Every October weekend across New England has a pumpkin festival, a harvest fair or a Halloween parade — here's where, laid out weekend by weekend so you can actually plan around them.
By mid-September, every parent in New England has heard the words "pumpkin festival" so many times it stops meaning anything. Fine. Here's the thing: there are roughly nine of them happening this October, and they are not the same event wearing different hats. One involves floating inside a hollowed-out pumpkin down a river in Maine. Another has an actual apple you can't identify, handed to a stranger, for science. This is the month New England shows off, and it deserves a proper map instead of a vague sense that "something's happening in Salem."
King Richard's Faire in Carver and Salem's Haunted Happenings run every weekend of the month, so they're left off the list below — this is for the one-weekend-only events, the ones you'd actually miss if nobody told you the date. Everything here traces back to the organizer's own site or a local news outlet; anywhere a 2026 date hadn't been posted yet, that's said plainly rather than guessed at.
Celebrating its 150th year, dating to 1876. Gate admission $12 for ages 13+, free for kids 12 and under. deerfieldfair.com
Sack races, hay rides, a mud pit, tug-of-war and fair games with prizes. $15 general admission, $10 ages 3–18, free under 3.
80+ vendors, food trucks, a DJ and a dog parade.
See Weekend 2 — it's still going the following weekend too.
People hollow out giant pumpkins, climb inside, and paddle or motor them down the Damariscotta River while thousands watch. The regatta is Sunday, Oct 11, noon–2pm; the kids' Pumpkin Derby is that morning. mainepumpkinfest.com
An old-fashioned country fair with dedicated kids'-focused days.
An oxen competition, a midway and a 1pm Children's Parade. Started in 1947, run by hundreds of volunteers. wfff.org
Friday is the pumpkin lighting. Saturday has the Great Pumpkin Weigh-in and a haunted trail; scarecrow-making runs Saturday and Sunday. milfordpumpkinfestival.org
Free admission. About 200 artists and craftspeople, plus antiques, on the village green.
Starts with the HONK! Parade of 25 bands; anyone can join the back and walk to Oktoberfest. cambridgeusa.org
Pony rides, a hay maze and hay jump, hayrides, a petting zoo and square dancing. $15 adults, free for kids 12 and under. berkshirebotanical.org
The "Pumpkingames" at noon Saturday include pumpkin bowling and a pumpkin relay. ashfieldfallfestival.org
Watch a working bog harvest, or pay extra to put on waders and get in the bog yourself. Only found on an aggregator site, not an official page — worth double-checking before you drive out.
The Topsfield Fair (Oct 2–12) and Maine's Fryeburg Fair (Sun Oct 4 – Sun Oct 11).
Sunday brings the carnival, live music, 100+ crafters and vendors, and free pumpkin decorating while supplies last.
Because of downtown construction, the festival center moves from Central Square to Railroad Square this year. explorekeene.org
Juried crafters and old-fashioned market vendors from across New England. yorkharvestfest.com
A craft fair, children's activities, eco-tours and the Oyster Shuck-Off. Ticketed; 2026 prices not yet posted. Runs rain or shine; pets aren't allowed.
Kids' activities alongside the seafood.
Runs across two weekends — see Weekend 4 for the Halloween-themed second half. wachusett.com
Kids trick-or-treat downtown and in Perkins Cove, plus a classic car show at Main Beach and the Dogtoberfest costume parade. ogunquit.org
Thousands of carved pumpkins, family activities, local artisans and live entertainment.
Cider pressing, butter churning, and mystery apple identification — bring an apple you can't identify and someone will tell you what it is. mofga.org
The Halloween-themed second weekend of the two-part AppleFest.
Anyone can dress up and march — no sign-up needed.
Dates, times and prices are from each event's own site or a local news source as of late September 2026 and can change — click through to confirm before you go, especially for anything more than a few weeks out.