Gurney’s in Montauk. Courtesy Indagare’s Callie Randall
In recent years, Montauk has gained a reputation for being the bohemian, easy-going sibling to the chic, see-and-be-seen Hamptons. Visitors have a few options: Gurney’s and the newer Gurney’s Star Island are often at the center of the Montauk scene, while Hero Beach Club’s laid-back atmosphere belies its host of wonderful, hands-on activities from surfing lessons to fishing to horseback riding.
For a Cozy Home Base in the Hudson Valley: Troutbeck, Hudson Valley
Troutbeck is a bucolic, family-friendly property near the Connecticut border on the eastern side of the Hudson Valley. Its 36 rooms and suites showcase modern, simple décor, and intimate public spaces, including a library and a sun room, offer multiple nooks for reading and boardgames. The 45-acre property has a pool and tennis courts along with yoga areas, three trout pools and easy access to hiking and biking trails.
For an Iconic New York Mountain Lodge: Mohonk Mountain House, Hudson Valley
The castle-like, Victorian-era Mohonk Mountain House has an enviable perch (pictured, top of page), overlooking a glacial lake and surrounded by 40,000 acres of forest. The all-inclusive resort is a window into another era of vacationing, with days spent canoeing, row-boating, hiking or biking, and meals taken in the grand dining room with panoramic views. Families return year after year and love the hotel’s spa.
Driving Vacations In Massachusetts
The Berkshires become one of America’s great cultural getaways each summer, when the Boston Symphony Orchestra decamps to Tanglewood. Here, as well as in Cape Cod, you’ll find several of Indagare members’ favorite East Coast hotels.
For a Wellness Retreat: Canyon Ranch, Lenox
Canyon Ranch Lenox, courtesy Canyon Ranch.
Canyon Ranch Lenox is a fitness, wellness and beauty mecca, with programmed stays gently pushing guests to become their best selves. That means a robust offering of workout classes, a dreamy spa and delicious, health-focused meals with the Berkshires as the backdrop.
For a Secluded, Refined Berkshires Hotel: Wheatleigh, Lenox
Wheatleigh, set in an 1890s palazzo-style home turned hotel, is all about refinement. Guests here—in one of just 19 rooms—take their time to relax, roam the property, enjoy gourmet dining and soak in views over the rolling hills and nearby Stockbridge Bowl lake.
For Adults-Only Luxury with Old World Soul: Blantyre, Lenox
Modeled after a Scottish manor, Blantyre transports guests to the early 20th century. Expect antique furnishings, including four-poster beds, toile wallpaper and silk curtains, along with wood-burning fireplaces and terraces overlooking the grounds. Days here are filled with croquet and lawn tennis, and evenings are black tie affairs, complete with multi-course dinners and piano music by candlelight.
For the Best Cape Cod Hotel: Chatham Bars Inn, Chatham
Chatham Bars Inn is a quintessentially New England resort, with a buzzy vibe, the area’s best restaurants, and a fresh, beachy aesthetic along the elbow of Cape Cod. It’s great for multi-generational families and groups of friends looking for prime beach access.
Driving Vacations In Maine
Just an hour and a half from Boston, southern Maine’s rocky coast beckons those in search of a slower pace, excellent seafood and charming hotels.
For the New England Foodie: White Barn Inn, Kennebunk
A White Barn Inn guest room courtesy White Barn Inn
Historic White Barn Inn, just a few minutes from town, comprises several classic clapboard cottages, a converted carriage house and the main inn, linked by flower-lined walkways and gardens. An Auberge Resort, it’s one of Maine’s most elegant boutique hotels, with just 26 rooms, a pool and spa and a stellar fine-dining restaurant serving contemporary New England fare.
For the Woods Meets Beach Experience: Hidden Pond, Kennebunkport
About a mile in from the beach, the woodsy Hidden Pond has a camp-like atmosphere—albeit with modern comforts like stone fireplaces, flatscreen televisions, Bose iPod docks, Frette linens and reliable WiFi. It’s split into two sections: adults-only one-bedroom bungalows and family-friendly two-bedroom cottages. Morning yoga and evening cocktails add a sense of community, along with two pools and a spa, though there’s plenty of opportunity for privacy, including biking to a quiet beach nearby or relaxing on your private porch swing.
Driving Vacations In Vermont
Vermont’s Green Mountains are actually greener today than they were 100 years ago, when most of them had been cleared for farmland. Now, they’re a forested wonderland, with wintertime skiing and fabulous summer hikes, plus a few standout hotels.
For Culture & Cuisine Lovers: Twin Farms, Barnard
Looking up at the main house at Twin Farms. Courtesy Twin Farms
The former estate of Nobel Prize–winning author Sinclair Lewis and his wife, journalist Dorothy Thompson has been transformed into one of Indagare’s most beloved boutique hotels: Twin Farms. Sprawling over 300 acres—complete with a covered bridge over a pond—this adults-only, all-inclusive retreat has a museum-quality art collection with works by the likes of Jasper Johns, Roy Lichtenstein and Bernice Abbott, as well as a lauded culinary program. This is laid-back luxury at its best, with plenty of activities—from canoeing around Copper Pond and wandering the crisscrossing trails that wind from the cabins down through forests and fields or just a lazy afternoon of reading.
For the Small Town New England Experience: Woodstock Inn, Woodstock
Overlooking a historic town green in the center of town, Woodstock Inn gives guests a sense of life in a historic New England village. Laurence Rockefeller built the hotel in 1969, and the country home-style rooms feature four-poster beds and cushioned window seats. Nearby, the Green Mountains offer year-round activities, though the inn’s 10,000-square-foot spa, Robert Trent Jones-designed golf course and onsite falconry mean there’s plenty to do on-property as well.
For the Storybook Setting: The Pitcher Inn, Warren
In tiny Warren, Vermont, the two-story Pitcher Inn welcomes guests with its double-decker front porch, lit by twinkling lights come nighttime). Individually designed guest rooms are whimsical without becoming kitschy. The “School” room, for example, emulates a one-room schoolhouse with vintage blackboards. Service is consistently warm and sincere: many staffers have spent decades on-property and are eager to help visitors take advantage of all central Vermont has to offer.
Driving Vacations In Rhode Island
Rhode Island is home to several of our favorite resorts and inns, ideal getaways for Bostonians and New Yorkers alike.
For a Classic New England Seaside Vacation: Ocean House at Watch Hill, Westerly
A view of Ocean House, Watch Hill, courtesy Ocean House
Ocean House at Watch Hill has been a beloved Rhode Island resort since it opened in the 1860s as a playground for East Coasters looking for a prime location on the Atlantic, subdued glamour and discreet privacy. Now, it offers foraging and cooking classes, a 12,000-foot spa, croquet and cocktails, squash courts and a putting green, movies on the beach and lobster boils and barbecues for its guests.
For the Yacht Crowd Party Scene: Gurney’s, Newport
On its own island just outside of Newport, this outpost of Gurney’s welcomes trendy New Englanders to its seaside Pineapple Club, with its saltwater outdoor pool, restaurant and bar, plus an edition of Scarpetta. The 257 guest rooms 18 suites—each with a water view—feature crisp, nautical lines and muted fabrics. In warmer months, guests can also take advantage of the kids’ club, marina and sailing school.
Contact Indagare to help us plan your East Coast road trip vacation.