Fall Festivals, PYO and other activities across New England

It’s October! That means apple picking, pumpkin carving and hayrides. It also means pumpkin regattas, a wife-carrying championship, traditional Oktoberfest Biergartens, and garlic ice cream. 

We put together a list of places all around New England with the best fall fun and unique perks! This is a list of events and activities, pick-your-own (PYO) and fall festivals, some for adults and some for kids, none of which are scary, and all of which have great food!


Tangerini’s Spring Street Farm – Millis

  • Admission $8 per person, includes hayride, pumpkin picking and decorating, hay maze and a free pumpkin when you leave!
  • $28 for a peck (10-12 lbs), $38 for half a bushel (20-24 lbs)
  • PYO apples, wildflowers

Connors Farm – Danvers

  • Mondays-Fridays: $9.99, $8.99 seniors, children under 2 are free; Saturdays & Sundays: $13.99; $12.99 seniors
  • $10.95 for 1/2-peck bag (approx. 5 pounds), $19.95 for 1-peck bag (approx. 10 pounds), $38.95 for 1/2-bushel bag (approx. 20 pounds)
  • PYO apples, corn maize, hayride, and pumpkin tetherball!

Boston Hill Farm – North Andover

  • Free admission
  • $20 for 1-peck bag (approx. 10-12 pounds), $40 for 1/2-bushel bag (approx. 20-24 pounds)
  • PYO apples that you can eat while you pick! They’ve also got apple cider and cinnamon doughnuts, sugar pumpkins and ice cream

New Hampshire

20th Annual Attitash Oktoberfest – Bartlett

  • October 7 – 8
  • Admission $12 for adults, $7 kids aged 6-20. Kids 5 and under are free.
  • Live Bavarian music, dancing, kids games, German food, and Oktoberfest Biergarten featuring local regional brewers

Pumpkin Weigh-off and Regatta – Goffstown

  • October 14 – 15
  • Free admission
  • The giant pumpkin weigh-off  takes place on Saturday and is followed by the regatta on Sunday, where people ride down the river in their enormous pumpkins. There’s also a 10K run and kids relay, pumpkin catapults, a giant pumpkin drop, and pumpkin races.

Somersworth Pumpkin Festival – Somersworth Plaza, Somersworth

  • October 14, 10 am – 4 pm
  • Admission: $12 for kids, adults are free
  • Everything is pumpkin themed! Pumpkin pie, pumpkin carving, pumpkin painting, pumpkin tossing, and pumpkin-themed games.


Green Mountain Orchards – Putney

  • Hayrides by appointment. Apple pie, apple cider doughnuts, hand-pressed apple cider, jams, butters, cheeses and maple products for sale!
  • PYO pumpkins, apples, peaches, plums, and berries

Pumpkin Festival at Cedar Circle Farm – Thetford

  • October 8, 10 am – 3 pm
  • Free admission for those who walk or bike! Suggested donation $10-15 per car
  • Horse-drawn wagon rides, pumpkin picking, raffles, enchanted forest for kids, live music, butternut apple crisp, pumpkin brownies, organic local ice cream and more.

The Great Pumpkin Walk – Essex Junction

  • October 30, 6 – 8:30 pm
  • Free admission 
  • For one night only, Maple Street Park will be lined with carved pumpkins! Plan to spend at least an hour walking through the street, and feel free to bring your own creation (drop off by 3 pm that day).


Pumpkin Train – Portland

  • October 21, 22, 28, 29
  • Admission $10 adults, $9 seniors, $6 kids, 2 and under free
  • Ride the train along Casco Bay and enjoy hot cider, cookies, decorating pumpkins, and exploring the museum

Harvest on the Harbor – multiple locations across Portland

  • October 17 – 22
  • Buy tickets in advance at harvestontheharbor.com (sales help fund Full Plates Potential, working to end childhood hunger in ME)
  • Flavors of Maine grand tasting event, Maine Lobster Chef of the Year competition, Harvest Happy Hour, Market on the Harbor, Harvest Crawl and Grand Tasting on the Harbor (wine, beer and spirits with views of Casco Bay while enjoying food from notable Maine chefs)

Sunday River Fall Festival Weekend – Newry

  • Oct 7 to Oct 8, 2017
  • North American Wife Carrying Championship, Kids’ Pumpkin Pie Eating Contest, New England Corn Hold Championship, Blue Mountain Arts and Crafts Fair, Wine Tent, concerts on Saturday and Sunday. Scenic Chairlift Rides to the Peak Lodge, free wagon rides and more.


Connecticut Renaissance Faire – Lebanon

  • Now until October 9
  • Admission $15 for adults, $10 for kids ages 7 – 15, kids free under 7
  • Explore a Medieval marketplace, jousting tilts, live music and magic shows
  • Admission $8 for adults, $7 for seniors, $1 for kids under 12
  • Rides, games and live music. Buy freshly harvested bulbs, deep fried garlic and garlic ice cream, and learn how to cook and grow garlic at home.

36th Annual Chowder Days Festival – Mystic Seaport

  • October 7 – 9, 9 am – 5 pm
  • Admission to the festival is included with admission to Mystic Seaport, but there is an additional charge for the food.
  • Try different varieties of chowder and bisque, horse and carriage ride, live music, scarecrow making, crafts and games.

Rhode Island

Harvest Festival – Newport Vineyards, Middletown

  • October 29, 12 – 5 pm
  • Admission: $25 per person, includes wine tasting
  • Grape stomping competition and pie eating contest, wine tasting, live music and sampling food by Vineyard chefs, and don’t forget to take a photo with a live wine statue.

Bowen’s Wharf Seafood Festival – Bowen’s Wharf, Newport

  • October 14-15, 2017
  • Free admission; fees for food and beverages
  • Celebrate National Seafood Month! Fresh, local seafood fish tacos, lobster rolls, fried calamari, signature cocktails, cold beer, and live music

Blackstone Valley Fall Foliage Train Ride – Woonsocket

  • October 22, 9 am
  • 7 hour train tour on the Providence and Worcester Railroad. Ride from Woonsocket to Putnam, and enjoy a 3 hour stop in for antique shopping, dinning, and the Putnam Fall Festival.

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