Press Release: Downtown Annapolis Celebrates Fall with Festivals, Giant Pumpkins, and Seasonal Fun

Office of Mayor Gavin Buckley
PRESS RELEASE

City of Annapolis
160 Duke of Gloucester Street
Annapolis, Maryland 21401

For Immediate Release:
Mitchelle Stephenson, 410-972-7724 or [email protected]

Downtown Annapolis Celebrates Fall with Festivals, Giant Pumpkins, and Seasonal Fun

ANNAPOLIS, MD (October 15, 2025) - Fall is in full swing in Annapolis, with festive activities, harvest-themed festivals, and giant pumpkins. Most of these events are free and family-friendly.

"Fall in Annapolis is about more than just pumpkins," said Annapolis Mayor Gavin Buckley. "it's about celebrating community, history, and the unique spirit of downtown."

GREAT PUMPKINS: The iconic Great Annapolis Pumpkins are back in downtown. Presented by Visit Annapolis & Anne Arundel County, the Downtown Annapolis Partnership, and the Maryland Office of Tourism, these giant pumpkins (some weighing more than 1,000 pounds) are on display on Main Street, Market Space, Maryland Avenue, West Street, College Avenue, and Compromise Street. These giant pumpkins are a favorite photo opportunity. Enjoy professional pumpkin carvings by local and regional artists on Thursday, October 24. The pumpkins will remain on display through November 2. Visit: https://www.downtownannapolispartnership.org/great-annapolis-pumpkins

MARYLAND AVE FALL FESTIVAL: From 10 a.m. to 6 p.m. on Sunday, October 19, enjoy live music, local vendors, food, and family-friendly activities along historic Maryland Avenue. Maryland Avenue will be closed to both traffic and parking on Sunday, Oct. 19 from 7 a.m. until breakdown of the festival. Visit: https://www.mascma.com/

WATERMARK FALL FOLIAGE CRUISE: On three dates (Oct. 19, 21 and 25), Watermark Cruises hosts a special fall foliage cruise with views of three Chesapeake Bay lighthouses. Details: https://watermarkjourney.com/events/fall-foliage-bay-lighthouse-cruise/

SCARECROW STROLL: Between October 25 and November 1, enjoy creatively-themed scarecrows along West Street, Maryland Avenue, and Main Street. The stroll is hosted by Inner West Street Association in partnership with Maryland Avenue and State Circle Association, and Downtown Annapolis Partnership. Visit: https://www.iwsannapolis.com/event-details/4th-annual-annapolis-scarecrow-stroll

DINNER UNDER THE STARS MASQUERADE BALL: From 4:30 to 11 p.m. on Wednesday, October 25, come out for the last "Dinner Under the Stars" event of the season. There will be a costume contest, drag bingo and outdoor restaurant service from all the dining establishments on the block (reservations recommended). Inner West Street (between Church Circle and Calvert Street) will be closed to both traffic and parking from 4 p.m. until midnight. Visit: https://www.iwsannapolis.com/event-details/masquerade-ball-drag-bingo-and-show

FIRST SUNDAY ARTS FESTIVAL HOLIDAY MARKET: 11 a.m. to 5 p.m. on Sunday, November 2 in the first block of West Street (between Church Circle and Calvert Street), featuring vendors, live music, and cafe dining. Inner West Street (between Church Circle and Calvert Street) will be closed to both traffic and parking from 9 a.m. to approximately 7 p.m. Visit: https://www.iwsannapolis.com/first-sunday-arts-festivals

MARITIME REPUBLIC OF EASTPORT TUG OF WAR: Noon on Saturday, November 8 on Second Street in Eastport. This charity fundraiser typically involves a rope stretched across Spa Creek, but due to the work at City Dock, the event this year will be exclusively held in Eastport. Live music, food, vendors and teams vying for bragging rights. Visit: https://themre.org/tug .

NAPTOWN FLEA MARKET: 1 to 6 p.m. on Sunday, November 9 at Market Space, this community market features live music and a mix of vendors selling vintage and handmade arts, clothes, records, goods, and collectibles. Visit: https://www.instagram.com/naptownflea/

TASTE OF FALL: 2 to 5 p.m. on Sunday, November 9 in the unit block of West Street with tastings from local restaurants, live music and more. Inner West Street (between Church Circle and Calvert Street) will be closed to both traffic and parking from noon to approximately 7 p.m. Tickets: https://www.eventbrite.com/e/taste-of-fall-on-west-street-tickets-1606767738559

For more information about events and locations of the Great Annapolis Pumpkins, visit Downtown Annapolis Partnership or Visit Annapolis .

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