The 8 Best Fall Festivals in Massachusetts!

Fall is in the air. Crisp days with the foliage ablaze in a variety of bright colors, and the harvest of local fruits and vegetables brings on a feeling of celebration. To welcome in the season, immerse yourself in all things fall with these excellent festivals in Massachusetts! 

1. The Big E, West Springfield, MA

The Big E hosts the biggest fair in the Northeast. Enjoy agricultural competitions, food contests, live music, midway rides and more. This is a typical big time fair with lots to offer the whole family.

2. Douglas Oktoberfest, Douglas, MA

At the Douglas Oktoberfest, there's plenty of beer, but this fall festival embraces its roots, too. Plenty of food vendors, arts & crafts, live music, and games fill the streets of downtown Douglas for an event that offers something for everyone in the family.

3. Cranberry Harvest Festival, Wareham, MA

Jump right into the cranberry bog as harvesting is taking place at Wareham’s Cranberry Harvest Festival. If you’d prefer to stay dry, however, there are pony rides, helicopter rides, wagon rides, several cooking demonstrations and loads of activities for kids.

4. Harpoon Octoberfest, Boston, MA

If you enjoy good beer, don't miss out on Boston's annual Harpoon Octoberfest at Harpoon Brewery. Enjoy live music and dancing, traditional German eats, and of course...delicious beer. Stop by this multi-day event for one of the biggest Octoberfest celebrations in New England. 

5. Berkshire Botanical Gardens Harvest Festival, Stockbridge, MA

One of the longest running festivals of this type, the Berkshire Botanical Gardens Harvest Festival is fun for the whole family. Check out the farmers market, tag sale, lots of delicious food and live entertainment.

6. Apple and Agriculture Days at Old Sturbridge Village, Sturbridge, MA

A visit to Old Sturbridge Village is in itself a wonderful adventure. Visiting during Apple Days is the perfect way to celebrate fall. Bob for apples. Play games with apples. Eat apple pie and a variety of other delicacies from the harvest. Experience apple harvest time from days gone by.

7. Wellfleet OysterFest, Wellfleet, MA

Enjoy oysters, scallops and more at the Wellfleet OysterFest. Take part in a shuck-off, enjoy live music and be sure to bring the kids. There are several activities in store just for them.

8. What the Fluff?, Somerville, MA

C'mon...who doesn't love Fluff?! This delicious festival is in celebration of one of the most underrated spreads: Fluff. Drawing 20,000 people each year, enjoy live music, cooking contests, and several Fluff-themed activities at this late September event. 

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May
26

Rhododendron Festival

10:00 AM
Heritage Museums and Gardens, Sandwich, MA
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May
26

Food Truck - Gonzalez Mexican

12:00 PM
Mighty Squirrel Brewing Company, Waltham, MA
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May
26

Food Truck - Chicken and Rice Guys

5:00 PM
Mighty Squirrel Brewing Company, Waltham, MA
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May
26
May
27

Rhododendron Festival

10:00 AM
Heritage Museums and Gardens, Sandwich, MA
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May
27
May
27
May
27
May
27

Food Truck - Empanada Dada

12:00 PM
Mighty Squirrel Brewing Company, Waltham, MA
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May
27
May
27

Food Truck - Kith and Kin

4:00 PM
Mighty Squirrel Brewing Company, Waltham, MA
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May
27

Food Truck - Chicken and Rice Guys

5:00 PM
Mighty Squirrel Brewing Company, Waltham, MA
Learn More
May
27

Lakeside Family Festival

6:00 PM
Saint John Neumann Church, East Freetown, MA
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May
28

Mass Sheep and Woolcraft Fair

7:00 AM
Cummington Fairgrounds, Cummington, MA
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May
28
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