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Best Harvest and Pumpkin Festivals Near Boston for Fall Family Fun

The Topsfield Fair is one of Boston's most beloved fall festivals and autumn traditions. Photo courtesy of the Topsfield Fair
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9/1/24 - By Lucie T

Crisp morning air, ripe apples, and school bells...all signs it's time for fall festivals near Boston! With so many harvest festivals and pumpkin festivals in New England, it can be hard to choose one for a family activity. We took the guesswork out of it by compiling a list of the best autumn fairs and festivals near Boston. These fall celebrations have good food, lots of fun activities, music, performances, and much more. And these fall extravaganzas are perfect for both parents and kids. Read on for our guide to fall festivals near Boston, from the city to the Berkshires. We'll help you find festival fun as big as the Topsfield Fair and the Big E.

For more great autumn activities, see our Fall Fun Guide. And don't forget to explore our events calendar for the latest fall fun in Boston and around New England!

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Have a grand olde time at a fall festival near Boston! Photo courtesy of King Richard's Faire
Have a grand olde time at a fall festival near Boston! Photo courtesy of King Richard's Faire

Best Festivals Near Boston for Fall Family Fun - September

Gloucester Schooner Festival

Gloucester - Wednesday, Aug. 28 - Monday, Sept. 2, 2024
Free
The Gloucester Schooner Festival takes place in America's oldest seaport over Labor Day Weekend. Events include the annual Mayor's Cup Race, schooner tours, a concert, a boat parade of lights, and fireworks. READ MORE

King Richard's Faire

Carver - Saturdays & Sundays, August 31 - Oct 20, 2024
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. READ MORE

Campfire Festival

Cambridge - Thursday, Aug. 30 - Monday, Sept. 2, 2024
Club Passim's Campfire Festival combines the idea of musicians sitting around the campfire playing music with a commitment to developing new talent in the Boston area.  READ MORE

Fall Festival Weekends at Smolak Farms

North Andover - Weekends in September & October 2024
Every weekend during September and October, the farm hosts a fall festival featuring weekly themes, live entertainment, carnival games, storytime, hayrides and more.  READ MORE

Greek Fest

Brookline - Friday, Sept. 6 - Sunday, Sept. 8, 2024
Free
The Annunciation Greek Orthodox Cathedral of New England is hosting their annual festival with lots of music and dancing, raffle prizes, a special door prize, face painting, balloon animals, and bouncy houses. READ MORE

Oktoberfest

Walpole - Saturday, Sept. 7 - Sunday, Sept. 8, 2024
This popular German fest features live entertainment, archery, kids’ games, target shooting, food, and (for the 21+ crowd) beer. READ MORE

Beverly Harbor Fest

Beverly - Sunday, Sept. 8, 2024
Free
  Visit waterfront Lynch Park for the annual Harbor Fest. The festival will include games and activities on the lawn, as well as a beer garden. There will also be live music and food trucks. READ MORE

Cambridge Carnival International

Cambridge - Sunday, Sept. 8, 2024
Free
Cambridge Carnival International is a celebration rooted in African traditions featuring live music, ethnic foods, and crafts from around the world. READ MORE

The Big E

Springfield - Friday, Sept. 13 - Sunday, Sept. 29, 2024
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.  READ MORE

Riverfest

Somerville - Saturday, Sept. 14, 2024
Free
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. READ MORE

Boston Local Food Festival

Boston - Sunday, Sept. 15, 2024
Free
The Boston Local Food Festival, overlooking historic Boston Harbor, is an outdoor, beginning-of-autumn celebration of the many virtues of locally grown and produced food. READ MORE

South Boston Street Festival

Boston - Saturday, Sept. 21, 2024
Free
This street festival features “The Best of South Boston” including over 100 merchants, restaurants, artists and community organizations, which will fill East Broadway. READ MORE

What the Fluff? Festival

Somerville - Saturday, Sept. 21, 2024
Free
  What the Fluff? A Tribute to Union Square Innovation is a lively festival celebrating the invention of Marshmallow Fluff and Somerville’s legacy of creativity. This year will feature live music, fluff-filled feasts, fun games, and zany activities. READ MORE

Roslindale Porch Fest

Roslindale - Saturday, Sept. 21, 2024
Free
Go porch hopping at this free family-friendly event featuring 63 porches and 100 performances.   READ MORE

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. READ MORE

Faire on the Square

Watertown - Saturday, Sept. 21, 2024
Free
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. READ MORE

Harvest Fest at Southwick's Zoo

Mendon - Friday, September 27 - Sunday, September 29, 2024
Southwick's Zoo in Mendon presents Harvest Fest, with craft vendors, live entertainment, and more. Harvest Fest is included with zoo admission. READ MORE

Annual Fall Festival at Weir River Farm

Hingham - Saturday, September 28, 2024
Spend time learning about the farm's livestock with educators, climb aboard a tractor, choose a farm “tattoo”, make a spooky mask or a wildflower seed “bomb”, and challenge your friends at corn hole and the potato spoon relay. READ MORE

Vermont Pumpkin Chuckin' Festival

Stowe VT - Sunday, September 29, 2024
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. READ MORE
Make some noise for the top fall festivals in Boston! HONK! Photo by Leonardo March, courtesy of the festival
Make some noise for the top fall festivals in Boston! HONK! Photo by Leonardo March, courtesy of the festival

Best Harvest and Pumpkin Festivals Near Boston for Fall Family Fun - October

Topsfield Fair

Topsfield - Friday, October 4 - Monday, Oct. 14, 2024
The Topsfield Fair is the quintessential country fair - traditional agricultural exhibits, big entertainment, rides, games, shopping, and great food. READ MORE

HONK!

Somerville - Friday, Oct. 4 - Sunday, Oct. 6, 2024
Free
This annual three-day free festival bringing brass bands from all over the United States and the world to Somerville for a celebration of music, community and activism. READ MORE

187th East Village Fair

Lexington - Saturday, October 5, 2024
Free
Celebrate the New England fall season on Saturday, October 5th from 10am-3pm at the 187th Annual East Village Fair in Lexington, MA READ MORE

Annual Harvest Festival at LexFarm

Lexington - Sunday, October 6, 2024
The Lexington Farmers' Market is celebrating all things autumn with live music, food and beverages, children's activities, and open houses for Silk Fields Farm and Arlington Brewing Company. READ MORE

Berkshire Harvest Festival

Stockbridge - Saturday, Oct. 12 - Sunday, Oct. 13, 2024
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. READ MORE

Mad Love Music Festival

Hingham - Sunday, Oct. 13, 2024
This outdoor festival features local musicians, food, drink, and activities for the whole family. READ MORE

Water Lantern Festival

Weymouth - Saturday, Oct. 19, 2024
Watch your unique lantern drift out into the water as it joins thousands of other lanterns carrying hope, love, happiness, healing, peace, and connection. Arrive before the ceremony to enjoy food, games, activities, vendors, and music. READ MORE

40th Annual AppleFest at Wachusett Mountain

Princeton - Saturdays & Sundays, Oct. 19 - Oct. 27, 2024
This all festival celebration includes over 100 craft exhibitors, a farmers' market, kids entertainment, and peak fall foliage viewing from the SkyRide. READ MORE

Fall Festival at the Arnold Arboretum

Boston - Saturday, October 19, 2024
Free
Celebrate autumn at the Arboretum at the first Fall Festival since 2008! Explore the eeriest elements of the Arboretum landscape for Halloween: poisonous plants, creepy insects, and oozing mushrooms, and learn how to identify poison ivy once and for all. READ MORE

Boston Book Festival: Copley Square

Boston - Saturday, Oct. 26, 2024
Free
Boston Book Festival hosts author presentations, panels, and hands-on demonstrations at outdoor venues throughout the Copley Square area, from Trinity Church to the Boston Public Library.  A street fair in the square features exhibitors and live music throughout the day.  READ MORE

Newton Harvest Fair

Newton - Sunday, Oct. 20, 2024
Free
For over 40 years Newton has celebrated the change of seasons and gathered as a community at the Harvest Fair in Newton Centre. READ MORE

New Hampshire Pumpkin Festival

Laconia, NH - Friday & Saturday Oct. 22 - Oct. 31, 2024
Free
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.  READ MORE

Places featured in this article:

Gloucester Harbor
Lynch Park
The Rose Kennedy Greenway
Union Square
South Shore Conservatory
Downtown Laconia