Giant Pumpkins & Fall Events in Downtown Annapolis

Annapolis, MD - Imagine strolling throughout downtown Annapolis and Eastport and finding giant pumpkins weighing over 1,000 pounds each. Annapolis is one of the few places you can enjoy that experience, It’s the perfect complement to all of the fall events in downtown Annapolis.

Visitors strolling through downtown Annapolis, the Annapolis Arts District, and Eastport will find gigantic pumpkins at multiple locations, nestled amidst straw bales in the downtown Annapolis and Eastport area. The pumpkin displays make the perfect backdrop to get your photos taken with friends, family, and pets.

Halloween weekend will kick off Friday, October 27th, with the Great Annapolis Pumpkins when local professional artists arrive to carve the giant pumpkins, turning them into jack-o-lanterns and works of art for all to enjoy.  Watching the carving is just as fun as seeing the finished works of art. Touring the giant Annapolis jack-o-lanterns is a free, must-attend family-friendly event.  Each jack-o-lantern has a fun personality that the public enjoys getting pictures with. This day is also the debut of the Annapolis Night Market at the Hillman Parking Garage.

The  Downtown Annapolis Partnership is pleased to work with partnering organizations for the fourth year in a row on this event.   We are grateful to our sponsors that make this free event possible, including Visit Annapolis and Anne Arundel County, Maryland Tourism, Downtown Annapolis Partnership, City of Annapolis, Arts Council of Anne Arundel County, Annapolis Arts District, Annapolis Waterfront Hotel, St. Anne’s Episcopal Church, Boatyard Bar & Grill, and others.

The Downtown Annapolis Partnership is hosting a photo contest through October 31 to encourage everyone to take selfies with the Great Annapolis Pumpkins.  Individuals who take a picture or shoot a video of themselves with any of the giant pumpkins and post it on social media along with the hashtags #GreatAnnapolisPumpkins, #Visit Annapolis, and #VisitMaryland will be entered for a chance to win gift cards to their favorite Annapolis-area businesses via random drawings throughout the month. 

Great Annapolis Pumpkin Locations for 2023:

  • Graduate Annapolis Hotel next to FinArt Gallery
  • Annapolis Visitors Center
  • St. Anne’s Episcopal Church
  • Maryland Inn
  • Maryland Avenue at State Circle
  • Market Space
  • Annapolis Waterfront Hotel
  • Boatyard Bar & Grill
  • Corner of Francis and Main Street (coming soon)

Additional fall activities in downtown Annapolis within a short stroll of the Great Annapolis Pumpkins include:

Sincerely,

Erik Evans | Executive Director | Downtown Annapolis Partnership