A True Berkshires Harvest

‘Tis the season for festivals, orchards, cider donuts, and ghosts

Pumpkin spice and thick-sweater devotees, your time has finally come. Fall, with all her brilliant reds and oranges, her bonfire smells, and her crisp mornings, has arrived. Even the most seasonally dispassionate among us doesn’t stand much of a chance against what is one of the most vibrant times of the year in the Berkshire region. 

Whole communities and municipalities gather to celebrate autumn. The weekend of September 20-22, 2024, the Town of Lee will fully immerse itself in Founders Weekend, complete with fireworks, a full parade with marching bands, food, and vendors. In North Adams, the annual Fall Foliage Parade on October 6, 2024, promises to be, quite literally, a fete de soleil as the theme this year honors The Greatest Show in North Berkshire and the beloved circus. All are invited to this decades-long tradition, just a block or two from MASS MoCA, Bright Ideas Brewing Co., and the delectable Craft Food Barn.

The 42nd annual Lenox Apple Squeeze on September 28th promises to be a fall family fun extravaganza of food, music, beer, artisans and artists, a kids’ carnival, and yes, apples. That same weekend, the Hancock Shaker Village 27th Annual Country Fair (September 28-29) welcomes visitors to enjoy Shaker crafts workshops, an incredible quilt show, an on-site farmer’s market, an antique car and tractor show, farm animal friends, and so much more. This is a true country fair on a beautiful property. Do not miss the iconic Round Barn. 

Another mainstay of Berkshire life is happening on the weekend of October 12-13, when the Berkshire Botanical Garden in Stockbridge will host its annual Harvest Festival, a beloved event featuring family-friendly entertainment, a beer garden, food trucks, and 80+ artisan vendors, all set against the backdrop of the brilliant autumn hills. And perhaps those autumn hills will inspire a trip on the Berkshire Scenic Railway Fall Foliage train ride, a one-hour scenic trip through the Northern Berkshires Mountains (departing from Adams, MA) on board restored, mid-century railcars. 

For many of us, the beautiful views also inspire a near-instinctual desire to go apple picking, eat cider donuts, drink spirits, and gather around bonfires. Hilltop Orchards in Richmond, MA offers a full seasonal experience of pick your own (PYO) apples, cider and wine tastings, hiking, and general exuberance. The apple cider donuts (and apples) at Bartlett’s Orchard, also in Richmond, are an institution, as is the heart-pumping, uphill terrain of the generations-old orchard. More views and treats can be found at Jaeschke’s Orchard at the base of Mt. Greylock, which offers apples (PYO), pears, plums, peaches, and pumpkins, not to mention a farm store jam-packed with pies, jams, and other local goods. 

Naumkeag Pumpkin Show, photo by David Edgecomb

The daytime adventures, brilliant colors, and warm drinks tend to extend into the twilight hours. The haunted sites and events in the region do not disappoint. The Berkshires are rich with storied estates, historic cemeteries, and haunted woods. The Mount in Lenox offers Storywalks and Ghost Tours at night, where spectral beings are often happy to make an appearance in high-up windows and candle lit hallways. (Be sure to walk through the pet cemetery in the woods.) Just a few miles from Edith Wharton’s estate, The Incredible Naumkeag Pumpkin Show fully embraces the spookier side of the season with thousands of jack-o-lanterns lighting up the property from September 27th to October 27th. Be sure to exit through the graveyard… 

Learn more about this special season in our region.

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