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 18 2025|
The Laconia Pumpkin Festival in Laconia, New Hampshire | 5 Best Pumpkin Festivals in New England
Photo Credit: CliffordPhotographyNH.comLooking 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 20-October 31, 2025
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.
Photo Credit : CliffordPhotographyNH.com
Vermont Pumpkin Chuckin’ Festival | Stowe, VT
September 28, 2025
It’s the ultimate game of fall one-upmanship. Held at Mayo Farm Events Field, 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 local charities. And a chili cookoff gives Stowe-area restaurants a chance to compete for glory, too.
Jack-o-Lantern Spectacular | Providence, RI
September 26 – November 2, 2025
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 10-13, 2025
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.
Photo Credit : Aimee Tucker
Laconia Pumpkin Festival | Laconia, NH
October 25, 2025
This beloved annual tradition brings the community together with thousands of carved pumpkins, live entertainment, food vendors, family-friendly activities, and more in the heart of downtown Laconia.
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.
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Pumpkin is a very nutritious food. Why oh why would you write about a pumpkinchunkin contest? How much better would it be for the residents of Pumpkintown to donate their unused pumpkins to people who would appreciate the nutritious fruit? Children who watch this waste of food get the idea that
it is okay to throw away edible food and call it “fun.”
Franklin County Pumpkinfest 2014 will be held on Saturday, October 18 in Turners Falls Massachusetts. Only in its fifth year, it is becoming a extremely popular festival with all ages, drawing visitors from outside the county as well as locals.
Check out the Jack O Lantern Blaze in Croton on Hudson NY. Well worth the ride and price of admission. Get tickets early as this event sells put.
Rightly said Anne. I too think think the pumpkins should be donated to families who will appreciate this fruit. So they can carve up a face on it, post a picture on a social media site, get lots of likes. And finally let the pumpkin rot outside.
Chucking pumpkins is different, and therefore wrong.
Most pumpkins get donated after the event to local pig farmers here in New Hampshire. Pumpkins make great nutritious food for animals, too.
We hope that one day our annual event (co-hosted by the Ridgefield Chamber of Commerce) “Giant Pumpkin Weigh Off” will be on this list! Come check it out, Sunday, September 28, 2014 in Ballard Park on Main Street in Ridgefield, CT. Free family fun! https://www.facebook.com/Ridgefieldpumpkinweighoff
Another great (yet not highly publicized…yet) pumpkin event happens in Newtown, CT each year. In 2011, after finding out that her friend was battling brain cancer, then 12-year-old Mackenzie Page decided that she needed to do something positive to help her friend. Mackenzie lives on Main Street in Newtown which is THE place to trick-or-treat on Halloween night. An average of 3,000 children participate on Main Street on that night and it’s a very social event. Knowing the type of foot traffic that they get and trying to brainstorm something to raise funds for her friend’s medical bills Mackenzie decided that her family could offer to display carved pumpkins on their front lawn, all to be lit up in a grand display, for a small donation. The money raised has been split between her friend and charity organizations such as Paul Newman’s Hole in the Wall Gang Camp. So far, this child, working almost single-handedly, has managed to raise a whopping $11,786.00. This year, as a junior in high school, Mackenzie plans to host the 4th annual Great Pumpkin Challenge. If you’re looking for a fall pumpkin event that will have you walking away feeling great consider donating to the Great Pumpkin Challenge in Newtown, CT. You can donate and have your pumpkin displayed or you can make a monetary donation online. Either way, it’s an incredible cause!
http://www.greatpumpkinchallenge.org/
Pumpkins Aglow is really great too and they have rides + a train ride included in admission. Really great with kids.
http://edaville.com/events.html#Carnival
Jack-o’lanterns are carted off to local pig farms after the Keene Pumpkinfest. Sugar pumpkins for eating are different than pumpkins used for jack-o’lanterns.
You missed the Milford NH Pumpkin Festival!! It’s awesome!
The Milford Pumpkin Festival traditionally runs over Columbus Day weekend in October. This year’s dates are October 9th through 11th. This is our 26th year, and each year as we get better and better! In 2014, attendance level over the 3 day festival was in excess of 35,000. Due to our proximity to so many large cities and other states, our attendees and tourists come from all over New Hampshire, the Boston metro area and the surrounding New England States. We just keep getting bigger and better each year, and as a result, we see an increase in media coverage, so there is even greater marketing potential for you this year than in years past!!
There are more activities planned for this year than ever before, with a spectacular fireworks display on Friday night; carnival rides; live entertainment and music on 2 stages featuring live bands throughout the weekend; a Haunted Trail; bouncy houses and a climbing wall; some of the best food in New England; craft vendors, face painting, pumpkin painting, and scarecrow making; a beer and wine tasting tent; a pumpkin catapult; the giant pumpkin weigh-in contest; and much MUCH more!
Another great festival is pumpkin on the pier in Milford, CT.
visit http://www.pumpkinsonthepier.org for more info. It is a great way to bring together all of New England’s beauty, the beach and the fall!
Lighten up, life is ment to be joyful
Although you did mention how the let it shine organization ran away from the Keene area that supported it for 25 years because few drunken college kids got rowdy on side streets away from pumpkin fest (I was there with my son and they weren’t on the main streets of pumpkinfest), you didn’t mention how the people in this area have banded together to create a real pumpkinfest in neighboring swanzey NH. The local businesses in Keene need your support, pumpkinfest brought in a lot of business that they depended on. So come to the one at the Cheshire fairgrounds and avoid Laconia. Show let it shine that tradition is important as well as supporting local businesses. Thank you
Stu –
No one is more disappointed than I that Pumpkinfest will not be held in Keene this year. Let it Shine, did NOT run away from Keene. City government refused to issue an event permit to the organizers, after the fracas on campus last year.
I’m glad that there is an alternative event at the Fairgrounds; however, it seems wrong to malign the folks who worked so hard to keep the event going after Center Stage abandoned it. I think no one has embraced the tradition of Pumpkinfest more than Ruth Sterling and Let it Shine. I also understand that Nancy Sporborg, founder of the Keene Pumpkinfest, has collaborated with the Laconia organizers to bring many of the Keene traditions to the new venue.
Regrettably, I will not be able to join the folks at the Fairgrounds, as we come from out of state and have planned to attend the Laconia event. Best of luck to you.
The web-site for the Milford Pumpkin Festival (celebrating it’s 26th year in 2015) is: http://www.milfordpumpkinfestival.org/
It’s FABULOUS!
Absolutely Stu…the Monadnock Pumpkin Festival at the Cheshire Fairgrounds is going to be amazing! I can’t wait…a carving contest, a costume contest, fright fest, so many new and fun activities!
Check out the 2nd Annual Rocky Point Farm Pumpkin Walk. A great event with many hand carved candle-lit pumpkins set in an enchanting woodland setting. Perfect for young children and their families. Roast a marshmallow then take a stroll through the candle-lit woods and view all the jack o lanterns. October 29 and 30th, 2015 — 6-8:30 pm each night. $5 adults, $3 kids 1-14, infants 0-1 year old free. Rocky Point Farm, 130 Rocky Point Ave, Warwick, RI http://www.rockypointblueberries.com
closed this year due to traffic problems
You are missing out on one of the best Pumpkin Festivals in New England… the “All Things Pumpkin” Festival which includes a Pumpkin Carving Competition and Expo, “All Things Pumpkin” Chef of the year Competition an “All Things Pumpkin” Tour which is a sleigh ride over the Jackson Historic Covered Bridge down into the Village of Jackson where the sleigh stops at businesses who bring out Pumpkin Tasting goodies to all the sleigh riders. This festival takes place along side the MOST popular NH event in October which is the “Return of the Pumpkin People”. Please be sure to add this to your fall foliage extravaganza.
The town and people of Jackson are the nicest and scenery absolutely stunning. The Pumpkin People and events are the best. Don’t miss a day of fun and excitement. Love town of Jackson.
Milford, NH has been one of the 1st Pumpkin Festivals in New Hampshire. To bad you have to look to the newest rather than the old ones running for years….
and one of the best.
Excellent write-up; as always. Thank you!
I heard from the organizers that after the Keene Pumpkin Festival wraps up in Keene NH, they give all of the used jack-o-lanterns to a local pig farm as food for farm animals.