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Great Annapolis Pumpkins

You are invited to explore Annapolis and find the giant pumpkins.
Take your picture with real pumpkins that are over 1000 pounds each and post pictures to your favorite social media pages for chances to win prizes from local businesses.
Use the hashtag #GreatAnnapolisPumpkin
s to be entered into the contest
These pumpkins will appear just after the first weekend in October and are all within an easy stroll of one another. 


The pumpkins will turn into Jack-o-Lanterns the Friddays before Halloween. Be sure to revisit Annapolis to see the area's largest Jack-o-Lanterns.

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Press release 2023 (revised 10/9/2023)

The Great Annapolis Pumpkins make their historic return and are larger than ever.

You are invited to explore Annapolis and find the giant 1000+ pound pumpkins.


ANNAPOLIS, MARYLAND – Imagine strolling throughout downtown Annapolis and Eastport and finding giant pumpkins weighing more than 1,000 pounds each. “Annapolis is one of the few places you can enjoy that experience,” says Erik Evans, Executive Director of the Downtown Annapolis Partnership and the Annapolis Arts District. “It’s the perfect complement to all of the fall events in downtown Annapolis including ghost tours that start near the Maryland Inn, a scarecrow walk along West Street, Halloween concerts at the USNA Chapel, the Fall Festival on Maryland Ave, a night market at Hillman Parking Garage and a pumpkin walk at the Hammond Harwood House that are all within a short stroll from the Great Annapolis Pumpkins.”  

"Annapolis and Anne Arundel County are bursting with adventures this October as we dive into another fall season filled with outdoor fun for everyone," says Kristen Pironis, Executive Director of Visit Annapolis & Anne Arundel County, and this year's leading sponsor. "Fall is one of the most magical times to visit our Capital City, and we're proud to support this one-of-a-kind, larger-than-life experience that simply adds to the visitor experience that makes the gateway to Maryland's Chesapeake Bay so special,” she added. The organization is pleased to serve as lead sponsor of the Great Annapolis Pumpkins and recommends weekend getaways to Anne Arundel County this fall to enjoy the Great Annapolis Pumpkins, local shopping and dining, and nearby attractions in the county that also include corn mazes, pick your own pumpkins, fall festivals, concerts, boat shows, historic home tours, and local wineries and breweries.


The giant pumpkins are purchased at a pumpkin weigh-off contest in Western Pennsylvania each year. Bumper Moyer, treks up there annually with funds from the sponsors and organizers to negotiate the purchase of the giant pumpkins directly from the farmers. Buying at auction is always tricky and you never know what size or how many you will be successful at purchasing until after the auction ends. This year the Downtown Annapolis Partnership was able to purchase  giant pumpkins of which 4 were over 1,000 pounds. two of the giant pumpkins were lost in transport back to Annapolis. However, this will still be the most extensive collection of giant pumpkins that Annapolis has ever seen Starting Monday, October 9th.  They get comments and stares every year as the giant pumpkin caravan makes its return trip to Annapolis, Maryland.  The City of Annapolis public works crews provided a forklift and crew to help Garden Girls and the Downtown Annapolis Partnership unload and place the giant pumpkins around downtown Annapolis.

Visitors strolling through downtown Annapolis and the Annapolis Arts District will find gigantic pumpkins at multiple locations.  Start at the Visitors Center at 26 West Street and they will help you find all the Great Annapolis Pumpkins that are 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. The pumpkins arrive the morning of Monday, October 9th. Unloading these gigantic pumpkins with forklifts is always an attention-getter and is immediately followed by people lining up to get their pictures taken with them.


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.


Erik Evans says the Downtown Annapolis Partnership is pleased to work with partnering organizations for the fourth year in a row on this event.  “We love seeing all the families that come to Annapolis to experience seeing something they may have never seen before.  Our goal is to provide a fun, safe way for individuals of all ages to enjoy a fall visit to Annapolis, Maryland.  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.


To encourage every to take selfies with the Great Annapolis Pumpkins the Downtown Annapolis Partnership is hosting a photo contest through October 31.  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


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

Oct 1-Nov 1 Ghost Tours

Oct 9- 31 Great Annapolis Pumpkins

Oct 14 St Anne Cemetery Tour 

Oct 20– Nov 1 Scarecrow Stroll 

Oct 21 Fall Fest on West

Oct 22 Maryland Ave Fall Fest 

Oct 22 Outdoor Movie Hocus Pocus

Oct 26 Halloween Bike Ride 

Oct 27 Great Annapolis Pumpkin Carvings

Oct 27-28 Halloween All Saints Concert 

Oct 27 Hammond Harwood House Pumpkin Walk 

Oct 27 Annapolis Night Market

Oct 28 Whispers of the Raven

Oct 29 Hammond Harwood Full Moon Tour

Oct 29 Outdoor Movie Psycho  

Oct 29 Haunted Verses Poetry


For more information on the Great Annapolis Pumpkins visit www.downtownannapolispartnership/great-annapolis-pumpkins 

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