Stockbridge, Massachusetts

Just 10 minutes south of downtown Lenox, you’ll find yourself in the charming village of Stockbridge, made famous by Norman Rockwell’s painting, Stockbridge Main Street at Christmas. Although much smaller and quieter than Lenox, Stockbridge still offers visitors an abundance of cultural and natural beauty all year long. Historic inns, sprawling estates, lush gardens, and genuine small town hospitality are just a few of the things that you’ll find in this quaint little town.

Start by taking a stroll down Main Street and you’ll feel as though you’ve taken a step back in time, with the village being one of the most well-preserved in the entire region. In fact, chances are you’ll be convinced that you’re walking through the exact scene depicted in Rockwell’s work!

Outside of the historic downtown, some of the village’s biggest claims to fame are museums honoring local world-famous artists, including Rockwell and Daniel Chester French. French, the sculptor of the Lincoln Memorial, had his home at Chesterwood, and today the mansion serves as a museum and sculpture garden containing his work.

But of course, no trip to Stockbridge would be complete without paying a visit to the Norman Rockwell Museum. The museum is home to the world’s largest collection of Rockwell art, with almost 600 original paintings and over 100,000 pieces of memorabilia providing a glimpse into the artist’s life. Additionally, the museum holds the very studio in which he worked, set up exactly as it was back in the 60s. Step inside and to see for yourself why he often referred to it as “the best studio yet”.

After exploring the museums and the downtown district, be sure to spend some time taking in the natural beauty of the area. The Housatonic River runs right through town, and with it, numerous trails bursting with greenery during the summer months. In addition, on a sunny day, the nearby Berkshires Botanical Garden makes for a beautiful spot to picnic and explore. It’s also a good idea to check their website in advance to plan around any upcoming events, especially in the summer and fall!

Last but not least, finish off your day with a stop at the Red Lion Inn on Main Street. Built back in the late 1700s, the hotel is also home to an award-winning restaurant with an extensive wine list. Even if you’re not all that hungry, nothing quite beats sitting out on the porch in a rocking chair and looking out into town with a nice cold drink in your hands.

Regardless of what your interests are, there’s certainly something to be enjoyed by everyone in Stockbridge, making it a quintessential stop on any trip to the Berkshires region.