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:


September 2015:

Gloucester Schooner Festival – Gloucester, MA – September 4-6, 2015
31st annual maritime and sailing event. Don’t miss the Sunday morning Parade of Sail!

Martha’s Vineyard International Film Festival – Vineyard Haven, MA – September 8-13, 2015
Explore the local area, live music and enjoy 40+ films from around the globe by international film makers.

Harvard Fall Festival – Harvard, MA – September 12-13, 2015
Family event with live music, kids carnival, fireworks, craft demonstrations and bbq food.

Somerville Dog Festival– Somerville, MA – September 13, 2015
5th annual event with dog sports demonstrations, silent auction and other activities. Free admission but donations are appreciated.

Taste of WGBH Food & Wine Festival – Boston, MA – September 17-20, 2015
Chef’s Gala, Wine and Craft Beer Paired Dinners, Brunch Bar, tasting event and Food Fight chef competition.

Wormtown Music Festival – Greenfield, MA – September 18-20, 2015
Three days of music and two days of camping at Camp Kee-Wanee.

The Big E – West Springfield, MA – September 18 – October 4, 2015
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. Discounted tickets available online prior to September 16th. Parking is $10 for cars. One day tickets are $8-12 with a $1 surcharge.

Spirit of Shrewsbury – Shrewsbury, MA – September 25-27, 2015
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.

Working Waterfront Festival – New Bedford, MA – September 26-27, 2015
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.

Scallop Festival – East Falmouth, MA – September 18-20, 2015
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.

Grotonfest – Gronton, MA – September 19, 2015
Enjoy food, arts & crafts, and displays from local businesses and non-profits at Legion Common.

Boxford Apple Festival – Boxford, MA – September 19, 2015
Held annually on the third Saturday in September by the Boxford Historical Society.

Beantown Jazz Festival – South End, Boston, MA – September 26, 2015
Annual event on the last Saturday in September. The 2015 theme is Jazz: The Voice of the People. 70,000 attend the block party to enjoy food, live music and family entertainment.

Amherst Apple Harvest Festival – Amherst, MA – September 26, 2015
29th 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.

North Quabbin Garlic & Arts Festival – Orange, MA – September 26-27, 2015
17th 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.

Allston Village Street Fair – Boston, MA – September 27, 2015
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.

October 2015:

Topsfield Fair – Topsville, MA – October 2-12, 2015
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.

Boston Harbor Islands Regatta – Boston, MA – October 3, 2015
The 11th 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 4, 2015
36th 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 9-11, 2015
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.

Riverside Blues & BBQ Festival – Greenfield, MA – October 10-11, 2015
5th 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.

Wellfleet OysterFest – Wellfleet, MA – October 17-18, 2015
15th 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.

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.

Berkshire Botanical Harvest Festival – Stockbridge, MA – Oct 10-11, 2015
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 10-11, 2015
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.

Nantucket Cranberry Festival – Nantucket, MA – October 10, 2015
13th 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.

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

Head of the Charles Regatta – Cambridge, MA – October 17-18, 2015
Hundreds of thousands come to the banks of the Charles River to row or watch the Regatta since it was started in 1965.

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.

Franklin County Falls Pumpkinfest – Turners Falls, MA – Oct 24, 2015

Great Pumpkin Fest – Worcester, MA.  October 24, 2015.  Held at Ecotarium.

Boston Vegetarian Food Festival – Boston, MA – October 24-25, 2015
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.

November 2015:

Boston Christmas Festival – Boston, MA – Nov 6-8, 2015
Shop from 300 craft vendors at the 29th annual event. Admission is $15 with kids under 15 free.

Franklin County CiderDays – Nov 7-8, 2015
21st 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.

Festival of Trees – Methuen, MA – Nov 19 – Dec 5, 2015

Paradise City Marlborough – Marlborough, MA – Nov 20-22, 2015

Gloucestor Tree Lighting – Nov 29, 2015

Last Year’s Events:

Cranberry Arts & Music Festival – Harwich, MA – September 14-15, 2014
Slater Park Fall Festival – Pawtucket, MA – September 13-14, 2014

Barnstable County Harvest Festival – Cape Cod, MA – September 28-29, 2013

Plymouth Barktoberfest – Plymouth, MA – October 4, 2014
Essex Clamfest – Essex, MA – October 25, 2014

HarvestFest – Rockport, MA – Oct 18, 2014

Northern Berkshire Fall Foliage Festival and Parade – North Adams, MA – October 5, 2014
Filmshift Festival – Somerville, MA – October 25-26, 2014
Great Pumpkin Fest | EcoTarium – Worcester, MA – October 25, 2014

Salem Harvest Fest – Salem, MA – October 25, 2014
 National Cranberry Festival – Edaville, MA – October 5-6, 2013
Drink Craft Beer Fall to Winter Fest – Boston, MA – Nov 14-16, 2014

Holiday Festival of Crafts – Worcester, MA – Nov 28-30, 2014

Other potential events:

Fall Fest on the Waterfront
Marblehead Spirit Days
Sturbridge Harvest Festival – Sturbridge, MA
Harbor Fall Festival – Weymouth, MA

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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