10 Unique Fall Festivals & Activities in MA

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Happy fall! In celebration of the start of fall season, we’re highlighting 10 festivals and activities over the next few months in Massachusetts.

In no particular order, here’s what’s in store!

Working Waterfront Festival in New Bedford, MA

Located at one of America’s largest fishing ports, this annual celebration always marks the seasonal transition — falling this year on September 28 and 29. The festival program guide gives a good overview of the fun that awaits, which runs from film screenings to fishermen’s contests. For a look at scenes from previous years’ festivals, click here. To get directions or survey nearby lodging options, just click here.

2nd Annual Fall Arts Festival in Cheshire, MA

The Berkshires are well known as an artistic hub, and the Arts Festival in Cheshire provides one of the best ways to enjoy the fruits of that labor. On October 5, attendees will be greeted by an enchanting array of local and regional crafts, including glass-blown pumpkins, photography, ceramics, woodwork and more. The festival will be held at the studios of 413 Glassworks, which you can find at 37 Nobody’s Road.

Ikebana: A Japanese Flower Exhibition in Boylston, MA

Folks interested in nature will get the chance to see something truly special this season at Tower Hill Botanic Garden. The botanical garden will honor the 55 anniversary of Ikebana, the Japanse art of flower arrangement, the weekend of October 4, with a dazzling display of floral formations. Directions to the garden are here, while hours can be found here.

Cranberry Harvest Celebration in Wareham, MA

The annual, family-friendly Cranberry Harvest Celebration in Wareham takes place this year on October 12 and 13, and was also recently named one of the Top 100 Events in North America, which will come as no surprise to seasoned attendees. For driving directions, click here.

Cranberry bog

Photo: Cranberry Bog via MOTT

Autumn Adventure in Florence, MA

Looking for a fast-paced fall activity that’ll get you some fresh air? Look no further than Ride Noho’s Autumn Adventure, which combines exercise, sightseeing and sociality in the foothills of the Berkshires. Over the course of four days, October 13–16, this fall event features bike rides of varying difficulty, culminating in a challenging ascent of Mount Greylock that rewards adventurers with a breathtaking vista. Tickets are available for purchase here.

Great Pumpkin Lighting and Stroll in Newburyport, MA

On Saturday, October 19, all folks are invited to bring a pumpkin to Market Square, where the jack o’ lanterns will be lit. After the lanterns have been lit, attendees can stroll the downtown area, taking in some fresh fall air and the pumpkins designed by local businesses. For some helpful tips on traveling to Newburyport, just click here.

Jack o lanterns

Photo: Jack o’ lanterns via MOTT

Applefest in Princeton, MA

Fall is the time for apple pie and pumpkins; you can find both and then a whole lot more on October 19 and 20 at Applefest! Held on the grounds of Wachusett Mountain, Applefest is one of Massachusetts’ most popular fall events, one that brings a variety of entertainment each year. A pie-eating contest, a giant pumpkin weigh-off and a lumberjack show are just of the unique attractions at this year’s show, which will also have an Oktoberfest Celebration. Tickets are available here.

Haunted Happenings in Salem, MA

Haunted Happenings is a Massachusetts classic and for good reason! Salem has a rich Halloween history, which is celebrated each year all throughout October. Theater productions, carnivals, and spooky tours of historic sites are just a few of the activities scheduled this year in Salem, which also features lots of enticing food options. Information on driving directions, parking and public transit can be found here. If you’re interested in a multi-day Haunted Happenings stay, you can rest comfortably in plenty of places.

Scary Salem

Photo: Salem Carnival via MOTT

Deerfield Christmas Sampler Craft Festival in West Springfield, MA

Is November too early to think about Christmas? Not for folks in West Springfield, who are brought together each year by the award-winning Deerfield Christmas Sampler Craft Festival. The festival features fine jewelry, artwork, clothing and, of course, ornaments from more than 200 exhibitors who hail from more than 10 different states. This year’s festival will take place November 15 – 17 and you can find directions here.

Paradise City Arts Festival in Marlborough, MA

Before you start carving the turkey, why not take in a world-class art festival in Marlborough? The Paradise City Arts festival will run from November 22 – 24 and feature a wide variety of hand-made crafts, as well as larger-scale pieces of art in the form of paintings and sculptures. Free parking and live jazz only add to the fun! You can find a list of the exhibitors here, along with a rundown of food options here.

Here in Massachusetts, the onset of fall always brings about a bevy of fun activity opportunities, as well as the incredible foliage for which New England is renowned. So, if you’re looking for a collection of additional Massachusetts fall adventures, click here.

What’s your favorite Massachusetts fall activity? Let us know in the comments!

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  • maryk32

    North Quabbin Garlic and Arts Festival Oct. 5 and 6 in Orange, MA celebrating its 15th year. Great family fun.
    Details at: garlicandarts.org

    • MassVacation

      That’s another good one! We’ll help spread the word as it approaches :)

    • Donna

      Yes don’t forget the North Quabbin Garlic and Arts Festival!! It is October 5th and 6th. In Orange, MA It’s a beautiful location, wonderful artisans, great food, great entertainment. Plus, the one thing many people don’t know about are the
      Energy Workshops. You’ll hear about every topic you can imagine, hoop gardening, fermenting, solar display and demonstration, the list goes on……All day on both Saturday and Sunday in the North Quabbin Energy tent in the upper left corner. See you there, it is worth the trip!

  • KristinaB

    Ipswich Illumination, September 28! 5th Annual!
    Bonfires floating on the Ipswich River, theatre, art show, music, family activities, poetry, food.

  • Jgrasmere

    Amherst Apple harvest festival. Sept 28 10am-4 pm. Proceeds to benefit Amherst Family Center.
    Lots of kids activities plus a cool kung fu demo at 2:00 pm!

    • MassVacation

      That’s a good one as well! We’ll help get the word out tomorrow. Thanks for letting us know :)

  • Elvira Herrera

    Wooooooow wishing so much to experience this..woooooow gosh!Love it.