Boston Fall Festivals – Fall 2021 MA Events

Boston Lights at Franklin Park Zoo - Boston, MA - Jul 23 to Oct 11, 2021
Experience the wonder of over 60 magnificent displays comprised of hundreds of beautifully crafted lanterns spanning Franklin Park Zoo’s 72 acres. Walk through glowing corridors of lotus and sunflowers, cranes and cherry blossoms, and a towering 87-foot-long Tyrannosaurus Rex tunnel!

Gloucester Waterfront Festival - Glouceser, MA - Aug 21 to Aug 22, 2021
Arts and crafts show with over 200 juried artisans, food vendors, authors and musicians from across the US bring a variety of arts and crafts (across all media) and literature. Includes family style entertainment including live music and performance arts. Free admission, goes on rain or shine, friendly leashed pets welcome.

BSV Oktoberfest - Walpole, MA - Sep 11 to Sep 12, 2021
Several thousand attend this two day Oktoberfest with German food, beer, games and even a full-contact medieval fighting exhibition. Location: 8 County St, Walpole, MA 02081

Swampscott Arts & Craft Festival - Swampsott, MA - Sep 11 to Sep 12, 2021
Annual arts & crafts show – free admission! Goes on rain or shine. Friendly leashed pets welcome.

Trails and Sails - Essex County, MA - Sep 17 to Sep 26, 2021
Two weekends of walks and water await you throughout Essex County, with over 150 free events at cultural, historic, and natural sites where you can walk, hike, sail, tour, and embark on other adventures

Boxford Apple Festival - Boxford, MA - Sep 18 to Sep 18, 2021
Held annually on the third Saturday in September by the Boxford Historical Society. Enjoy crafters, tours of a 1760 Holyoke-French House, food including apple favorites, and music

Oktoberfest at DBco - Dorchester, MA - Sep 18 to Sep 19, 2021
Kick off Oktoberfest with fresh Oktoberfest beers in traditional German liter steins, traditional food, live German band and more!

Soulful Bliss Arts and Music Fest - Boston, MA - Sep 18 to Sep 18, 2021
Inaugural arts and music festival on Spectacle Island. “Soulful Bliss” is an artistic movement expressed in various mediums by local artists, bringing a soulful experience to advocate for the arts and music. Ticket includes roundtrip ferry from Long Wharf North, live music and arts, smores on the beach, cardio dance class, snacks and a swag bag, and more. Food available for purchase including Night Shift beer

Fluff Festival - Somerville, MA - Sep 22 to Sep 26, 2021
Fluff, the marshmallow confectionary in a jar, was invented in 1917 in Union Square. This festival celebrates that invention with over 15,000 people, and features musical performances, a cooking contest, Fluff-themed games and activites, and of course, treats made with Fluff!

Boston Latino International Film Festival - Boston, MA - Sep 24 to Oct 3, 2021
Annual event featuring films made by Latinos, about various themes and in different genres

Grotonfest - Groton, MA - Sep 25 to Sep 25, 2021
Enjoy food, arts & crafts, and displays from local businesses and non-profits at Legion Common. Since 1979.

Topsfield Fair - Topsville, MA - Oct 1 to Oct 11, 2021
Held annually since the first cattle show in 1820. Giant pumpkin weigh-off, Essex County pageant, sheep show, goat show, racing pigs, farmyard, petting zoo, kiddie korral and more.

Harpoon Octoberfest - Boston, MA - Oct 1 to Oct 2, 2021
Octoberfest has been going strong in fall at Harpoon in Boston for more than two decades. It includes Harpoon beer, German food, Oompah bands, chicken dancing, keg bowling game, and German chocolate cake-eating contest. Location: 306 Northern Avenue, Boston, MA 02210

NB Oktoberfest - New Bedford, MA - Oct 2 to Oct 2, 2021
It’s a local fundraiser sponsored by the South Coast Business Alliance, featuring local, seasonal craft brews and live music. It runs from 3:00 pm to 12:00 am. Almost 50 total brews including 35 regional beers, sangria, cider & gluten free beer as well. Location: Pier 3, New Bedford

Textile River Regatta - Lowell, MA - Oct 3 to Oct 3, 2021
Annual event on the Merrimack River.

Harpoon Dogtoberfest - Boston, MA - Oct 3 to Oct 3, 2021
This fundraising event welcomes dog lovers and their furry friends to the Harpoon Brewery to celebrate Octoberfest! Stretch those legs with a 1-mile fun run/walk with your pup, then join our “barking lot” party with the freshest Harpoon beer, food trucks and music. We’ll even have a Harpoon Dog Beer made from a 100% malted barley mash with powdered peanut butter directly to the kettle boil! This “beer” contains no alcohol or hops (which is poisonous to dogs), and it is non-carbonated. Proceeds from the event will benefit the Kenary Brain Tumor Research Fund at Dana-Farber Cancer Institute as well as the MSPCA.

Honk! Festival - Somerville, MA - Oct 9 to Oct 9, 2021
For 2021, a more decentralized festival as well as virtual activities. Normally: A festival of activist street bands. You’ll hear honking horns, beating drums and see flags waved by people of all ages, classes, ethnicities and backgrounds.

Boston Marathon - Boston, MA - Oct 11 to Oct 11, 2021
The famous 125th marathon harkens back to the 1897, after the success of the first marathon competition in the preceding year’s Olympics, making Boston the world’s oldest annual marathon, and it is one of six of the World Marathon Majors. About half a million spectators take in the marathon along the course, and about 30,000 runners participate every year.

Head of the Charles Regatta - Boston, MA - Oct 22 to Oct 24, 2021
Hundreds of thousands come to the banks of the Charles River to row or watch the Regatta since it was started in 1965.

Boston Vegetarian Food Festival - Boston, MA - Oct 23 to Oct 23, 2021
Hosted by the Boston Vegetarian Society and held at Reggie Lewis Athletic Center with free admission, free food sampling, free speaker presentations, free parking, kids activities and more.

Castleberry Fall Craft Festival - Wilmington, MA - Oct 23 to Oct 24, 2021
Over 150 of the region’s finest artisans will display and sell their American made arts and crafts plus a “food sampling” extravaganza will be presented with such gourmet specialty food delights. Indoor, rain or shine with plenty of free parking.

Spooky Sips - Walpole, MA - Oct 28 to Oct 28, 2021
For 2021, a virtual Halloween wine sampling event. Enjoy Halloween bottles, candy pairings, a costume contest, and more!

Boston Christmas Festival - Boston, MA - Nov 5 to Nov 7, 2021
Shop from 300 craft vendors just in time for the holidays. Admission is $14 with kids under 14 free. Held at the Seaport World Trace Center.

New England Craft and Specialty Food Festival - Topsfield, MA - Nov 12 to Nov 14, 2021
Over 200 of the region’s finest artisans will display and sell their American made arts and crafts plus a “food sampling” extravaganza will be presented with such gourmet specialty food delights. Indoor, rain or shine with plenty of free parking. There is a discount coupon for admission on the linked event website

Paradise City Marlborough - Marlborough, MA - Nov 19 to Nov 21, 2021
The city features 175 American artists and master crafters who compete in a number of talent areas. An annual event at the Royal Plaza Trade Center.

Festival of Trees - Methuen, MA - Nov 19 to Dec 4, 2021
Features 200+ spectacular, shiny, sensational trees, mini-trees and wreaths, which you can win.

Greater Newburyport Turkey Trot - West Newbury, MA - Nov 25 to Nov 25, 2021

Castleberry Faire - Wilmington, MA - Nov 26 to Nov 28, 2021
Over 250 of the region’s finest artisans will display and sell their American made arts and crafts plus a “food sampling” extravaganza will be presented with such gourmet specialty food delights. Indoor, rain or shine with plenty of free parking. There is a discount coupon for admission on the linked event website

Parade of the Big Balloons - Springfield, MA - Nov 26 to Nov 26, 2021
Main Street in downtown Springfield will be filled with people, bands, motorized contingents, huge balloon characters and more on the day after Thanksgiving, as the Spirit of Springfield launches the annual Parade of the Big Balloons. The helium-filled balloons will include the 75-foot Cat In the Hat, the MGM Lion balloon, and a balloon of the American flag. The rest of the parade will feature cold-air inflatables that rise 20 feet in the air. Don’t miss the arrival of Santa near the end!

Vineyards Artisans Festival - West Tisbury, MA - Nov 26 to Nov 27, 2021

New England Holiday Craft Spectacular - Hanover, MA - Dec 4 to Dec 5, 2021
Over 150 of the region’s finest artisans will display and sell their American made arts and crafts plus a “food sampling” extravaganza will be presented with such gourmet specialty food delights. Indoor, rain or shine with plenty of free parking. There is a discount coupon for admission on the linked event website