Funtober Fall Festivals

Fall Massachusetts Festivals

There is great diversity in the fall festivals in Massachusetts available.  The selection of harvest and seafood festivals in September and October makes for an excellent second act to follow up on Oktoberfest in Boston.

We hope you enjoyed last year’s list.  We will be updating this information for 2016 over the next few weeks.  Stay tuned!

Last Major Update:


Fall Festival Organizer? Advertise Here.
More than 500,000 people came to Funtober last year looking to attend a fall festival and another 500,000 were specifically interested in attending an oktoberfest. We can help increase attendance at your event through a sponsored listing, coupon giveaway, cross-promotion or other creative marketing initiative. Special deals for nonprofits. Please see our advertising page or contact us for more information.

September 2016

Pawtucket Arts Festival – Pawtucket, MA – August 26 – September 25, 2016

Gloucester Schooner Festival – Gloucester, MA – September 2-4, 2016
32nd annual maritime and sailing event. Don’t miss the Sunday morning Parade of Sail!

Martha’s Vineyard International Film Festival – Vineyard Haven, MA – September 6-11, 2016
Explore the local area, live music and enjoy 40+ films from around the globe by international film makers.

Boston Comedy Arts Festival – Sept 7-11, 2016
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.

South Shore Irish Festival – September 10-11, 2016

Somerville Dog Festival– Somerville, MA – September 11, 2016
6th annual event with dog sports demonstrations, silent auction and other activities. Free admission but donations are appreciated.

Bershires to Boston Bicycle Tour – Sept 14-18, 2016
Not a race or fund raiser, this event will feature over 165 riders from around the world who tour over 240 miles of Massachusetts countryside.

Taste of WGBH Food & Wine Festival – Boston, MA – September 15-18, 2016
Chef’s Gala, Wine and Craft Beer Paired Dinners, Brunch Bar, tasting event and Food Fight chef competition.

Wormtown Music Festival – Greenfield, MA – September 16-18, 2016
Three days of music and two days of camping at Camp Kee-Wanee.

FreshGrass – North Adams – Sept 16-18, 2016
Plenty of live entertainment at 87 Marshall Street in North Adams.  Features awards and workshops.

The Big E – West Springfield, MA – September 16 – October 2, 2016
The biggest fair in the Northeast, with nearly 1.5 million people attending in 2014. Circus spectacular, mardi gras parade, agricultural competitions, arts & crafts, food contests, live music and midway. Parking is $10 for cars. One day tickets are $8-12 with a $1 surcharge.

Boxford Apple Festival – Boxford, MA – September 17, 2016
Held annually on the third Saturday in September by the Boxford Historical Society.

Scallop Festival – East Falmouth, MA – September 23-25, 2016
50,000+ attend this three day event. Arts & crafts show, live music, inflatable ride park, food court and more. Admission is $7 per person. Children 6-12 are $2 with younger kids free. Formerly the Bourne Scallop Festival.

Beantown Jazz Festival – South End, Boston, MA – September 24, 2016
Annual event on the last Saturday in September. The 2015 theme is Jazz: Peace Supreme. 70,000 attend the block party to enjoy food, live music and family entertainment.

Fluff Festival – Somerville – Sept 24, 2016

Grotonfest – Gronton, MA – September 24, 2016
Enjoy food, arts & crafts, and displays from local businesses and non-profits at Legion Common.

Allston Village Street Fair – Boston, MA – September 25, 2016
A family friendly event 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.

Amherst Apple Harvest Festival – Amherst, MA – September 24, 2016
30th annual event is held on the Amherst Town Common and runs from 10 AM to 5 PM. Arts & crafts, local food, children’s games and silent auction. Free admission. This is a fundraising event for the Amherst Family Center, a free drop-in support center for families with children up to five years of age.

Spirit of Shrewsbury – Shrewsbury, MA – September 24-25, 2016
A community festival 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 – September 24-25, 2016
18th annual event. 100 booths of farmers, artists and community organizations. Raw garlic eating contest and chef demos. $5.00 per day for adults, weekend pass $8.00, kids 12 and under free, free shuttle and parking too.

HUBweek – Sept 25 – October 1, 2016

Boston Latino International Film Festival – Sept 29 – October 2, 2016

Topsfield Fair – Topsville, MA – Sept 30 – October 10, 2016
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.

October 2016

Boston Harbor Islands Regatta – Boston, MA – October 1, 2016
The 12th annual race will attract more than 100 boats and raise money for the Boston Harbor Islands National and State Park. Race starts at 11 AM. After party follows conclusion.

Textile River Regatta – Lowell, MA – October 2, 2016
37th annual event on the Merrimack River.

Festival of the Hills – Conway, MA – October 4, 2015
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 – October 7-9, 2016
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 – October 8, 2016
14th annual event runs from 11 AM – 4 PM. Watch the cranberry harvest, enjoy live music, petting zoo, hay rides, antique tractor displays and children’s activities. Free admission. Parking is $15 per car.

Riverside Blues & BBQ Festival – Greenfield, MA – October 8-9, 2016
6th annual event with bbq contest, blues and beer. Admission is $5 with bbq sampling for an additional $5 and beer sampling on Saturday for $20.

Berkshire Botanical Harvest Festival – Stockbridge, MA – Oct 8-9, 2016
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.

Ashfield Fall Festival – Ashfield, MA – October 9-10, 2016
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.

Wellfleet OysterFest – Wellfleet, MA – October 15-16, 2016
16th annual event from 10 AM to 5 PM 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.

Great Pumpkin Fest – Worcester, MA.  October 22, 2016.
Held at Ecotarium.  This Halloween event features over 1000 carved pumpkins, live entertainment, family fun with trick-or-treating, displays and more.

Essex Clamfest – Essex, MA – October 22, 2016
Food and fun with lots of vendors.  The highlight is the annual Clam Chowder Tasting competition in Memorial Park.

Boston Vegetarian Food Festival – Boston, MA – October 22-23, 2016
Run by the Boston Vegetarian Society and held at Reggie Lewis Athletic Center. Free admission, free food sampling, free speaker presentations, free parking, kids activities and more.

Head of the Charles Regatta – Cambridge, MA – October 22-23, 2016
Hundreds of thousands come to the banks of the Charles River to row or watch the Regatta since it was started in 1965.

Franklin County Falls Pumpkinfest – Turners Falls, MA – Oct 29, 2016

November 2016

Boston Christmas Festival – Boston, MA – Nov 4-6, 2016
Shop from 300 craft vendors at the 30th annual event. Admission is $15 with kids under 14 free.  Held at the Seaport World Trace Center.

Franklin County CiderDays – Nov 5-6, 2016
22nd 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.

Boston Comedy Festival – November 16-19, 2016

Paradise City Marlborough – Marlborough, MA – Nov 18-20, 2016
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 – Dec 3, 2016

Future Events – 2017

If we find the dates for a festival next fall (September or October 2017) which does not have an event in 2016, we will post them here.

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!

September 2015:

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 2015:

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

Applefest at Wachusett Mountain – Princeton, MA – October 17-18, 2015
Fall Festival with foliage skyrides, family entertainment, pony rides, clowns, climbing wall (for kids) 75 vendor booths at the craft fair.

November 2015:

Gloucestor Tree Lighting – Nov 29, 2015

Find other fun things to do in Massachusetts in October:

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


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