Fall is the time for fun in the Berkshires. Amazing foliage, unique events, seasonal treats, and a classic harvest vibe make it the perfect destination for all kinds of travelers. Fall in the Berkshires is absolutely magical. There’s no shortage of things to see and do – here are some ideas to get you started.
Get Outdoors
The Berkshires is loaded with all kinds of hikes and trails for anyone who is up for a walk. Saturdays and Sundays throughout September and October, you can go on a free Housatonic Heritage Walk through the region, led by local experts. Tour buildings, explore the Appalachian Trail, and learn about the history and heritage of some of the area’s biggest attractions.
Take one of the various routes up Mount Greylock, the tallest mountain in Massachusetts. If you make it to the top, you’ll be rewarded with stunning views of Western Massachusetts, Vermont, and New York. The Ashuwillticook Rail Trail is a flatter option, making for a lovely, accessible scenic walk along the Cheshire Reservoir and Hoosic River.
More adventurous types might enjoy checking out the ziplining at Catamount, the mountain coaster at Jiminy Peak, or the aerial park at Ramblewild for higher-octane ways to explore the outdoors.
Go on a Road Trip
The legendary Mohawk Trail Scenic Byway is one of America’s oldest scenic routes, winding its way through Western and North Central Massachusetts. Along the way, stop by North Adams and Adams to experience some picturesque Massachusetts small towns. And don’t miss the route’s iconic Hairpin Turn, one of the best overlooks in Massachusetts.
For a more intimate drive, try the Jacob’s Ladder Scenic Byway through the Southern Berkshires. For over 100 years, the trail has been a destination for motorists – it was the first highway built over mountains in the country. Today, it’s a great way to explore some of Massachusetts’s more rural areas.
See Some Foliage
Peak colors usually arrive between late September and mid-October, and can last until the beginning of November. If you can get the timing right, you’re in store for some of the most unique and beautiful scenery in the country. In addition to the drives and hikes above, you can find fall colors throughout the region.
Chesterfield Gorge, a state park, is a wonderful landscape with expansive rock cliffs, dramatic waterfalls, and lots and lots of trees. In Pittsfield, the Canoe Meadows Wildlife Sanctuary provides ample opportunities to see a variety of wildlife in addition to the perfect fall colors. And at Bartholomew’s Cobble reservation in Sheffield is the perfect spot to see the whole panorama of the Housatonic River Valley.
You can also see amazing foliage in towns throughout the Berkshires. Stockbridge (where you’ll find Naumkeag and the Norman Rockwell Museum), the Hancock Shaker Village in Pittsfield, and Lee are local favorites.
Must-Eats
Apple picking and apple cider are two not-to-be-missed classic fall rituals. If you’ve never had an apple cider donut, now is your chance. Local farms and bakeries all have their own unique recipes, and you’ll definitely want to try them all. Also keep your eye out for local breweries and wineries like Bright Ideas Brewing, Hot Plate Brewing, and Balderdash Cellars.
Pack your bags
Keep an eye on Berkshires.org, Mohawk Trail, and 1Berkshire for more local events and more trip ideas. When you’re in the Berkshires during the fall, you can’t go wrong. Just be warned – once you experience the region at its best, you may never want to leave.
