It’s (almost) Fall, and we made the ultimate list of ALL THE FALL events and family activities happening in Annapolis and Anne Arundel County!
This is the best time of the year for festivals, corn mazes, haunted houses, and pumpkin patches! We did all the research, so you don't have to!
Scroll down for a list of all the fun Fall activities to enjoy with your family this season throughout Anne Arundel County, MD.
This guide will keep growing as new events pop up, because our local businesses are endlessly creative (and we LOVE cheering them on!)
Hosting an event? Email us ([email protected]) to be added! It's FREE, and we can’t wait to spotlight you!
*Please note – While we make every effort to cross-check 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 we can correct them. Thanks for your help!
This guide is presented by Luminis Health. Fall fun can sometimes come with a few tumbles. Whether it’s a twisted ankle at soccer practice or a broken bone from a weekend adventure, Luminis Health Orthopedics is here to help. We’re open seven days a week, including evenings and weekends, to care for the bumps and bruises that come with being active.
From Friday night lights to pumpkin patch playdates, we’ve got your whole family covered. Booking an appointment is as easy as ordering a pumpkin spice latte.
Booking an appointment is as easy as grabbing your phone!
FALL FESTIVALS + PUMPKIN PATCHES
Butler’s Orchard Pumpkin Festival (Montgomery County)
Dates: September 20th – November 2nd | Wednesday – Friday: 1-6pm + Saturday – Sunday, and Columbus Day: 9am-6pm
Address: 22222 Davis Mill Road | Germantown, MD 20876
It’s back again for another year! The 45th Annual Pumpkin Festival starts September 20th and runs through November 2nd. We’ve made a few updates to improve your Festival experience, and we are so excited to have you at Butler’s, whether it’s your first visit or 45th visit! Children under 24 months old are FREE.
Clark's Elioak Petting Farm + Pumpkin Patch
Dates: September 16th - November 2nd
Address: 10500 Clarksville Pike, Ellicott City, MD 21042
Visit with our friendly farm animals-goats, sheep, cows, pigs, a donkey, ponies, bunnies, chicks, an emu, turkeys, ducks. Feed can be purchased to feed the goats, too. Large pumpkins, mini pumpkins, gourds, bumpy pumpkins, white pumpkins for sale by the pound. Hay wagon rides, pony rides, Fairy Forest + so much more!
Councell Farms Field of Fun (Talbot County)
Dates: NOW - End of October | 9:30am-5:30pm
Address: 11773 Old Skipton Road | Cordova, MD 21625
At Councell Farms, we believe that a trip to the field of fun should be a yearly tradition for families! Come spend a morning, an afternoon or all day at Councell Farms Field of Fun! Here at Councell Farms we LOVE our families! Grandparents who are joining their families at the Field of Fun are FREE! With 20+ farm related activities, including the corn maze, jumping pillow, combine slide and pumpkin patch, there’s something for everyone at Councell Farms’ Field of Fun. We are open 7 days a week from mid September until the last weekend of October, weather permitting. We also sell delicious local apples, fresh apple cider, and a large selection of jams and jellies. Be sure you also look at our fall decorations, including gourds, Indian corn, straw bales, corn stalks and mums for sale.
GET TICKETS (children 2 + under FREE!)
Gaver Farm (Frederick County)
Dates: August 29th – November 2nd | 10am-6pm Daily
Address: 5501 Detrick Road | Mt Airy, MD 21771
Celebrate the vibrant colors and crisp air of autumn at the Fall Fun Festival at Gaver Farm! Running throughout September and October, this family-friendly event offers over 65 exciting attractions, making it the perfect destination for a day of fun, laughter, and unforgettable memories. Explore the 2025 “Fun to the Core” Corn Maze, featuring everything apples. It’s a 7-acre corn maze, perfect for all ages. This maze combines the thrill of exploration with the joy of discovery. Whether you’re working together as a family or racing against friends, our corn maze promises a day of fun and excitement. Meet Our Friendly Barnyard Animals: Get up close and personal with our friendly barnyard animals, including goats, sheep, cow, alpacas, pigs, donkey, pony, bunnies, peacocks, turkeys, ducks and chickens. Kids (and adults!) love the opportunity to feed and interact with our goats, creating cherished memories and learning about farm life along the way.
GET TICKETS (kids under 24 months are FREE!)
First Sunday Arts Festival
Dates: October 5th + November 2nd | 11am
Address: West Street | Annapolis
Inner West Street Association is the proud sponsor of Maryland's premier art festival. From May through November, thousands of visitors enjoy shopping along beautiful West Street in downtown historic Annapolis. Check out over 100 vendors, live entertainment, cafe dining, and so much more!
Homestead Gardens’ Fall Festival Weekends
SEE THE NEW BREWERY, PLAYGROUND + 2025 FALL FESTIVAL VIBES
Dates: Weekends from September 27th to October 27th |Saturdays + Sundays | 10am – 4pm
Address: 743 W Central Avenue | Davidsonville, MD 21035
Join us for Fall Festival Weekends at Homestead Gardens. Give your family the same enchanting experiences you had as a child; seeing the barnyard animals, taking hay rides, picking out pumpkins and connecting with the community. Create new traditions and make unforgettable family memories.
GET TICKETS (Kids 3 and under are FREE!)
Knightongale Farm Fall Festival
Dates: September 27th - October 26th | Weekends ONLY 10am-5pm
Address: 3924 Solomons Island Road | Harwood, MD 20776
Pumpkin picking at Knightongale Farm has become a long-standing tradition for many families and friends. In addition to the pumpkin patch and corn maze we offer face painting, pedal tractors to ride, hayrides, barnyard basketball, Jump Pad, Mega Slides and petting animals. Paid activities include apple cannons, pony rides and face painting. Food and drinks also on-site for purchase, plus brewery, winery, vineyard ... and so much more!
GET TICKETS (kids 2 + under are FREE!)
Light House Pumpkin Patch
Dates: Opening Day Sept 27th through October | Thursdays + Fridays | 2-6pm and Saturdays + Sundays | 10am-6pm
Address: St. Martin’s Church | 1120 Spa Road | Annapolis, MD
An Annapolis Tradition! Light House Pumpkin Patch Volunteers from all over Annapolis will be selling pumpkins to support the Light House - Homeless Prevention Support Center.
MD Corn Maze: Get Lost in the Land of Oz
WATCH THE VIDEO from two years ago
Dates: NOW - November 2nd
Address: 389 Gambrills Road | Gambrills, MD 21054
There are so many fun activities included with your ticket: Hay Pyramid, Corn Pits, Jump-Pad, Feed the Animals, Ziplines, Tight Ropes, Pedal Tractors, Broom Swings, Tractors, Petting Zoo, Hayrides, Bubbles, Slingshots and an 8-Acre Corn Maze. Pony rides are an extra fee. Come hungry to enjoy the food trucks, vendors and visit the general store to go shopping!
GET TICKETS (Kids 2 + under are FREE on weekends)
Himmel’s Landscape & Garden Fall Festival
Date: October 11-12th & 18-19th | 9am - 4pm
Location: 4374 Mountain Road, Pasadena
Join us for games, food trucks, market, pumpkins, decor, and more!
Maryland Avenue Fall Festival
Dates: October 19th | 10am-5pm, rain or shine
Address: Maryland Avenue + State Circle | Annapolis
Join the businesses of historic Maryland Avenue for the return of their annual Fall Fest, now in its 54th year. Do not miss the ‘Halloween Pup Parade,’ live music and performances, fun for the kids, delicious food, a beer garden, unique jewelry and clothing vendors, antiques, and art, as well as fair trade, handmade, sustainable goods, and so much more in the heart of Historic Annapolis!
Montpelier Farm Fall Festival
Dates: Open Select Dates NOW - November 2nd
Address: 1720 Crain Highway | Upper Marlboro, MD, 20772
Welcome to an exciting day at our Fall Festival, packed with fun and perfect for photo ops! Savor delicious treats, refreshing drinks, and shop at our farm markets. Dive into the farm festivities with adorable animals, exhilarating playgrounds, a Trike Track, Barnyard Basketball, Giant Hill Slides, ride-on pig races, and so much more!
GET TICKETS (Kids under 2 are FREE!)
4th Annual Annapolis Scarecrow Stroll
Dates: October 25th - November 1st
Address: Throughout Annapolis
Welcome to the 4th Annapolis Scarecrow Stroll! Scarecrows will line the streets of downtown Annapolis on West Street, Maryland Avenue and Main Street. Deadline for entry is Friday, October 17, 2025. Check-in will be in front of Annapolis Collection Gallery 55 West Street, Thursday, October 23rd, 4-6pm. At check-in you will receive a name tag, pole assignment and ties to secure your scarecrow. The Annapolis Scarecrow Stroll is hosted by the Inner West Street Association in partnership with Maryland Avenue and State Circle Association and Downtown Annapolis Partnership.
ADULTS ONLY
Boatyard Beach Bash | Concert for a Cause
Date: September 20th | 4-10pm
Address: Annapolis Maritime Museum | 723 Second Street | Annapolis, MD 21403
Tickets: $150 — your all-inclusive pass to crafted cocktails, gourmet bites, and six unforgettable hours of entertainment by the Bay. Join us for the Annapolis Maritime Museum & Park’s 20th Annual Boatyard Beach Bash , headlined by world-class musicians and members of the iconic Jimmy Buffett’s Coral Reefer Band. Let yourself be whisked away to Key West as you immerse yourself in the incomparable talent of world-class musicians. This year is in memory and in honor of Jimmy Buffett.
Blazers . Bourbon . Cigars
Date: September 25th | 6-9pm
Address: William Paca House & Garden | 186 Prince George Street | Annapolis
Join Historic Annapolis at the Annual Blazers, Bourbon, Cigars! Connect with a wide network of influential community members – the region’s top business leaders, entrepreneurs, professionals, and visionaries representing our diverse community – in the picturesque William Paca Garden. While you network, enjoy bourbon, whiskey, and other fine liquor tastings, premium cigars, and delightful food from the area’s top chefs. This popular annual fundraiser supports Historic Annapolis and our mission to Preserve . Protect . Connect. 21+ only. Event is held rain or shine.
FREE Community Sunset Dance Workout with Moms in Motion and LIVE DJ Deezy
Date: October 11th | 5:30pm
Address: Annapolis Town Center
Join Moms in Motion for a FREE high-energy, dance fitness class featuring Baltimore’s own DJ Deezy—spinning the hottest tracks as the sun goes down! Let’s turn the evening into a full-blown dance celebration—100% FREE and open to all! Powered by The Annapolis Town Center, Toastique Annapolis & Dr. Kinney, this day is all about celebrating self-care and wellness.
Providence of Maryland’s 2025 Harvest Bash- Oktoberfest Edition
Date: October 11th | 7pm
Address: Providence Greenhouses & Gardens | 370 Shore Acres Road | Arnold, MD
Join us for a night of great food, drink and company in celebration of the season and in support of Providence’s mission. Providence’s Harvest Bash – Oktoberfest Edition Features Entertainment by the Dan Haas Band, All Your Favorite Bash Foods, Plus Traditional Bavarian Cuisine & Cocktails, Exciting Raffles & Live Auctions, Shop Providence Pottery & Fall Decor, Fireside Biergarten & More! We can’t wait to spend an unforgettable night with you under thousands of twinkling lights and a canopy of stars in our enchanting Greenhouse & Gardens!
The Cultured Somm Wine Tasting Events + Classes
The Cultured Somm, Anne Arundel County's premiere Wine Education, Events, & Travel company, invites all Anne Arundel Moms and friends to celebrate Fall at one of our October or November Wine Tasting Classes! Full Schedule with Details and Ticket Purchase link is available Here. Purchase tickets by Friday October 3rd for any/all of our 4 upcoming Classes offered on 10/15, 10/24, 10/28, and 11/6 and receive $15 off each/every ticket purchased by entering the Code: AAMoms at Venmo checkout.
October 15th: 7 to 9 pm Around the World: A Tasting Exploring 6 Different Global Wines
The world of wine is vast and spans many different regions of the globe. Break out of your wine rut and expand both your palate and your horizons while learning about new wines and winemaking styles in this 2-hour mini-master class highlighting both centuries old traditions and cutting-edge techniques in global winemaking. Everyone from the most seasoned oenophiles to those newer to the world of wine will not want to miss this special chance to take a virtual trip around the world with our globe-trotting sommelier Stephanie, a former U.S. diplomat with a vast and deep knowledge of not just the wines, but the people, places, stories, and traditions that make them so special. Pricing: $125 per person
October 24th is World Champagne Day and there is no better way to celebrate than to take this special class with Annapolis’ Champagne Expert - our founder Stephanie Schmid. You’ll learn about France’s storied champagne houses & traditions, how champagne is crafted, & where to find the best deals on this effervescent pleasure. We’ll enjoy 4 different Champagnes over the course of our tasting, including a special vintage Champagne. You’ll be sure to leave this class with a list of the perfect sparklers to add joie de vivre to all your holiday gatherings. Pricing: $135 per person
Why should the kids have all the fun? You won’t want to miss this special HalloWine Class and Celebration where Stephanie shares all her tricks to successfully pairing wine with food and lots of treats, including 6 delicious wines starting with Champagne, with each wine paired with a different artisanal cheese and classic Halloween candy. Costumes strongly encouraged! Witch way to the wine? Pricing: $110 per person
In this class, we’ll learn all about the art of food and wine pairing through the lens of Thanksgiving Dinner. We’ll enjoy 4 different wines that pair perfectly with classic Thanksgiving dishes while enjoying small artisanal bite versions of classics from roasted turkey with stuffing to pumpkin pie. You will leave class feeling sated and ready to wow your Thanksgiving guests with your wine knowledge and finds! Pricing: $85 per person
The Lash Lounge Ghouls and Glow Lash + Tan Open House
Date: Tuesday, October 21st | 6-8pm
Address: Lash Lounge Annapolis | 1907 West Street, Annapolis
We’re so excited to invite you to Ghouls & Glow: Lash + Tan Open House — a night of glam, glow, and Halloween fun! It’s the perfect night to bring your besties, see what The Lash Lounge and pop-up Bella Tans is all about, and celebrate spooky season with a glow.
Hansel Hill Farm Brew-Ha-Ha-Halloween
Date: October 24th | 6-9pm
Address:1017 Hansel Drive | Millersville
A 21+ night at Hansel Hills Farm featuring our signature, best-tasting-ever decaf (hot or cold brew), Pherm Brewery pours, costumes encourages + ID required. FREE entry!
ARTS + CRAFTS + STORYTIMES
FREE Home Depot In-Store Kids Workshop
Date: October 4th | 9am-noon
Address: Home Depot | Annapolis
Join Us at 9 a.m. on the First Saturday of Every Month. While Supplies Last.
Capital SUP Taylor Swift Paddle + Bracelet Making
Date: October 4th | 10-11:30am
Address: Eastport location
Swifties unite! Paddle to a Taylor Swift playlist and make friendship bracelets post-paddle. Fun for all ages.
Mini Makers Halloween Playdate
Date: October 23rd + 24th | 10:00am
Address: 623 Baltimore Annapolis Blvd, Severna Park
All the Mini Makers fun but with a spooky, magical twist. Get ready for themed art projects, games, and lots of Halloween excitement!
Pumpkin Walk at Hammond-Harwood House
Date: October 24th | 4-6pm
Address: 19 Maryland Avenue | Annapolis
Join us for our annual Pumpkin Walk! Come celebrate the spooky season with games, crafts, snacks, storytelling, face painting, and a costume parade around the mansion. This event will also feature a brief tour of the mansion to introduce children to colonial superstitions and the special architecture of the Hammond-Harwood House. Wear your best costume for the selfie station! This family event is an Annapolis tradition not to be missed! Costumes encouraged. Beer and wine will be available for purchase. Annapolis’s favorite Fox, Frolic the Fox, will join our event this year! Frolic will lead our costume parade and make magic in the garden with the children! We will sing, play, dance, prance, pretend and tell stories in the garden. It’s always fun when we get an extra sprinkle of fairy dust with our friend Frolic.
Mr. Paca’s Garden Storytime: “Trick or Treat on Scary Street” by Lance Bass
Date: October 25th | 10am
Address: 186 Prince George Street | Annapolis
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, plus time to explore the Paca Garden following the story hour. Let’s go on a pumpkin hunt in our amazing Boxwood Parterre. Make sure you wear your Halloween costume!
Create Your Own Trick or Treat Tote Bags
Date: October 25th | 10:30am
Address: Annapolis Library
Join us on the Saturday before Halloween to decorate and customize your own Trick or Treat tote bags! We will provide reusable tote bags for you to spookify and take home with you!
Halloween Booktacular Party
Date: October 30th | 4:30-8pm
Address: Wyrd Bookstore | 135 Mitchells Chance Rd, Edgewater
Join Wyrd Bookstore for story time for kids at 4:30, costume contest with prizes, literary costumes encouraged, open mic ghost stories – sign up in advance if you can, spooky drinks and treats, fun for families, couples, singles! Don’t miss this!
Halloween Storytime + Parade
Date: October 31st | 10:30am
Address: Discoveries Library at the Mall
Join us for a frightfully fun time! Start with a spooky storytime, followed by a colorful costume parade, and topped off with a monster mash dance party.
CONCERTS + PERFORMANCES
Annapolis Baygrass Music Festival
Dates: September 20th + 21st
Address: Sandy Point State Park | 1100 E College Avenue | Annapolis
More than just a music festival, Baygrass is a vibrant celebration of community, conservation, and connection. Located on the breathtaking beachfront of the Chesapeake Bay, Baygrass brings together a rich blend of music rooted in progressive bluegrass, Americana, and improvisational jam, all while championing two vital causes—protecting the Chesapeake Bay and promoting mental health awareness. Best of all, every song, every sunset, and every shared moment helps create a lasting impact—making Baygrass a festival where fun and purpose come together in perfect harmony.
2025 Art in The Park
Date: October 5th | 1-5pm
Address: 760 Ritchie Hwy, Severna Park
Join us for the Fifth Annual Art in The Park... an indoor/outdoor festival celebrating Art in all its forms, presented by Cafe Mezzanotte and The Severna Park Voice. This year's LIVE Music is Ahmed Warshanna's ISHTA, with special guest Gracie Jay. PLUS a dozen Local Artists and Local Art Galleries, Wine Garden (with Beer and Cocktails), All-You-Can-Eat Gourmet Picnic, and more!
FREE Kids Concert and Pumpkin Painting
Date: October 25th | 2pm
Address: Mother’s Grille | 969 Ritchie Hwy, Arnold
Free pumpkin painting and kids' songs performed by Aaron Hawkins.
USNA Annual All Saints’ Day/Halloween Concert
Dates: October 31st | 7pm + 10pm and November 1st | 7pm
Address: USNA, Naval Academy Chapel | 121 Blake Road | Annapolis
The USNA annual Halloween Concert is a spectacular event of music, light, drama, and dance. One of the most popular events on the Yard, this production is an experience you will not soon forget! This electrifying concert features Monte Maxwell, Chapel Organist, with the multi-faceted talents of midshipmen in a presentation that has drawn record-breaking crowds into the Naval Academy Chapel. A wide variety of music from multiple genres, including the famous Toccata and Fugue in D Minor, are featured in this concert celebrating the triumph of good over evil and All Saints’ Day. The incredible performances, special effects, and grand finale will leave you on the edge of your seat!
Pasadena Theatre Company’s NARNIA The Musical
Dates: November 14-23rd
Location: Anne Arundel Community College
Step through the wardrobe and into a world of wonder in “Narnia: The Musical”. Join the Pevensie siblings as they stumble into an enchanted land where mythical creatures roam, an evil White Witch rules with icy cruelty, and a great lion named Aslan leads the fight for freedom. Get ready to believe in the impossible— Narnia awaits!
HAUNTED HOUSES
Six Flags Kids BOO Fest
Dates: Select dates, September 13th - November 2nd
Address: 13710 Central Avenue | Bowie, MD 20721
Around every corner at Kids Boo Fest is spook-tacular entertainment that families and friends can enjoy together. From magical mazes to larger-than-life scarecrows and so much more, Kids Boo Fest at Six Flags America is safe, exciting fun for everyone.
Madhaunter's Madhouse (Loundon County, VA)
Dates: Ever weekend starting Sept 27 - Nov 1 | 7pm
Address: 37658 Legard Farm Road | Purcellville, VA 20132
Terrors are abound at Madhaunter’s Madhouse in Purcellville, Virginia. The unspeakable and frighteningly real horror visages that stalk every corner here are genuinely evil, as you will be terrified and filled with bloodcurdling screams. Madhaunter’s Madhouse is a petrifying attraction for any thrill-seeker. Chosen as the “#1 Must-See Haunt” in Virginia by thousands of scare-loving fans at TheScareFactor.com, Madhaunter’s Madhouse haunted attractions continue to achieve popular and critical success with the accolade of “Top Haunt” in 2016-2019, 2022-2024 by industry experts at FrightFind.com.
Arundel Volunteer Fire Department Station 7 Terror Trail
Dates: Open Weekends October 3rd - November 1st
Address: 2380 Davidsonville Road | Gambrills, MD
A family-friendly haunt with activities for everyone. We have a scary Terror trail recommended for 8 years and older and offer activities for younger children at the ticket booth and families can enjoy our Boo Haunt loop – geared for those under 8 years old. We are supporting the Arundel Volunteer Fire Department. All proceeds from the Haunted Trail.
Special Historic Hauntings
Dates: Thursdays, Fridays + Saturdays in October | 7:30pm
Address: Annapolis, MD, United States
Our spirited guide will lead you through the dark alleys, spooky side streets, and lesser-known haunted sites of the old and creaky town of Annapolis.
DOG-FRIENDLY EVENTS
AmericanK9's 2nd Annual Paws and Pumpkins Fall Fest
Date: October 4th | 11am-3pm
Address: 3869 Birdsville Road | Davidsonville, MD
Join us for a fun-filled day at the American K9 Dog Ranch in Davidsonville as we celebrate the beauty of fall with our furry friends! The Paws and Pumpkins Fall Fest is a dog-friendly festival that offers a variety of activities for dogs and their owners to enjoy. Not to worry, there will be activities for adults and children too including a vendor market, face painting, photo booth, live music, costume contest, pumpkin painting station and more!
Barktoberfest
Date: October 4th | 11:30am -6pm
Address: 1906 Towne Center Blvd | Annapolis
Join us for the third Barktoberfest with steins and canines as we celebrate German-style beer, bavarian food, and pawesome four-legged friends. We'll be hosting our crowd-favorite dog fashion and costume show with two options: general Halloween fun and German/Oktoberfest themed. Sip on both imported and locally crafted Oktoberfest style brews and there will be plenty of yard games again. The SPCA of Anne Arundel will be the main benefactor of the festival and their volunteers will be showing off pups and pouring beers! Our stein-holding contests was incredibly competitive last year so don't miss to see who this year's champ is! There will also be plenty of fall photo opportunities!
Paws at the Mall Halloween Pawty
Date: October 19th | 1-3pm
Address: Paws at the Mall, Annapolis Mall
Join us for fun, festive activities such as Face Painting, Halloween Themed Photo Booth for Humans & Pets, Bake Sale for both Humans & Pets. And...An Online Halloween Costume Contest! Bring your furry friend in their best costume into Paws, get a photo taken by one of our staff members, have it uploaded on our Facebook page, and whoever receives the most likes on their photo (within 24 hours) will win a $15 gift card to Paws at the Mall.
Sandy Point State Park Pet Costume Contest
Date: October 25th | 4:30pm
Address: Sandy Point State Park
Bring your four-legged friend to Sandy Point State Park for a fun afternoon at the Pet Costume Contest on Saturday, October 25, 2025, from 4:30 to 5:30 p.m. Dress up your pet and show off their best look for a chance to win “Best Dressed Pet.” Pets must be leashed, and park entry is $3 per vehicle.
FALL EVENTS
Eastport Oktoberfest
Date: September 19th - 21st | 12pm
Address: 418 Fourth St, Annapolis, MD 21403
Don’t miss: Gravity keg tapping outside at 5pm Friday. Stein and a .5 L pour for $17 ($12 for just stein). Local sausages, pretzel roll w/ sauerkraut. Favorite beer. Beginning of fall. SIXTH Annual Forward Oktoberfest!
Drive-In Movies on Forest Drive
Dates: September 26th + October 24th
Address: 117 Hillsmere Dr | Annapolis
Annapolis’ Small Businesses on the SOuth FOrest Drive Corridor (SOFO) hold Summer Drive-In Movies Under the Stars on the fourth Friday of the month through October. Food and drinks can be purchased from Grump’s Cafe.
September 26: The Hunt for Red October + October 24: Moana 2
Capital SUP Fall Paddle Festival
Date: September 27th | 10am-2:30pm (30-minute sessions)
Address: Quiet Waters Park
Celebrate the season at our family-friendly Fall Festival! Expect paddling, games, and plenty of autumn fun.
West Annapolis Oktoberfest
Date: September 28th | 11am-4pm
Address: Annapolis Street
It’s always a party, always the place to be! Live music, local vendors, great food, cold beer, and an unbeatable neighborhood vibe. Don’t miss your chance to be part of the most beloved street festival of the year.
Let’s Be Friends Brunch
Date: September 28th | 11am-3pm
Address: The Woodlands at Homestead Gardens
This Fall, we’re bringing the community together again—this time with crisp air, cozy vibes, and bold seasonal style. The Let’s Be Friends Brunch: Fall Edition is more than an event—it’s an experience designed to inspire, connect, and celebrate creativity through fashion, food, and fellowship. Join us for an unforgettable afternoon featuring: A curated fall-style brunch experience, Live music & soulful sounds, A Bohemian Black Fall fashion presentation, Beauty & wellness activations, Local vendor marketplace & pop-up shopping, Interactive photo moments & styling tips, Kids Korner with fall crafts + play, Swag bags, raffles, and surprises throughout the day.
Capital SUP Pedals + Paddle
Date: October 2nd | 5:30-7pm
Address: Eastport location
Join us for an active day of customer flower bouquet making and paddling.
Annapolis Powerboat Show
Dates: October 2-5 | Thurs- Sat: 10am-6:30pm, Sunday 10am - 5pm
Address: City Dock | Annapolis
October brings the transformation of Ego Alley and Annapolis Harbor into a boater’s dream, as floating docks create a temporary marina showcasing new and premiering boats and the latest in boating accessories, equipment and apparel during the Annapolis Powerboat Show. Whether you are a boater, angler, or just getting started, you will want to grab your family and head to downtown Annapolis and soak in the boating lifestyle, catch up with old boating friends, and make new ones as you walk the docks.
Children’s Theatre of Annapolis Fall Festival
Date: October 3rd | 5:30-9:30pm
Address: 1661 Bay Head Road | ANNAPOLIS, MD 21409
Join us as we celebrate the beauty of the season at our annual Fall Festival! Bring your family and friends to enjoy Haunted Attraction (family-friendly spooky attraction), Face Painting, Arts and Crafts, Games, Live Performances, Local Vendors, Food Trucks, and More!
Flea Market, Tractor Pull, and Maryland State Jousting Championship
Date: October 4th
Address: Anne Arundel County Fairgrounds | 1450 General's Highway | Crownsville
FREE Beech Grove Farm Farm Festival
Date: October 4th | 10am - 3pm
Address: 1575 Underwood Road Gambrills, MD 21054
If you’re looking forward to crisp, cool mornings, fields of autumnal gold, hillsides aglow with flaming color, food cooked over the fire, hay rides, armfuls of mums on the front porch, and the turning over of the agricultural season (whether it be your garden or the local farmer’s fields and herds), come join us to celebrate! We’ll have a variety of activities for the family: pony rides, hay rides, a moon bounce, and more. Live entertainment and local, hot food. Mums and garden resources. Admission is free. Farm-sponsored activities will be cash only. Stay tuned for future announcements as we add to the plans for a family day of fun on the farm!
Chesapeake Arts Center’s 11th Annual Arts in the Park FREE Community Festival
Date: October 4th | 11am-3pm
Address: 194 Hammonds Lane | Brooklyn Park
Join us in celebrating the 11th Annual Arts in the Park Free Festival at Chesapeake Arts Center! This signature community event brings together over 1,000 local residents, artists, and organizations for a day full of live entertainment, hands-on art activities, local vendors, delicious food, and creative fun for all ages. This year’s festival promises to be our biggest and most vibrant yet—with new features, returning favorites, and a few surprises in store. We can’t wait to celebrate with you—see you there!
Wild Kid Acres 5-Year Anniversary Celebration
Date: October 4th | 6-9pm
Address: 731 Central Ave E | Edgewater
Celebrate five years of farm fun at the Wild Kid Acres 5-Year Anniversary Celebration! Join us for an unforgettable evening filled with: A delicious farm-to-table dinner Live music Dancing Pony rides Roping demonstrations Engaging farm tours Wild Kid Acres is devoted to providing farm-based education and community experiences, and to producing regenerative, sustainable and accessible food. Wild Kid Acres is owned by a minority, veteran, and beginning farmer, Gerardo Martinez. The 5 acres Anne Arundel county farm property was purchased in 2019. Upon purchasing the property, Gerardo and his family set out to convert the unofficial dump into a thriving homestead using climate-smart agricultural practices. The family built the home and all the infrastructure surrounding the farm by hand. Orginially from the inner city and migrant families themselves, Gerardo and his family also wanted to ensure that their new homestead could serve as a model for other young families looking to find alternative ways to redevelop properties.
Annapolis Sailboat Show
Dates: October 9-12th | Thurs- Sat: 10am-6:30pm, Sunday 10am - 5pm
Address: City Dock | Annapolis
Sailors from around the globe gather in beautiful downtown Annapolis every October for the Annapolis Sailboat Show. This annual celebration of sailing features floating docks lined with sailboats from manufacturers around the world. Multihulls, monohulls, cruisers, racers, sailing dinghies and more. Show tents line the shore, stocked with the latest in nautical gear and accessories, electronics, communication equipment, sails, rigging, education, charter companies, clubs and more. Seasoned and novice sailors alike are invited to expand their horizons and connect with fellow sailors during this internationally acclaimed show.
Celebrate You
Date: October 11th | 8:30am-6:30pm
Address: Annapolis Town Center
Annapolis Town Center, Toastique Annapolis and Dr. Kinney are bringing you a day to celebrate self-care and wellness! Join us for meditation, fitness, taste of the town center, vendor village, kid’s corner and so much more!
Art @ The Park
Dates: October 11th + 12th | 10:00am - 4:00pm
Address: Quiet Waters Park
Join us to celebrate the 35th year of Art @ the Park. It is a great gathering of Music, Visual Arts, food trucks and activities for the younger crowd along with live performances and demonstrations. The festival is free, but the $6 per car entry fee into the park still applies. PLEASE NOTE: this year, the event will be OUTDOOR ONLY. The Visitor Center and Blue Heron Center, where we normally host indoor vendors, will be under renovation. All vendors will be outside and will need 10’ x 10’ tents.
Kinder Farm Park Fall Fun Day
Date: October 11th | 10am-3pm
Address: 1001 Kinder Farm Road | Millersville, MD
Join us for our Fall Fun Day on Saturday, October 11, 2025, from 10:00 AM until 3:00 PM. This year’s event will be scaled down a bit. Tickets will be sold on the day of the event for the following popular activities: • Pumpkin Patch • Straw Maze • Face Painting • Hayrides.
Day of the Dead Festival
Date: October 11th | 1-6pm
Address: Edgewood Avenue | Annapolis
Celebrate Día de los Muertos in Annapolis!Join us on Edgewood Avenue in the Design District (between McGuckian & Virginia Streets) for a vibrant Day of the Dead Festival! There will be Live music, Artists & vendors, Delicious food and Fun for the whole family!
Homegrown & Handmade OctoberFest
Date: October 12th | 11am-3pm
Address: Sand & Silo Marketplace | 8567 Fort Smallwood Road, Pasadena
THE one-of-a-kind farmers & artisans market you’ve been waiting for! Inside Sand & Silo Marketplace you’ll find original art, jewelry, décor, furniture, gifts, and apparel. Out front, our lot is packed full of incredible farmers, bakers, food trucks, makers, and artisans bringing you the best of the season! From produce, eggs, meats, seafood, sourdough, spices, teas, body care, pies, drink mixes, pickles, dog treats, cookies, pizza, coffee, olive oil, olives, jams, jerky, peppers, and honey… there’s truly nothing we didn’t think of! Come for the food, fun, and community—stay for the heart of supporting local! Convenient parking with overflow available around back!
Hansel Hill Farm Boo Basket Pick-Up + Halloween Fun
Date: October 17th | 4-5:30pm
Address: 1017 Hansel Drive | Millersville, MD
FREE Boo Baskets for the first 50 families filled with goodies and coupons from local small businesses. Stay and play for just $7 in advance and $10 at the door for a not-so-spooky hayride, pumpkin decorating, inflatable corn maze, and animal time on the farm.
Golden Gatherings: HERE! A Pop-up Shop
Date: October 17th - November 9th
Address: 6 Fleet Street • Downtown Annapolis
Featuring 70 LOCAL ARTISTS & MAKERS in a boutique setting! This shop is benefiting Bosom Buddies Charities & Pinked Perspective
Capital SUP Halloween Paddle
Date: October 18th | 9:30-11am
Address: Eastport location
Get in the spooky spirit with our festive Halloween Paddle! Costumes are encouraged for this fun on-water event.
Annapolis Pride Parade and Festival RESCHEDULED
Date: October 18th | 10am-4pm
Address: Maryland Hall | Annapolis
Get your costume ready for some spooky fun!!!! The Annapolis Pride parade and festival will be held on October 18. Parade starts at 10 am at kick off at 10 a.m. at Calvert and Bladen streets, proceeding around Church Circle and along West Street to end at Amos Garrett Boulevard. The festival runs from 11 am - 4 pm at Maryland Hall and the Bates Athletic Complex!
28th Annual Oyster Festival
Date: Saturday, October 18th | 11am-5:30 pm
Location: 1418 E West Shady Side Rd, Shady Side
Come out for the festival and our biggest fundraiser of the year and enjoy the day on our broad green lawn on the banks of the West River in Shady Side. This year we have double the bands, more vendors and more hours of fun for you to enjoy! Good community company, fine regional music, an array of choice gifts for purchase, a cash raffle, local food and drink and the best oysters anywhere.
Halloween on the Farm
Date: October 19th | 11am-2pm
Address: Dragonfly Acres Farm | 1278 Meyers Station Road | Odenton, MD
Join us for our 4th Annual Halloween on the Farm! Come in your best costumes, enjoy our rescue farm and our modestly decorated Boo Trail & Nature Nooks. It is destined to be a Spooktacular time for all! We are excited to welcome back Baked By Isabella so our guests may enjoy freshly made baked goods and cookies for sale. Take a peek at our flyer with all of the fun "things to do" and follow us for more updates as we approach one of our favorite events of the year! ALL AGES & ALL ABILITIES WELCOME.
Maryland Avenue Fall Festival
Date: October 19th | 10am-5pm
Address: Maryland Avenue, Annapolis
Our Fall Festival is one of the longest-running in our state! Our festivals take place on the first two blocks of Maryland Avenue between State Circle and Cumberland Court.
Haunted Harbour Day
Date: October 25th | 10-12:30
Address: 2512 A Solomons Island Road, Annapolis
Throw on a spellbinding costume and join us for Haunted Harbour Day! This interactive experience is filled with thrilling activities and spooky giveaways. THIS FREE, FAMILY-FRIENDLY HALLOWEEN EVENT INCLUDES: Free Trick-Or-Treat Bag, Trick-Or-Treating, Children’s Costume Contests, Free Giveaways, Balloon Artist, Pumpkin Decorating & Glitter Tattoos!
Waugh Chapel Family Fall Festival
Date: October 25th | 12-2pm
Address: 1417 S Main Chapel Way, Gambrills
Autumn’s Call, Fun for All! Join Waugh Chapel Towne Centre on South Main Chapel Way for our annual Family Fall Festival! Visit for balloon art, live music, pumpkin decorating, kids activities, visits from Waugh Chapel Towne Centre businesses, and more. It’s fun for the whole family can enjoy! Hope to see you for a Waugh-nderful time.
TRUNK OR TREAT EVENTS
Homestead Gardens Tractor Treat
Date: Thursday, October 16th | 4pm - 7pm
Address: Homestead Gardens | 743 W Central Ave, Davidsonville
Homestead Gardens is hosting a unique community event that highlights local agriculture: the Tractor Treat! Farmers from Anne Arundel County have been invited to bring their tractors and equipment for a Halloween-themed trunk-or-treat. Children 12 and under can visit each tractor to trick-or-treat and learn more about the tools used in local farming.
FREE Macaroni Kid Trunk or Treat at Baysox Stadium
Date: October 18th | 3-6pm
Address: 4101 Crain Highway | Bowie, MD 20716
Annual Trunk or Treat inside the Baysox Stadium!
Arundel Olympic Swim Center Pumpkin Plunge
Date: October 19th | 12:30pm
Address: Arundel Olympic Swim Center | 2690 Riva Road, Annapolis
Get ready for a splash of spooky fun at the Arundel Olympic Swim Center Pumpkin Plunge! Swim among floating pumpkins, find your perfect gourd, and enjoy a Trunk-N-Treat in the parking lot afterward! $13 per person | Ages 3+ (must be toilet-trained)
FREE Halloween Spooktacular at the Severna Park Community Center
Date: October 24th | 5-8pm
Address: Severna Park Community Center | 623 Baltimore Annapolis Blvd | Severna Park
Mark your calendar for October 24th and join us for Halloween Spooktacular presented by KMA Law Office! This FREE event is open to all. Bring your family and friends for some trunk or treating, games, crafts and more!
FREE Annapolis Recreation and Parks Fall Harvest Festival
Date: October 25th | 10am-2pm
Address: Pip Moyer Recreation Center
Calling all ghouls and goblins! Get ready for a spooktacular time at Harvest Fest! Enjoy FREE family fun with a spooky magic show, face painting, hay rides, a pumpkin patch and Trunk-o'-Treating! Come celebrate with costumes, candy and community fun. Featuring your FAVORITE characters like Bluey, Glinda & Elphaba from Wicked, Princess Tiana, Spider-Man, Miles Morales, and Rumi from K-Pop Demon Hunters.
Trunk or Treating at The Lodge Annapolis
Date: October 25th | 12-4pm
Address: The Lodge Annapolis | 177 Jennifer Road
Something spooky and sweet is coming! Join us for Trunk or Treating at The Lodge! Bring the kids (costumes encouraged) and enjoy pumpkin painting, free kids meals, and more! Let’s make it a night to remember. Want to participate with your car? Be sure to register on our website. Space is limited!
Anne Arundel County Police Department (Southern District) Trunk or Treat
Date: October 25th | 5-7pm
Location: 35 Stepheny’s Lane, Edgewater
Mark your calendars! This is the ultimate family-friendly event to kick off the spooky season. We’re getting the trunks ready and filling them with treats—all you need to bring are the creative costumes! Don’t miss out on the festivities.
Trunk or Treat By TruCentered Chiropractic Care
Date: October 28th | 4:30-6:30pm
Address: 2525 Riva Road | Annapolis
Join us for a fun-filled Trunk or Treat with music, games, treats, and pumpkin decorating! Perfect for the whole family!
FUNDRAISING EVENTS
Calm for a Cure Fundraiser + Beer Release
Date: September 19th | 6pm
Address: Pherm Brewing
Join Us for a night of music, community, and purpose. Your ticket funds year-round complimentary massages, facials, and healing sessions for cancer patients and caregivers through the Harmony Foundation. Your ticket = 1 wellness service for a cancer patient or caregiver. Celebrate with the exclusive Calm for a Cure beer release at Pherm Brewing. Enjoy DJ, dancing, food from Garten Eats, raffles & silent auction prizes. Be part of a community bringing calm, comfort, and connection where it’s needed most!
Join Us for the Together in Teal Walk to End Ovarian Cancer
Date: September 21st | 8:30am-12pm
Address: Annapolis Mall
The National Ovarian Cancer Coalition – Central MD Market invites you to their annual Together in Teal Walk. This family-friendly event raises awareness of ovarian cancer — a disease with no screening test — while honoring survivors, remembering loved ones, and raising funds to support NOCC’s mission. Enjoy entertainment, kids’ activities in the Spirit Tent, refreshments, a “Chance to Win” tent, a parade of Sling Shot Riders, a 1.5-mile Walk, and a special performance from the Naptown Brass Band!
7th Annual Custom Cars, Cocktails and Change Gala
Date: September 27th | 6-11pm
Address: Live! Casino & Hotel Maryland
For over 25 years, Vehicles for Change has been a lifeline for families and individuals seeking a way forward. We believe in second chances. We believe in stable transportation. We believe in careers, not just jobs. And we believe that the road to opportunity starts with a single key in the ignition. Each year, our Custom Cars, Cocktails & Change Gala is more than a night of celebration—it’s a movement powered by community, compassion, and change. And this year, we need you more than ever. Use code KATIE for $50 off your ticket.
Mochas in Motion
Date: October 19th | 11am-1pm
Address: 1160 Reece Road | Severn
Join the Anne Arundel County Mocha Moms for Mochas in Motion — a fun and empowering fitness fundraiser supporting breast cancer awareness and local women’s wellness initiatives. This high-energy event features three dynamic classes — Zumba, Strength Training, and Yoga — designed to get you moving, smiling, and feeling strong. Bring your yoga mat, hand weights, and positive energy as we sweat for a cause and celebrate sisterhood in motion.
Fish For A Cure Fishing Tournament + Shore Party
Date: November 1st | 6am + 5-9pm
Address: Safe Harbor Annapolis | 519 Chester Ave | Annapolis
Fish For A Cure (F4AC) is an unmissable experience on fishers’ yearly calendars. Celebrate with a great day of fishing on the Chesapeake Bay followed by the Shore Party where we’ll celebrate the competition for the biggest fish and most dollars raised through the Paul C. Dettor’s Captain’s Challenge. No matter the size of your fish or the amount of money you raise, you can be sure to have a good time! You should be happy in knowing that you are helping F4AC realize its mission of raising funds for cancer care in our community. Fish For A Cure (F4AC) 2025 will host a Shore Party from 5-9 p.m. at the Safe Harbor Annapolis. There will be food and beverages served from multiple bars, a dance floor, and more. Plus, the winners of the Tournament and Paul C. Dettor Captain’s Challenge will be announced at the party. For those not registered in the F4AC tournament, party tickets are $175 per person. All proceeds will support the Cancer Survivorship Program at Luminis Health Anne Arundel Medical Center’s Geaton and JoAnn DeCesaris Cancer Institute and its vital programs that directly benefit patients and their families in our community.
Hosting an event? Email us at [email protected] to be added! It's FREE, and we can’t wait to spotlight you!
Grab your calendar, share this guide with your friends, and let’s fill the season with family fun and small-business love!
HAPPY FALL + have fun!
Do you LOVE this guide? Check out our other guides HERE, including the Indoor Activities Guide + The Local Moms Network Ultimate Baby Guide + MORE!
