Lay of the Land
Connecticut: Litchfield County
With maple-shaded lanes dotted with white clapboard houses, Litchfield County, a two-hour drive north of New York City, is home to such idyllic small towns as Woodbury, Kent, New Preston and Washington. This northwestern corner of Connecticut consists of lush farm-like landscapes of rolling hills punctuated with stone walls, clusters of forest and the occasional covered bridge crossing the Housatonic River.
The county boasts some of the richest soil in New England, producing such mouthwatering organic fruits and vegetables as berries, peaches, apples and potatoes. The local restaurants take pride in this, and dining at the Mayflower Grace and in its surroundings is excellent.
Blantyre, Wheatleigh and Canyon Ranch are all located minutes away from each other near Lenox, Massachusetts, in the Berkshires. A three-hour drive from New York City and two hours from Boston, they are popular resorts for long weekends and boast nearby attractions like the music festival Tanglewood, the dance company Jacob’s Pillow, the Williamstown Theatre Festival and museums like the Sterling and Francine Clark Art Institute, MassMoCA and myriad historic homes and gardens. The region is also acclaimed for its excellent fishing, hiking and golf opportunities.
Cape Cod: Chatham
Sitting at the elbow of Cape Cod, Chatham is a charming town that feels like a traditional, albeit posh, New England whaling village. With a beautiful coastline (known for frequent seal sightings), it is often considered the most upscale destination in Cape Cod and is an excellent option for travelers seeking a quieter scene than on Martha’s Vineyard or Nantucket. The town center consists of just one charming street boasting a handful of restaurants, two bars, a candy shop and a couple t-shirt stores. Visitors should also visit Seashore Drive, a beautiful street with elegant homes and lighthouse. The best hotel option is Chatham Bars Inn, which boasts stunning views, delicious food and a welcoming staff.
The easiest way to get to Chatham is by car. It is a five- or six-hour drive from New York City, and two hours from Boston. Alternatively, visitors can fly into Barnstable airport (20 miles away) or arrange a charter flight into the private Chatham airport (2 miles away).
Rhode Island: Watch Hill
A part of the larger town of Westerly, Rhode Island’s coastal village of Watch Hill rose to prominence in the late 19th century when it was the summer destination of choice for many East Coast elite. The town occupies the most southwestern point of the state (excluding Block Island, which lies 13 miles off the coast and can be seen on a clear day), which contributes to its status as one of the most private summer enclaves on the east coast, in stark contrast to the gilded grandeur of nearby Newport. Despite its exclusive status, which has attracted the likes of Clark Gable, Henry Ford, and, more recently, Taylor Swift, Watch Hill is a family-oriented community (it boasts the oldest operating flying horse carousel) known for its Victorian-style architecture and small town atmosphere. Long weekenders usually stay at one of two resorts, the grand dame Ocean House or the charming Weekapaug Inn.
Woodstock, home to Woodstock Inn, is located in central Vermont, just under a five-hour drive from New York and around two-and-a-half hours from Boston. There are also Cape Air flights from both New York and Boston to Lebanon airport, which is located in Lebanon, New Hampshire, twenty minutes from Woodstock.
Barnard, home to Twin Farms, is located in central Vermont, just north of Woodstock. It’s a drive of five hours from New York, three from Boston. The closest airports are Lebanon, NH (forty minutes away) and Burlington, VT (seventy-five minutes away).
There’s an airport in Burlington, Vermont, which is seven miles north of the town of Shelburne, home to Shelburne Farm.
Maine: Portland and Kennebunkport
The land of lighthouses and lobster, Maine is the country’s northeast most state and boasts over 200 miles of rocky coastline. Located on the southern coast, Portland is the state’s largest city and exudes New England charm with cobblestone streets and a picturesque harbor, home to dozens of restaurants and shops. Twenty miles south of Portland is Kennebunkport, a quiet harbor side village, known for its stately mansions and laid-back summer scene.
When to Go
In the summer, the gardens of New England are in full bloom and meals are often served al fresco. Warm weather sports include kayaking, biking, archery and hiking. In the winter, there’s snowshoeing and cross-country skiing. It’s hard to top New England in early October, when the fall leaves are at their peak. Winter is also popular, especially the week between Christmas and New Year’s, as there are good ski resorts located throughout the region.