Fall Festivals for Families in Boston 2025

Fall Festivals in Boston and Greater Boston for 2025

King Richard's Faire
Carver - Saturdays & Sundays, Sat Aug 30- Sun Oct 19, 2025
A visit to King Richard’s Faire, New England’s largest and longest-running Renaissance festival that is tucked away on 80 acres of enchanted forest, offers a full day of live, interactive entertainment. Visit the website here.

Fall Festival Weekends at Smolak Farms
North Andover - Weekends in September & October 2025
Every weekend during September and October, the farm hosts a fall festival featuring weekly themes, live entertainment, carnival games, storytime, hayrides and more. Visit the website here.

Riverfest
Somerville - Saturday, Sept. 13, 2025
Free Admission
Riverfest is the culmination of a summer of activity at Assembly Row with live local music, dozens of local artists, free children’s activities, a sidewalk sale, and of course the annual fireworks show over the Mystic River. Visit the website here.

Faire on the Square
Watertown - Saturday, Sept. 13, 2025
Free Admission
The Faire offers a wide variety of free activities for children and adults including children's rides and activities, musical entertainment and food, crafts sales, and dance performances. Visit the website here.

Mystic River Celebration
Medford - Saturday, Sept. 21, 2024
Free
Watch live musician performances, browse local artisan crafts, get to know local businesses and organizations, eat food, and take part in any number of fun activities for all ages including a Knucklebones play area for kids. Visit the website here.

Harvest Fest at Southwick's Zoo
Mendon - Saturday, September 27 - Sunday, September 28, 2025
Southwick's Zoo in Mendon presents Harvest Fest, with craft vendors, live entertainment, and more. Harvest Fest is included with zoo admission. Visit the website here.

Annual Fall Festival at Weir River Farm
Hingham - Saturday, September 27, 2025
Spend time learning about the farm's livestock with educators, climb aboard a tractor, choose a farm “tattoo”, and enjoy live music. Visit the website here.

187th East Village Fair
Lexington - Saturday, October 4, 2025
Free Admission
Celebrate the New England fall season on Saturday, October 4th at the 187th Annual East Village Fair in Lexington, MA. Visit the website here.

Annual Harvest Festival at LexFarm
Lexington - Sunday, October 5, 2025
The Lexington Farmers' Market is celebrating all things autumn with live music, food and beverages, children's activities, and beer from Arlington Brewing Company. Visit the website here.

Newton Harvest Fair
Newton - Saturday & Sunday, Oct. 18 & 19, 2025
Free Admission
For over 40 years Newton has celebrated the change of seasons and gathered as a community at the Harvest Fair in Newton Centre. Visit the website here.

Annual AppleFest at Wachusett Mountain
Princeton - Saturdays & Sundays, Oct. 18 - Oct. 26, 2025
This all festival celebration includes over 100 craft exhibitors, a farmers' market, kids entertainment, and peak fall foliage viewing from the SkyRide. Visit the website here.

Pumpkin & Harvest Festivals Worth the Day Trip

The Big E
Springfield - Friday, Sept. 12 - Sunday, Sept. 28, 2025
The Big E, or Eastern States Exposition, is a New England autumn tradition and the ninth-largest fair in North America. The Big E features entertainment, major exhibits, The Big E Super Circus, the Avenue of States, and dazzling thrill shows. Visit the website here.

Vermont Pumpkin Chuckin' Festival
Stowe VT - Sunday, September 28, 2025
Stowe Vermont's 14th annual festival of pumpkin catapulting features live music, food trucks, children's activities, and a chili cook-off among area restaurants. Visit the website here.

Topsfield Fair
Topsfield - Friday, October 3 - Monday, Oct. 13, 2025
The Topsfield Fair is the quintessential country fair - traditional agricultural exhibits, big entertainment, rides, games, shopping, and great food. Visit the website here.

Berkshire Harvest Festival
Berkshire Botanical Garden, Stockbridge
Saturday, Oct. 11 - Sunday, Oct. 12, 2025
Enjoy live music and entertainment, fresh local and artisan food and refreshments, a plant sale and farmer's market, pony and hay rides, haunted house, hay jump, regional vendors, as well as some surprises still in the works. Visit the website here.

New Hampshire Pumpkin Festival
Laconia, NH - Saturday, October 25, 2025
Free Admission
An annual tradition in New Hampshire's Lakes Region, this free, family-oriented festival is known for its pumpkin tower, built with donated pumpkins carved at home or on site, as well as rides, activities, music, and food. Visit the website here.

LexFUN! Fall Extravaganza
Lexington - Sunday, Oct. 26, 2025
Free
This year’s fall gathering will feature apple cider donuts, entertainment, and a chance to meet with local sponsors and preschools. Kids are welcome to attend in their costumes and participate in the annual Halloween Parade! Visit the website here.

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