Fall Festivals

in Pittsfield

Fall harvest season brings a host of family-friendly festivals in Pittsfield.Spending your autumn days surrounded by beautiful fall foliage is an absolute must, and what better way to experience the season than to enjoy a fall festival or two? Explore Best Of Fall Festivals 2025 Events Happening In Pittsfield.

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Fall Festivals in Pittsfield

Sat, 06 Sep

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384 Webster Mill...

FULL MOON MAZE MADNESS

Fall Festivals from nearby cities

Sat, 13 Sep

•

Chelmsford Lowel...

Sunflower Festival 2025

17+ Interested

Free
Sat, 27 Sep

•

436 Salem Street...

Haverhill's Woofstock

7+ Interested
Sat, 20 Sep

•

4 Hollis St, Pep...

Pepperell Fall Festival 2025
Fri, 12 Sep

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Downtown Leominster

Leominster Food Truck Festival

10+ Interested
Sat, 18 Oct

•

118 N River Rd, ...

2025 Fall Corn Maze Craft Fair
Sat, 11 Oct

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Hooksett Legion ...

3rd Annual Pumpkin Fest Psychic & Craft Fair

6+ Interested
Sat, 27 Sep

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Lynn Ferry Terminal

1st Annual Lynn Food Truck & Craft Beer Festival

9+ Interested
18-19 Oct

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Rockingham Hill Farm

2025 Southern Vermont Flannel Festival
Sat, 20 Sep

•

York Woods Tree ...

5th Annual Fall Festival

4+ Interested