7 Places to Stay for Your Fall Foliage Berkshires Getaway

North Adams is a prime jumping-off point for an all-encompassing New England foliage tour. The town is a cultural hub – it’s the home of the Massachusetts Museum of Contemporary Arts (Mass MoCA) and the summer home of the Boston Symphony Orchestra and the Bang on a Can Summer Festival.

Nearby Route 7 is one of the best highways in the state for leaf-peeping from North Adams to Sheffield, passing through some of the most beautiful towns and villages in New England – Pittsfield, Lenox, Stockbridge, and Great Barrington. Along the way, you will pass picturesque country farms and orchards nestled amid rolling hills and drenched in warm autumn hues.

The Mount Greylock Scenic Byway begins south of North Adams and goes through Mount Greylock State Reservation. The byway grants access to the breathtaking 3,491-foot Mt. Greylock and other attractions like the Appalachian Trail, Ashuwillticook Rail Trail, and Natural Bridge State Park. The region has enchanting woodland trails, a wildlife sanctuary, and nature and cultural center. There are numerous spots to catch a glimpse of autumn’s glory.

Williamstown is home to stunning visual and performing arts that perfectly complement an autumn foliage vacation. The hip college town is home to summer stock theater festivals and the noted Clark Art Museum, a rare institution that focuses on artistic expression, research, and higher education. The Williams College campus in Williamstown hosts several distinguished events, and just walking across the campus during the colors season is something to behold.

In Williamstown, you’re likely to see folks sipping a cold brew or iced tea from one of the town’s eclectic coffee shops in the late-afternoon glow of the sun, or catch a few college kids playing Frisbee on the college quad. From cute antique shops and bookstores to chic gastro pubs and taverns, Williamstown has a little something for anyone seeking to expand their horizons.

For lodging, there are a few wonderful choices within 15 miles of North Adams, Jiminy Peak, and Williamstown. First, consider an inn right in the heart of downtown. A contemporary inn with a nod to the town’s vibrant history is perfect if you want to walk to everything in North Adams. A second option is a more rural retreat, such as a mid-century bed and breakfast on private acreage with a more secluded environment.

Pittsfield and the surrounding area allow you to take in the fall colors on two or four wheels. The 11,000-acre Pittsfield State Forest has more than a few spots for a memorable photo or two along its more than 30 miles of trails.

When you’re not taking in Mother Nature’s wonderment, the Berkshire Museum in Pittsfield showcases the rich natural history, culture, and art of the Berkshires. The Barrington Stage Company has first-rate performances throughout the year. The Hancock Shaker Village in Hancock and Pittsfield have roots dating back to the 18th Century as a former Shaker commune. South of Pittsfield, Jacob’s Pillow dance center and school in Beckett hosts one of the oldest internationally acclaimed summer dance festivals annually.

Monument Mountain outside of the town of Lenox has challenging hiking, but the 360-degree views at its peak are more than worth it. Nearby Lenox Mountain and the Mahanna Cobble Summit comes in a close second place for its bird’s-eye view of the fall colors explosion. With 15 miles of well-maintained tree-lined trails, Kennedy Park in Lenox is another big draw during the autumnal switch for its rich hues. Kennedy Park is perfect for those looking for an easy hike to view the fall leaves. Head to the top for beautiful views while you relax in the gazebo. Kennedy Park and Lenox Mountain both offer fun horse-riding outings so you can take in the colors as you clip-clop along select trails.

Charming Stockbridge is home to top-notch attractions like the Berkshire Theater Festival and the Norman Rockwell Museum. The Norman Rockwell Museum has the largest collection of Rockwell’s work, many of which were inspired by Stockbridge and the surrounding towns.

The Lenox-Lee-Stockbridge vicinity has a wide selection of inns, hotels, resorts, and bed and breakfasts that are second to none. There are Colonial inns that capture the ambiance of the late 18th Century but have been fully renovated with contemporary amenities like Wi-Fi, cable TV, and updated bathrooms.

There are cozy bed and breakfasts that have been converted from private residences or other establishments and have a long history of greeting notable guests over the years, including poets, politicians, artists, and other intellectuals. Loaded with history and tradition, accommodations vary from historic residences in the middle of town to rural estates on more private roads only a few miles from the downtown core.

A little further south, the best foliage views are part of a central loop that includes Becket, Hinsdale, Dalton, Pittsfield, West Stockbridge, and Lenox. A loop through Stockbridge, Housatonic, Great Barrington, and Devonfield is slightly shorter in length but equally stunning.

Jacob’s Ladder Scenic Byway is another picture-perfect favorite that follows U.S. Route 20 from Lee through Becket, Chester, Huntington, and Russell. The 35-mile stretch of road traverses along dramatic cliffs and thick woodland groves with gorgeous views along the way. There are plenty of opportunities to stop off and explore. The Appalachian Trail, the Becket Land Trust Quarry, Chester-Blandford State Forest, Jacob’s Pillow, Keystone Arch Bridges, and October Mountain Forest are just a few of the highlights.

The 13-mile drive from Stockbridge south to Great Barrington is short but mesmerizing during the fall colors. Monument Mountain Reservation is west of Route 7, just to the south of Monument Valley Road. Further south, you’ll drive through Fountain Pond State Park and Housatonic Flats Reserve before you reach the outskirts of Great Barrington. If you turn on Monument Valley Road, head south to connect with Stony Brook Road. It turns into Blue Hill Road and leads to Beartown State Forest, a popular park with hiking and scenic views.

Bash Bish Falls State Park on the Massachusetts-New York border just southwest of Great Barrington has an immaculate single-drop waterfall (the highest in the state) that makes for a flawless fall colors hike. The state park is about a 25-minute drive from Great Barrington via Massachusetts Highway 41 South (MA-41) and Mt. Washington Road.

The most southern stretch of the Berkshires – from Great Barrington south into northern Connecticut – offers bountiful eye candy all the way to North Canaan, Lakeville, and Norfolk. There are three different routes you can take south that have excellent scenery and places to sightsee along the way. Massachusetts Highway 33 (MA-33) is the easternmost route, traveling through Hartsville and New Marlborough. The more traveled Route 7 will take you through Sheffield. To the west, MA-41 follows Mt. Washington State Forest south to Salisbury, Connecticut.

There are a few top-rated inns, lodges, and bed and breakfasts in the southern Berkshires that shouldn’t be missed. From spotless guest rooms and contemporary amenities to in-house dining choices that are out of this world, each Berkshires inn has something different that sets it apart from the norm. Hotels and inns in the Berkshires pride themselves on giving their guests the ultimate New England colors experience!