Top 5 Berkshire Fall Events and Festivals

The Berkshires offer stunning mountain views, convenient access to New York City and Boston, and plenty of local attractions and amenities. With fall just around the corner, homebuyers can learn more about the area while also meeting local residents at the following events and festivals.

 

August 30-September 4, Chatham, NY

 

This annual fair takes place over a six-day span during Labor Day weekend. Visitors have a chance to see a variety of performances, including a concert by Grammy-winning country music artist Travis Tritt, the Cincinnati Circus, the Demolition Derby, and the Painted Pony Rodeo. The fair also features fun competitions, delicious food from local vendors, and midway rides and games. Visitors can purchase tickets by mail order, at local businesses, or at the gate. Admission is free for children 12 and under.

 

September 14-17, Lee, MA

 

Lee Founders Weekend provides a great way to sample some of the best foods in the area and appreciate all that the historic town of Lee has to offer. Visitors can browse through booths filled with handcrafted goods and sample food from several local restaurants. This annual event also features a parade and a Latino festival, as well as family-friendly activities and entertainment. This year’s event, which takes place from 8 AM to 5 PM each day, celebrates the town’s 240th birthday.

 

September 17, Great Barrington, MA

 

This much-loved triathlon gives participants a chance to put their athletic skills to the test while also raising money for a good cause. Proceeds from this event benefit Berkshire United Way. The triathlon includes 27 miles of biking, 6 miles of running, and 5 miles of canoeing, kayaking, or stand up paddle boarding. Spectators can cheer contestants and take in beautiful views from Great Barrington to Lenox, then join a post-race celebration at the Tanglewood Music Festival in Lenox. The races start promptly at 9:30 AM.

 

September 23-24, Lenox, MA

 

This annual event, which takes place on Housatonic Street in Lenox, marks the start of the fall season in the Berkshires. Visitors can join in this apple harvest festival and enjoy live entertainment and activities for all ages, including musical performances. This event also includes a street fair featuring booths run by local vendors and artists. The festival starts at 10 AM on Saturday and ends at 5 PM on Sunday.

 

October 1, North Adams, MA

 

This year’s 62nd annual North Adams Fall Foliage Parade features a magical theme with fairies, wizardry, and more. The parade kicks off at 1 PM on Curran Memorial Highway and ends on Ashland Street. Those who attend the parade can see a wide range of impressive floats, hear live bands and other musical performances, and mingle with locals. This parade, which is a beloved local tradition, celebrates the beginning of the fall foliage season in the North Adams area.