Take a “Gourd-geous” Day Trip: The Great Annapolis Pumpkins Are Back! 🎃
Just 45 minutes from Old Town, Annapolis serves up pumpkins, photos, and fall charm.
ANNAPOLIS, MD – If you thought Old Town Alexandria had charm in the fall, wait until you stroll the historic streets of Annapolis surrounded by giant pumpkins weighing up to 1,500 pounds! The Great Annapolis Pumpkins are rolling back into town this October, and they’re just begging to be part of your next autumn adventure.
Picture this: Forklifts unloading monster pumpkins the size of small cars onto Main Street, Market Space, and Maryland Avenue. By mid-October, these massive gourds are perched in front of Annapolis landmarks like St. Anne’s Church, St. John’s College, the Annapolis Waterfront Hotel, and more—all easy walking distance from each other.
Snap a selfie with one of these gentle giants, tag #GreatAnnapolisPumpkins and @VisitAnnapolis, and you could win prizes from local shops and restaurants. (Tip: Bring a friend or the kids—these pumpkins are some of the most Instagrammed things in town!)
And don’t just stop with the pumpkins:
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Catch a Fall Festival – The Annapolis Pride Parade, Maryland Avenue Fall Fest, or the Annapolis Night Market are perfect pairings with your pumpkin quest.
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See the Magic Happen – On October 24, local artists (including Food Network’s Nancy Baker) will carve the pumpkins into jaw-dropping jack-o’-lanterns. Come back after dark to see them glow—there’s nothing else like it in Maryland!
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Explore & Indulge – While pumpkin-spotting, browse boutiques filled with fall fashions, grab oysters by the waterfront, or join a ghost tour for a spirited twist.
Easy Alexandria Day Trip
Annapolis is just a quick 45-minute drive from Old Town Alexandria, making it the perfect mini-getaway. Spend the day pumpkin-hunting, dining, shopping, and soaking up the colonial charm. Then head home with a camera roll (and maybe a pumpkin spice latte) full of memories.
“The Great Annapolis Pumpkins puts a festive twist on fall in our historic downtown—with a dash of spooky style,” says Kristen Pironis of Visit Annapolis. “It’s a ‘gourd’ time for visitors and locals alike.”
So grab your scarf, pack your phone charger, and head to Annapolis this October. These pumpkins won’t be around forever—by Halloween, they’ll be transformed into the area’s biggest jack-o’-lanterns.
🍂 When: Pumpkins arrive October 6 and stay through early November
📍 Where: Downtown Annapolis (pick up maps at the Visitors Center, 26 West St.)
💲 Cost: Free!
For the full pumpkin map and details on fall events, visit VisitAnnapolis.org.
