Fall Massachusetts Festivals

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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.

TD Bank Hub on Wheels - Boston, MA - Sep 15, 2019
Boston’s annual bicycling ride. There are two routes, including a short downtown route, and both of which start and finish on City Hall Plaza. A portion of registration fees benefit Boston Children’s Hospital.

German American Business Council of Boston Oktoberfest! - Boston, MA - 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!

Ipswich Ale Oktoberfest - Ipswich, MA - Sep 28 to Aug 28, 2019
Held at the Brewer’s Table at Ipswich Ale, with a pay-as-you-go Oktoberfest, with their Chucktoberfest and more on tap, German food, live music, and stein-hoisting competition.

Allston Village Street Fair - Boston, MA - Sep 29, 2019
A family friendly event celebrating the rich diversity of neighborhood residents, with two outdoor stages, live bands, street performances, international food court, artists and an amusements area. Free parking and free shuttle bus service from the Guest Street Parking Garage.

Fall Fest at Chatham Bars Inn Farm - Brewster, MA - Oct 5, 2019
You can stroll through the farm and fields of their 8-acre farm socializing and stopping along the way to toast and taste flavorful creations by four top chefs. Also featured will be specialty cocktails created with Chatham Bars Inn’s own private label Maker’s Mark bourbon as well as Coastal Encounter, a hoppy pale ale created specifically for Chatham Bars Inn by Mayflower Brewery. Tickets are $130 per person and all guests must be 21+.

Octopurr Fest - Rochester, MA - Oct 6, 2019
An annual fundraiser for It’s All About the Animals, Inc, with vendors, raffle, silent auction, face painting, music, and tours of the shelter.

Berkshire Botanical Harvest Festival - Stockbridge, MA - Oct 12 to Oct 13, 2019
Up to 10,000 show up to this family friendly event with arts & crafts, entertainment, food trucks, and silent auction to support educational programs at the Garden.

Bing Comic Con - Springfield, MA - Oct 26, 2019
One day event featuring over 50 tables of artists, writers, and other creatives, cosplay contest, music, lunch and other refreshments, and more, at Trinity United Methodist Church, from 11am-5pm. $5 admission at the door.

Somerville Dog Festival - Somerville, MA - Sep 13, 2020
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.

South Shore Irish Festival - Marshfield, MA - Sep 19 to Sep 20, 2020
Enjoy live entertainment on multiple stages, corn hole tournament, tug of war competion, Irish magic show, Irish storytelling and more

HUBweek - Boston, MA - Sep 30 to Oct 2, 2020
Bringing together individuals and organizations in pursuit of their mission – convening and celebrating the change makers doing impactful work at the intersection of art, science, and technology in Boston and beyond

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.

Wormtown Music Festival - Greenfield, MA - Jan 1 to Sep 15, 2019
Canceled for 2022, look for their return in 2023. Normally: Three days of music and two days of camping at Camp Kee-Wanee.

Labor Day Hyannis Craft Festival - Hyannis, MA - Sep 4 to Sep 5, 2021
Over 100 juried artisans will display and sell their American made works, plus sample specialty foods

Bike MS: Ride the Vineyard - Concord, MA - Sep 18, 2021
Bike MS is more than a ride. It’s an experience grounded in camaraderie and marked by passion, inspiration, determination and pure enjoyment. It will be an experience you’ll never forget, shared with new friends and old.

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

Night Shift Oktoberfest - Everett, MA - Sep 25 to Sep 26, 2021
Prost to lagers, pretzels, and all things fall. Night Shift Brewing is offering up new beer releases, Oktoberfest flights, German food and music, stein hoisting competition and more.

Newburyport Oktoberfest - Newburyport, MA - Oct 16, 2021

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

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

Thanksgiving Eve Party at Howl at the Moon Boston - Boston, MA - 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!

Parade of the Big Balloons - Springfield, MA - 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!

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

Boston Lights at Franklin Park Zoo - Boston, MA - Jul 22 to Sep 25, 2022
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 20 to Aug 21, 2022
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.

Kill Tide Arts & Crafts Festival - Brewster, MA - Aug 27 to Aug 28, 2022
Arts and crafts vendors. Free Admission, rain or shine event. Friendly pets on a leash are welcome.

Beer Fest of Ale - Princeton, MA - Aug 27, 2022
Annual Beer Fest of Ale will feature over 40 local and national breweries! Come enjoy a day of sampling, food, live music, and entertainment. You will receive a free Beer Fest of Ale sampling glass with purchase as well as 25 sampling tickets! This is a 21+ Event.

Gloucester Schooner Festival - Gloucester, MA - Sep 1 to Sep 4, 2022
Annual maritime and sailing event. Don’t miss the Sunday morning Parade of Sail!

Labor Day Sale, Music and Craft Beer Party - Princeton, MA - Sep 2 to Sep 5, 2022
A full weekend of fantastic sales on equipment at their annual MTNside Labor Day Sale, plus Saturday-Monday is the Music and Craft Beer Festival.

Martha’s Vineyard International Film Festival - Vineyard Haven, MA - Sep 6 to Sep 11, 2022
Explore the local area, live music and enjoy 40+ films from around the globe by international film makers, plus conversations with filmmakers and others, live musical events, and more

Challenge Walk MS: Cape Cod - Hyannis, MA - Sep 9 to Sep 11, 2022
Come together for an endurance walking event fueled by your passion and your steps. 3 days and 50 miles towards a world without MS

BSV Oktoberfest - Walpole, MA - Sep 10 to Sep 11, 2022
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 10 to Sep 11, 2022
Annual arts & crafts show – free admission! Goes on rain or shine. Friendly leashed pets welcome.

Canal Diggers 5K - Worcester, MA - Sep 10, 2022
Run a 5k through the town of Worcester, then party at the end with food, a concert, kids race and activities, and some pints of cold Harpoon! (Check the event website for some parking suggestions)

The Big E - West Springfield, MA - Sep 16 to Oct 2, 2022
The biggest fair in the Northeast, with nearly 1.5 million people attending in recent years. Circus spectacular, mardi gras parade, agricultural competitions, arts & crafts, food contests, live music and midway.

Trails and Sails - Essex County, MA - Sep 16 to Sep 25, 2022
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 17, 2022
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 17, 2022
Kick off Oktoberfest with fresh Oktoberfest beers in traditional German liter steins, traditional food, live German band and more!

Cystic Fibrosis Cycle for Life – Rhode Island - Wesport, MA - Sep 17, 2022
CF Cycle for Life is a fully-supported ride with different route options. From breakfast to the cycle post party, you can enjoy fully stocked rest stops every 10-12 miles, bike mechanics for bicycle maintenance and repair, ride marshals to cheer you along the way and plenty of support vehicles to help you complete the ride. This unique event empowers participants to take action and demonstrate their fight in finding a cure for cystic fibrosis in a tangible, emotional and powerful way.

BBQ Fest at Wachusett Mountain - Princeton, MA - Sep 17 to Sep 18, 2022
Head up to Wachusett Mountain for some of the finest vendors in the area for this tasty event which also features live music, craft fair and farmers’ market, contests and cooking demos.

Soulful Bliss Arts and Music Fest - Boston, MA - Sep 17, 2022
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 17, 2022
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!

Oktoberfest Weekend at Cape Cod Beer - Hyannis, MA - Sep 17 to Sep 18, 2022
German food, Cape Cod Beer and live music at this family friendly event. Free admission on Sunday

Notch Oktoberfest - Salem, MA - 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

Wellfleet OysterFest - Wellfleet, MA - Sep 19 to Oct 16, 2022
Annual event celebrating oysters, clams and shellfishing. Oyster shuck-off competition, cooking demonstrations, arts and crafts, live music, road race and children’s activities. Proceeds fund a local scholarship, community grants and other local initiatives.

FreshGrass - North Adams, MA - Sep 23 to Sep 25, 2022
Plenty of live entertainment, workshops, and more in North Adams.

Spirit of Shrewsbury - Shrewsbury, MA - Sep 24 to Sep 25, 2022
A community festival, first held in 1996, celebrating the culture and history of the area. Parade, 5K, fishing derby, craft fair, children’s talent show, car show, scarecrow contest and more.

Grotonfest - Groton, MA - Sep 24, 2022
Enjoy food, arts & crafts, and displays from local businesses and non-profits at Legion Common. Since 1979.

Duxbury Oktoberfest - Marshfield, MA - Sep 24, 2022
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+

KidsFest at Wachusett Mountain - Princeton, MA - Sep 24 to Sep 25, 2022
Two days filled with entertainment, shows, giveaways, vendors, activities and more, all for kids and families

Topsfield Fair - Topsville, MA - Sep 30 to Oct 10, 2022
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 - Sep 30 to Oct 1, 2022
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

New Englad Super Megafest Comic Con - Framingham, MA - Sep 30 to Oct 2, 2022
Three days of fun including a costume contest, celebrity Q&A panels, artist sketches, cosplay party, car show, comic book and collectible sale, and more! Kids under 6 are free, and tickets are available for individual days or the whole weekend for both adults and children 6-12.

Douglas Octoberfest - Douglas, MA - Oct 1, 2022
Douglas’ most popular local event is its Octoberfest street fair. There’s lots of entertainment, rides and games. Proceeds from many food booths, games, and childrens’ activities go to support local community groups. Main St, Douglas

NB Oktoberfest - New Bedford, MA - Oct 1, 2022
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

Mashpee Oktoberfest - Mashpee, MA - Oct 1, 2022
Annual Oktoberfest held at Mashpee Commons and hosted by the city’s recreation department.

OktoberFest at Wachusett Mountain - Princeton, MA - Oct 1 to Oct 2, 2022
This is the season for beautiful foliage, tasty beer and camaraderie among friends! Raise your steins and toss the empty kegs as you eat, drink and celebrate with live German music, contests, shows, craft and farmers’ market vendors, and activities for the whole family.

Nantucket Harvest Festival - Nantucket, MA - Oct 1 to Oct 2, 2022
Visitors can expect to learn about the history of cranberry farming on Nantucket through educational displays and harvesting demonstrations, participate in family activities, sample delectable cranberry treats and other New England classics, or simply enjoy the music and the spectacular autumn scenery, plus tons more fun. Parking is $25 per car. This event combines Nantucket’s two favorite fall events, the Cranberry Festival and the Island Fair.

North Quabbin Garlic & Arts Festival - Orange, MA - Oct 1 to Oct 2, 2022
100 booths of farmers, artists and community organizations. Raw garlic eating contest and chef demos.

Boston Vegetarian Food Festival - Boston, MA - Oct 1 to Oct 2, 2022
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.

Textile River Regatta - Lowell, MA - Oct 2, 2022
Annual event on the Merrimack River.

Harpoon Dogtoberfest - Boston, MA - Oct 2, 2022
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.

Festival of the Hills - Conway, MA - Oct 2, 2022
Pre-festival events on Saturday include pancake breakfast, art show, used book sale, community turkey dinner and more. Sunday includes 10K road race, live music, food vendors, fresh pressed cider, crafts fair, skillet-toss contest and other activities.

Honk! Festival - Somerville, MA - Oct 7 to Oct 9, 2022
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.

Ashfield Fall Festival - Ashfield, MA - Oct 8 to Oct 9, 2022
Arts & crafts, local foods, live music, dancing, children’s activities including face painting, giant pumpkin and tallest sunflower contests. Admission is free. Donations encouraged for parking.

Oktoberfest in Harvard Square - Cambridge, MA - Oct 9, 2022
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

Chatham’s Pumpkin People in the Park - Chatham, MA - Oct 14 to Oct 31, 2022
A fabulous event where Chatham local businesses, and others create unique and fascinating display with Pumpkins. Every year the creativity gets better and better. Thousands of visitors pose for photo opps with the “People.”

Another Anime Convention - Westford, MA - Oct 14 to Oct 16, 2022
Another Anime Convention is a run by people who love Japanese culture especially Japanese animation. It is a place for fans to gather for a three day convention to enjoy events, special guests and other media that celebrate aspects of Japanese culture.

Applefest at Wachusett Mountain - Princeton, MA - Oct 15 to Oct 16, 2022
Wachusett Mountains’ most popular fall festival celebration including over 100 craft exhibitors, a farmers’ market, kids entertainment and peak fall foliage viewing from the SkyRide. Also enjoy live music, Apple Pie Baking and Eating Contests, along with additional family entertainment. Tickets available for $11 a day for adults, plus a festival package and a festival season pass to all four of their festivals.

Head of the Charles Regatta - Boston, MA - Oct 21 to Oct 23, 2022
Hundreds of thousands come to the banks of the Charles River to row or watch the Regatta since it was started in 1965.

Oktoberfest Amherst - Hadley, MA - Oct 22, 2022
The event will take place 12 – 5 PM at the nonprofit Young Men’s Club in Hadley, MA. Proceeds will create two college funds for low income families in the area.

Chatham Oktoberfest - Chatham, MA - Oct 22, 2022
Held at Kate Gould Park is this Oktoberfest with great beers, bratwurst, cupcake contests, kid’s games, and Pumpkin People in the Park. Event takes place between 10:30 am to 4:30 pm. The huge pumpkin people will remain on display through Halloween.

Essex Clamfest - Essex, MA - Oct 22, 2022
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

Great Falls Festival aka Pumpkinfest - Turners Falls, MA - Oct 22, 2022
The annual festival is held on Avenue A in Turners Falls, MA.

Castleberry Fall Craft Festival - Wilmington, MA - Oct 29 to Oct 30, 2022
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.

Boston Christmas Festival - Boston, MA - Nov 4 to Nov 6, 2022
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.

Franklin County CiderDays - Deerfield, MA - Nov 4 to Nov 6, 2022
Annual event celebrating all things apples. Orchard tours, cider-making, apple cuisine and more. Amateur Cider Competition, hard cider tasting, cidermaking workshop, apple pancake breakfast.

Fall Food Truck Festival - Princeton, MA - Nov 5, 2022

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

Lighting of the Pilgrim Monument - Provincetown, MA - Nov 11, 2022
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 11 to Nov 13, 2022
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 18 to Nov 20, 2022
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 18 to Nov 30, 2022
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.

ZooLights at Zoo New England - Stoneham, MA - Nov 18 to Jan 8, 2023
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!

Festival of Wreaths - Nantucket, MA - Nov 19 to Nov 26, 2022
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.

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

Concord Turkey Trot - Concord, MA - Nov 24, 2022
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.

Greater Newburyport Turkey Trot - West Newbury, MA - Nov 24, 2022

Boston Volvo Thanksgiving Day MS Run - Allston, MA - 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.

Northborough Turkey Trot - Northborough, MA - Nov 24, 2022
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 24, 2022
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 24, 2022
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.

Gobble Gobble Gobble Thanksgiving Race - Somerville, MA - Nov 24, 2022
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 24, 2022
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.

Castleberry Faire - Wilmington, MA - Nov 25 to Nov 27, 2022
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

Vineyards Artisans Festival - West Tisbury, MA - Nov 25 to Nov 26, 2022
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.

Lowell City of Lights Parade and Festival - Lowell, MA - Nov 26, 2022
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.