We made the ultimate list of ALL THE HOLIDAY events in Annapolis and Anne Arundel County!
We did all the research (so you don’t have to), organized everything by category, event date, and added direct links to everything in ONE BIG LIST!
Please email me at [email protected] and I’ll add it to the guide!
This year’s Holiday Guide is proudly presented by Erica Baker, Associate Broker & Vice President with TTR Sotheby’s International Realty.
The holidays are a time to gather, reflect, and enjoy the moments that make a place feel like home. As a trusted real estate resource throughout Anne Arundel County, Erica is honored to support clients as they navigate where they are now and where they’re headed next.
Whether you’re settling into a new space, exploring future possibilities, or simply embracing the season in your own way, this guide was curated with your lifestyle and our community in mind.
From cherished local traditions to festive events and the small businesses that give this area its charm, consider this your go-to source for holiday inspiration.
And if you’re looking for thoughtful guidance on your next real estate move, Erica is here to provide clarity, strategy, and a supportive experience at every step. See what she’s sharing here!
Want to stay in the know about listings in your area? Sign up here for a curated listing email!
Erica Baker | Associate Broker, Vice President | 410.919.7019 | ericabaker.co
FREE HOLIDAY PARKING DOWNTOWN ANNAPOLIS
Between Thanksgiving and New Years
Use Parkmobile to Get Two Hours Free at Meters + One Hour Free at Mills-Hillman Garage
TREE LIGHTINGS
Annapolis Town Center Tree Lighting
November 20th | 5:30pm
Join us for our 18th annual tree lighting! The Greater Annapolis Ballet will perform at 5:30pm, DJ and giveaways begin at 6pm and Santa arrives to join our friend, Jamie Costello, to lead the countdown to light the tree! Purchase a warm beverage from Tatte and we will have cookies for the kids - compliments of Whole Foods!
Homestead Gardens Grand Illumination
November 22nd | 5-8pm
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.
Grand Illumination Tree Lighting Downtown Annapolis
November 30th | 3-5:30pm
The Downtown Annapolis Partnership joins the City of Annapolis as they ring in the holiday season in downtown Annapolis. The Grand Illumination annual tree lighting takes place near the Market House every year on the Sunday after Thanksgiving. The celebration begins at 3:00 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.
Grand Illumination Event Schedule:
3:10–3:40 p.m. – Annapolis Symphony Academy Aquarius Wind Ensemble performs a selection of holiday orchestral music
3:45–3:55 p.m. – Edge Dance Complex Company Performance
4:00–4:30 p.m. – Naptown Sings & Plays Performance
4:00–4:30 p.m. – Storytime, cookies, hot chocolate, and nutcrackers for kids inside Zachary’s Jewelers
4:30–4:50 p.m. – Chesapeake Ballet Performance (outside Zachary’s)
4:50–5:15 p.m. – The Talent Machine Company Performance
5:15 p.m. – Remarks by guests followed by Santa, Mrs. Claus, and Elfie arrive to light the tree.
Glen Burnie Town Center Tree Lighting
December 3rd | 5:30-7:30pm
Mark your calendars for the Glen Burnie Town Center Tree Lighting—the perfect way to kick off the holiday season! This free, fun-filled event is great for the whole family. Free parking is available at the Henry L. Hein Building Garage. Join us for Free Ice Skating (5:30-6:30 PM), Visit with Santa, Live Music & County Exhibitors, Holiday Marketplace & Hot Cocoa, Toys for Tots donations, and more!
Annual Tree Lighting at Waugh Chapel Towne Centre
December 2nd | 5:30pm
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!
Crofton Country Club Holiday Tree Lighting + Santa Visit
December 3rd | 5:45pm
Join us at 5:45 PM out front for caroling with the St. Elizabeth Ann Seton Choir, Tree Lighting, and Santa’s arrival escorted by Arundel Volunteer Fire truck. Santa will be escorted inside to meet the children. Everyone can enjoy hot chocolate, cookies, and make and take crafts while you wait to visit Santa. AVFD will be accepting donations.
PHOTOS WITH SANTA
Bass Pro Shops Santa’s Wonderland
NOW- December 24th
Stop by to visit Santa and receive FREE 4×6 photos with Santa AND a FREE sharable video! Stop in during the weekday for FREE weekday giveaways including wooden ornaments and bass cookie cutters.
Santapolis | A Magical Holiday Experience
NOW - December 24th
Discover a holiday experience unlike any other! Santapolis is more than a photo—it’s a festive journey the whole family will love. From hands-on kids’ activities and interactive holiday fun to multiple enchanting photo stops along the way, every moment builds anticipation before your visit with Santa himself.
FREE Photos with Santa at Homestead Gardens Davidsonville + Severna Park
November 29th - December 20th
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!
Santa is Coming to Mother's
December 6th | 12-3pm
Delight in an enchanting afternoon filled with festive cheer. Kids and adults alike will be captivated by the joyous atmosphere. Enjoy delectable treats, festive activities, and the chance to meet Santa himself! Capture memorable moments and embrace the spirit of giving. Don’t miss out on this delightful celebration—mark your calendars and bring your family for a day of holiday fun!
Sensory Santa at TruCentered Chiropractic Care
December 9th | 1-5pm
A sensory-friendly Santa visit means you can interact however feels comfortable - close up or from across the room. This event is completely FREE for your family. This year, we're partnering with Gold In Fight—a local foundation supporting families navigating childhood cancer. Every dollar you choose to donate goes directly to local families who need it most during the holidays. And because I believe in the power of this community, Dr. Bryant is personally matching every donation dollar-for-dollar. That means your $25 becomes $50. Your $100 becomes $200. Your generosity literally DOUBLES its impact.
Santa Visits the Trail Parks
December 13th | 9am-2pm
The holiday season is hitting the trails! Join us for a special day of scheduled visits with Santa and his helpers along the B&A, Broadneck Peninsula, and WB&A Trails. This is a fun community event where Santa will be handing out candy canes and collecting non-perishable food items for the Anne Arundel County Food Bank.
9am Jones Station Road + 9:45am Hatton-Regster Green
10:15am | Broadneck Library
11:30am | Odenton-Babbington Green
1pm | Earleigh Heights Ranger Station
1:45pm | Harundale Shopping Center
HOLIDAY SHOWS + PERFORMANCES
The Nutcracker at Zachary's Jewelers
November 30th | 4-5:30pm
Join us for one of Annapolis’ most magical holiday traditions! Zachary’s Jewelers welcomes families for The Nutcracker — a joyful celebration created especially for children. The afternoon begins inside our store with a heartwarming storytelling of The Nutcracker, complete with hot chocolate, cookies, and the magic of the season. The first 100 children will receive a complimentary nutcracker keepsake to take home — a cherished reminder of the day. Register now to reserve your spot.
The Nutcracker by Severna Park High School
December 7th | 12:30pm + 3:30pm
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!
What’s Up? Media’s Nutcracker Tea
December 7th | 10am, 1:30pm + 5pm
Celebrate a beloved holiday tradition at the DoubleTree Hotel in Annapolis on December 7, 2025. Enjoy a delightful buffet with all the trimmings, an enchanting Nutcracker performance by The Edge Dance Complex, and a special visit from Santa and Mrs. Claus with photos and a classic Christmas story. A magical event for the whole family — plus a special gift for every child!
Greater Annapolis Ballet’s The Nutcracker
December 12th - 14th
Experience the magic of the season with Greater Annapolis Ballet’s beloved annual production of The Nutcracker, a timeless holiday tradition for the whole family! Featuring a live orchestra, stunning custom costumes, and the extraordinary talent of our GAB dancers, this production brings Tchaikovsky’s classic score to life in a breathtaking display of artistry, wonder, and holiday spirit.
Ballet Theatre of Annapolis Presents The Nutcracker
December 13th - 21st | Maryland Hall
Be a part of something new! This holiday season, experience the world premiere of Annapolis’s own Nutcracker with Ballet Theatre of Maryland. The familiar story takes on local significance through vibrant dancing, historic costumes, and festive sets. Beloved characters like Clara, her enigmatic Uncle Drosselmeier, and the brave Nutcracker return with new depth as their stories weave into the history of 19th-century Annapolis.
BREAKFAST + DINNER WITH SANTA
Cookies and Cocoa with Santa
December 6th | 11am
Witness the magic of Christmas through a child's eyes. Join us for cookies, hot cocoa, story time, and a visit from the jolly guy himself! Santa just might have his bag full of cheer for the kids. (HINT! Great photo opportunity for parents!)
Cookies and Cocoa with Santa
December 12th | 5-8pm
Join us for our annual Cookies & Cocoa with Santa. Shop for last minute holiday gifts, enjoy crafts, a movie & treats and of course get your picture taken with Santa. This event is FREE! Bring your family & friends and spend the evening with us.
Cookies and Cocoa with Santa at Earleigh Heights Volunteer Fire Company
December 14th | 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. This continues to be a free event! 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.
Brunch with Santa at Ram's Head Tavern Annapolis
December 14th | 10am - 2pm
Santa is coming to town! Join us for a festival family fun brunch. Santa stops by for a visit 11AM - 1PM!
Dinner with Santa at Coconut Joe's
December 17th | 6-10pm
Grab you little elves and join us for a magical night by the water filled with festive fun, delicious food and the big man himself- Santa Clause! Gifts for all the kids! Family-friendly dinner vibes, holiday lights and plenty cheer.
HOLIDAY LIGHTS, PARADES + TOURS
Experience a New Holiday Tradition: ICE! Featuring The Polar Express™
NOW - January 4th
Celebrate Christmas in Washington, D.C. with a visit to ICE! featuring The Polar Express™ to experience the classic holiday story in real life through larger-than-you-can-believe ice sculptures. Ride down thrilling frozen slides, wander through awe-inspiring tunnels, and capture the coolest pictures with your family throughout this frozen attraction.
Use code PARTNER25 for 25% off ICE tickets!
Jolly Express Cruise
November 22nd - January 1st
Annapolis' favorite holiday activity makes its return for the 2025 holiday season. Miss Anne will be adorned with reindeer spirit for an intimate 45-minute “sleigh ride” along Spa Creek. Captain Santa or Mrs. Claus will be at the helm, and an elf will be on board serving hot cocoa and good cheer. 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 are donated to Historic Annapolis. Ticket includes the cruise and your first cup of hot cocoa.
2025 Deep Creek Lighted Boat Parade
November 22nd | 5:30pm
This year is going to be bigger and brighter than ever! This year we’re adding a judging panel to crown the Best Decorated Boat. Last year we had a record 34 boats participate and raised over $1,500 for charity. The winning captain also took home nearly $800 in prize money! After the parade, join us at Donnelly’s Dockside for the official after party.
The Backyard's Christmas Market
November 22nd - December 23rd
The most wonderful time of the year is nearly here; where you can rock around our Christmas TREES 🌲 TRAIL ❄️ & MARKET 🎁 starting this Sat Nov. 22-Dec. 23rd. Starting 11/29, we will have outside vendors on the weekends (Mistletoe Market), along with a NEW Christmas Trail (Winter Wonder Walk), filled with many surprises! If you thought the Farmer’s Market was hype, just you wait!
Lights on the Bay
November 23rd - January 1st
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.
Willow Oak North Pole Lights Walk
November 28th - December 28th (select dates only 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.
Special Historic Holiday Tours
November 29th + 30th + Saturdays and Sundays in December
This daytime walking tour of Annapolis features many of the stories from our traditional evening Holiday Candlelight Stroll, with some extra bonuses. Meet your period-attired guide inside our cozy 188 Main Street office where you can enjoy a festive apple cider drink. Stroll with your lantern-lead guide around Maryland’s capital city, trimmed in greenery for the season. You will hear holiday traditions of times past and present as you walk by colonial mansions, Victorian homes, and quaint shops.
Jingle Bell Hayride at Kinder Farm Park
December 6th | 10am-1pm
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. Warm drinks by Stony Man Coffee Truck. Cost is $10.00 per person plus a small processing fee. Children 2 and under are Free but may be asked to ride on accompanying adult's lap. All Children 10 and under must be accompanied by an adult.
Pasadena Boat Parade
December 6th | 3pm - close
The Annual Pasadena Christmas Boat Parade is back on Saturday, December 6th, and we’re celebrating BIG at Broken Oar Bar & Grill! Come by early and grab the best spot on the water — we’ll have A visit from Santa himself, A live DJ spinning holiday jams, Spiked hot chocolate for the grown-ups, Treats for the kiddos, and more! It’s one of our favorite local traditions, and we can’t wait to share the night with our Broken Oar family!
The Eastport Yacht Club's Lights Parade
December 13th | 6-8pm
It’s one of the best nights of the year in Annapolis! Dozens of boats in all shapes and sizes covered in thousands of colored lights parade through the Annapolis Harbor for two magical hours. The joy that parade night brings continues thanks to sponsor generosity. Proceeds are shared with EYC Foundation that works year round to support local diverse and under represented youth through interactive and on-the-water learning, a career expo, and marine and maritime trade school and college scholarships. All are welcome to apply to have their boat in the parade! Why just watch the parade when being in the parade is so much more amazing!
HOLIDAY SHOPPING EVENTS
Sleigh Bells Ring HERE. a pop-up shop
Open daily until December 21st
Located right off Market Square, behind Fed House we have over 80 LOCAL makers and something for EVERYONE on your list, at all price points! We also have the BEST decor, cards, ornaments and gourmet treats!
Upcoming events:
Friday 11/21 - PINK FRIDAY (a movement to shop small before “Black Friday”) Pink cupcakes & Tipsy Wine Tasting 4-6pm
Friday 11/28 - PLAID FRIDAY (instead of “Black Friday”) Free Plaid Scarves for the first 75 shoppers + Gray Wolf
Saturday 11/29 - SMALL BIZ SATURDAY Free cookies by Mulberry Treats +Gray Wolf
Thursday 12/4 Midnight Madness I Gray Wolf, CAnE, Book Signing with Kate Myers & Michelle Douglas
Friday 12/5 GIVE BACK Event benefiting Bernie House, 5-8pm (more details to come)
Monday 12/8 Multiple Author Book Signing, WE Lead, Vol.3 6-8pm
Thursday 12/11 Midnight Madness II Gray Wolf, CAnE, Book Signing with Kate Myers & Michelle Douglas
Sunday 12/14 - Charm Bar, 11am-4pm
Thursday 12/18 Eleventh Hour (aka Midnight Madness III) Gray Wolf & CAnE
Girls Night Out Homestead Gardens
November 19th (Davidsonville) + November 20th (Severna Park) | 5-8pm
Sample, Sip & Shop in our beautifully decorated store, fully transformed into a holiday wonderland. Enjoy exclusive treats, warm beverages, and festive bites as you browse. Take advantage of our special GNO discount—25% off your total purchase (some exclusions apply). Whether you’re looking for unique gifts, seasonal décor, or simply a bit of holiday inspiration, this is your one-stop shop for everything you need to make the season bright.
Shannon + Vivi's Holiday Party at Mango and Main
November 21st | 5-7pm
We’re throwing a holiday party for our besties & YOU’RE INVITED! We’ll have bubbly and charcuterie (ofc!), permanent jewelry, FREE gifts with purchase, and the BEST meaningful, thoughtful gifts for everyone on your holiday lists! “Pink Friday” is a nationwide effort to help you “shop small FIRST!” and lots of stores downtown are participating… so call your girlfriends and plan a shopping day!
Mistletoe & Martinis: Providence of Maryland’s Holiday Sip & Shop
December 2nd | 6-9pm
Get into the holiday spirit at Providence’s Mistletoe & Martinis holiday event — a cozy evening of shopping, sipping, and seasonal cheer. Browse one-of-a-kind gifts, decor, hand-made pottery from Providence Pottery & Arts Studio, and fresh holiday greens from Providence Greenhouses’ — including cedar garlands, noble fir wreaths, mistletoe, and poinsettias. Warm up with complimentary seasonal martinis, and enjoy holiday snacks by our fire pit under a canopy of twinkling lights.
Midnight Madness
December 4th, 11th, and 18th
Late-night holiday shopping lights up the streets with twinkling lights, special discounts, seasonal treats, and unique gifts in one of the city’s most festive traditions.
Sip N' Shop Howliday Pawty
December 5th | 6-9pm
Join us for an evening of festive fun as we prepare for Christmas and enjoy great company! Our gym will be transformed into an exclusive holiday market featuring 15+ local vendors, live music, raffles, delicious handheld food, and plenty of holiday cheer. Guests will also enjoy wine, shopping, and special St. Martin’s merchandise — perfect for kicking off your holiday season in Bulldog style!
Sip. See. Shop. 2025
December 5th | 4-8pm
Jen Denney is hosting her third annual holiday pop-up at her home, featuring an incredible lineup of local, women-owned small businesses. This year’s group is bursting with creativity, style, and one-of-a-kind gifts you’ll actually want to give (and maybe keep for yourself).
Atticus+Wolf Salon Grand Opening
December 5th | 5-8pm
Sip. Shop. Eat. Vibe. Come check out Atticus+Wolf Salon in Edgewater! Shop local vendors, eat local eats and meet the crew that helped build this edgy, modern, boutique style hair salon.
West Annapolis Holiday Market
December 6th | 11am-4pm
From hot chocolate, to holiday shopping to a visit with Santa Claus (11am - 1pm), you won't want to miss this year's Holiday Market! Located in the parking lot of 20 Ridgely, at the corner of Annapolis Street and Giddings Avenue.
Vintage Christmas Market at Wildberry
December 6th | 1-5pm
Join Wildberry + dozens of local small businesses for an outdoor market on the farm! The Wildberry Farm to Table Food Trailer will be serving hot food + beverages. FREE totes for the first 50 guests! FREE holiday themed balloon animals for guests! Beer + Wine Garden! Roaming Santa! Live music! Free admission, leashed dogs allowed. Rain Dates: Sunday 12/7 + Sunday 12/14 1pm-5pm
Severna Park Community Center Holiday Market
December 7th | 1-5pm
Bring your family, your friends, or even just yourself and shop local. Not only will you find perfect presents, but you’ll also be supporting your local community – it’s the gift that keeps on giving! Mark your calendars and enjoy a stress-free shopping experience!
Holiday Magic on the Farm
December 7th | 2-5pm
What’s on the list of fun? Local Vendors for early shopping & supporting local businesses! Delicious Baked Goods for Sale. Fresh Coffee for Sale. Complimentary Hot Chocolate Bar. Several Photo Ops. Meet Our Farm Animals. Bonfire - Gather with Community. Enjoy Nature & Share our Space. Parking is first come, first serve.
15th Annual Taste & Sip Extravaganza
December 9th | 5-8pm
You are cordially invited to attend the 15th Anniversary of our Holiday Taste and Sip, one of the most well-attended and anticipated events of the year. Enjoy an evening of fantastic food, libations and music where you can sample offerings from our local restaurants, bakeries and liquor stores in a wonderfully festive atmosphere. Great networking, live holiday entertainment, an amazing silent auction, a jewelry raffle, cash bar and more. Open to Chamber Members and the public.
Sweat and Holiday Shop
December 10th | 6-8pm
Join us for a 45-minute bootcamp-style workout followed by holiday shopping from your favorite, local vendors. The workout will be from 6-6:45pm and shopping until 8pm. Don’t forget your water bottle and yoga mat.
Heroes Holiday Market
December 14th | 8-11am
Join us for the 6th annual holiday market featuring your favorite local vendors!
Holiday Pop Up at Severna Park Community Center
December 14th | 11am-2pm
Find some unique holiday gifts or treat yourself to a few goodies! Don't stress about wrapping, we've got you covered with our FREE gift-wrapping service on all Pop-Up Shop purchases! Also, don't miss out on our festive Gift Basket Raffle! Delicious pancakes & goodies from the Pancake Peeps! Spread the holiday cheer and support local businesses at the same time. We can't wait to see you there!
Pherm Brewing Holiday Sip N Shop
December 14th | 112pm
ICE SKATING
Glen Burnie Outdoor Ice Skating
NOW until the end of February
Glen Burnie’s ice rink has everything you need for a perfect family outing—free parking, free storage lockers, and the cutest penguin skate helpers for beginners. For rentals, you can choose from double-bladed, figure, or hockey skates!
Quiet Waters Park Ice Skating
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. Rink is closed on TUESDAYS.
HOLIDAY TRAIN DISPLAYS
Homestead Gardens Train Davidsonville
NOW - December 31st
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
NOW - December 31st | 10am - 6pm
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 Marley Station Mall
November 22nd - January 4th
Visitors will enjoy a selection of O-scale model train displays featuring old favorites like Thomas the Train, as well as new additions like SpongeBob! Charm City LUG returns this year with not one, but TWO new Lego displays! Willy Wonka will also be handing out some special door prizes, so be sure to bring the family for a day of fun! This is a FREE event for all ages, however, donations are greatly appreciated. All proceeds go to keeping the trains running and supporting the Emmanuel Lutheran Church's food pantry and emergency fund for local families in need. See the train schedule.
DOG FRIENDLY EVENTS
Lights + Leashes
November 21st + 22nd | 5-8:30pm
Experience the magic of "Lights on the Bay" on foot with your furry friends at our exclusive Lights & Leashes event! This two-night-only opportunity allows you and your pets to walk through the dazzling light displays, enjoy the festive atmosphere, and create unforgettable memories together. Tickets on sale each evening at the gate!
Pet Santa Nights at Annapolis Mall
November 24th, December 1st + 8th | 4-7pm
Bring your furry family members for a special holiday photo with Santa!
FREE Santa Paws Pet Photos with Santa
December 4th | Severna Park + December 5th Davidsonville | 4-7pm
Join us for a heartwarming holiday tradition where pets take center stage. Bring your dogs, cats, or other companions for a festive photo opportunity with Santa in front of a beautifully decorated backdrop at all our Homestead Gardens retail locations. Guests will capture their own photos, so don’t forget your phone or camera to snap the perfect holiday memory. Amid the twinkling lights and cheerful atmosphere, this event is the perfect way to include your four-legged family members in your holiday traditions.
Sea Dog Pet Boutique Santa Photos
December 7th | 1-3pm
The event is free, and we will be accepting donations for a local animal charity!
HOLIDAY EVENTS
Jingle and Mingle Holiday Party
November 21st | 6-10pm
Kick off the holiday season with your co-workers and colleagues at this year's Jingle & Mingle Winter Wonderland Holiday Party at the Doordan Institute at Luminis! Various ticketing options are available including discounted party packs so you can bring the whole crew!! After enjoying a fantastic spread of food from local vendors and signature Vintage Views cocktails, you'll be able to bid on some fantastic silent auction items (including the wreaths from the decorating contest), network with colleagues, take selfies with Santa and more! Attire: Winter white encouraged!
Great Annapolis Gingerbread Houses
November 22nd - December 20th | 10am - 4pm
Enter now for the Great Annapolis Gingerbread House decorating contest! Houses will be on display from November 22nd thru December 20th at the Annapolis Visitors Center on West Street. Winners will be announced on Dec 7th at the Annapolis Chocolate Binge Festival.
Bubbles + Baubles
December 3rd | 5:30-7:30pm
Join Wrabyn for a luxurious night of French champagne tastings led by The Cultured Somm, caviar and light bites by La Ruche, and 15% off all Lizzie Fortunato jewelry. Each pour is designed to unfold through the evening to make for an exclusive shopping experience. The evening includes a take-home gift bag featuring a bottle from the pour and bespoke treats to savor later.
Winter Wonderland at the Y in Pasadena
December 5th | 5-7pm
Join us for a magical celebration of the season! Our Winter Wonderland is a fun, family-friendly event highlighting all the holidays. Enjoy holiday-themed crafts, festive activities, and an opportunity to connect with the community. Come make memories, share the joy, and kick off the holiday season with fun for everyone!
Annapolis Chocolate Binge Festival
Sunday December 7th
The Annapolis Chocolate Binge Festival takes over the first block of West Street, in a family-friendly celebration of all things chocolate. 2025 marks the 11th year of the event. Be sure to also check out the Gingerbread House contest! With the help of Visit Annapolis and Anne Arundel County, the festival is hosting a Gingerbread House decorating contest! The contest is open to anyone: church groups, kids, bakers, businesses, etc., and there are winners for 1st, 2nd, and 3rd place. All houses will be displayed at the Visitor Center at 26 West Street.
The Cultured Somm’s The Most Wonderful Wine of the Year Class: Festive Holiday Wines for Entertaining, Gifting & Celebrating All Season Long
December 10th | 7-9pm
In this class we'll explore celebratory wines chosen to elevate your Holiday entertaining and pair well with festive fare. From Christmas dinner to New Years Eve parties, for hostess gifts and presents by the Menorah or under the tree, The Cultured Somm will ensure you have the perfect wines - red, white, & sparkling - to wow your guests and impress your favorite oenophile!
Santa Speedo Run
December 13th | 11am
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!
2026 Polar Bear Plunge
January 23rd - January 31st
The Polar Bear Plunge is part of Maryland's history. For the past 29 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 $4.75 million this year and register for the 2026 Plunge!
HANUKKAH EVENTS
Parade of Light
December 14th | 5:30pm
Join us for a spin at the annual Menorah Car Parade here in Annapolis. An experience you won't want to miss! Parade Destination - City Dock - Annapolis, MD at approximately 5:45pm where we will kindle a giant menorah and celebrate the festival of lights. Participation in the Menorah Parade and Lighting is FREE. Your donation will help cover the costs of this wonderful and vital program.
MILITARY BOWL 2025
Go Bowling Military Bowl Parade | Budweiser Clydesdale Miracle in Annapolis
December 26th | 2:30pm -4:30pm
The Go Bowling Military Bowl Parade draws thousands of fans to Downtown Annapolis and along the parade route proceeding through city streets, starting on Calvert Street downtown and eventually proceeding out West Street before concluding at Maryland Hall. The Parade includes the Budweiser Clydesdales, youth groups, community groups, military-themed groups, youth football teams, participating team marching bands and spirit groups and more. The Parade is free to attend and open to the general public. A Budweiser Clydesdale Miracle in Annapolis includes food trucks, vendors, games, activities and more for adults and children!
Military Bowl Pub Crawl
December 26th | 4-9pm
Each bar will have drink specials. The list of participating bars will be available in a few weeks.
Go Bowling Military Bowl Tailgate + Game
December 27th | 8 - 10:30am
Game at 11am
Tickets are now on sale for the 2025 Go Bowling Military Bowl at the Navy-Marine Corps Memorial Stadium in Annapolis! The Military Bowl Official Tailgate Festival takes place in the parking lot outside Navy-Marine Corps Memorial Stadium. For fans, the first stop of the Go Bowling Military Bowl experience is the Tailgate Festival. Visit the booths. Take selfies. Get giveaways. Purchase official Bowl gear. See the Clydesdales and more! The Tailgate is free and open to the public. Food and beverages from local establishments are available for purchase. For information about hosting a booth in the tailgate, contact Marc Goldman, Senior Director of Partnerships, [email protected].
NOON YEAR'S + NEW YEAR'S EVE EVENTS
Noon Year's Eve Celebration at Annapolis Library
December 31st | 11:30am
Help us bring in the New Year 2026 with crafts and music! A countdown and celebration will occur right before noon with dancing following.
Noon Year's Eve at Chesapeake Children's Museum
December 31st | 10am-12pm
Count down to noon with us with noise makers, silly hats, and traditions from around the world!
Watermarks New Years Eve Annapolis Yacht Party
December 31st | 8-10pm
Enjoy a complimentary glass of bubbly for the adults and a cup of cocoa for the kids, and a front-row seat of Annapolis’s fireworks display.
'80s New Year's Eve Bash at O'Loughlin's
Get ready to rewind and celebrate! We are throwing the ultimate New Year’s Eve ’80s Party featuring the Doug Segree Band, and this is more than just a party—it’s the official kick-off to our 40th year!
The Choptank Annapolis New Year's Gold Party
December 31st | 8pm
Ring in 2026 at our exclusive New Year’s Eve party! Join us on the rooftop at The Choptank Annapolis for an unforgettable night with an open bar, rooftop views, live DJ, and a champagne toast at midnight. Early bird pricing available ~ Grab your tickets today!
FIRST DAY HIKES
Enjoy the holidays with your friends and families! See you around Annapolis! Stay warm + have fun!
We're constantly updating this list, so check back for updates! If we're missing your favorite holiday event, please email us at [email protected] to be added to the guide!
*Please note – While we 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!
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