The Berkshires Blog

Autumn Awaits

By Kim Ostellino

Leaf peepers flock to New England, and as soon as the first crisp autumn evening appears, they come looking for colorful scenery, festive communities, and tasty fall treats. The famed hills of the Berkshires are one of the most sought out destinations for foliage fun. Aside from stunning fall colors that frame the landscape, the Berkshires offers visitors a multitude of picturesque hiking trails, placid lakes for canoeing or kayaking, apple orchards, wineries, and several autumnal events.

Apple picking is one of the area’s favorite pastimes. There are orchards dotted prolifically across the Berkshires, making it easy to have fun even if your schedule is tight. Bartlett’s Orchard in Richmond has been in business for more than fifty years. They offer their customers apple picking as well as bags of ready to purchase apples from a wide variety of apple breeds. A visit to their farm store is a must. There you’ll find fun gift items, local food products, and a bakery counter featuring their famous cider donuts!

Richmond is also the home of Hilltop Orchards and Furnace Brook Winery and a visit to this idyllic farm is a wonderful way to spend a day in the Berkshires. Here you can sit lazily in Adirondack chairs while sipping on a glass of wine from their winery. In season, they have live music, wine tastings, and tractor rides around the property. Be sure to allow yourself some time to soak up the vibrant scenery. When you’re ready for picking, the orchards are only a short walk from the store and winery so you’ll be able to leave with your own bag of handpicked apples.

Take in the scenery, we'll wait.

Location: Lakeview Orchard in Lanesborough, Photo Credit: Ogden Gigli

Another orchard that you should not miss is Lakeview Orchard. This picturesque orchard overlooks Hoosac Lake in Lanesborough. Be sure to visit their farm stand and bakery after you have had your fill of apple picking.

Along with panoramic views and numerous outdoor activities, the Berkshires celebrates the fall season with fun festivals and events. In mid-September, the town of Lee holds their Founders Day Weekend with food tasting’s from area restaurants, a street fair, a parade that is a favorite with kids of all ages, and also a Latino Festival.

This is one of the most anticipated festivals every year.

Location: Lenox; Photo Credit: Kim Ostellino

The Lenox Apple Squeeze (Sept. 23 & 24) promises to be bigger and better than ever. Art and craft vendors, food booths, and farm stands line the streets of Lenox’s historic downtown and now they have added live music all weekend long. That same weekend you can enjoy the 20th Annual Country Fair at Hancock Shaker Village.

In October, the 62nd Annual Fall Foliage Parade happens in North Adams. The festival includes a craft fair, road race, and several live performances. The parade enters its 62nd year and this year’s theme is Magic in the Berkshires, acknowledging everything magical going on in the Berkshires from witchcraft and wizardry atop Mount Greylock to fairies in Adams and at Arrowhead.

At Ioka Valley Farm in Hancock, surround yourself with options that will make happy every member of the family. Take a free hayride on their “Giant Pumpkin” wagon over to the pumpkin patch to pick your own and explore the corn maze. Try your best to win a free pumpkin in their water balloon slingshot game, or lend a hand with feeding the farm animals. Plenty of gifts and souvenirs to choose from at the farm stand, and a Calf-A serving Ioka’s roast beef and maple BBQ sandwiches.

Take a ride with your friends.

Location: Ioka Valley Farm, Photo Credit: Laura Brennan

As the autumn season winds down, it brings one of the county’s most treasured events, the Berkshire Botanical Gardens Harvest Festival. With live music, craft booths, mouthwatering foods, a plant and tag sale, and fun activities for kids, there is guaranteed to be something for everyone.

The Berkshires offers visitors something for every season, but autumn in the Berkshires truly delights. So pack up the car and come visit us this fall and be sure to snap lots of photos and share your Berkshire love with us by using #intheberkshires.


Kim is a freelance writer, devoted to bringing the best of the Berkshires to locals and visitors alike through her website, Berkshire Girl Online. She is an avid hiker and kayaker, who also loves to explore the cultural and historical sites of the Berkshires.