Hartford to Berkshires: Great Barrington, Lenox & Greylock Road Trip
Route: Hartford ➔ Great Barrington, MA (via CT-44 W & US-7 N, ~60 miles) ➔ Lenox/Stockbridge, MA (~15 miles) ➔ Mount Greylock (via US-7 N & MA-2 E, ~50 miles) ➔ return to Hartford (via I-90 E to I-91 S, ~120 miles).
Highlights:
This road trip takes you into the scenic Berkshire Mountains of western Massachusetts a region known for culture, quaint towns, and outdoor beauty. From Hartford, drive northwest on CT Route 44, a scenic rural highway that will treat you to classic New England countryside. In about 1.5 hours you’ll arrive in Great Barrington, MA, a charming small town frequently named one of the best small towns in America (Smithsonian Magazine even ranked it #1 in a past list). Stroll Great Barrington’s Main Street for unique shops, cafes, and a friendly small-town vibe. If it’s summer and you’re a music fan, note that nearby Lenox is home to the famous Tanglewood Music Center the Boston Symphony Orchestra’s summer home where daytime rehearsals or evening concerts happen regularly. Check the schedule ahead of time; if a concert aligns with your visit, it might be worth a stop in Lenox on your way through.
Continue a short drive north to Stockbridge, MA. This postcard-perfect town is home to the Norman Rockwell Museum, which houses the world’s largest collection of original Rockwell paintings including many beloved images of American life (Stockbridge’s own Main Street was the setting for Rockwell’s famous “Stockbridge Main Street at Christmas” painting). Take some time to visit the museum or even just enjoy the grounds. In the center of Stockbridge, you can also peek into the Red Lion Inn a historic inn established in 1773 that has been welcoming travelers for over two centuries. Even if you don’t stay or dine there, the lobby and porch are filled with New England charm and history.
At 3,491 feet, Mount Greylock is the highest point in Massachusetts, and it’s your next destination. Drive north through Pittsfield and pick up the Mount Greylock Scenic Byway (access is seasonal, generally open late May through October, weather permitting) which winds up to the summit. At the top you’ll find the Massachusetts Veterans War Memorial Tower, a 93-foot monument built in 1932 that crowns the peak. On a clear day, the summit provides panoramic views extending 60–90 miles in all directions you might catch sight of New York’s Catskills, Vermont’s Green Mountains, and even a bit of New Hampshire and Connecticut. There are picnic spots near the summit (and a rustic lodge, Bascom Lodge, which offers refreshment in season), so it’s a great place to breathe the mountain air and maybe enjoy a picnic if you packed one. Snap some photos of the sweeping vistas and the Art Deco-style memorial tower and savor the accomplishment of reaching the top of Massachusetts.
After enjoying the mountain, start making your way back toward Hartford. If time permits and you’d like a different route home, you can swing east through the northern Berkshires and pick up I-91 South via Greenfield, MA. This adds a bit of time but takes you through the lovely Pioneer Valley (with views of the Deerfield River and Mount Sugarloaf) for a change of scenery. Otherwise, the quickest return is to head south to the Mass Pike (I-90) and take it east to I-91 South in Springfield, then straight down to Hartford. Either way, it will be roughly 2.5 hours back. (As a bonus option for art lovers with more time, North Adams near Mount Greylock is home to MASS MoCA, a vast contemporary art museum housed in an old factory complex. It’s one of the largest modern art centers in the U.S., and could be a fantastic add-on if you choose to extend the trip with an overnight stay in the North Adams area.)
Pro Tip: The Berkshires are wonderful in every season, but each comes with considerations. Fall (late September through October) brings spectacular foliage colors to the mountains it also brings more tourists, especially on weekends, so roads can be slower and lodging fills up quickly (book ahead if you plan to stay overnight during peak foliage season). Summer offers cultural events like Tanglewood concerts, Jacob’s Pillow dance festival, and more, which make weekends lively but occasionally busy on the roads and in town centers. In winter, this route transforms into a ski trip Ski Butternut in Great Barrington or Catamount on the NY-MA border are popular for skiing and snowboarding. If you go in winter, check the weather and be aware that the Mount Greylock summit road is closed in snow and ice (the scenic byway is typically closed late October through late May), so you might skip the drive up Greylock in the winter months.
Pro Tip: Always carry a bit of cash in small bills when exploring the back roads you may come across honor-system farm stands selling fresh apples, maple syrup, or homemade goods in these rural areas. This itinerary is very flexible: you could easily turn it into a relaxing weekend by staying overnight in a town like Lenox or Williamstown (for example, to visit the Clark Art Institute or Williams College Museum of Art, in addition to MASS MoCA). But even as a day trip, you’ll get a delightful taste of small-town New England charm and mountain vistas, all just a couple hours from Hartford. It’s a lot of ground to cover in one day, but if you start early, you’ll come home with plenty of stories (and photos) from the highest peaks and quaintest villages of western New England.