The Berkshires Blog

Fair Hopping in the Fall

By Lisa Green

In the Berkshires, September ushers in a panoply of fairs and festivals that take on a whole different air from summer’s outdoors events. Many of them mark the arrival of the harvest season, while some celebrate the history of their towns and the thriving nature of the communities and towns that make the Berkshires such a joyous place to visit.

For instance, Pittsfield, whose downtown area (renamed “Upstreet”) was recently named the first cultural district in western Massachusetts by the Massachusetts Cultural Council, offers twice- monthly arts, culture and food street fairs on North Street. On the First Fridays ArtsWalk, which falls on September 6, shops and restaurants become galleries for the works of local artists (the works stay up for the month), and many artists open their own studios to the public.  Third Thursday, on September 19, is a true street fair. North Street is closed to traffic — but open to local food and crafts vendors, nonprofit organizations, and four stages featuring local bands. The September event’s theme is Festa Italiano, so you can expect to find a taste of Italy from beginning to end.

What could be more appropriate than WordFest at The Mount, the spectacular estate of American author Edith Wharton? It’s the site for a stimulating celebration of ideas, words and literature. WordFest, scheduled for September 20-21, honors the living legacy of Edith Wharton by bringing acclaimed writers to the Lenox treasure. There’s poetry on the Terrace, a “Literary Death Match,” author readings, and many conversations with authors.

New to the Berkshires this year is What’s Out There Weekend Berkshires hosted by The Cultural Landscape Foundation. This event will take place on September 21-22 and offers a wealth of historic landscapes to explore for FREE, including important sites along the African American Heritage Trail, historic farmsteads and town commons,Jacob’s Pillow and Tanglewood performance spaces, and iconic landscape design at Naumkeag. This is a great addition to the Fall line up in the Berkshires and should be chock full of great information about our cultural landscape that you might not know.

The town of Lee celebrates its birthday with Founder’s Weekend, September 20-22. This charming (and burgeoning) downtown is listed in the National Register of Historic Places.  The event-packed weekend includes the Chamber’s Corn Cookoff (featuring local corn prepared with sweet and savory recipes), and lots of family fun: live music, tastings, a parade, entertainment, and sidewalk sales.

Two other annual events showcase the Berkshires’ distinctive autumn spirit. The Country Fair at Hancock Shaker Village, September 28-29, celebrates the bounty of the harvest with agricultural demonstrations, wagon rides, a farmers market, and a huge tent filled with regional crafters and artisans. There’s also a food tent, and the second annual Chicken Games (we hear the chickens are training hard), the always-anticipated pie contest, and the juried Harvest of Quilts. Finally, although it falls on the same weekend as the Country Fair, don’t miss the Lenox Apple Squeeze Weekend. Located in the center of this elegant town, the venerable annual event celebrates all things apple (pies, cakes, cider, even pizza). Kids will love the hay and pony rides, and there are crafts and antique stalls to peruse while sipping some fresh, local cider.
Lisa Green is a freelance writer and advertising director of