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Harvest Festivals

One of the delights of living in the Berkshires is autumn! Visitors come from all over the world to look at our gorgeous foliage. We have researched harvest festivals so you may join in the exciting celebrations of this glorious season.

September 27-29

Chatham, New York
Chatham Farm And Art Tour allows visitors to see the diverse faces of farming, providing educational and entertainment opportunities for all ages.
Saturday, September 27 from 10AM to 4PM.

Lenox, Massachusetts
35th Lenox Apple Squeeze and Harvest Festival is one of the most famous and memorable “squeezes” of the season. The street fair has food, rides, shopping, and long music, all set amongst the changing colors of the Berkshire Mountains.
Saturday & Sunday, September 27 & 28.

Pittsfield, Massachusetts
Hancock Shaker Village Country Fair celebrates the bounty of the harvest with agricultural demonstrations, wagon rides, a fabulous Farmers Market and huge tents full of the best local and regional crafters and artisans.
Saturday & Sunday, September 27 & 28, 10AM to 5PM.

October 3- 4

Pittsfield, Massachusetts
8th Annual Berktoberfest bringing some of the absolute finest craft beers in the northeast United States together under the big tents.
Saturday, October 3, 12PM-6PM.

Lenox, Massachusetts
Annual Medieval Faire The historic Jacobean-Revival estate will revert to days gone by when chivalry and armored tournaments were a way of life.
Sunday, October 4, 10AM-4PM.

North Adams, Massachusetts
59th Annual Northern Fall Foliage Parade celebrates the theme of Transportation with vehicles, trains, bikes, and balloons.
Sunday, October 4, 1PM.

October 9-11

Salisbury, Connecticut
The Salisbury Fall Festival takes place for three days over Columbus Day Weekend. Activities throughout the town include a pancake breakfast, craft and artisans vendors, live music, hay rides and beer tasting.
October 9-11, See schedule for each day.

Stockbridge, Massachusetts
Berkshire Botanical Garden Harvest Festival celebrates the community and showcases area artists and crafters in a large tent, a pumpkin toss, pony and hayrides. Performances will come to life throughout the day.
Saturday & Sunday, October 10th & 11th.

Warren, Connecticut
Warren Fall Festival. Garden Tractor Pull. Antique Tractor Pull. Pumpkin Cannon. Wamago Timber Team. Blacksmiths Demos. Rummage Sale. Balloon Sculpting. Magic Show. Petting Zoo. Martial Arts Demonstration. Country Crafts. Fire Truck Rides. Live Music. Zip Line. Delicious Food.
Saturday & Sunday, October 10th & 11th, 10AM to 5PM (rain or shine).

October 17

Hillsdale, New York
Hillsdale Pumpkin Festival. A full day of fun events for family and friends of all ages, including live music, bake sale, face painting, pumpkin carving and raffles.
Saturday, October 17th.

October 25

Kent, Connecticut
38th Annual Kent Pumpkin Run. The five mile run begins at noon and the USATF certified course starts and finishes at Kent Green in front of Town Hall. Join the festivities at the start/finish area - music, refreshments, face painting, Halloween fun and much more. Post- race party for all!
Sunday, October 25th.