Every fall roundup is organized by state, which is useless. Nobody plans a Saturday by state — you plan it by how long everyone can survive in the car.
📅 September 2, 2026 · GOkidOZ Boston · 5 min read
Yes, this is a real sport: racers in hollowed-out giant pumpkins. Photo: Jens Berlin, Wikimedia Commons (CC BY-SA 3.0)
So here's the season sorted the way we actually think about it — 25 festivals in four tiers, from home-by-nap-time to worth-an-overnight. All dates confirmed as of this week.
🚗 Under an hour
The Saturday-morning tier — home by nap time
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Fall-O'ween on the Farm
📍 Drumlin Farm, Lincoln · Sat, October 24 · 9am–5pm
Mass Audubon's version of Halloween, on a working farm with actual animals. The closest thing on this list to a sure thing for the under-eight crowd.
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Harvest Fest at Southwick's Zoo
📍 Mendon · Sat, September 26 · rain date the 27th
Included with zoo admission, so you get the animals either way.
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Worcester Day of Play Festival
📍 Elm Park, Worcester · Sat, September 19 · 11am–4pm · rain date the 20th
Free, and Elm Park itself is worth the drive.
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Hollis Hills Farm Apple Festival
📍 340 Marshall St, Fitchburg · September 19–20
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Marlborough Food Truck & Arts Festival
📍 Downtown Marlborough · Sunday, September 13
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Sturbridge Harvest Festival
📍 Sturbridge Common · October 17–18
Pair it with Old Sturbridge Village and you have a full day.
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Waters Farm Fall Farm Days
📍 Waters Farm, Sutton · October 17–18
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West Boylston Fall Fest
📍 Goodale Park — park at the WB schools · Sat, October 25 · 11am–4pm
⛰️ The Wachusett run
Princeton, about an hour — something nearly every October weekend
Wachusett Mountain is the easiest single place to plan around, because if one weekend doesn't work, the next one will.
BBQFest
Oktoberfest
AppleFest, weekend one
AppleFest, weekend two
BooFest
Now in its 42nd year and extended to two weekends because of demand, AppleFest lands during peak foliage: craft vendors, a farmers' market, live music at noon and 3pm daily, magic and circus shows, roaming characters, and apple pie baking and eating contests.
The SkyRide is the real draw — foliage from a chairlift, no hiking required, and small children think it is the best thing that has ever happened to them. Note that dogs and coolers aren't allowed at Wachusett festivals.
🌾 Ninety minutes west
Worth the drive, but pack snacks
The Avenue of the States at The Big E — the Massachusetts building. Photo: liz west, Wikimedia Commons (CC BY 2.0)
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The Big E
📍 West Springfield · September 18 – October 4
New England's largest fair, with a genuinely clever hook for kids: the Avenue of the States, where all six New England statehouses are reproduced at scale and you can walk through every state in an afternoon. Plus carnival rides, farm animals, food trucks and a real concert lineup.
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Kids Boo Fest at Six Flags New England
📍 Agawam · September 26 – November 1 · select dates
Trick-or-treat trails and gentle themed activities aimed at younger children.
Check your ticket carefully. Fright Fest runs at the same park on the same calendar, with haunted attractions, scare zones and roaming characters. Confirm which event you've booked and which hours you're arriving — plenty of families have learned this one the hard way.
🛏️ Worth an overnight
Two to four hours — make a weekend of it
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Damariscotta Pumpkinfest & Regatta
📍 Damariscotta, Maine · October 9–12
This is the one. Growers raise Atlantic Giant pumpkins to 400–700 pounds, the pumpkins are hollowed out and decorated, and then volunteer captains climb inside and race them down the Damariscotta River. Ten to fifteen thousand people come to watch.
There's also a pie-eating contest, a buskers' stage at Elm Street Plaza, a dessert contest at Skidompha Library, and a scavenger hunt for kids using mini jack-be-little pumpkins.
If your child sees one thing this fall, make it a grown adult paddling a hollowed-out squash.
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Common Ground Country Fair
📍 Unity, Maine · September 25–27
The 50th annual, run by the Maine Organic Farmers and Gardeners Association: more than a thousand exhibitors, draft horses, sheepdogs, spinners, weavers, woodworkers and all-organic food courts.
Children 12 and under get in free — but you still have to reserve their ticket in advance, which trips people up every year. Advance sales run through September 23.
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Northeast Kingdom Fall Foliage Festival
📍 Vermont — rotating towns · September 27 – October 4
The festival moves to a different Northeast Kingdom town each day. Check the schedule and pick your day.
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Fall for St. Johnsbury
📍 St. Johnsbury, Vermont · October 10–11
With foliage train rides.
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Fryeburg Fair
📍 Fryeburg, Maine · October 4–11
Maine's biggest agricultural fair.
🍎 New Hampshire, if you're heading north anyway
Easy add-ons to a foliage trip
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Apple Harvest Day
📍 Downtown Dover · Saturday, October 3
Free, roughly 400 crafters, an apple pie contest and a 5K. Around 50,000 people turn out, so go early and park further out than you think you need to.
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Somersworth Pumpkin Festival
📍 Somersworth Plaza, Main Street · Sat, October 10 · 10am–3pm
Pumpkin painting, carving, throwing, bowling and golfing. Yes, pumpkin golf.
📝 A few honest notes
Dates shift. Rain dates get used, small-town festivals move, and a couple of these were listed as confirmed by organizers but can still change. Check the organizer's own site the week of — not a roundup, including this one.
The free ones are often the best ones. Worcester Day of Play, Dover Apple Harvest Day and Somersworth Pumpkin Festival cost nothing and are run by people who live there.
Foliage peak moves north to south: the Northeast Kingdom peaks late September into early October; Massachusetts is usually mid-to-late October. If foliage is the point of the trip, drive north early in the season and stay closer to home later.
Always confirm with the organizer before you drive: wachusett.com · mainepumpkinfest.com · mofga.org · massaudubon.org. Cross-checked against Worcester Central Kids Calendar, NH Magazine, New England Travel Journal, WWLP and Mommy Poppins Boston.