The Most Charming Small Towns in America? LandVest Knows Them Too

A Closer Look at Stockbridge, MA
and Woodstock, VT


Big 7 Travel recently published a list of The Top 50 Most Charming Small Towns in America. New England made 10 appearances, snagging the top two spots: Stockbridge, MA at number 1 and Woodstock, VT at number 2.

Stockbridge, MA

Stockbridge_CCStockbridge is a quintessential New England small town in the Berkshires, Western Massachusetts. Stockbridge’s vibe feels like it is right out of a Normal Rockwell painting because…it is. The artist made the town his home and the centerpiece of his work. The Norman Rockwell Museum is one of the highlights of Stockbridge, where you can view all 323 Rockwell Saturday Evening Post covers.

If you prefer sculpture, visit Stockbridge’s Chesterwood. The summer home of Daniel Chester French, who created the Lincoln Memorial in Washington, DC, offers numerous examples of his work set among lovely architecture and gardens.

Stockbridge’s quaint Main Street is one of the main reasons it earns the top spot. The town square hosts happenings year-round, surrounded by traditional picture-perfect shops and restaurants. There’s plenty to do in Stockbridge: visit historic inns, museums, gilded age mansions, religious shrines, and the Berkshire Botanical Garden, on top of walks in the hills as well as evenings at the Boston Symphony Orchestra’s home in Stockbridge. Tanglewood and the new Linde Center offer music and entertainment year-round.

Cindy Welch, who heads up LandVest’s work in the Berkshires, is a longtime resident. Here are five of Cindy’s favorite things to do in and around Stockbridge:

  1. You can’t say you have truly visited the town of Stockbridge unless you have spent time sitting in the rocking chairs on the porch of the Red Lion Inn!
  2. Just one door down from the Red Lion is the Williams Country Store, a throwback to yesteryear with lots of penny candy and toys you loved as a kid…and your children will too.
  3. If you are a gardener or simply enjoy seeing the beauty of unique and well-tended landscapes, the Berkshire Botanical Garden is the place to explore and admire.
  4. If you are looking for a night out with live theatre, the Berkshire Theatre Festival is one of the oldest professional performing arts venues in the Berkshires, celebrating its 92nd anniversary this year
  5. Pack a lunch and head up to Olivia’s Overlook to enjoy long views over Kripalu and Stockbridge Bowl, then hike the trails leading to the Pleasant Valley bird sanctuary.

Intrigued? You can have your own country retreat, gilded age mansion or garden for quiet puttering.

Woodstock, VT

Like Stockbridge, Woodstock has been a longtime destination for a retreat from the city, supporting the most valuable real estate off the water and slopeside in New England.

The Rockefeller family, keen-eyed seekers of beautiful real estate, stewarded beautiful property next to the village center, which became the Marsh-Billings-Rockefeller National Historic Park, with miles of gentle carriage roads through grand forests. Adjacent Billings Farms gives visitors a chance to meet their doe-eyed Jersey cows and sample their homemade ice cream, a short walk from the Woodstock Inn on the village green. Summers are relatively cool and winters are full of outdoor activities, with plenty of skiing options from the cozy slopes at Suicide Six to the big mountain at Killington and Okemo. The equestrian hub of South Woodstock centers around Green Mountain Horse Association, with every weekend from spring through fall. Competitors mingle with locals around the big tables at the South Woodstock Country Store and over pizza in the tavern at the Kedron Valley Inn (which you will recognize from the iconic Budweiser Holiday commercial).

We asked Dia and Story Jenks, Chris Lang and Ruth Kennedy Sudduth to share five favorite things to do in and around Woodstock:

  1. Walk up the Mt. Tom trails from the center of town to the star (lit during the holidays) with a spectacular view of Woodstock village,
  2. Pick up lunch from the Woodstock Farmer’s Market and eat out at the picnic tables by the river – aka the LandVest summer office.
  3. Putter around the creaky wood floors of Gillingham’s General Store for local and hard-to-find items, especially chocolate!
  4. Take a lunch meeting in nearby Silver Lake in Barnard, swimming and chatting.
  5. Enjoy the Spa at the Woodstock Inn!

Woodstock’s hills are dotted with remarkable properties, ranging from classic farmsteads with big red barns to rambling ski houses tucked in the woods to chic modernist boxes opening to the views. Here are some examples of LandVest available properties and solds:

For more properties near Stockbridge, click here.
For more properties near Woodstock, click here.

During this time, our LandVest Berkshires and Woodstock experts are here to advise remotely or at an appropriate social distance!