Adjacent to Skip Barber, the Interlaken Resort & Conference Center (74 Interlaken Rd, Lakeville, 860-435-9878; from $149) is loaded with amenities like a full-service spa, and sits on the shore of Lake Wononscopomuc (CT’s deepest); quintessential old-school hotels dot the countryside. 1 The White Hart Inn (15 Undermountain Rd, 860-435-0030; from $150), housed in a former home which dates back to 1806, is smack in the middle of Salisbury’s Village Green. Tucked away in the woods, the farmhouse-turned-Inn at White Hollow Farm (558 Lime Rock Rd, Lime Rock, 860-435-8185. From $125) has all of four guest rooms, each with its own bathroom. The property is intersected by the Appalachian Trail.

Regardless of where you stay, drop your bags and head over to the White Hart’s Tap Room for a glass of liquor-infused apple cider and a mammoth chicken potpie. Uneven wood floors, William Morris wallpaper-wrapped dining rooms and a roaring fireplace establish an authentic country-time vibe. The bar is a favorite with locals on weekends—particularly faculty members from the neighboring Hotchkiss boarding school—so grab a pint and make nice.

Winter hikes abound in the area: Lion’s Head is a short but vigorous ascent to sweeping views of the Berkshires from its 1,738-foot peak. Bear Mountain takes athleticism to another level; the six-mile trail rewards with panoramic vistas of the region from the top—the tallest in Connecticut.

Weary hikers, or those just looking to ease into the day with the morning newspaper, are mainstays at the perennially bustling 2 Chaiwalla Tea Room (1 Main St, Salisbury, 203-435-9758). A huge selection of exotic teas and open-faced sandwiches are served up in a room that multitasks as owner Mary O’Brien’s dining room (she lives upstairs with her son Liam). If you can justify the splurge, don’t miss the side table loaded with home-cooked berry cobblers and carrot cakes.

Shopping in Salisbury is great if you have a country house or just know someone who does. A string of home-good stores line one side of the street: The many rooms of A Perfect Pair (2 Main St, Salisbury, 860-435-0128) are loaded down with Simon Pearce glassware, monogrammed toiletry cases and Caspari napkins; Passports Collection (14 Main St, Salisbury, 860-435-8855) features Asian-inflected goods, such as shagreen eyeglass cases, beaded opal necklaces and lacquered trays. Just down the road, Agapanthus (329 Main St, Lakeville, 860-435-8900), dedicated to the gardening set, offers everything from cashmere blankets to woven baskets. As you head back to New York, detour past 3 Lou’s Relics (351 Millerton Rd, Lakeville, 845-452-5820), an antiques-laden barn packed with old crystal, paintings of parrots and rooms piled high with furniture.

Though just 100 miles outside the city, these tiny sleepy towns, which are edged up against the Berkshires, are a pleasant reminder that nature and a more low-key way of life aren’t that far away—but just close enough not to make us too uneasy with their unnatural lack of noisy traffic and cell reception.

THE TAB

One night, two people

Car rental (with gas) $120
hotel $150
+ Meals $80

TOTAL $350

Take I-87N to the Taconic State Pkwy North. Merge onto US-44, which takes you straight through Salisbury.

TRAVEL TIME 2hrs

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