Massachusetts' Scenic Berkshire Mountain Town Is Known For Festivals, Art, Gardens, And Charming Stays

Massachusetts is full of scenic spots, from the eastern coastline and islands to the western Berkshire Mountains towns like the quiet, romantic retreat of Lenox. Vermont might come to mind first when considering New England foliage drives, but the Berkshires is an underrated fall destination with rolling hills ablaze with color. Stockbridge is a vibrant fall getaway, but it is also a year-round location known for art, festivals, gardens, historic homes, and charming inns. The epitome of a picturesque, small New England town, Stockbridge pulls above its weight when it comes to cultural attractions. If you feel like you're walking in a Norman Rockwell painting, that may literally be the case. Rockwell lived in Stockbridge in the later years of his life and the local scenery as well as his neighbors are featured in his art. If you go to the town's -– and one of the region's -– most popular attractions, the Norman Rockwell Museum, you'll see his painting "Stockbridge Main Street at Christmas (Home for Christmas)." Stockbridge takes historic preservation seriously and even has an annual December celebration that brings antique cars to Main Street to reenact the depiction in the painting. Stunning gardens burst to life in spring and summer, and summer also brings one of America's most famous classical music festivals.

Berkshire County covers the entire west side of the state with Stockbridge in about the middle of the north-south sliver. Stockbridge is about two hours west of Boston, two hours north of Manhattan, and an hour and 15 minutes northwest of Hartford, Connecticut. 

Norman Rockwell was an iconic chronicler of American culture. His subjects included kids at soda fountains and nosy neighbors. He also depicted serious subjects like Ruby Bridges being escorted to school during desegregation. His "Golden Rule" mosaic — which depicts a group of people reflecting different nationalities, races, and religions — hangs in the United Nations. Don't miss the lower level of the Norman Rockwell Museum, which displays his Saturday Evening Post covers, and stroll around the bucolic campus which includes his barn studio.  

If you're visiting Stockbridge between May and October, take a turn around the 24-acre Berkshire Botanical Garden where you'll find a variety of flowers and plants in themed areas. These include the Pond Garden, the Foster Rock Garden, the Daylily Walk Garden, the Children's Discovery Garden, the Wildflower Meadow, the Woodland Garden, and others. Topiary lovers should seek out Lucy's Garden where elephants and chairs are shaped from boxwood, yew, and arborvitae. 

Two historic homes in Stockbridge are also draws for lovers of art and gardens. The man responsible for the Lincoln Memorial in Washington, D.C., and the Minute Man sculpture in Concord, Massachusetts, Daniel Chester French lived and worked at Chesterwood. On 122 acres, Chesterwood houses hundreds of French sculptures, and the grounds include a studio garden and woodland walk. Another Gilded Age mansion, Naumkeag is decorated with original furnishings, and is on 8 beautifully landscaped acres with formal gardens, meadows, and farmland.

Upwards of 350,000 people spread out their blankets on 500 acres of grass every year and enjoy world-class classical music performances every year at the Tanglewood festival. Situated between Lenox and Stockbridge on Route 183, Tanglewood also hosts some popular music performances — particularly the Boston Symphony Orchestra — as well as speakers and food and wine events. Smaller festivals take place at area cultural institutions, including Chesterwood's performing arts and speakers' series and Naumkeag's spring Daffodil & Tulip festival. 

The most famous place to stay in Stockbridge is The Red Lion Inn, which dates to 1773 and has a monopoly on lodging with its eight buildings. Even if you don't stay here, it's worth a visit to explore the public spaces, dine, or sit in a rocking chair on the wraparound porch and people watch. Guest rooms, which have printed wallpaper, four-poster beds, and wingback chairs, start at roughly $200 per night– though it can be more or less depending on the date — and amenities include a pool and hot tub. On the road from Stockbridge to Lenox, the Georgian-style Inn at Stockbridge sits on 6 acres with 13 rooms in three buildings: the Main House (rooms have sitting areas), Cottage House (fireplaces), and Barn (decks and fireplaces). Offering a pool, fitness center, breakfast, and bar, the inn charges in the general ballpark of $400 per night. There are also romantic retreats in Lenox and just past Stockbridge, a top-rated bed and breakfast that transports you to the English countryside in Lee.