Family-friendly events


The Tanglewood season has ended and the summer residents have departed.  Yet throngs of weekend visitors from the Capital Region and beyond flock to the nearby Berkshires each fall. And it’s not only to see the foliage.  In the Berkshires,  fall ushers in an abundance of outdoor fairs, festivals and special events, marking the arrival of the harvest and honoring the historic past of its colonial-era towns. Most of all, it’s fun, with family-friendly events at all venues.
 The town of Lenox plays host to two September events – the Lenox Tub Parade and the Apple Squeeze.
 If you thought “Lifestyles of the Rich and Famous” started with that popular TV series, you’d be wrong. In actuality, the Berkshires is known for its Gilded Age “cottages” where the elite from the big cities summered. A tradition from that era is the focus of an annual fall event – the Lenox Tub Parade. A reenactment of the cottagers parading through Lenox to celebrate the end of summer will take place on Saturday, September 13 at 1:30. Organized by the Colonial Carriage and Driving Society, the parade starts at Shakespeare and Company on Kemble Street where the horses and carriages gather. This historic venue provides the perfect locale to kick off the parade. The participants then proceed to the center of Lenox, circling it twice. Upon returning to Shakespeare and Company, the festivities continue with a horse and carriage driving competition.
What could be more American than apple pie? But the Apple Squeeze also features apple cider, apple cakes, and anything you can possibly imagine featuring apples – even apple pizza! It’s a great street fair with a variety of activities, including hay and pony rides for the kids, craft demonstrations, antique stalls, sidewalk sales, live music and much more. This year, the venerable town event will be held on September 27 and 28. “The Apple Squeeze draws families outdoors,” says Lindsey Schmid, Director of Marketing for the Berkshire Visitors Bureau. “Besides helping us kick off the foliage season, they also boost our economy by shopping in local stores.”
A cherished tradition is on again at the Berkshire Botanical Garden in nearby Stockbridge.  The Harvest Festival, a fund raiser for the Garden’s educational programs, will be held this year on Columbus Day weekend (October 11 and 12).  Adults will enjoy tag sales, live music, a silent auction, a plant sale, and a farmers market.  The highlight of the festival is the 100-plus local and regional vendors who display their wares. Serious shoppers or those just browsing will find anything from jewelry to birdhouses to wearable art to maple syrup. For the kids, there’s a hay jump, a hay maze, a haunted house (back by popular demand) and a petting zoo. Festival attendees have the added pleasure of enjoying the Garden in its autumn splendor.  Communications and Marketing Director Brian Cruey says, “Don’t miss the mums, asters, and fall crocuses. They’re in their glory this time of year.”
Attention all outdoor enthusiasts. Would you enjoy climbing the tallest peak in the Berkshires? Join all the folks who want bragging rights and sign up for the Adams Mt. Greylock Ramble which, like the Harvest Festival, falls on Columbus Day weekend (October 12 and 13).  Enjoy the beautiful view from the peak at the altitude of 3,491 feet.  A free shuttle will be provided round trip for hikers from Adams to the base of Mt. Greylock. The first 2,000 hikers will receive certificates of accomplishment by reaching the summit.  The Ramble is a relatively easy walk, with hikers of all ages participating.
If the arts are more your thing, the North Adams Open Studios on October 18 and 19 will be your go-to event this fall. Dozens of artists open their studios to the public in locations ranging from downtown North Adams storefronts to the formerly abandoned mills, now converted for artist usage. You can walk or hop the trolley to navigate the studios.  Mass MoCa has become a partner in this event (the Massachusetts Museum of Contemporary Art) and a major draw in attracting artists to the area. The event demystifies how artists create, and event goers can get up close and personal with the artists and their works.
Get your rolling pins ready for the pie contest at the Hancock Shaker Village’s Country Fair on September 27 and 28. Located in Pittsfield (on the border of Hancock), this fair has the added bonus of its unique setting. Visitors can also tour the historic Hancock Shaker Village, a major Berkshire tourist destination.  Established in the 1780s, the 750-acre Village preserves the legacy of the Shakers.  Regular admission to the Village gives access to the Country Fair. A diverse assortment of local artisans, food vendors and farmers are featured in this festival celebrating the harvest. Lindsey Schmid of the Berkshire Visitors Bureau comments, “This fair has something for everyone. Mom can look at quilts while the kids observe the farm animals on the property.”
Autumn is the second busiest season in the Berkshires and is driven by the fall foliage. The Berkshires offers the quintessential New England experience with a variety of offerings on any given weekend from the beginning of September through end of October.

 For more information on fall events, check out the Berkshire Visitors Bureau at


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