Fall Massachusetts Festivals

Find a Massachusetts fall festival to attend in 2019. Our events calendar for September, October and November 2019 has things to do across Massachusetts including activities in Boston, Worcester, and Springfield. Our list includes festivals celebrating the local harvest, food, music, beer, Oktoberfest and more.

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Boston Fall FestivalsWorcester Fall Festivals

2019 Festivals

Gloucester Waterfront Festival - Glouceser, MA - Aug 17 to Aug 18, 2019
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 24 to Aug 25, 2019
Arts and crafts vendors. Free Admission, rain or shine event. Friendly pets on a leash are welcome.

Gloucester Schooner Festival - Gloucester, MA - Aug 30 to Sep 2, 2019
Annual maritime and sailing event. Don’t miss the Sunday morning Parade of Sail!

Labor Day Sale, Music and Craft Beer Party - Princeton, MA - Aug 30 to Sep 2, 2019
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.

Labor Day Hyannis Craft Festival - Hyannis, MA - Aug 31 to Sep 1, 2019
Over 100 juried artisans will display and sell their American made works, plus sample specialty foods

Martha’s Vineyard International Film Festival - Vineyard Haven, MA - Sep 3 to Sep 8, 2019
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

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.

South Shore Irish Festival - Marshfield, MA - Sep 7 to Sep 8, 2019
Enjoy live entertainment on multiple stages, corn hole tournament, tug of war competion, Irish magic show, Irish storytelling and more

BSV Oktoberfest - Walpole, MA - Sep 7 to Sep 8, 2019
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

Canal Diggers 5K - Worcester, MA - Sep 7, 2019
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)

Swampscott Arts & Craft Festival - Swampsott, MA - Sep 7 to Sep 8, 2019
Annual arts & crafts show – free admission! Goes on rain or shine. Friendly leashed pets welcome.

Beer Fest of Ale - Princeton, MA - Sep 7, 2019
First 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.

Somerville Dog Festival - Somerville, MA - Sep 8, 2019
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.

The Big E - West Springfield, MA - Sep 13 to Sep 29, 2019
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.

Wormtown Music Festival - Greenfield, MA - Sep 13 to Sep 15, 2019
Three days of music and two days of camping at Camp Kee-Wanee.

Notch & Karl’s Oktoberfest - Salem, MA - Sep 14, 2019
Hosted by Notch Brewing and Karl’s Sausage Kitchen. Liter pours, German food, Bavarian music, and more!

Cystic Fibrosis Cycle for Life – Rhode Island - Wesport, MA - Sep 14, 2019
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.

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.

FreshGrass - North Adams, MA - Sep 20 to Sep 22, 2019
Plenty of live entertainment, workshops, and more in North Adams.

Trails and Sails - Essex County, MA - Sep 20 to Sep 29, 2019
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

Night Shift Oktoberfest - Everett, MA - Sep 21, 2019
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.

Fluff Festival - Somerville, MA - Sep 21, 2019
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!

Boxford Apple Festival - Boxford, MA - Sep 21, 2019
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

Funktoberfest - Hyannis, MA - Sep 21, 2019
German food, Cape Cod Beer and Oktoberfest Challenges at this family friendly event. Competitions include the CornHole Toss, Growler holding, hop counting and others. Free admission.

Oktoberfest at DBco - Dorchester, MA - Sep 21, 2019
Kick off Oktoberfest with fresh Oktoberfest beers in traditional German liter steins, traditional food, live German band and more!

KidsFest at Wachusett Mountain - Princeton, MA - Sep 21 to Sep 22, 2019
Two days filled with entertainment, shows, giveaways, vendors, activities and more, all for kids and families

Boston Latino International Film Festival - Boston, MA - Sep 25 to Sep 29, 2019
Annual event featuring films made by Latinos, about various themes and in different genres

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!

Another Anime Convention - Chelmsford, MA - Sep 27 to Sep 29, 2019
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.

Spirit of Shrewsbury - Shrewsbury, MA - Sep 28 to Sep 29, 2019
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.

North Quabbin Garlic & Arts Festival - Orange, MA - Sep 28 to Sep 29, 2019
100 booths of farmers, artists and community organizations. Raw garlic eating contest and chef demos. $10.00 per day for adults, free shuttle and parking too.

Grotonfest - Gronton, MA - Sep 28, 2019
Enjoy food, arts & crafts, and displays from local businesses and non-profits at Legion Common. Since 1979.

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.

BBQ Fest at Wachusett Mountain - Princeton, MA - Sep 28 to Sep 29, 2019
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.

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.

HUBweek - Boston, MA - Oct 1 to Oct 3, 2019

Topsfield Fair - Topsville, MA - Oct 4 to Oct 14, 2019
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, 2019
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

Oktoberfest Amherst - Hadley, MA - Oct 5, 2019
The event will take place 12 – 6 PM at the nonprofit Young Men’s Club in Hadley, MA. Proceeds will create two college funds for low income families in the area.

Mashpee Oktoberfest - Mashpee, MA - Oct 5, 2019
Annual Oktoberfest held at Mashpee Commons and hosted by the city’s recreation department.

Douglas Octoberfest - Douglas, MA - Oct 5, 2019
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 5, 2019
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

OktoberFest at Wachusett Mountain - Princeton, MA - Oct 5 to Oct 6, 2019
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.

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+.

Festival of the Hills - Conway, MA - Oct 6, 2019
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.

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.

Textile River Regatta - Lowell, MA - Oct 6, 2019
39th annual event on the Merrimack River.

The Taste of WGBH Food Wine Festival - Boston, MA - Oct 10 to Oct 13, 2019
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.

Honk! Festival - Somerville, MA - Oct 11 to Oct 13, 2019
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.

Nantucket Cranberry Festival - Nantucket, MA - Oct 12, 2019
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. Watch the cranberry harvest, enjoy live music, petting zoo, hay rides, antique tractor displays and children’s activities. Free admission. Parking is $20 per car.

Ashfield Fall Festival - Ashfield, MA - Oct 12 to Oct 13, 2019
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.

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.

Oktoberfest in Harvard Square - Cambridge, MA - Oct 13, 2019
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 18 to Oct 28, 2019
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.”

Wellfleet OysterFest - Wellfleet, MA - Oct 19 to Oct 20, 2019
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.

Head of the Charles Regatta - Boston, MA - Oct 19 to Oct 20, 2019
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 19 to Oct 20, 2019
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.

Duxbury Oktoberfest - Duxbury, MA - Oct 19, 2019
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!

Applefest at Wachusett Mountain - Princeton, MA - Oct 19 to Oct 20, 2019
This event also has an Oktoberfest celebration with German cuisine, beer garden and live music.

Great Falls Festival aka Pumpkinfest - Turners Falls, MA - Oct 19, 2019

Applefest - Princeton, MA - Oct 19 to Oct 20, 2019
Enjoy this fall festival with over 100 craft vendors, a farmers’ market, kids activities, a view of amazing fall foliage on SkyRide, live music, a Giant Pumpkin contest, apple pie baking and eating contests and more!

Boston Hard Cider and Doughnut Fest - Boston, MA - Oct 19, 2019
Part bar hop, part sweet celebration! Featuring (6) bars & restaurants, premium hard cider & 2,000 doughnuts! The official kick off to fall season has arrived! Head to The Greatest Bar for registration, then head to local spots for more. With the official event wristband, participants receive $1-$2 doughnut, $4 drink specials

Chatham Oktoberfest - Chatham, MA - Oct 26, 2019
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 12:00 pm to 4:00 pm. The huge pumpkin people will remain on display through Halloween.

Essex Clamfest - Essex, MA - Oct 26, 2019
Food and fun with lots of vendors. The highlight is the annual Clam Chowder Tasting competition in Memorial Park.

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.

Castleberry Fall Craft Festival - Wilmington, MA - Oct 26 to Oct 27, 2019
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.

Franklin County CiderDays - Deerfield, MA - Nov 1 to Nov 3, 2019
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 3, 2019

Boston Christmas Festival - Boston, MA - Nov 8 to Nov 10, 2019
32nd annual. Shop from 300 craft vendors just in time for the holidays. Admission is $15 with kids under 14 free.  Held at the Seaport World Trace Center.

Boston Comedy Festival - Somerville, MA - Nov 13 to Nov 16, 2019
This four day festival features hundreds of comedians from around the world for comedy shows, workshops, and special events.

Boston Comedy Arts Festival - Cambridge, MA - Nov 13 to Nov 16, 2019
Lots of entertainment and workshops at this annual event. Over 300 artists perform in a wide variety of musical and comedy acts. Features sketch, standup, and improv comedy for 5 days of non-stop fun. Held at ImprovBoston near Central Square T station.

New Englad Super Megafest Comic Con - Framingham, MA - Nov 16 to Nov 17, 2019
Two 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.

New England Craft and Specialty Food Festival - Topsfield, MA - Nov 16 to Nov 17, 2019
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 22 to Nov 24, 2019
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 22 to Dec 7, 2019
25th annual.

Castleberry Faire - Wilmington, MA - Nov 29 to Dec 1, 2019
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

New England Holiday Craft Spectacular - Hanover, MA - Dec 7 to Dec 8, 2019
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

Past Events

We know that you want current events. But we often don’t have dates for the current year. We leave those events with their link here so that you can look for the new dates yourself. We hope you don’t mind!

Boston Harbor Islands Regatta - Boston, MA - Sep 8, 2018
Annual race will attract more than 100 boats and raise money for the Boston Harbor Islands National and State Park. After party follows conclusion.

Valley Kids Festival and Craft Fair - Amherst, MA - Sep 29, 2018
A yearly fall celebration with fun for the whole family, including outdoor games, arts and crafts, food vendors, and more

Cambridge 5k Oktoberfest - Cambridge, MA - Oct 7, 2018
German themed 5K road race that starts at 9:30 AM followed by an Oktoberfest sponsored by Cambridge Brewing. Registration includes race shirt plus food and beverages at the after-party. The event benefits the Cambridge Family & Children’s Services. Location:1 Kendall Square, Cambridge, MA

Great Pumpkin Fest - Worcester, MA - Oct 12 to Oct 28, 2018
Held at Ecotarium. This Halloween event features over 1000 carved pumpkins, live entertainment, family fun with trick-or-treating, displays and more.

Newburyport Oktoberfest - Newburyport, MA - Oct 13, 2018

Oktoberfest at First Parish Canton - Canton, MA - Oct 20, 2018
First Parish Unitarian Universalist, Canton, will once again hold its annual Oktoberfest on October 20. Featuring Canton’s own Double Eagle Oktoberfest Band, this rollicking event will offer music, sing-alongs, dancing, the unique Stumpf Fiddle contest, and all the German food you care to eat. So come help celebrate the harvest season in traditional German style – get out your Lederhosen and Dirndls and come have a great time!

September:

Working Waterfront Festival – New Bedford, MA – 2017
They are not holding this event in 2016. The next one will be in 2017! Celebrate fall at America’s largest commercial fishing port with cooking demonstrations, fishermen’s contests, live music, fresh seafood and walk the decks of a scalloper. Admission is free.

October:

Cranberry Harvest Celebration – Wareham, MA – October 10-11, 2015
12th annual event over Columbus Day weekend. Celebrate the harvest of the top food crop in Massachusetts.

Williamstown Film Festival – Williamstown, MA – October 15-18, 2015

November:

Gloucestor Tree Lighting – Nov 29, 2015

Find other fun things to do in Massachusetts in fall:

Oktoberfest in Massachusetts
Massachusetts Corn Mazes
Massachusetts Ghost Tours
Haunted Houses in Massachusetts
Massachusetts Pumpkin Patches

3 thoughts on “Fall Massachusetts Festivals

  1. Doug Potoksky says:

    Ashfield Fall Festival is the one to not miss! Perfect for a little New England town festival. Bring the kids! Lot of things to do and see. And just think cell phones do not work

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