A weekend in the Berkshires

Full of quaint villages and pretty scenery, The Berkshires, in Western Massachusetts are a popular destination from Boston or NYC. And for a good reason, as it’s a pleasant place to spend a long weekend.

On my visit to the Berkshires in July 2022, we stayed in an Airbnb in Housatonic, which is close to lots of things, but is a town with not much there, although I totally recommend the Berkshire Mountain Bakery and ExtraspecialTeas right in town.

SEE

Berkshire Botanical Garden, a small and pretty botanical garden which is good for an hour or two strolling around the gardens.

Chesterwood, the home, studio, and gardens of sculptor Daniel Chester French, offers guided tours of his studio and gardens or you can opt for the self-guided garden only tour, which is what we did on the day of our visit. There are rotating outdoor sculpture displays in the woods and gardens.

A great place for a hike is Monument Mountain, there are trailheads on both sides of the mountain as well as several options for routes. The trail to Flag Rock from Route 183 is about 3 miles round trip and is not too steep. For a more dramatic hike, park at the Route 7 trailhead and take the Hickey Trail to the Peekskawso Peak Trail for a little bouldering and some views.

Edith Wharton’s home, The Mount is a fabulous place to visit. There are short trails to walk, outdoor sculptures, pretty gardens, and a house to tour, so lots of interesting things to see both inside and outside.

Tanglewood is the summer home of the Boston Symphony Orchestra.

We managed to catch movie night - The Empire Strikes Back - one night when we were there, which was a lot of fun.

There are outdoor concerts all summer long as well as some daytime activities, like Saturday morning yoga.

EAT

The Red Lion Inn in Stockbridge has a lovely porch where you can sit and have a drink and the Courtyard is a great place to eat lunch.

Great Barrington is a larger town and has more dining options and we found ourselves there several times for dinner. One night we got takeout pizza from Baba Louie’s, another night we ate at Xicohtencatl, which was happy to take a reservation for a larger party, and the final night in town we ate at farm to table restaurant, The Prairie Whale.