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.

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Boston Fall FestivalsWorcester Fall Festivals

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.


Oktoberfest at Jacob Wirth - Boston, MA - to
You’ll find various breweries with Oktoberfest beers take over the taps during September and October at Jacob Wirth, a classic European restaurant that offers a menu of German specialties throughout the year. They haven’t posted a calendar of events for 2016 yet.

Gloucester Schooner Festival - Gloucester, MA - Sep 2 to Sep 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 - Sep 6 to Sep 11, 2016
Explore the local area, live music and enjoy 40+ films from around the globe by international film makers.

Boston Comedy Arts Festival - Cambridge, MA - Sep 7 to Sep 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 - Marshfield, MA - Sep 10 to Sep 11, 2016

BSV Oktoberfest - Walpole, MA - Sep 10 to Sep 11, 2016
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

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

Festival of the Hills - Conway, MA - Sep 11 to Sep 11, 2016
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.

Bershires to Boston Bicycle Tour - Sunderland, MA - Sep 14 to Sep 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 - Sep 15 to Sep 18, 2016
Chef’s Gala, Wine and Craft Beer Paired Dinners, Brunch Bar, tasting event and Food Fight chef competition.

The Big E - West Springfield, MA - Sep 16 to Oct 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 - Sep 17 to Sep 17, 2016
Held annually on the third Saturday in September by the Boxford Historical Society.

Marion Oktoberfest - Marion, MA - Sep 17 to Sep 17, 2016
Organized by Marion’s Pythagorean Lodge Ancient Free and Accepted Masons. German food including bratwurst, kanckwurst, sauerkraut and pastries served from noon to 8 PM. German music by Alpenblumen Musikanten from 12-4 pm. German dancers from 2 to 6 PM. The Bavarian Brothers play from 4-8 PM. Cost is $10. Kids under 12 are free.

Scallop Festival - East Falmouth, MA - Sep 23 to Sep 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.

John Harvard’s Brwery Oktoberfest - Framingham, MA - Sep 23 to Sep 23, 2016

Duxbury Oktoberfest - Duxbury, MA - Sep 23 to Sep 23, 2016

Spirit of Shrewsbury - Shrewsbury, MA - Sep 24 to Sep 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.

Beantown Jazz Festival - Boston, MA - Sep 24 to Sep 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.

Amherst Apple Harvest Festival - Amherst, MA - Sep 24 to Sep 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.

Fluff Festival - Somerville, MA - Sep 24 to Sep 24, 2016

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

North Quabbin Garlic & Arts Festival - Orange, MA - Sep 24 to Sep 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.

Cape Cod Beer - Hyannis, MA - Sep 24 to Sep 24, 2016
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.

Night Shift Oktoberfest - Everett, MA - Sep 24 to Sep 24, 2016

Allston Village Street Fair - Boston, MA - Sep 25 to Sep 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.

HUBweek - Boston, MA - Sep 25 to Oct 1, 2016

German American Business Council of Boston - Boston, MA - Sep 27 to Sep 27, 2016
Held at Jacob Wirth Restaurant.

Boston Latino International Film Festival - Boston, MA - Sep 29 to Oct 2, 2016

Topsfield Fair - Topsville, MA - Sep 30 to Oct 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.

Harpoon Oktoberfest - Boston, MA - Sep 30 to Oct 1, 2016
Oktoberfest has been going strong in fall at Harpoon in Boston for more than two decades. 2015 was Harpoon’s 25th annual Boston Oktoberfest of beer, music, and Fall in New England. On Friday, the event goes from 5:30 PM to 11 PM. On Saturday, the party goes from 1 PM to 7 PM. 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 Lowell - Lowell, MA - Sep 30 to Oct 1, 2016

Boston Harbor Islands Regatta - Boston, MA - Oct 1 to Oct 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.

Oktoberfest Marshfield - Marshfield, MA - Oct 1 to Oct 1, 2016
Event features New England’s largest and most thrilling midway. This is an authentic styled Oktoberfest featuring great beers and both domestic and international beer gardens. Lots of good German styled foods, games, tastings, fiesta shows, and demonstrations. Even contest of skill such as the Beer Mug obstacle course.

Bogie’s Oktoberfest - Beverly, MA - Oct 1 to Oct 1, 2016

Douglas Octoberfest - Douglas, MA - Oct 1 to Oct 1, 2016
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. Location: Main St, Douglas, Massachusetts

Heritage Weekend Oktoberfest - Marlborough, MA - Oct 1 to Oct 1, 2016

NB Oktoberfest - New Bedford, MA - Oct 1 to Oct 1, 2016
It’s a local fundraiser sponsored by the South Coast Business Alliance. It features local, seasonal craft brews and live music at the 10th annual event. 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: State Pier Ferry Terminal of New Bedford

Mashpee Oktoberfest - Mashpee, MA - Oct 1 to Oct 1, 2016
28th annual Oktoberfest held at Mashpee Commons and hosted by the city’s recreation department.

Textile River Regatta - Lowell, MA - Oct 2 to Oct 2, 2016
37th annual event on the Merrimack River.

Cambridge 5k Oktoberfest - Cambridge, MA - Oct 2 to Oct 2, 2016
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

Honk! Festival - Somerville, MA - Oct 7 to Oct 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 - Oct 8 to Oct 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 - Oct 8 to Oct 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 to Oct 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.

Oktoberfest Massachusetts - Boston, MA - Oct 8 to Oct 8, 2016

First Parish Canton’s Oktoberfest - Canton, MA - Oct 8 to Oct 8, 2016
Unitarian Universalist congregation in Canton MA will be holding an Oktoberfest event on Saturday, 8-October.

Ashfield Fall Festival - Ashfield, MA - Oct 9 to Oct 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.

Oktoberfest in Harvard Square - Cambridge, MA - Oct 9 to Oct 9, 2016
The 38th 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

Wellfleet OysterFest - Wellfleet, MA - Oct 15 to Oct 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.

Applefest - Princeton, MA - Oct 15 to Oct 16, 2016
Fall Festival with foliage skyrides, family entertainment, pony rides, clowns, climbing wall (for kids) 75 vendor booths at the craft fair.

Oktoberfest Amherst - Hadley, MA - Oct 15 to Oct 15, 2016
The second Octoberfest is scheduled to take place on Saturday October 15, 2016 & Sunday October 16th in case of rain. 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. We have upped our capacity to 2,000 people and we are also upgrading our marketing, media coverage, staging, and sound ten fold.

Applefest at Wachusett Mountain - Princeton, MA - Oct 15 to Oct 16, 2016
This event also has an Oktoberfest celebration with German cuisine, beer garden and live music.

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

Head of the Charles Regatta - Boston, MA - Oct 22 to Oct 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.

Boston Vegetarian Food Festival - Boston, MA - Oct 22 to Oct 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.

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

Chatham Oktoberfest - Chatham, MA - Oct 22 to Oct 22, 2016
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.

Franklin County Falls Pumpkinfest - Turners Falls, MA - Oct 29 to Oct 29, 2016

Boston Christmas Festival - Boston, MA - Nov 4 to Nov 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 - Deerfield, MA - Nov 5 to Nov 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 - Somerville, MA - Nov 16 to Nov 19, 2016

Paradise City Marlborough - Marlborough, MA - Nov 18 to Nov 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 to Dec 3, 2016

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

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

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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