The holidays are coming up quickly and there are so many fun holiday things to do in Annapolis + Anne Arundel County!
I did all the research (so you don’t have to 😉), and organized everything by category + dates, with direct links to everything in ONE BIG LIST! 🙌
The guide will be updated as more events are announced!
Am I missing your event? Please email me at [email protected] and I’ll add it to the guide!
This guide is generously sponsored by Western Shore Veterinary Hospital. When your pet’s adventures lead to unexpected injuries or health concerns, they're there to help. Their experienced team offers comprehensive care during our regular business hours, including wellness services for puppies and kittens, surgery, dental care, and specialized support to help pets navigate their golden years.
From playful pups to senior cats, they've got your whole family covered!
Booking an appointment is easy – just give Western Shore Veterinary Hospital a call!
FREE HOLIDAY PARKING DOWNTOWN ANNAPOLIS
Thanksgiving to New Years Day using ParkMobile
Two Hours Free at Meters, One Hour Free at Hillman Garage
TREE LIGHTINGS
Grand Illumination at Homestead Gardens
November 16th | 5-8pm
Kick off the holiday season with a spectacular tradition at Homestead Gardens! Join us for an unforgettable evening at our annual Grand Illumination, where the magic of the holidays comes alive. With over 250,000 lights illuminating the stunning grounds of our Davidsonville, MD and Smyrna, DE locations, you’ll be transported to a winter wonderland filled with twinkling lights, festive displays, and holiday cheer.
Annapolis Town Center Annual Tree Lighting Ceremony
November 21st | 6-8pm
Join us for a festive Tree Lighting at Annapolis Town Center with live performances, holiday treats, Santa, and lots of seasonal cheer!
Family Friendly Activities include Reindeer Food – Take-home bottles with “reindeer-friendly” snacks, Holiday Glitter Tattoo Station – Festive designs for kids, Holiday Balloon Twisting – Get your holiday-themed shapes like Santa hats, candy canes, and reindeer hat, Magic Mailbox – Mrs. Claus will stamp children’s letters to Santa at the Magic Mailbox before and after her stage reading.
There will also be a DJ, LED Lights, Firetruck and Brass Band. Enjoy Sips & Snacks from Vintage Views Mobile Bar, Reba’s Funnel Cakes, Stony Man Coffee and More!
Santa arrives to help light the tree around 7:45 pm. Festivities will be located on the boulevard near P.F. Chang’s and the East Village Boathouse.
Tickets are free and required for headcount purposes.
Downtown Annapolis Grand Illumination
December 1st | 4pm
The Downtown Annapolis Partnership joins the City of Annapolis as they ring in the holiday season in downtown Annapolis. The celebration begins at 4:00 pm with dancing and carols by local groups. The annual Christmas Tree lighting ceremony will include carolers, music, and general merriment! This event is free and open to the public. Join Santa, Mrs. Claus, and Elfie as they arrive to light the Christmas Tree.
Event Schedule 2024
4 -430 Naptown Sings
4 -430 Storytime Nutcracker inside Zachery's
430-450 Chesapeake Ballet
4:50 - 5:15 Talent Machine
515 -Tree Lighting with Santa
Glen Burnie Town Center Tree Lighting
December 3rd | 5:30-7:30pm
Join us for an evening filled with festive cheer! Enjoy a visit with Santa, live music, free ice skating, and treats like hot cocoa. Local businesses and county exhibitors will also be joining in on the fun!
Annual Tree Lighting at Waugh Chapel Towne Centre
December 3rd | 6pm
Join us for our Annual Tree Lighting Ceremony at Waugh Chapel Towne Centre. Meet us on South Main Chapel Way to kick off the holiday season with live performances from local groups and a special message from Santa. Plus–enjoy complimentary hot chocolate and a giveaway!
Hot Chocolate and a giveaway start at 5:30pm! Our celebration begins at 6pm! Or tune into our Facebook live at 6:00pm from home–don’t forget to chat with us virtually during the show! We hope to see you there!
City of Bowie Holiday Tree Lighting
December 7th | 5-7pm
Bundle up for caroling outdoors, followed by Santa and Mrs. Claus’ arrival atop the Bowie Volunteer Fire Department’s ladder truck. Children are invited to do a holiday craft while waiting for an exciting visit with Santa. There will be various food trucks on site starting at 5 p.m., with the Bowie State University Chorus leading the carols, leading up to the tree lighting at 6 p.m.
Admission is free, but feel free to spread some extra holiday joy by bringing a non-perishable donation for the Bowie Food Pantry.
SANTA PHOTOS + EVENTS
Santapolis: A Magical Holiday Experience at The Annapolis Mall
NOW-December 24th
To make a reservation and pre-purchase a photo package, click HERE.
Reservations are recommended but not required. Walk-ups are always welcome and will be accommodated on a space-available basis.
Bass Pro Shops Santa’s Wonderland
NOW- December 24th
Stop by to visit Santa and receive FREE 4x6 photos with Santa AND a FREE sharable video! Stop in during the weekday for FREE weekday giveaways including wooden ornaments and bass cookie cutters.
Make Your FREE Santa Photo Reservation Up to 7 Days in Advance.
Santa’s Cottage at Annapolis Town Center
November 22nd-December 24th
Experience the magic and capture the spirit of the holiday season with a visit to Santa’s Cottage where you will meet Santa himself and take home a photo for the whole family to treasure. Reservations encouraged. Walk-ins accepted. Check out the upcoming special events!
Santa Photos at Marley Station Mall
NOW - December 24th
Don't miss Santa pictures at Marley Station Mall! Walk ups welcome every day until closing time. Please Note: Multiple families are scheduled during the selected 15-minute time.
Jolly Express Cruise
November 23rd-January 1st
Annapolis' favorite holiday activity makes its return for the 2024 holiday season. Miss Anne will be adorned with reindeer spirit for an intimate 45-minute "sleigh ride" including hot cocoa, holiday music, and good cheer. Captain Santa or Mrs. Claus will be at the helm during this festive evening cruise on Spa Creek. Blankets will be available to stay warm and cozy. This is the perfect opportunity to start a family holiday tradition. In the spirit of the season, a portion of proceeds will be donated to Historic Annapolis. The ticket includes the cruise and your first cup of hot cocoa.
Photos with Santa at Homestead Gardens
November 30th-December 22nd (weekends only)
We are excited to bring back FREE photos with Santa for the holiday season, offering families and friends the chance to capture magical moments together. Whether you’ve been naughty or nice, Santa’s ready to make your holiday extra special! Check out all the important details below to make sure you’re ready when Santa comes to town.
Santa Claus is Coming to the Old Town Bowie Welcome Center
December 1st | 12:30-1:30pm
Visit the Old Town Bowie Welcome Center and capture the season's joy with a picture alongside Santa between 12:30 and 1:30 p.m. Also stop by the Railroad Museum to watch the trains whiz by on this busy train travel day (10 a.m. to 4 p.m.)
Jingle Bell Hayride at Kinder Farm Park
December 7th | 10am-1pm
Come join us in the holiday fun at Kinder Farm Park! Enjoy a festive hayride, snacks, warm drinks, roast marshmallows, visit the holiday decorated farmhouse and Meet Santa and Mrs. Claus Between 10:00 AM and 1:00 PM. Children 2 and under are Free but may be asked to ride on accompanying adult's lap. Hayrides last about 20-25 minutes. You are encouraged to bring a nonperishable food item for a food drive to be given to SPAN (Serving People Across Neighborhoods) during this holiday season.
SOFO's Photos with Santa at Annapolis Fire Department
December 7th | 10am
Bring your little ones to capture the joy as they share holiday wishes with Santa! With festive music, light refreshments, and memories waiting to be made, this event is all about celebrating the magic of the season. Don’t forget to bring your camera to snap those priceless moments!
Swim with Santa at Arundel Olympic Swim Center
December 7th | 10:30am-12pm
Event starts at 10:30 am and ends at 12:00 pm. Fee includes pool time, a picture with Santa and a stuffed stocking. Bring a swimsuit and goggles and visit with Santa. $12 Register early space is limited. Register at aarecparks.org/registration, Activity #38112.
Family friendly events for ages 3 years and above. Must be fully toilet trained, no swim diapers allowed.
FREE Kid + Dog Photos with Santa at Mother's Peninsula Grille
December 8th | 11:30am-1:30pm
FREE photos with Santa for kids and pets!
Cookies + Cocoa with Santa at Earleigh Heights Volunteer Fire Company
December 8th | 2-4pm
There will be various cookies, cocoa, and milk for all to enjoy. Lunch items will be for sale. Crafts, activities, and fire prevention material will be available for the children, as supplies last. Donation boots will be placed around the hall for those willing to contribute to help offset cost. Photos will Santa will be available to purchase for $5. Any questions, please reach out to [email protected].
This continues to be a free event!
Dragonfly Acres Christmas on the Farm
December 8th | 2-5pm
Our second ever Christmas event and this one is going to be extra special. It is an event we started last year to give back to our surrounding communities for all the support they’ve given us throughout the year!
Join Us to Meet Our Farm - Hands on Interaction, Bonfires for S’mores, Small Holiday Crafts, Christmas Photo Ops, Pictures with Santa, Holiday “Sleigh” Rides, Sensory Friendly Environment, Hot Chocolate/Coffee/Cookies, Local artisans, crafters and homemade goods (still accepting inquiries for tables if interested) and more!
Cookies + Cocoa with Santa at the Severna Park Community Center
December 13th | 5-8pm
Stop by to enjoy the Holiday Gift Marketplace, Santa's Elf Workshop, Holiday Movie & Treats, Photos with Santa, Festive Photo Booth, Holiday Crafts and so much more!
Visit with Santa on the B&A Trail
December 14th | 10am-3pm
Visit with Santa and his helpers as they hand out candy canes and collect non-perishable food items for the Anne Arundel County Food Bank! In the event of rain, this event will be held at Earleigh Heights Ranger Station from 10:00 a.m. - 1:00 p.m.! Notifications will be posted if decided. We hope to see you on the trail!
Saturday Fun with Santa at the Bowie Gym
December 14th | 10am-1pm
Come see Santa in a festive environment with moon bounces, live holiday music, face painting, and a balloon twister. Families with children ages 10 and under are welcome.
A donation of a new and unwrapped toy for the toys for tots drive is welcome, but admission is free.
SENSORY FRIENDLY SANTA
Sensory Friendly Santa at Annapolis Town Center
December 8th | 9-10:30am
We invite families with kids of all ages and abilities to join us for a sensory friendly environment that supports neurodiverse guests with an inclusive environment. Children with sensory sensitives can enjoy the magic of Santa with a safe and comfortable experience. Make memories in a sensory friendly environment with reduced lighting and music and meet a sensory-friendly trained Santa and staff to support families and kids with special needs.
Annapolis Mall Sensory-Friendly Santa
December 8th | 9-10:30am
Sensory Santa is a sensory-friendly opportunity for children with special needs and their families to enjoy a private photo session and visit with Santa Claus in a calming environment before the mall opens to the public.
Each child in attendance will receive a free plush and bag full of holiday goodies.
Reservations are not required. Walk-ups are always welcome!
Sensory Santa Experience with TruCentered Chiropractic
December 13th | 1-4:30pm
‘Tis the season….to get holy-joly and very merry! With the festivities and holiday plans well underway, it can also be a very overwhelming time of year - especially for children with Sensory Processing Disorders, NeuroDeflective Disorders, Autism Spectrum Disorder, developmental differences, or any child who is sensory sensitive. For our friends You’re invited to bring together those you love most for a festive and sensory-friendly Santa day!
8 minute time slots to visit with the legendary (and sensory-friendly!) Santa Todd who is patient, kind, and experienced with working with truly everyone. Sessions will take place in a private space with no music and crowds. Festive decorations as well as weighted blankets, and fidget toys will be provided. Photos are optional and will happen with continuous lighting (not flash!). The building and space is wheelchair accessible, and will have a dedicated waiting space with activities.
This opportunity is complimentary, however donations are greatly appreciated and will be sent to Gold In Fight (GIF) in an effort to raise funds for local families who have children battling childhood cancer.
HOLIDAY SHOWS + PERFORMANCES
Guava Jelly Performs at The Annapolis Mall
November 20th, December 4th + December 18th | 10:30am
Ready to move and groove? Join us at Crate & Barrel Court on Wednesday's from 10:30 - 11:15 for a fun-filled family event with Guava Jelly! This Annapolis-based duo will bring their Caribbean rhythms to the mall, creating the perfect midweek music break for you and your little ones! Don’t miss out on this FREE, family-friendly concert series! Come ready to sing, dance, and create some unforgettable memories!
Children's Theatre of Annapolis Holiday Cabaret with Santa
December 7th | 2-5pm
Showcasing live performances, vendors, holiday snacks + games, & a visit from Santa and his bag of gifts! This promises to be a wonderful and joyous holiday celebration.
A Colonial Yuletide
December 7th | 2-5:30pm
You are cordially invited to celebrate a colonial holiday with Historic Annapolis! Bring the entire family to welcome yuletide at the William Paca House and Hogshead Trades Museum. It’s the year 1774! Experience the holiday traditions, music, and stories of Christmases past. Spend a fun afternoon with us at this joyous celebration! Your Colonial Yuletide admission includes both sites, and you may begin your experience at either location.
Discoveries Library Nutcracker Storytime + Preview
December 8th | 2pm
Join us for the story of the Nutcracker and a preview of the ballet by The Chesapeake Ballet Company.
Belair Mansion Magic Elf Hunt
December 13th-15th + 20th-22nd | 12-4pm
Calling all Elf Hunters! The elves are missing from the North Pole and Santa believes they are hiding at Belair Mansion…again! Are you a certified elf hunter? Come to Belair Mansion and prove your skills and earn your official elf-hunting badge. Help return those naughty elves to the North Pole in time for Christmas.
Free. No reservations are needed.
The Nutcracker at The Dance Center at Severna Park Community Center
December 13th | 6pm + December 15th | 12:30pm
Step into the magical world of sugar plum fairies and toy soldiers this festive season! We invite you to join us and experience the enchanting tale of The Nutcracker! Perfect for the whole family, this timeless classic will spark your imagination, touch your heart, and transport you to a winter wonderland like no other. So, save the date, and let's keep the tradition alive! You won't want to miss out on this spectacular celebration of the holiday season!
The Talent Machine Presents - A Jolly Holiday 2024
December 13th-23rd | Indian Creek High School
Join the Talent Machine Company and experience the magic of the season with our annual holiday show, A Jolly Holiday! This high energy production will enchant audiences of all ages. The show will feature a cast of 42 talented children, ages 7-18 from all over the region, along with Rudolf, Frosty, Santa and the Elves!
With captivating choreography and heartwarming holiday music, A Jolly Holiday is a timeless celebration of the holiday season, offering an unforgettable experience for families. From classic carols to contemporary favorites, the production promises a mix of joyful tunes, delightful dance numbers, and beautifully designed sets featuring a magical toy room that comes to life!
The Nutcracker: Ballet Theatre of Maryland at Maryland Hall
December 14th-22nd
Discover the wonder of this timeless holiday tradition and allow yourself to be magically swept away by the tale of the young heroine Clara and her adventures to rescue her beloved Nutcracker from the Rat Queen’s evil spell. Travel with Clara through the whirling Kingdoms of Snow and Sweets to the place where the possibility of dreams, the magic of Christmas, and the wonder of the child merge to reveal her destiny. Experience the power and beauty anew as the mysterious Drosselmeier transports you and Clara back in time to capture the spirit of the holiday season through the language of dance and theatre.
ASO Presents Holiday Pops at Severna Park High School
December 14th | 3pm
Get ready to experience one of the most beloved traditions in Annapolis—the Annual Holiday Pops concert! This festive season, join the Annapolis Symphony Orchestra and 70 world-class musicians as we bring the joy, beauty, and warmth of the holidays to life with a dazzling mix of classical music, carols, and heartwarming holiday tunes.
BREAKFAST + DINNER WITH SANTA
Brunch with Santa at 100 Lots
December 7th | 10:30am-12:30pm
Santa is taking a break from his busy schedule to fly down for brunch at 100 Lots! We will have a hot chocolate bar set up and crafts for the kids.
Brunch with Santa at Eastport Yacht Club
December 8th | 11am-1:30pm
EYC membership and reservation required.
Brunch with Santa
December 8th | 10am-2pm
Dinner with Santa at Coconut Joes
December 11th + 18th | 6-10pm
Get ready for a holly jolly evening with the big guy himself! Bring the family, share your wish list, and enjoy a night full of elfin’ good fun, delicious food, and festive cheer! Snap pics with Santa, Feast on your favorites and Make magical memories. Don’t miss this sleigh-worthy night – it’ll be yule fun for everyone!
Email at [email protected] to reserve your spot!
Breakfast with Santa at The Lodge Annapolis
December 14th | 9:30am-12pm
Bring the whole family to The Lodge Annapolis for Breakfast with Santa. Enjoy a delicious meal, festive activities, and a visit with Santa Claus himself.
Breakfast with Santa at Tuscan Prime Italian Chophouse
December 15th | 10am
Santa is coming to Tuscan Prime! Reserve your table this December 15th and enjoy a delicious brunch, and get your picture taken!
City of Bowie Breakfast with Santa
December 21st | 9-11am
Bring the family to visit Santa, eat breakfast, make crafts, and watch a magician. Hurry! This event is only open to 90 participants and sells out quickly!
Sign up for an intergenerational Breakfast with Santa on December 21 at the Bowie Senior Center. The fun begins at 9 a.m. with a hearty breakfast of pancakes, sausage, fruit, juice and coffee. Then, get a photo taken with Santa, be entertained by roving magicians, and make holiday crafts. Registration opens in November and the registration deadline is December 1 or whenever the 90 available slots are filled.
Admission is $5. Children 2 and under are free. Registration is required.
Annapolis Maggiano's Breakfast with Santa
December 22nd | 9-11am
Santa Claus is coming to town, and he's stopping by to enjoy a delicious breakfast with all the good boys and girls. This event is the perfect opportunity to share your Christmas wishes and snap a memorable photo with Santa.
STORYTIMES + CRAFTS
Library Nutcracker Storytime + Preview
November 20th | 6pm
November 30th | 1:30pm
December 8th | 2pm
Join us for the story of the Nutcracker and a preview of the ballet by The Chesapeake Ballet Company.
Mini Makers Winter Wonderland
December 5th + 6th
Mr. Paca’s Garden Storytime: Bear Stays Up for Christmas
December 17th | 10am
Mr. Paca’s Garden Storytime is a fun hour full of reading and activities in the William Paca Garden, a secret treasure in the Historic District of Annapolis. Each program is designed for little ones, 3-7 years, with a book reading, song, and craft/art project.In Bear Stays Up for Christmas, we discover that giving is one of the best Christmas presents of all. Join us as we sing and dance in anticipation of the holidays! We will create a special Christmas craft!
Advance registration is required, space is limited.
Lafayette’s Farewell Tour: Open House & Story Time
December 14th | 12-4pm
Join Watermark for an open house and story time with author, Selene Castrovilla, who will share her acclaimed picture book Revolutionary Friends: General George Washington and the Marquis de Lafayette. Young readers will love learning how and why Lafayette sailed to America and helped us win our liberty. Signed books will be available for purchase.
CHRISTMAS LIGHTS, PARADES + TOURS
Snowflake Alley
Off Main Street in downtown Annapolis across from Chick n Ruth’s Delly.
ICE At Gaylord National Resort
November 15th-December 28th
ICE! featuring "A Charlie Brown Christmas" is a dazzling, immersive, story-driven holiday showplace complete with larger-than-life ice sculptures, thrilling frozen slides, and awe-inspiring tunnels. Come experience the splendor of the holiday season at Gaylord National. Presented by PEPSI®. More than 40 world-renowned master artisans spend more than six weeks hand-carving approximately 6,000 blocks of ice to create this one-of-a-kind Christmas attraction! With more than 17,000-square-foot and 14 immersive scenes, here's a peek at some of our favorite scenes you won't want to miss!
Holiday Spirit Tour: Yuletide Traditions at the William Paca House
November 22nd-December 9th
You’ll be guided through this home of a Signer of the Declaration of Independence by your knowledgeable docent on a one-hour, candlelit tour. Enjoy the elegant decorations, learn about 18th century Annapolis and Maryland holiday traditions, and how the Paca household prepared for their holiday guests. The historic home is ready to greet you with music, garlands, a sweet treat, and a take-home recipe!
2024 Lights on the Bay MD
November 24th - January 1st | Sunday-Thursday: 5-9pm + Friday + Saturday: 5-10pm
Get ready for a dazzling holiday tradition that lights up the season with joy, wonder, and a whole lot of fun—all while supporting the SPCA! Gather your friends, family, and furry companions for an unforgettable evening filled with sparkling lights, festive vibes, and the warm feeling of giving back.
Winter Festival of Lights at Watkins Regional Park
November 29th-January 1st | 5-9pm
We can’t wait for the Winter Festival of Lights! The dazzling lights are back this year to help spread some holiday cheer. Our official opening day is Friday, November 29 at 5 pm. We’ll see you and your family there!
North Pole Lights Walk at Willow Oak
November 29th-December 28th | select dates 4:30-8pm
Take a self guided walk to the North Pole! Let the North Pole Fairy send you on your way through the garden flowers and arctic animals to the North Pole Palace. Visit Santa in the Garden Cabin. Take pictures in Santa’s magical sleigh. New scenes are added every year!
Pets are not allowed, only service dogs. The trail is about 1/2 mile long with many stops along the way. The path is brick, stone and woodland, strollers and wheelchairs can access it but some areas may be harder than others to navigate. In case of inclement weather you can use your tickets another evening. Tickets are non-refundable but can be used another night
Pasadena Boat Parade
December 7th | 5pm
The annual boat parade starts in Nabbs Creek, near the Broken Oar Bar & Grill, goes up and down Stoney Creek, and ends on Rock Creek at PYY Marine. Boaters and Santa return to THE BROKEN OAR at 7:30pm bringing Christmas cheer to all! There will be Christmas Music, a Kiddie Corner, a special drink menu for all ages, and plenty of viewing areas for all! Santa will be handing out treats and taking requests for Christmas presents from kiddies young and old from 7:30pm-9pm.
The Magic of Christmas at Anne Arundel County Fairgrounds
December 13th: 6-9pm, December 14th: 4:30-9pm + December 15th: 4:30-9pm
Step into a world of enchantment with The Magic of Christmas! This year, hop on a dazzling hayride and marvel at over half a mile of stunning light displays, leading you straight to Santa’s workshop! Journey through a wonderland of 100 illuminated Christmas trees and seize the chance to meet Mrs. Claus and Santa Claus to share your Christmas wishes! All proceeds support Anne Arundel County Fairgrounds. Food and beverages available at an additional charge.
Children 5 and under ride free!
Eastport Yacht Club Lights Parade
December 14th | 6-8pm
It's a beloved Annapolis tradition! Every year on the second Saturday in December, magic happens on the water of the Annapolis Harbor—boats suddenly appear out of the cold winter night illuminated with thousands of colored lights and crewed by jolly revelers!
HOLIDAY TRAIN DISPLAYS
Homestead Gardens Train Davidsonville
November 1st-December 30th
The holiday train display at the Davidsonville Homestead Gardens gets bigger + better every year! It’s the perfect FREE place to bring your train-obsessed kids, browse new plants, and shop for holiday home decor.
Homestead Gardens Trains Severna Park
November 1st-December 30th
The display only has one track but it’s full of intricate details, twinkling lights and the train makes fun noises + whistles. Kids can walk around the entire display and get up close to see the train and characters. We loved the big selection of kids gifts, the dancing Elf display, and the 3D glasses to see different figures in the Christmas trees! The train display is FREE to see and open during store hours.
Holiday Train Garden at Kenilworth
NOW until January 5th
Visit the lower level of the Shops at Kenilworth to enjoy the annual Train Garden display, sponsored by The St. Paul’s Schools and GBMC Healthcare. My friend Angie made a visual scavenger hunt for the littles to make their visit even more fun.
Holiday Train Garden at Marley Station Mall
November 23rd-30th + December 1, 6, 7, 8, 13, 14, 15, 20, 21, 22, 23, 24, 26, 27, 28, 29, 30 + 31 + January 3-5
The Holiday Train Garden at Marley Station Mall will be reopening for the 2024 holiday season. Join us on opening day 11/23 for a fun filled day of model train displays, door prizes, and giveaways. Come see our all new displays including Andy's room (Toy Story), Willy Wonka's chocolate factory, new Thomas the Train displays, slot car display, and more!
Maryland Hall Holiday Trains
November 15th - December 23rd (times vary via Maryland Hall)
Hosted at Maryland Hall for the Creative Arts in Annapolis during the holiday season, features an original display with two themes: 1) Where's Waldo Train Station and Zoo complete with scavenger hunt from the book Where's Waldo and 2) Alfred Hitchcock's 1959 movie North by Northwest.
HOLIDAY FESTIVALS + CONTESTS
The Great Annapolis Gingerbread Houses
November 24th-December 1st
The Annapolis Chocolate Binge Festival will be hosting their annual Great Annapolis Gingerbread Houses Contest event sponsored and held at Visit Annapolis & Anne Arundel County. All ages are encouraged to enter a decorated house for the contest to be held during Annapolis Chocolate Binge Festival. Judging will take place starting Sunday, November 24th thru Sunday, December 1st at 3pm. Winners will be announced at the festival at 3:30. Decorated winners will be on display until Friday, December 20th.
Annapolis Chocolate Binge Festival
December 1st | 11am-4pm
Start off the December holiday season with some fun and indulge your sweet tooth at the annual Annapolis Chocolate Binge Festival. Take a chocolate tour along West Street with chocolate vendors selling various chocolate specialties, including chocolate truffles, caramels, bars, fudge, cookies, cakes, martinis, French macaroons, cupcakes, pies, brownies, and more. You can also complete your holiday shopping at our holiday market at the Annapolis Chocolate Binge Festival featuring local artisans with a wide range of handmade items including jewelry, pottery, candles, wood turnings, ornaments, clothing and more.
TICKETS ARE $5 AND FREE ADMISSION TO AGES 12 AND UNDER
Anne Arundel Chamber of Commerce Jingle and Mingle Holiday Party
December 4th | 6pm
Celebrate the season with your co-workers and colleagues at the Chamber's Jingle & Mingle Holiday Party at The Atreeum at Soaring Timbers. We have several options for you to attend the Holiday Party including discounted party packs so you can bring the whole crew!! We'll have a fantastic silent auction along with our wreath auction.
HOLIDAY SHOPPING EVENTS
Himmel's Holiday Village
November 21st - December 24th
Join us at Himmel's Holiday Village for five magical weeks of family-friendly holiday events and artisanal shopping at 4374 Mountain Rd. in Pasadena, MD. Running from November 21 to December 24, 2024, our holiday village features a wide variety of local vendors, delicious food trucks, and live music to get you into the festive spirit. Enjoy free hot chocolate, meet Santa Claus every Saturday and Sunday, and explore exciting activities perfect for all ages. Come experience the best holiday shopping and entertainment in Pasadena, and make your season truly unforgettable!
HERE. a pop-up shop 50th
November 15th-December 22nd
It's our 50th pop-up since 2013! Celebrate with us by shopping over 85 LOCAL makers this holiday season! See the calendar for special events & late nights!
Quiet Waters Park Holiday Artisan Market
November 13th-January 5th
Explore unique handcrafted items from talented local artists perfect for holiday gifts or personal treasures. Reception Nov 17, 1:30pm-3:30pm in the Visitors Center.
Homestead Gardens Girls Night Out
November 20th | 5-8pm | Davidsonville location
November 21st | 5-8pm | Severna Park location
This signature event promises to be a magical night filled with festive charm, perfect for kicking off the holiday season in style. Whether you’re coming with your best friends or looking to enjoy a special evening out on your own, this event is designed to delight and inspire everyone who attends. Sample, Sip & Shop in our beautifully decorated store, fully transformed into a holiday wonderland.
FREE
Pink Friday Shopping Downtown Annapolis
November 22nd | 10am-5pm
Plaid Friday Downtown Annapolis Shopping
November 29th | 11am-5pm
Wear plaid on the day after Thanksgiving and come stroll and shop downtown Annapolis! Support your local small businesses + shop small!
Small Business Saturday Downtown Annapolis
November 30th | 10am
Small Business Saturday has become an annual event for our downtown Annapolis business districts. It has been over 11 years since we started celebrating our small local businesses on this day. These are the businesses that make your community unique and special. Every day we all vote with our dollars on which businesses we want to see continue to be in our communities. Shopping at your favorite Small Business on this day brings the community together to reinforce to our local business owners that you appreciate them, as they appreciate you.
The day is devoted to supporting your local independent retailers and restaurants. Have fun and shop in Downtown Annapolis at your favorite small business. Enjoy the special hometown service and the unique selection you find from your locally owned retailers.
Providence Pottery & Arts Studio Holiday Market
November 30th | 10am-2pm
Join us for a festive day of holiday shopping this Small Business Saturday at the Providence Pottery & Arts Studio Holiday Market! On Saturday, November 30th, from 10:00 AM to 2:00 PM, browse a wide selection of handcrafted holiday pottery, seasonal gifts, home décor, and more from Providence Pottery and a curated section of guest vendors. Whether you're looking for that perfect gift or a statement piece for your holiday table, you'll find something for everyone. We also offer gift certificates and fun "Paint Your Own Pottery Kits" for creative gift-giving. Don't miss this opportunity to support Providence of Maryland and bring home something unique for the holidays.
Midnight Madness Annapolis
December 5th, 12th + 19th | 4pm-midnight
The streets will be filled with entertainment and holiday decorations, and the shops will have refreshments and sales. It is the perfect opportunity to get your holiday shopping done and see why Annapolis is ranked as one of the Top Christmas Toowns in the nation. Bring your friends and family and enjoy the holiday season together. When we shop locally, we reinvest in our community and help our downtown businesses thrive.
Providence Greenhouses Holiday Decor Sale
December 6th + 7th | 9am-1:30pm
Embrace the spirit of the season with a delightful selection of holiday plants and décor, including vibrant poinsettias, fresh greenery, and beautifully crafted wreaths. We are not offering trees for sale.
West Annapolis Holiday Market
December 7th | 11am-5pm
Join us, along with our beloved local businesses, welcoming neighbors, and talented artisans, at the Annual West Annapolis Holiday Market! Wander among festive, light-adorned trees, savor a warming seasonal drink, and immerse yourself in the spirit of the holidays. It’s the perfect way to kick off the season with community, cheer, and giving. This event is sponsored in part by our friends at @rarbrew & @chessieswharf who undoubtedly know how to throw a party.
Wildberry Farm Vintage Christmas Market
December 7th + 14th | 2-6pm
Join Wildberry + over 60 unique small businesses over two Saturdays for an outdoor Christmas Market! The Wildberry Farm to Table Food Trailer will be serving hot foods + beverages. Plus enjoy a roaming Santa, live music + more!
Free admission, leashed dogs allowed.
Glen Burnie High School Winter Craft Fair
December 7th | 9am-3pm
Get your holiday shopping done at the 41st annual Glen Burnie High School Winter Craft Fair benefiting the GBHS Band Boosters. Join us as over 140 crafters display their unique arts and crafts. Shop for one of a kind wood crafts, soap and body products, candles, home goods, jewelry, glassware, holiday decorations, dog treats, candy and many more handmade items. Lunch and snacks are available. Admission is free. We hope to see you there!
Saint Martin's Howliday Pawty
December 7th | 6-9pm
It will be a night full of delicious handheld food, wine, vendors, raffles, and live music. Our school's gym will be transformed to an exclusive holiday market including 30+ local vendors, gift wrapping table, school merchandise, and more!
Heroes Holiday Market
December 8th | 8-11am
Join us on Sunday December 8th from 8-11am as we welcome over 35 of your favorite local small businesses, Santa and his crew and our 4th Annual Heroes Market raffle to benefit the River Arts District Asheville. Artists, bakers, creative gifts, clothing and more!
We’ve been in contact with Santa and he has confirmed that he and his beautiful wife will be there for photos, list sharing and plenty of holiday shopping!
FREE admission!
Olde Severna Park Holiday Shop + Stroll
December 8th | 4-7pm
Wander the Shops of Olde Town Severna Park for Holiday Cheer, Fun, and Gift Buying! Live Music, Vendors, Samples are all part of the Charm in our “Little” Hometown Village.
Annapolis Holiday Market
December 12th-15th
The market will be filled with a wide range of art, crafts, food, and handmade gift items from local and regional art, craft, and food vendors. This type of holiday market is also known as a Kris Kringle Market or Christmas Market. The Annapolis Holiday Market is now in its third year this holiday market will feature over 120 artisans and specialty food vendors.
Severna Park Farmers Market Christmas Market
December 14th | 8am-12pm
The Severna Park Farmer’s Market is holding its’ seventh annual outdoor Christmas Market! We’re so happy to announce this wonderful variety of local vendors who will be here with us for this one-day-only market.
Current Dermatology "Favorite Things" Holiday Week
December 16th-20th | 8am-4pm
Join us for a week of holiday cheer, fabulous savings, and exclusive surprises showcasing some of our favorite things — just in time to treat yourself or check off your holiday gift list!
What to Expect:
10% off all Gift Cards – Treat yourself or a loved one
Goodie Bags with every gift card purchase – packed with sample products and chances to win surprise gifts, including:
- Full-sized products from SkinBetter and Alastin
- Free vials of Dysport and Daxxify; and
- Gift cards up to $2,000 toward a treatment of your choice!
Our providers will also be available throughout the week to discuss our newest treatments and devices, giving you the chance to learn more about what’s best for you and your skin goals.
The Ultimate Girls Night Out, Charms before Midnight!
December 19th | 7pm
Charms by Bre is returning to Perpetual Skin, for a happy hour before Downtown Annapolis' Midnight Madness. Your ticket includes Bracelet making workshop led by Bre, custom made jewelry, which you get to take home for yourself or someone else, $11/unit tox - save for later, or be treated same night, Discounted Skincare and Giftcards, Raffle Giveaway Entry and Hors d'oeuvres and beverages.
5Ks + FITNESS
18th Annual Thanksgiving Day Turkey Trot 5K Fun Run
November 28th | 9am
The run is a gorgeous tour of downtown Annapolis and will benefit Girls on the Run Greater Chesapeake. This event is not officially timed, but we will have a finisher's clock at the end of the run. Once again we will award several prizes for the best turkey costumes. Are you ready to get creative? Strollers, kids, and dogs are welcome to join in the fun!
2024 DeCesaris Prout Cancer Foundation - Jingle Bell Run
December 7th | 9am
This annual fundraiser is designed to raise awareness for lung and ovarian cancers. The Jingle Bell Run/Walk is geared towards the general public as an incentive to participate in a healthy lifestyle while offering an opportunity to educate everyone about early detection of lung and ovarian cancers. In addition, the event is also designed to raise much needed funds to support various educational research programs and patient services.
Jingle + Mingle Dance Work Out, Flower Workshop + Holiday Cocktails
December 10th | 6:30pm
Grab your bestie, dress in your holiday spirit, and join us for a holiday class! We'll be dancing to our favorite holiday tunes, followed by a happy hour provided by @followfrannie. Get into the holiday spirit with a hands-on flower arranging session. We will be designing holiday flower boxes filled with fresh florals, berries, dried flowers that will ring in the holiday cheer. Whether you’re a beginner or a seasoned flower enthusiast, you’ll leave with a beautiful centerpiece to share or keep!
Annapolis Santa Run
December 15th | 5:45pm
Come help us make Christmas morning a little brighter for our neighbors in need. We will be escorting Santa around our area on Sunday December 15th collecting new, unwrapped toys that will then be delivered to families in need before Christmas morning. We are scheduled to stop at Cape St Claire Elementary School at 5:45pm, however weather and/or traffic can impact this time. We make every effort to arrive on time!
Santa Speedo Run at O'Brien's Oyster Bar
December 16th | 11am-3pm
Annapolis' most unique holiday tradition continues! Drop off your donations then join us for Christmas carols, photos, the RUN then an after party with the Timmie Metz Band featuring Tambo!
HO HO HO Dance Party
December 17th | 6:30pm
Grab your bestie, dress in your holiday spirit, and join Moms in Motion for our Holiday Dance Party with Class Act Performing Arts. We'll be dancing to our favorite holiday tunes, followed by a happy hour with some festive goodies provided! ADULTS ONLY!
Naptown Half Marathon & 10K/5K
December 21st | 7:30am
This year we are partnered with the FRIENDS OF ANNE ARUNDEL TRAILS to help their mission in promoting, protecting and enhancing the multimodal trails of Anne Arundel County. Be sure to show off your Holiday Cheer this year, as we will be giving out Santa Caps to all! Prizes for the most festive runners will also be given out too! We can't wait to spend the holiday with you!!
FUNDRAISING EVENTS
Rally for Riley
November 23rd | 2:30-6pm
Let’s come together as a community for Riley, a brave 10-year-old fighting stage 4 Neuroblastoma. Diagnosed at just 5 years old, Riley and his family need our support now more than ever. Rally for Riley is a massive health and wellness event dedicated to raising funds for Riley’s treatment and support for his family as they navigate his battle with cancer. Join us shop local vendors, register for fitness classes, enjoy the spa room, enter to win amazing raffle baskets, and immerse yourself in wellness while giving back! Enjoy a variety of wellness services including IV therapy, vitamin injections, hyperbaric oxygen, lymphatic drainage, acupuncture, and more. 100% of the proceeds go directly to Riley’s family, so his mom, Ashley, can take off work to be by his side.
JollyFest 2024
December 14th | 4-8pm
Join us for a festive evening of craft beer, food, live music and Santa! Adult tickets include dinner and 4 hour open bar. Kids eat, drink and enjoy the festivities for free! All proceeds benefit RareOlive's LNPK gene therapy research project at UTSW.
2025 Polar Bear Plunge
January 24th - February 1st
The Polar Bear Plunge is part of Maryland's history. For the past 28 years, thousands of plungers have jumped into the icy waters of the Chesapeake Bay all in support of Special Olympics Maryland. Your dedication to the athletes and Unified® teammates is impactful and has created countless inclusion experiences across the state of Maryland. Help us reach our goal of $4 million this year and register for the 2025 Plunge!
DOG-FRIENDLY EVENTS
SPCA Lights and Leashes
November 22nd + 23rd | 5-9pm
For two nights only, bring your furry friend and walk through the light show on foot! It’s a pawsitively magical evening that supports the SPCA of Anne Arundel County. All dog walkers must exit the course by 10:00 PM.
Santa Paws at Annapolis Town Center
November 26th, December 3rd, 10th + 17th | 4-7pm
Join us at Santa’s Cottage for Pet Photos with Santa! Capture the perfect holiday memory with the entire (furry) family from 4-7 pm.
Pet Photos with Santa at Annapolis Mall
December 2nd, 9th + 16th | 4-7pm
We’ve reserved special times for your furry friends to join in your family photos with Santa. Each pet will receive a free special treat. While supplies lasts. Pets must be leashed or in a carrier. Reservations are recommended but not required. Walk-ups welcome.
Santa Paws 2024 at Homestead Gardens
December 4th | 4-7pm | Severna Park Location
December 6th | 4-7pm | Davidsonville Location
This heartwarming holiday event is designed for your furry friends to enjoy, alongside their human companions. It’s the perfect opportunity to capture festive memories with a photo of your pet and Santa in a magical setting. Amid twinkling lights and holiday cheer, your pets will have the chance to pose with Santa in front of a beautifully decorated backdrop. You’ll be in charge of snapping the photo, so be sure to bring your phone or camera to immortalize the special moment. The festive atmosphere will make it a truly memorable experience for both you and your pets.
FREE
FREE Kid + Dog Photos with Santa at Mother's Peninsula Grille
December 8th | 11:30am-1:30pm
FREE photos with Santa for kids and pets!
FREE Dog Photos with Santa at Sea Dog Pet Boutique
December 8th | 1-3pm
@dogsofannapolis will be photographing your pups, and you’ll get your photos digitally sent to you after the event. The event is free, but we will be accepting donations for a to be determined animal charity.
MILITARY BOWL 2024
A Budweiser Clydesdale Miracle on West Street
December 27th | 3pm
Don't miss seeing these majestic animals. This year the horses will be parading on West Street!
Military Bowl Game
December 28th | 1pm
This year's game will feature teams from the ACC and the American Athletic Conference, kicking off at 5:45 p.m. ET and televised on ESPN.
Schedule of Events with more information to come!
1pm: Military Bowl Parade
2pm: Tailgate Festival
5:45pm: Kickoff
For the first time, the Military Bowl will be played in prime time... click here to read more!
ICE SKATING
Glen Burnie Outdoor Ice Skating
November 20th - December 3rd
Online Reservations Are Highly Recommended - We Do Sell OutSkating Tickets Are For Up To 2 Hours of SkatingTickets Can Be Purchased Up to Two Weeks in AdvancePlease Arrive Within 10 Minutes of Your Scheduled Reservation Time.
Quiet Waters Park Ice Skating
NOW until TBD
The Quiet Waters Park Ice Rink is located in front of the Visitor Center and offers a pleasant and safe environment to enjoy ice skating outdoors. We have skates, helmets, and we sharpen skates on-site. Come out for fun with family and friends. Ice skating lessons will be available throughout the season for all levels. Email [email protected] for more information.
Monday, Wednesday, Thursday + Friday: 3-9pm and Saturday + Sunday 9am-9pm | Rink is CLOSED on Tuesdays
Holidays (when AA County public schools are closed) 10am-9pm. Adult $7.00, Senior (60 years and over) $6.00, Child (12 years and under) $6.00, Ice Skate Rental $3.00
HANUKKAH EVENTS
Celebrate Hanukkah at The Annapolis Town Center
December 25th-January 2nd
We invite the community to join us and gather with friends and family in celebration of the Hanukkah season. The Festival of Lights begins on Dec 25th and the Menorah will proclaim and celebrate the miracle of Hanukkah with each candle we light through Jan 2nd.
Chabad of Anne Arundel County Parade of Light
December 29th | 5:30pm
Join us for a spin at the annual Menorah Car Parade here in Annapolis. An experience you won't want to miss! The parade will be leaving Safeway in Annapolis at 5:30pm so please be there at 5:00pm if you are planning on joining the parade. Parade Destination - City Dock - Annapolis, MD at approximately 5:45pm where we will kindle a giant menorah and celebrate the festival of lights.
NOON YEAR'S + NEW YEAR'S EVE EVENTS
Noon Year’s Eve at the B&O
December 31st | 10am-1pm
Ring in the New Year at the B&O with themed New Years Activities! Create your celebratory party hat and mirror ball, then head over to our Resolution Station and set your goals for the new year! No New Year’s Celebration would be complete without the chance to see the ball drop, make a toast (with apple juice), and celebrate with confetti poppers! Don’t forget to commemorate this great day out with family with photos topped off with balloons and props. Train rides will be available at 11:00 am and 1:00 pm. Tickets are available for purchase on-site.
New Year’s Eve at Noon at EcoAdventures
December 31st | 11am-12:30pm
We're having a New Year's at NOON! Lots of little ones can't stay up until midnight... WE can't even stay up until midnight...), so Eco Adventures is speeding up the clock so your kids can celebrate New Year’s Eve at Noon! Join Eco Adventures for an unforgettable time with an animal show ! Then countdown to noon and watch the "Ball" drop into our gator pond in grand style while we feed Walle our gator! AND PARTY with us as we will have a dance-off party, Make a craft, green screen pictures, and of course...New Year’s Eve Hats and party favors!! It's countdown time to a New Year so blast off with us... Five, four, three…two.. Happy New Year 2025!!!
Noon Year’s Eve Celebration at Discoveries Library
December 31st | 11:30am
Celebrate the New Year by counting down to noon at our special party just for kids who won't make it to midnight!
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New Year's Eve Fireworks Annapolis
December 31st | 9pm
The City of Annapolis will put on a fireworks displays at Susan Campbell Park. This family-friendly event has been drawing tourists to the shores of Annapolis for years! The spectacle of the fireworks from the shores or on one of the many charter boats in the county makes for a festive and exciting way to ring in the new year!
New Year’s Eve Gold Party at The Choptank Annapolis
December 31st | 8pm
Starting at 8 pm you can enjoy an open bar featuring spirits and cocktails, passed apps and a standing buffet, live entertainment and the best view of the fireworks!
New Year's Eve at Acqua al 2
December 31st | 9:30pm
Indulge in an array of passed and displayed hors d’oeuvres, including Scallop and Prosciutto Bites, Grilled Lamb Lollipops, Tuna Crudo Bites, Burrata Crostini, Arancini di Riso, and more (full menu can be found here.) Our ticket includes access to an open bar featuring six handcrafted cocktails, alongside beer, wine, sparkling, and non-alcoholic options. For any additional beverages, a cash bar will be available.
Dance the night away with live DJ beats as we celebrate from 9:30 PM to 1:30 AM in the heart of Annapolis. This is the perfect way to welcome 2025 in style—don’t miss out!
Enjoy the holidays with your friends and families! See you around Annapolis! Stay warm + have fun!
I'll be updating this list over the next couple of weeks so check back for updates! If I'm missing your favorite holiday event, please email me at [email protected] to be added to the list.
*Please note – While I make every effort to crosscheck links and event details, we always encourage you to do the same before making final plans. If details are missing or incorrect, please let us know so I can correct them. Thanks for your help!
