The Berkshires in western Massachusetts lie in the picturesque Appalachian Mountains. A road trip through the area comes with breathtaking scenery including rolling hills, farmland, rivers, and quaint towns filled with historic buildings and antiques. In the winter, you can ski and snowshoe, and in the spring and summer, you can hike to your heart’s content. In the fall, the leaves on the oak and maple trees put on a show of red, yellow, and orange color against the evergreens that will leave you marveling at the wonders of nature.
The following road trip would be especially memorable during the changing of the leaves. You could rush along in a straight line and cover these 35 miles in about an hour. But you’ll have a better time if you detour to small towns, bike along a rail trail following the river, ride a vintage train, visit Norman Rockwell’s studio, walk around a Shaker village and pet baby lambs, enter the library where Herman Melville wrote Moby-Dick, and get your culture fix at a renowned art gallery.
With all the highlights of this road trip, you could easily spend a day or two — or perhaps a week — in the Berkshires.
Stockbridge
This town, with roots in the 1700s, transports you to a gentler, quieter era, when people knew their neighbors and sat on their front porches in their rocking chairs as kids played in the yard.
Stockbridge, deep in the Berkshires, is a great choice for a stay of a day or more before taking off on your road trip. Artist Norman Rockwell called Stockbridge home, and his house and studio are open for tours. Guides take you through the museum and discuss the many works of art on display. You are also invited to bring a sketch pad and charcoals, sit outside on the benches, and create your own picture of the lovely Berkshires. The shop offers all kinds of souvenirs decorated with Norman Rockwell paintings.
Another popular place in Stockbridge is the Naumkeag estate. For a taste of elegant life here in the late 1800s, tour this 44-room mansion and then wander through the gardens, including the Afternoon Garden, Tree Peony Terrace, Rose Garden, Evergreen Garden, and Chinese Garden.
Chesterwood is the beautiful home of Lincoln Memorial sculptor Daniel Chester French. You’ll find his work exhibited in the gardens. His studio will be of particular interest to those who love art, as it contains models and works in bronze and marble.
Relax at the Berkshire Botanical Garden during your visit to Stockbridge. Spend as much or as little time as you wish in this “museum of living things.” The 24 acres of gardens are open daily and feature plants native to the Berkshires. The topiary animals of the gardens are a favorite. Check the website for classes on everything from form and texture in planning a garden to how to make a garden tool belt.
To immerse yourself in the history of the Berkshires, stay or eat at the iconic Red Lion Inn. Opened as a tavern in 1773, the Red Lion served as a stop for stagecoaches traveling from Albany, New York, to Boston. Today, not only is the original, updated inn open, but accommodation choices include village houses and a historic firehouse. Enjoy breakfast, lunch, or dinner in one of the four restaurants. The dinner menu features New England clam chowder and entrees ranging from seafood to a turkey dinner with all the trimmings.
Lenox
After leaving Stockbridge, you may want to stop just 10 minutes north on Route 7 in the town of Lenox.
The Lenox Station Museum is open every Saturday between Memorial Day and Labor Day. Visit the restored railway station and ride the Jitney train a short distance to get a feel for the heyday of rail travel.
The Mount in Lenox was once the home of author Edith Wharton. She called the estate “a spacious and dignified house,” and it has been restored to look like it did when she lived there in the early 20th century. This splendid estate is open March through October. The mansion offers various tours, including an evening ghost tour. Yes, the house is believed to be haunted!
If you are craving time out in nature, the Pleasant Valley Wildlife Sanctuary will delight you. Wander around on more than 1,000 acres of lush plants, trees, and blooms. Landscapes include forests, meadows, and wetlands, all set against Lenox Mountain. Whether you want an easy walk or a more demanding hike, you’ll find it here. You’re likely to see beavers and their dams and dens along the way. The trails are open from dawn to dusk every day except Monday.
Pittsfield
Continue north to Pittsfield, a town best known as the home of author Herman Melville. You can tour Arrowhead, the house where Melville wrote Moby-Dick. Purchased by the Berkshire County Historical Society, Arrowhead is being restored to the way it was in Melville’s time. The library where Melville worked had been converted to a bedroom over the years, but now it is again a library and looks like it did in the mid-1800s.
To learn about the art and history of the Berkshires, head to the Berkshire Museum in Pittsfield. It features displays on art, nature, and science that appeal to people of all ages. You’ll find an aquarium, a permanent collection of paintings, and a hands-on exhibit called the Curiosity Incubator.
Hancock
Continue north on Route 7 from Pittsfield for about 9 miles. In Lanesborough, head west on Brodie Mountain Road. After 5 miles, you’ll reach Hancock, near the New York-Massachusetts border. The main draw here is the Hancock Shaker Village, a living history museum.
The Hancock Shaker Village aims to bring the history of the Shakers to life and preserve their stories for future generations. The village encompasses a garden, walking trails, a barnyard, and buildings that cover all aspects of Shaker life. Start at the visitor center and pick up a map of the 5-acre village. Be sure to see the amazing round stone barn, the schoolhouse, and the meetinghouse. Take the walking trail to visit the orchard, gardens, and farm buildings. The pumpkin patch is especially fun in the fall.
The baby animals are, of course, quite popular. Lambs, calves, and newborn piglets all live at the village. And you can say hello to Veruca, the 1,400-pound pig.
Lanesborough
Retrace your path back to Route 7 and Lanesborough. This is where you’ll want to stop if you enjoy bike rides. Starting in Lanesborough, the Ashuwillticook Rail Trail is a former railroad corridor that’s now a 10-foot-wide paved scenic rail trail. It runs through the towns of Cheshire and Adams, meandering along for more than 12 miles through the Hoosac River Valley. Biking, walking, rollerblading, and jogging are all allowed.
You can park at the southern end of the trail at the entrance to the Berkshire Mall in Lanesborough. Or you can drive up Route 8 and enter the trail at various points. The trail is open from dawn until dusk.
If you’re wondering about the tongue twister of a name, it’s a Native American word that means “the pleasant river in between the hills.” And that’s a perfect description for the scenery along this path.
Adams
The train station in Adams is where you can climb aboard the Hoosac Valley Train for an enjoyable ride. Sit back and let the engineer drive while you savor the views out your window. The hour-long ride covers 10 miles and runs on Saturdays and Sundays.
Buy your tickets online and meet at the visitor center on Hoosac Street in Adams.
Mount Greylock
The highest peak in Massachusetts is Mount Greylock, at 3,491 feet. It lies in a state park with more than 70 miles of trails. The Appalachian National Scenic Trail runs through the park, too.
The visitor center entrance is just north of Lanesborough. If you’re coming from the Ashuwillticook Rail Trail or the Hoosac Valley Train ride, go west to enter Mount Greylock State Reservation.
Drive on the road that winds up around the mountain to arrive at the summit. From here, the panoramic view reaches as far as 90 miles and takes in five states. Bascom Lodge provides a place to eat as well as overnight accommodations. The road up the mountain is open from mid-May through mid-October. It may be open in the winter if weather permits.
If you want to hike, grab a trail map at the visitor center. Then you can hike as much or as little as you wish. The park is open from dawn until dusk all year long.
Williamstown
Next, take Route 8 north from Adams and then Route 2 west, or take Route 7 north from Lanesborough, turning east on Route 43. You’ll be driving through peaceful farmland either way.
Williamstown, home of Williams College, has all the pluses of a city that hosts a liberal arts school. The Williams College Museum of Art has been named one of the finest college art museums in the country. And the school hosts the Williamstown Theatre Festival in July and August.
If you are in town for only a short time, be sure to spend a few hours at The Clark. This art institute features works by French Impressionists as well as American art, including paintings, sculptures, drawings, and silver. You’ll find the artwork of Winslow Homer and John Singer Sargent and works from the Renaissance to the early 20th century.
The Williamstown Rural Lands Foundation’s website has all the information you’ll need to set out on a hike in the area. All levels and lengths of hikes are available. An interactive map will help you plan so that you get the maximum enjoyment from your time outside.
Are you staying more than a day here? Consider crossing north into Vermont for a day trip. Drive north on Route 7 for about 20 minutes, and you will cross the state line and arrive in the town of Bennington. Head to the Battle Monument, which is both historic and an ideal place to take in the tree-filled view. It commemorates a Revolutionary War battle that took place in 1777. At more than 300 feet tall, the monument allows you to gaze out at the hills of Vermont.
The small town is a great place to see historic architecture and stop for a snack or lunch. If you’re delighted by covered bridges, look for the Burt Henry Covered Bridge and the Silk Covered Bridge.
Pro Tip: Many of the stops on this road trip are open from May through October. If you are going to the Berkshires for winter sports, I’d recommend Hancock as a base. The nearby Jiminy Peak is a premier ski resort. Then, as weather permits, you can venture to the other towns in the Berkshires.
This road trip, if taken in the fall, carries you along through a dazzling show of colorful foliage. Discover quaint houses and shops, search for antiques, stroll along paths in lush gardens, dig into the history of the region, and end your day with a delicious dinner of regional food. Everyone will find something fun to explore in the Berkshires!
