New England

Best Pumpkin Festivals in New England

Looking for phenomenal fall celebrations? These annual events are the best pumpkin festivals in New England!

By Kim Knox Beckius

Sep 29 2022


The NH Pumpkin Festival in Laconia, New Hampshire | 5 Best Pumpkin Festivals in New England

Photo Credit :

Looking for a list of the best pumpkin festivals in New England? Backroads of New England (Voyageur Press, 2012) author and Yankee Travel Editor Kim Knox Beckius names these annual events the best pumpkin festivals in New England.

Best Pumpkin Festivals in New England

Pumpkintown USA | East Hampton, CT
September 17-October 31, 2023

Your GPS won’t recognize Pumpkintown, Connecticut, but keep your eyes peeled as you drive through East Hampton on Route 66. When you see adorable orange-headed beings at the side of the road, you’ve found New England’s most whimsical Halloween attraction. Pumpkintown USA is the rare destination that amuses all ages, even the littlest zomboys and ghouls. And more characters await on a 20-minute hayride. Affordable admission fees benefit the Sandy Peszynski Breast Cancer Foundation.

Best Pumpkin Festivals in New England
The NH Pumpkin Festival in Laconia, New Hampshire | 5 Best Pumpkin Festivals in New England
Photo Credit :

Vermont Pumpkin Chuckin’ Festival | Stowe, VT
TBD, 2024

It’s the ultimate game of fall one-upmanship. Held at Stoweflake Mountain Resort & Spa, the Pumpkin Chuckin’ Festival challenges kids and adults to build a better trebuchet: a modern version of the medieval catapult. Spectators watch pumpkins soar … and smash. But for competitors, this is a serious intellectual exercise. Low-cost entry and admission fees support the Lamoille Family Center. And a chili cookoff gives Stowe-area restaurants a chance to compete for glory, too.

Jack-o-Lantern Spectacular | Providence, RI
September 29 – October 31, 2023

Lines can be long at Providence, Rhode Island’s Roger Williams Park Zoo, but the artistry on display will mesmerize you. This isn’t simply an outdoor gallery of 5,000 illuminated jack-o-lanterns (some 125 of which are intricately etched); special effects transform zoo pathways into a Halloween fantasyland. Artisan carvers from Passion for Pumpkins whittle rinds throughout the show’s run to keep the display fresh. Included in Yankee‘s 2021 feature “31 Ways to Fall for Autumn.”

Damariscotta Pumpkinfest & Regatta | Damariscotta, ME
October 6-9, 2023

It begins serenely on a May morn, when hundreds of giant-pumpkin seedlings are distributed free to volunteer growers. By Columbus Day weekend, the Midcoast Maine town of Damariscotta has succumbed to pumpkinsanity. After a weigh-off with big cash at stake, humongous gourds become artworks, go on parade, and plummet 180 feet onto derelict vehicles. Their smaller kin are hurled, catapulted from cannons, or prepped to race in an unpredictable Pumpkin Derby. The hilarity peaks when costumed racers paddle and motor some of the largest specimens in a madcap Pumpkinboat Regatta.

New England pumpkin festivals
Find pumpkins, cider doughnuts, and more fall vibes at Wilson Farm just a short drive from Boston.
Photo Credit : Meredith Hanson

Bonus Pumpkin Pick! Wilson Farm | Lexington, MA

Wilson Farm is an editor-approved spot for fall pumpkin vibes within a short drive of Boston. Every autumn weekend through Halloween, the popular farmstand/bakery adds homemade apple cider donuts, hot and cold apple cider, and caramel apples to their lineup of seasonal treats.

This post was first published in 2017 and has been updated.

Best Apple Orchards in New England
Best Corn Mazes in New England
Guide to New England Pumpkin Patches
Best Halloween Events in New England