The Berkshires Massachusetts
The Berkshires Massachusetts

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Fall Festivals

bike rider on fall roadNothing captures the lively spirit of New England like an outdoor fall festival. The Berkshires has a bevy of events to visit this season. Visit our complete Calendar of Events for listings of even more things to do this fall in the Berkshires.

September kicks off with the popular Josh Billings RunAground Triathlon on Sunday, Sept. 16. This 31st annual event is the oldest and largest bike, canoe/kayak, run triathlon in the country. Set in Great Barrington, the course consists of a 27-mile scenic bike ride, a 5-mile canoe or kayak sprint around Stockbridge Bowl and finally a 6.2 mile run that ends at a festival in Tanglewood with music, food, festivities, a Kids Fun Run and more.

In the town of Lee you’ll come across a small town family affair worth of a painting by the late artist at Founders’ Weekend Celebration, Sept. 28 – 30. The three-day celebration of the 230-year-old town that was named for General Charles Lee of the Continental Army is stuffed with activities, including the Taste of Lee Festival on Sept. 28. Bake sales benefit high school sports teams; there are children’s activities and face painting, tap dancing on Main Street, live acoustic music, tours of the 19th century First Congregational Church and a pumpkin carving contest.

pumpkins That same weekend on Sept. 30 is the 52nd Annual Fall Foliage Parade in North Adams, which starts promptly at 1 p.m. This year’s theme focuses on transportation, so expect a parade filled with moving vehicles of all kinds, from cars and bicycles to planes, trains and balloons. Leading up to the parade there is an Autumn Arts Festival Craft Fair, Saturday, Sept. 29, the annual leaf hunt and the first annual charity bed race.

The town of Lenox will also be abuzz Sept. 29 – 30 with its annual Apple Squeeze celebration. The point of the weekend is to enjoy all things apple - apple pies, apple cakes, apple cider and even apple pizza. There will also be hay and pony rides, a children’s dog show, craft demonstrations, sidewalk sales and much more.

The oldest and longest-running event of the season is Botanical Garden’s Harvest Festival, Oct. 6 – 7. The 73rd annual family event includes a haunted house, a hay maze, crafts, animal exhibits, family games and the always popular Hay Jump. Stages will be set up for the never-ending list of folk, bluegrass and country music acts that perform throughout the weekend and there is a giant tag sale and a silent auction that benefits the Botanical Gardens’ educational programs.

Other events this season include the 10th Annual Country Fair at Hancock Shaker Village Sept. 29 – 30, which includes a scavenger hunt and pie contest couple at movie

Film buffs will want to secure tickets to the 9th annual Williamstown Film Festival, which attracts more than 3,000 people each year. The 11-day festival will be held Oct. 26 – Nov. 4.