Solitude, Steeples and Smart Luxury: An Insider’s Guide to Litchfield County, Connecticut

For years, New Yorkers have quietly slipped into Litchfield County, Connecticut, for weekends away from the city, bypassing the default trio of the Hamptons, Hudson Valley and Catskills. Technically the southern edge of the Berkshires, this northwest corner of Connecticut has a character all its own with historic town greens, working farms reborn as vineyards and winding roads lined with stone walls. The scenery alone could carry the trip, but Litchfield Hills, as the region is sometimes called, has evolved into far more than a postcard backdrop.

Today, the county’s 26 towns balance old New England charm with a sophisticated undercurrent. In Salisbury, Lakeville and Cornwall, farmhouses that look modest from the road conceal carefully restored interiors, while in Washington and Litchfield, discreet weekenders from Manhattan blend into a social scene that still orbits around the local farmers’ market. Fall brings out the best of the area: foliage blazing red and gold, antique fairs popping up in barns and harvest festivals filling the greens.

It’s also a destination that rewards curiosity. Spend the morning hiking the Appalachian Trail near Kent, the afternoon browsing New Preston’s design-forward boutiques, and the evening over a farm-sourced dinner at Community Table. Winter slows the pace but sharpens the experience, with ski jumps that rival Vermont, cross-country trails with smashing vistas, or a fireside drink in a centuries-old inn. Whether it’s a quick reset or a long weekend, Litchfield County delivers an escape that feels both chic and unpretentious. Ahead, a guide to seven essential towns and where to stay, shop and eat in each.

Litchfield

Litchfield has always carried a certain clout. America’s first law school still sits just off the Green, and the surrounding streets are so perfectly kept that the Colonials and Victorians read more like stage sets than private homes. But 2025 Litchfield isn’t stuck polishing brass—it’s newly flush with hotels that signal the town’s second act. The Abner, carved out of the 1890 courthouse, now pours cocktails on a rooftop cheekily dubbed The Verdict, while its restaurant deals in tavern fare with sharper edges. A few blocks away, Belden House & Mews reimagines a 19th-century mansion into 31 rooms by Champalimaud Design, with Reed Hilderbrand’s gardens keeping the grounds as spiffy as the interiors. Heritage still anchors the scene, particularly architecturally, with midcentury gems by icons like Marcel Breuer and John Johansen scattered in the hills beyond. On the plate, West Street Grill has been the town’s dining stage since 1990. One night it’s Clooney, Murray and Wes Anderson; the next, a birthday crowd from the city. For a nightcap, Litchfield Distillery pours complimentary bourbon tastings daily, no reservations needed.

Bantam

If Litchfield is the county’s anchor, Bantam is its dining room. Former Manolo Blahnik execs Anthony Yurgaitis and the late George Malkemus put this tiny borough on the national food map with their Arethusa Farm orbit. Arethusa al Tavolo still leads the fine-dining pack, with menus supplied by the farm across the street, while the dairy shop keeps churning out ice cream, cheese and butter with a following big enough to warrant extended hours every October. West Shore Seafood by Bantam Lake serves lobster rolls at picnic tables, and Krafted Brew Lab keeps caffeine levels steady with small-batch coffee and salted chocolate chip cookies. Step outside town and White Memorial Foundation opens up 4,000 acres of trails, marshes and boardwalk loops—a midweek walk here feels like you have the place to yourself, with herons overhead and leaves flaring gold. Bantam also carries a creative streak. At the Bantam Arts Factory, an old switch plant on the river, Dumais Made produces ceramic lighting and furniture alongside sculptors, perfumers and tile makers who thrive in its sunlit, high-ceilinged studios. Just down the road, master potter Guy Wolff is still throwing museum-quality clay vessels, each stamped with the weight marks that have made his work an obsession for collectors and decorators alike.

Washington

Washington could be considered the county’s polished center of gravity, thanks largely to a single stellar hotel. Washington Depot, the twin town’s casual core (and reportedly a source of inspiration for the fictional Connecticut town of Stars Hollow in Gilmore Girls), delivers the basics with charm: The Po Café for coffee and sandwiches, Hickory Stick Bookshop for a new read, and the Scoville Memorial Library for a quick browse. Outside the Depot in Washington proper, the Mayflower Inn & Spa, an Auberge Resorts property, remains the region’s marquee stay. Its 58 acres of manicured gardens, Celerie Kemble–refreshed interiors and The Well spa program draw a mix of design insiders and wellness seekers. Dining within the inn splits between the Garden Room, where chef José Ramírez-Ruiz crafts hyperlocal menus, and the Tap Room, a cozier pub-style alternative. Beyond the gates, G.W. Tavern offers hearty tavern fare, while Washington Pizza House handles the weeknight carb fix. Outdoors, Steep Rock Preserve remains Washington’s calling card: a patchwork of Shepaug River trails, ridge climbs and the 1870s railroad tunnel cut into the hillside. This is a place that blends cultivated calm with small-town utility—a weekend that can swing from spa treatments to muddy boots.

Kent

Kent punches above its weight with enough culture and outdoors to stretch a weekend. Kent Falls State Park (open daily, 8 a.m. to sunset) packs Connecticut’s tallest waterfall into a short, crowded climb, best tackled early. Macedonia Brook State Park offers the longer loop over Cobble Mountain, where fall hatches on the Housatonic below make the river one of the Northeast’s premier fly-fishing classrooms. Downtown, Swyft dials out wood-fired pizzas with hot honey pepperoni, while its upstairs sibling Ore Hill runs on tasting menus and reservations. RT Facts, set in the vast Kent Barns space, is where decorators lose hours among 7,000 square feet of antiques and custom furniture. When the day winds down, the Kent Collection fills the lodging gap with a trio of smartly renovated stays: the Firefly Inn, the Victorian and the Garden Cottages. Each delivers a different flavor—historic bones, private rentals or casual suites—but all keep you walking distance from restaurants, shops and the gallery circuit. While Kent looks like a Norman Rockwell cover on arrival, its edges are certainly sharper than that. 

New Preston

New Preston barely clears a crossroads, yet its one-block rise above the falls feels like a design district in miniature. Plain Goods sets the tone with a meticulous edit of heritage textiles, ceramics and fashion; Pergola Home layers rare plants and Japanese pottery into a gallery-like greenhouse; and Privet House tempts with antique glassware and cult-status linens that somehow make a new set of napkins feel essential. It’s the kind of block that convinces even second-home minimalists to haul back trunkloads. The food scene matches the impressive retail curation. The Smithy Café at 9 Main functions as the village canteen, serving soups, grilled cheese and salads to locals who don’t bother with menus. The Owl flips from espresso in the morning to natural wine and small plates after dark. For dinner, Community Table delivers the county’s most Copenhagen-adjacent cooking, where Nordic techniques meet Connecticut farms in a tasting menu worth planning your night around. Before the day tilts toward sunset, take to the Connecticut Wine Trail and stop at Hopkins Vineyard above Lake Waramaug: estate-grown flights poured against ridgeline foliage, a reminder that you’re still in New England even if the scene reads more, well, old England.

Cornwall

Cornwall is the county’s postcard that never faded; its ruby-red West Cornwall Covered Bridge has spanned the Housatonic since 1864. In the height of autumn, the shot of scarlet timber over gold water all but defines Connecticut fall. The river isn’t just a backdrop, though. Its upper stretches are a mecca for fly fishers, with state-designated pull-offs and fly-fishing-only zones that keep the banks busy with waders every autumn weekend. The hills climb into Mohawk Mountain, a family-run ski area since the 1940s that keeps its edge by staying no-frills and legit. It’s now part of the Indy Pass, which means your lift ticket here also buys bragging rights across a network of independent hills nationwide. Come winter, it’s laps without Vermont lift lines; in summer and fall, the trails flip into ridge walks with views that push straight across to the Berkshires. Cornwall itself plays things spare. Lodging is mostly farm stays, cottages, or B&Bs hidden down dirt lanes; food means a packed picnic or a detour to Kent or Litchfield. 

Salisbury

The northwest edge of the county, practically grazing the Berkshires, is where you’ll find Salisbury and its neighbor Lakeville. Salisbury’s Main Street still reads quintessentially New England: Sweet William’s Coffee & Bakery for morning fuel, Johnnycake Books for rare finds, and the Scoville Memorial Library—the nation’s first publicly funded library—anchoring one end of town. At the other end, the White Hart Inn sets the tone with rooms, a restaurant and its convivial Tap Room. Lakeville, just down the road, orbits around Lake Wononscopomuc, Connecticut’s deepest natural lake, where fall mornings mean mist over the water and locals walking Town Grove. Hikers get their fix on the Appalachian Trail, climbing to Lion’s Head or Rand’s View for wide-open Berkshires panoramas. Motorsport crowds head to Lime Rock Park, which turns the valley into a theater of engines every summer and fall, capped by its Historic Festival each Labor Day weekend.