Boston Fall Festivals – Fall 2024 MA Events

Head of the Charles Regatta - Boston, MA - Oct 18 to Oct 20, 2024
Hundreds of thousands come to the banks of the Charles River to row or watch the Regatta since it was started in 1965.

Harpoon Dogtoberfest - Boston, MA - Oct 6 to Oct 6, 2024
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.

Topsfield Fair - Topsville, MA - Oct 4 to Oct 14, 2024
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 4 to Oct 5, 2024
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. Check out Dogtoberfest with your pup that weekend too! Location: 306 Northern Avenue, Boston, MA 02210

BSV Oktoberfest - Walpole, MA - Sep 7 to Sep 8, 2024
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

Lowell City of Lights Parade and Festival - Lowell, MA - Nov 25 to Nov 25, 2023
The Annual City Of Lights Holiday Parade welcomes the holiday season with the arrival of Mr and Mrs Claus and the traditional lighting of JFK Plaza and the Wannalancit smoke stack. In addition to a parade and tree lighting at City Hall, enjoy the festival of wreaths, pictures with Santa, carolling, the Holly Jolly Trolley, holiday movie screenings, ice skating, food trucks, holiday craft market and more.

Vineyards Artisans Festival - West Tisbury, MA - Nov 24 to Nov 25, 2023
Thanksgiving weekend show – This largest holiday art show by Islanders, features many holiday gifts such as one of a kind winter hand-made sweaters, hand-made soaps, Island lavender, and fine crafts including leather and vintage material bags, wood butcher block cutting boards, and so much more. The best part of coming to the Vineyard Artisan Festivals is meeting the artists and listening to how they love there art and enjoy making these beautiful gifts. Great food and live music. A $2.00 parking fee is for the Vineyard Artisans Scholarship Fund, which awards several scholarships to graduating MV High School students for studies in the Arts each year.

Castleberry Faire - Wilmington, MA - Nov 24 to Nov 26, 2023
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

WCRC Wild Turkey Trot - Salisbury, MA - Nov 23 to Nov 23, 2023
2023 – This year the Winner’s Circle Running Club has moved their annual 5K to Salisbury! It will be run Thanksgiving morning. They feature runner and family friendly trails and post race refreshments. The new course, which is primarily on a rail trail, offers a fast and flat but scenic course

Northborough Turkey Trot - Northborough, MA - Nov 23 to Nov 23, 2023
Each Thanksgiving morning, close to 1,000 runners and walkers gather at the Marion E. Zeh school on Howard Street in Northborough to raise money for the Northborough Food Pantry. Over the years, the Turkey Trot has raised more than $65,000 for the Northborough Food Pantry. This year, support Northborough families in need by helping subsidize summer camps through the Northborough Recreation department.

Feaster Five Thanksgiving Day Road Race - Andover, MA - Nov 23 to Nov 23, 2023
5k or 5 Mile, plus Kids K fun run. The Proceeds from the race benefit the The Bellesini Academy, The Merrimack Valley Y, the MVS high school scholarship fund, and Groundwork Lawrence

Dreamcatcher Classic - Weymouth, MA - Nov 23 to Nov 23, 2023
Proceeds go to Dreamcatcher Scholarship for Weymouth High School students to assist with athletic fees and new Julie Rodick Scholarship Fund for Weymouth High School graduates.

Concord Turkey Trot - Concord, MA - Nov 23 to Nov 23, 2023
This family friendly events has attracted over 2,000 runners each year and benefits the Open Table of Concord and Maynard. Proceeds have also supported local youth running programs.

Gobble Gobble Gobble Thanksgiving Race - Somerville, MA - Nov 23 to Nov 23, 2023
The Gobble Gobble Gobble Gobble starts and ends in Davis Square (at the heart of Somerville), features a unique 4 mile course, and offers a fun opportunity to start Thanksgiving on a high and healthy note! Proceeds benefit Somerville Homeless Coalition, Somerville Track PAC, and Dilboy VFW Veterans Relief Fund.

Franklin Park Turkey Trot 5K - Dorchester, MA - Nov 23 to Nov 23, 2023
The Franklin Park Coalition’s now-famous Turkey Trot started in 2013. After another record-breaking year, with more than 1,400 runners participating in 2019, it went virtual in 2020, but the Turkey Trot is back to its orgins in 2021 (with appropriate safety protocals in place). With runners and walkers coming primarily from the neighborhoods that border the park, including Roxbury, Dorchester, Jamaica Plain, and Mattapan, the Turkey Trot is the largest Thanksgiving Day race in the City of Boston.

Festival of Wreaths - Nantucket, MA - Nov 20 to Nov 25, 2023
The Festival of Wreaths is the NHA’s kickoff celebration to the holiday season! This community driven event features an array of beautifully crafted wreaths made by islanders from local businesses, non-profits, schools, and organizations. From traditionally decorated greens to unconventional arrangements, the Festival of Wreaths truly captures the creativity of Nantucketers! Visitors can bid on their favorite wreaths in a silent auction to benefit the NHA’s year-round outreach efforts. FREE for NHA members and Island Residents.

Festival of Trees - Methuen, MA - Nov 18 to Dec 2, 2023
Features 200+ spectacular, shiny, sensational trees, mini-trees and wreaths, which you can win. Opening gala with limited tickets and tapas as well as select senior-only dates later in the month.

Paradise City Marlborough - Marlborough, MA - Nov 17 to Nov 19, 2023
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.

ZooLights at Zoo New England - Stoneham, MA - Nov 17 to Jan 7, 2024
This winter wonderland takes you on a stroll through the Zoo, along tree-lined paths lit by twinkling lights. Spanning the Zoo’s 26 acres, walk through the beautifully lit Yukon Creek and see black bears, a bald eagle, Canada lynx, arctic foxes, and even reindeer!

Lighting of the Pilgrim Monument - Provincetown, MA - Nov 11 to Nov 11, 2023
Each year, PMPM lights the Pilgrim Monument to commemorate the landing of the Mayflower Pilgrims in Provincetown Harbor.

New England Craft and Specialty Food Festival - Topsfield, MA - Nov 10 to Nov 12, 2023
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

Boston Christmas Festival - Boston, MA - Nov 3 to Nov 5, 2023
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.

Castleberry Fall Craft Festival - Wilmington, MA - Oct 28 to Oct 28, 2023
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.

Essex Clamfest - Essex, MA - Oct 21 to Oct 21, 2023
Food and fun with lots of vendors, entertainers, and arts and crafts. The highlight is the annual Clam Chowder Tasting competition in Memorial Park. Chowder tasting admission is $10

Boston Vegetarian Food Festival - Boston, MA - Oct 14 to Oct 15, 2023
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.

Oktoberfest in Harvard Square - Cambridge, MA - Oct 8 to Oct 8, 2023
Annual Oktoberfest attended by 200,000 includes legendary HONK parade, Sam Adams Beer Garden, 50+ international food vendors, multiple stages of live entertainment and sidewalk vendors along with family friendly

NB Oktoberfest - New Bedford, MA - Oct 7 to Oct 7, 2023
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

Honk! Festival - Somerville, MA - Oct 6 to Oct 8, 2023
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.

Textile River Regatta - Lowell, MA - Oct 1 to Oct 1, 2023
Annual event on the Merrimack River.

Grotonfest - Groton, MA - Sep 30 to Sep 30, 2023
Enjoy food, arts & crafts, and displays from local businesses and non-profits at Legion Common. Since 1979.

Cinefest Latino Boston Film Festival - Boston, MA - Sep 27 to Oct 4, 2023
Annual event featuring films made by Latinos, about various themes and in different genres. Formerly called the Boston Latino International Film Festival (BLIFF)

Somerville Dog Festival - Somerville, MA - Sep 24 to Sep 24, 2023
Annual event with dog sports demonstrations, silent auction, vendors and other activities for the whole family (including your pup!). Free admission but donations are appreciated.

Fluff Festival - Somerville, MA - Sep 23 to Sep 23, 2023
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!

Duxbury Oktoberfest - Marshfield, MA - Sep 23 to Sep 23, 2023
Participants will enjoy beers provided by local craft brewers, including special fall seasonal releases, plus German red and white wines. They’ll serve up a dinner of hearty, traditional, Bavarian fare, and celebrate the season dancing to lively music! Join in the fun and enter contests for the Best Dirndl and Lederhosen costumes, hefty stein-holding, and yodeling! 21+

Boxford Apple Festival - Boxford, MA - Sep 16 to Sep 16, 2023
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

Trails and Sails - Essex County, MA - Sep 15 to Sep 24, 2023
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

Gloucester Waterfront Festival - Glouceser, MA - Aug 19 to Aug 20, 2023
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.

Boston Lights at Franklin Park Zoo - Boston, MA - Aug 4 to Oct 29, 2023
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!

Soulful Bliss Arts and Music Fest - Boston, MA - Jul 29 to Jul 29, 2023
2023 – moved to July, will see if it moves back to fall next year. Description: 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

Boston Volvo Thanksgiving Day MS Run - Allston, MA - Nov 24 to Nov 24, 2022
The Boston Volvo 5k and the Wilmington Thanksgiving Day MS Run have combined into this annual event. Run while raising funds for MS research while working up an appetite for pie.

Essex Turkey Trot - Essex, MA - Nov 20 to Nov 20, 2022

Cranfest and - Plymouth, MA - Nov 11 to Nov 12, 2022

Notch Oktoberfest - Salem, MA - Sep 18 to Sep 18, 2022
Classic German fare, desserts, and cold session beer for sale will greet you at this Oktoberfest, along with the musical talents of an authentic German band

Oktoberfest at DBco - Dorchester, MA - Sep 17 to Sep 17, 2022
Kick off Oktoberfest with fresh Oktoberfest beers in traditional German liter steins, traditional food, live German band and more!

Swampscott Arts & Craft Festival - Swampsott, MA - Sep 10 to Sep 11, 2022
Annual arts & crafts show – free admission! Goes on rain or shine. Friendly leashed pets welcome.

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

Parade of the Big Balloons - Springfield, MA - Nov 26 to Nov 26, 2021
Canceled for 2022 due to helium shortage . Normally: 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!

Thanksgiving Eve Party at Howl at the Moon Boston - Boston, MA - Nov 24 to Nov 24, 2021
Turkey is good, but booze is better! Celebrate the long holiday weekend with some live music, dancing and drinks, with featured drinks, games, dancing and a great night out!

Newburyport Fall Half - Newburyport, MA - Nov 7 to Nov 7, 2021
Half marathon with start & finish in Cashman Park.

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!

The Taste of WGBH Food Wine Festival - Boston, MA - Oct 8 to Oct 11, 2020
A three day festival with events and activities across the city, featuring the best culinary talents of the area, including Chef’s Gala, wine and craft beer paired dinners, tasting event and Food Fight chef competition. Educational seminars, live music, and more! All-inclusive tickets get you into all events for one price, plus a wine glass to use for sampling.

German American Business Council of Boston Oktoberfest! - Boston, MA - Sep 25 to Sep 25, 2019
Celebrate this year’s Oktoberfest at Democracy Brewery, a cool new brewery reminiscent of a German-style beerhall right in the heart of Downtown Boston. They’ll have their own private room, Democracy Brewing’s beer will be flowing and they’ll will have German-style food to accompany the festivities!

Oktoberfest at Olde Magoun’s Saloon - Somerville, MA - Sep 4 to Sep 28, 2019
A month of Oktoberfest specials leading up to an all-day Oktoberfest starting with the Bayern Munich match at 9:30am, German food served from noon, ceremonial keg tapping of Paulaner Weisn tapped at 12:30, and music from noon to 8.