Fall in Maryland is packed with can’t-miss events festivals, but the fun doesn’t end with October! From parades and pumpkins to holiday markets, light displays and family-friendly traditions, there’s plenty happening from October through December. Whether you’re planning a weekend of fall activities or looking ahead to the holiday season, here are some of the top festivals and events happening in and around Annapolis.
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October Festivals & Events You Can’t Miss
Annapolis Pride Parade & Festival, October 3, Downtown Annapolis
Unite in Pride! Celebrate Pride with your community, dress in your rainbow best, and stroll around the festival. There will be vendors, food trucks, and lots of fun activities and performances.
Greenstreet Gardens Fall Fest, Oct. 3-Nov. 8, Lothian
Make a day of fall fun at Greenstreet Gardens! Get lost in the five-acre corn maze, hop aboard a hayride, explore the pumpkin patch, and say hello to the farm animals. Kids can also bounce on the jumping pillow, dig into the corn pit, conquer the tire tower, ride the cow train, and get their faces and hair painted. Local organizations and food trucks will be serving up food each weekend, and the Corn Cob Cafe will have snacks and drinks available for purchase.
Maryland Renaissance Festival, October 3-25, 1821 Crownsville Road, Annapolis
Come dressed in your 15th century best and join in on the merriment! There will be fantastic performances, food stalls, and vendors selling unique, handmade products.
Maryland Corn Maze, October 3-November 8, 389 Gambrills Road, Gambrills
Wander through the corn maze and enjoy plenty of fun, themed nights with friends and family. Participate in farm games, meet some furry friends, and grab a pumpkin on the way out.
Annapolis Sailboat Show, October 15-18, Annapolis City Dock, Annapolis
Head on down to the docks, appreciate sailboats from all over the world, and get the newest gear from the tents that line the shore.
Maryland Avenue Fall Festival, October 18, Maryland Avenue, Annapolis
Bring the whole family down to Maryland Avenue and shop local vendors, have a delicious meal, and dance along to catchy music.
USNA Halloween All Saints’ Day Organ Concert, October 30-31, Naval Academy Chapel, Annapolis
Additional October events
Country Calling, October 2-3, Ocean City
The International Edgar Allan Poe Festival & Awards, October 2-4, Lexington Market Plaza, Baltimore
Family Fall Fest, October 3, VFW Post 160, Glen Burnie
Galesville Maritime Heritage Festival, October 3, Galesville
Rock-Tober Fall Festival, October 3, Rock Hill Beach Community, Pasadena
5th Annual Riviera Beach Fall Fest, October 4, Riviera Beach Community Park, Pasadena
Lifeline 100 Century Ride, October 4, Kinder Farm Park, Millersville
First Sunday Arts Festival, October 4 & November 1, West Street, Annapolis
Annie Awards, October 5, Maryland Hall, Annapolis
Annapolis Powerboat Show, October 8-11, Annapolis City Dock, Annapolis
Fall Vendor Craft Fair, October 10, Glen Burnie Elks Lodge #2266, Severn
Harvest Bash: Passport to Italy Edition, October 10, Providence Greenhouses & Gardens, Arnold
Tractor Treat, October 15, Homestead Gardens: Davidsonville, Davidsonville
Party in the ‘Port: Boat Show Edition, October 17, Eastport Yacht Club, Annapolis
DragonFest 2026, October 17, Pier 4 Marina, Annapolis
Jug Bay Ghost Paddle, October 17, Jug Bay Wetlands Sanctuary, Lothian
3rd Annual Paws and Pumpkins Fall Fest, October 17, Davidsonville
Art @ the Park, October 17-18, Quiet Waters Park, Annapolis
Calm for a Cure, October 18, Even Keel Wellness Spa, Various Locations
Anchors & Artisans Pop-Up Market, October 18, Annapolis Town Center, Annapolis
Maryland Ave Fall Festival, October 18, Maryland Avenue, Annapolis
Ignite Annapolis, October 20, Maryland Hall, Annapolis
Sunfest, October 22-25, Ocean City Boardwalk, Ocean City
Blue Crab Cupcakes 5th Annual Trunk or Treat, October 23, 1580 Whitehall Rd., Annapolis
Halloween Spooktacular, October 23, Severna Park Community Center, Severna Park
Bountiful Harvest: Costumes & Cocktails, October 23, The Atreeum at Soaring Timbers, Annapolis
Trick or Treat Trail, October 24, SPCA of Anne Arundel County, Annapolis
Family Fall Festival, October 24, Waugh Chapel Towne Centre, Gambrills
Porchfest, October 24, Annapolis
Haunted Harbour Day, October 24, Annapolis Harbour Center, Annapolis
Feast on the Farm, October 24, Mas Que Farm, Annapolis
Annapolis Scarecrow Stroll, October 24-November 2, Downtown Annapolis
Halloween Whodunit 3, October 29, Rams Head On Stage, Annapolis
Candlelight: A Haunted Evening of Halloween Classics, October 29, Maryland Hall, Annapolis
Pumpkin Walk, October 30, Hammond-Harwood House, Annapolis
November Festivals & Activities You Can’t Miss
Bay Bridge Run, November 8, Chesapeake Bay Bridge
Don’t miss your one and only opportunity this year to cross the Chesapeake Bay Bridge on foot!
Lights on the Bay, November 23-January 3, Sandy Point State Park, Annapolis
Come experience the dazzling, sparkling lights of this beloved holiday tradition! Bring your entire family—including your pets—and get in the festive spirit while supporting the SPCA of Anne Arundel County.
Fleet Feet Sports’ Annual Thanksgiving Day Turkey Trot, November 26, 318 6th Street, Annapolis
Run or stroll through downtown Annapolis on Thanksgiving Day! Everyone is welcome to participate, including families with kids, dogs, and strollers. You’ll be supporting Girls on the Run Greater Chesapeake.
North Pole Lights Walk, November 27-December 30, Willow Oak Flower & Herb Farm, Severn
Meet the North Pole Fairy, visit the flowers and arctic animals, and say hello to Santa!
Grand Illumination, November 29, Annapolis
Celebrate the beginning of the holiday season with a beautiful, festive tree lighting, dancing, and carols by local singers.
Additional November Festivals & Events
Eastport vs Annapolis Tug of War, November 7, Spa Creek Bridge, Annapolis
Fish for a Cure Tournament and Shore Party, November 7, Annapolis
Early Christmas Fall Flea Market and Craft Fair, November 7, Benson-Hammond House, Linthicum Heights
OysterFest, November 7, Chesapeake Bay Maritime Museum, St. Michaels
SPAN’s Turkey Trot, November 7, Kinder Farm Park, Millersville
PUMC Craft Fair, November 7, Pasadena United Methodist Church, Pasadena
Gun and Knife Show, November 7-8, Anne Arundel County Fairgrounds, Crownsville
Veterans Classic, November 11, United States Naval Academy: Alumni Hall, Annapolis
Jingle Bell Bargains Yard Sale & Holiday Vendor Market, November 14, Walnut Hill Farm, Davidsonville
Waterfowl Festival, November 13-15, Downtown Easton
St. Martin’s Christmas Mart, November 14, St. Martin’s-In-The-Field Episcopal Church, Severna Park
Tastings & Tunes: Wine & Beer Fest on West, November 14, 60 West Street, Annapolis
The Gothic Market, November 14-15, Maryland State Fairgrounds, Timonium
Girls Night Out, November 18, Homestead Gardens: Davidsonville, Davidsonville
Girls Night Out, November 19, Homestead Gardens: Severna Park, Severna Park
Lights & Leashes, November 20-22, Sandy Point State Park, Annapolis
Garden of Lights, November 20-January 3, Brookside Gardens, Wheaton
Holiday Model Train Garden Grand Opening, November 21, Marley Station Mall
Great Annapolis Gingerbread Houses, November 22-December 20, Annapolis Visitor Center, Annapolis
Y Turkey Trot Charity 5K, November 26, The Greater Annapolis Y in Arnold, Arnold
19th Annual Holiday Tree Lighting, Mid-Late November (TBD), Annapolis Town Center
December Festivals & Events You Can’t Miss
Midnight Madness in Downtown Annapolis, December 3, 10, & 17, Downtown Annapolis
Explore the winter wonderland of Annapolis with its decorated and festive storefronts! Save on your holiday shopping with great deals and experience free live entertainment on the streets.
Annapolis Chocolate Binge Festival, December 6, Annapolis
Satisfy your sweet tooth and buy all kinds of chocolate, candy, baked goods, and more! Stroll through the holiday market, dance along to live music, and spend quality time with your loved ones under West Street’s Holiday Light Canopy.
Eastport Yacht Club Lights Parade, December 12, Annapolis Harbor
Get up close to the Annapolis Harbor and watch dozens of boats decorated in colorful lights cruise by.
The Nutcracker: Ballet Theatre of Maryland, December 12-20, Maryland Hall, Annapolis
Holiday Pops at Maryland Hall, December 18, Maryland Hall, Annapolis
Holiday Pops at Severna Park HS, December 19, Severna Park HS, Severna Park
New Year’s Eve Fireworks, December 31, Annapolis
Ring in the new year with your loved ones and watch a spectacular fireworks display over Annapolis. Top viewing spots are City Dock, Spa Creek Bridge, Eastport Waterfront, and Quiet Waters Park.
Additional December Festivals & Events
Photos with Santa, Early December (TBD), Uncharted, Annapolis
Menorah Lighting at Annapolis Town Center, Early December (TBD), Annapolis
Brigade Holiday Market, Early December (TBD), Dahlgren Hall, USNA
20th Annual Holiday Drive, December 5, Fence & Deck Connection, Millersville
West Annapolis Holiday Market, December 5, West Annapolis
Annapolis Holiday Market, December 4-13, 1040 Annapolis Mall Road, Annapolis
Christmas Bazaar 2026, December 5, The Vine Natural Health Center, Forest Hill
Cookies & Cocoa with Santa, December 11, Severna Park Community Center, Severna Park
Annapolis Striders Anniversary Run 15K, December 13, Quiet Waters Park, Annapolis
Keep the Fall Fun Going!
Can’t get enough of fall? Neither can we! Whether your perfect fall day means getting lost in a corn maze, hunting for the perfect pumpkin or filling a basket with freshly picked apples, we’ve got you covered. Check out our guides to even more fall fun around Annapolis and beyond:
- Your Ultimate Annapolis Guide to Corn Mazes
- Your Ultimate Annapolis Guide to Pumpkin Patches
- Your Ultimate Annapolis Guide to Apple Picking
Annapolis Pride Parade & Festival Returns With Family-Friendly Fun