Boston Moms’ Guide to Fall Fairs and Festivals

In addition to all things pumpkin and apples, New England does a great fall fair. Some of these terrific events are a bit further than metro Boston (here’s to you, Big E), but it can be a super fun day trip adventure! Grab the kids and your funnel cake money and check out one of these autumn (or late-summer!) festivals!

Boston Moms' Guide to Fall Fairs and Festivals - Boston Moms Blog

What :: Fisherman’s Feast, Boston’s Oldest Italian Festival
Where :: Boston’s North End on North, Fleet, and Lewis Streets
Highlights :: It’s an Italian Festival in the North End — food! There’s also live music and the famed “Flight of the Angel.”

What :: Martha’s Vineyard Agricultural Society Fair
Where :: West Tisbury Fairgrounds, Martha’s Vineyard
Highlights :: Rides, games, shucking contests, skillet toss, horse pull, woodsmen competition, fiber-arts tent, and dog and livestock shows.

What :: Marshfield Fair
Where :: 140 Main Street, Marshfield
Highlights :: It’s the 151st year of this premier South Shore fair. The fair draws hundreds of competitors in 4-H, arts and crafts, agricultural, and horticultural events. There is a farmer’s market, games, rides, animal shows, tractor pulls, live music, and entertainment.

What :: Plymouth Waterfront Festival
Where :: Water Street, Plymouth
Highlights :: Kids games and inflatables, Ducky Dash Race, food trucks, car show, and live entertainment.

What :: Clustertruck Food Festival
Where :: Kalon Farms, Lancaster
Highlights :: More than 25 food truck options, including dessert. Also, artisan vendors, craft brewing from Wachusett Brewing Company, and live music.

What :: Sterling Fair
Where :: Sterling Airport, 121 Greenland Road, Sterling
Highlights :: Friday night fireworks, kiddie tractor pulls, kids frog jumping contest (bring your own frog or they will let you borrow one!), skillet tossing, log sawing contest, horse and ox pulls, and a Lego building contest.

What :: Natick Days Community Festival
Where :: Main Street, Natick
Highlights :: Mini golf, a moonwalk, bungee challenge, pony rides, big trucks from the DPW, raffles, Big Daddy racing, photo booth, and an obstacle course.

What :: The Big E
Where :: 875 Memorial Avenue, West Springfield
Highlights :: The better question is what doesn’t the Big E have? Parades, big-name concerts (Ice-T!), animal exhibits and demonstrations, food and craft vendors, rides, street performances, a 5K, butter sculptures, and so much more!

What :: Davis Mega Farm Festival
Where :: 142 Redstone Hill, Sterling
Highlights :: Live music, food, craft beer and wine, family fun attractions, and campfire sites.

What :: Pete & Gerry’s Organic Eggs Festival at the Farm
Where :: Prowse Farm, 5 Blue Hill River Road, Canton
Highlights :: Live music (including kids’ sets), backyard games, pop-up performances, locally-sourced food vendors and craft brews, farmer’s market, and kids activities.

What :: 42nd Annual Corn Festival
Where :: South Shore Natural Science Center, 48 Jacobs Lane, Norwell
Highlights :: Hay rides, pony rides, hand drumming demo, corn kernel pit, arts and crafts, 4-H animals, and live music.

What :: What the Fluff? A 100th Anniversary Celebration of Fluff!
Where :: Union Square, Somerville
Highlights ::  Musical performances, a cooking contest, Fluff-themed games, activities, antics and fun for every age, and Fluff treats of every sort!

What :: 28th Annual KidsFest at Wachusett Mountain
Where :: 499 Mountain Road, Princeton
Highlights :: Kids’ entertainment, shows, giveaways, vendors, activities, a BMX bike show, live music, and dancing.

What :: Chinatown Main Street Lantern Festival
Where :: Rose Kennedy Greenway (Chinatown Park), 70 Beach Street, Boston
Highlights :: A variety of traditional Chinese performances, including lion dances, Chinese folk dances, and martial arts demonstrations!

What :: South Shore Irish Festival
Where :: Marshfield Fair Grounds, 140 Main Street, Marshfield
Highlights :: Traditional Irish storytelling, Irish music and dancing, and all things Irish!

What :: Topsfield Fair
Where :: 207 Boston Street, Topsfield
Highlights :: Swifty swine racing and swimming pigs, acrobatics show, monster trucks, axe women loggers, Royal Canadian Mounted Police show, human cannonball, and a hot dog eating contest.

What :: Maynard Fest
Where :: Nason and Main Streets, Maynard
Highlights :: Trackless train ride, sidewalk vendors, food trucks, and free family entertainment, including live music.

What :: The Berklee Beantown Jazz Festival
Where :: Columbus Avenue, west of Massachusetts Avenue, for six blocks to Burke Street.
Highlights :: Boston’s biggest block party — a free, annual, outdoor public concert. There is world-class music on three stages, phenomenal food and drink, arts, crafts, and unique gifts.

What :: Cranberry Harvest Celebration
Where ::  158 Tihonet Road, Wareham
Highlights :: Admission includes continuous viewing of the wet harvest operations, animal demonstrations, live music, cooking demonstrations, and many children’s activities.

What :: 35th Applefest at Wachusett Mountain
Where :: 499 Mountain Road, Princeton
Highlights :: Over 100 craft exhibitors, a farmers market, kids entertainment, and peak fall foliage viewing from the SkyRide. Also enjoy live music, the giant pumpkin weigh-off, apple pie baking and eating contests, along with additional family entertainment.

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After an illustrious career in politics (including stints on Capitol Hill and on a presidential campaign) and then reinsurance (yeah, that was a career change), Emily decided to once again make a bold move and stay at home after her first daughter was born. Daughter number two came shortly thereafter, and when daughter number three made her debut it became an official girl tribe! The Fahle girls keep super busy and active exploring their beloved town of Scituate and all that Boston and the South Shore have to offer! Emily is currently experiencing getting along with an infant who believes mom is a Holstein, a preschooler who is smarter than her, and a 2-year-old who has drama in her veins. Emily never knew coffee and wine would be such an essential part of her day.