The county of Litchfield includes 26 towns (places like Washington, Kent, New Preston, Warren, and West Cornwall) and occupies the northwest corner of Connecticut. The landscape is storybook New England, with rolling hills, endless woodlands, green fields, and streams. It’s just about two and a half hours by car from Manhattan, almost three from Boston. The most recent U.S. census marks the area as the least densely populated in Connecticut. But those are just numbers. The Litchfield list of names tells a different story. They’re not movie stars (for the most part) or party girls, but the county is undeniably packed with what used to be known as men and women of substance: Diane von Furstenberg is in New Milford, Philip Roth in Warren, Graydon Carter in Roxbury, Jasper Johns in Sharon, Henry Kissinger, Anne Bass, Agnes Gund, and Oscar de la Renta in Kent, Danny Meyer and Joan Rivers in Washington, Meryl Streep in Salisbury.
So just how did this 920-square-mile stretch of Connecticut with such a high-powered citizenship and close proximity to Manhattan become the red-hot center of the simple life?
This is a place where George Malkemus, the president of Manolo Blahnik, breeds prizewinning cattle at his Arethusa Farm in Litchfield. New York investor Terry Fitzgerald and his wife, Libby, raise all-natural Black Angus beef at their Greyledge Farm in Bridgewater. People get their coffee at Marty’s in Washington Depot or Nine Main in New Preston. The 96-year-old Goshen Fair—garden tractor pull at 10 a.m.! Rabbit judging at 12! Woodcutting demonstration at 5!—is a mainstay of the summer calendar. And the hot list to be on is Marble Valley Farm’s weekly e-mail update of what’s in season (“the organic blueberries are here!”), recipes included.
Litchfield County insiders may prize the region’s peace and privacy, but there are still plenty of reasons for visitors to come. And plenty do. They drive about two and a half hours from Manhattan (not including a burger–and–onion rings break at the Red Rooster Drive-In on Route 22 in Brewster, New York) or about three hours from Boston. Their long weekend should, invariably, include stops at the following (starting from the south).
This town is home to Mayflower Inn & Spa, opened in 1992 ($400–$1,600; 118 Woodbury Rd.; mayflowerinn.com). It’s a “country house hotel” with four-poster beds and chintz-covered chairs, but the spa, redone in 2006, brings it into the 21st century. After a one-hour Sweet Surrender massage, drive to town and get a coffee at Marty’s (6 Green Hill Rd.; seeyouatmartys.com), browse the aisles at the Hickory Stick Bookshop (2 Green Hill Rd.; hickorystick bookshop.com), and view contemporary photography at KMR Arts (2 Titus Rd.; kmrarts.com). Down the road is Finial Home & Garden (13 River Rd.; 860-868-2577) and Grape in the Shade (13 River Rd.; 860-868-9119) for vintage Chanel cuffs, Oscar de la Renta shifts, and ostrich-feather pillbox hats. The Pantry is perfect for lunch (5 Titus Rd.; 860-868-0258), and for dinner it’s local watering holes like G. W. Tavern (20 Bee Brook Rd.; gwtavern.com) or the bar at Mayflower.
Begin with coffee and croissants at Nine Main Bakery & Deli (9 Main St.; 860-868-1879). Then go to Dawn Hill Antiques for 18th- and 19th-century Swedish settees (from $12,000; 11 Main St.; dawnhillantiques.com). At J. Seitz & Co. (9 E. Shore Rd.; jseitz.com) the focus is more contemporary, with organic Italian duvets ($350) and leather clutches from Argentina (from $600). Pergola (7 E. Shore Rd.; pergolahome.com) offers rare botanicals, driftwood mirror frames (from $400), and Jack Staub’s illustrated book 75 Remarkable Fruits for Your Garden ($20). Most remarkable is the waterfall out back. For dinner Oliva is a favorite for grilled calamari stuffed with lemon and prunes, and Gorgonzola–and–caramelized onion pizza (18 E. Shore Rd.; 860-868-1787).
Winvian is a 113-acre resort with 18 themed cottages (the nautical Maritime, the wood-paneled Camping). There’s a 5,000-square-foot spa and the White Memorial Foundation for kayaking and canoeing. Even if the place is booked, come for the restaurant, recently opened to nonguests and headed by Ducasse and Boulud alum Chris Eddy (rooms, $1,450–$1,950; 155 Alain White Rd.; winvian.com). And though a fifties mail-order business made White Flower Farm’s bulbs and blooms available across the country, there’s nothing like walking through rows of paperwhites and perennials (167 Litchfield Rd.; whiteflowerfarm.com).
Bartley Johnstone is a decorator by trade, but at her shop B. Johnstone (4 N. Main St.; 860-927-1272) she assembles objects from across categories and eras: forties red-and-white glass tumblers ($65 for a set of eight), linen tunics ($140), and gently worn Balenciaga bags and Manolo Blahnik mules from local closets. At R. T. Facts (22 S. Main St.; rtfacts.com) down the street, Greg and Natalie Randall have an eclectic mix—19th-century doors, footed bathtubs, Italian garden sculpture. A few doors away is Belgique for chocolates (1 Bridge St.; 860-927-3681). Richard J. Lindsey Bookseller (15 N. Main St.; 860-927-3025) specializes in out-of-print titles like Pierre-Joseph Redouté’s Les Roses ($4,000). And if a weekend cannot go by without a Pilates session, Victoria Schumacher offers private classes at her Bedford Studio off the main street ($95 for one hour; 14 Old Barn Rd.; 860-927-5232).
Richard Lambertson, of the handbag design duo Lambertson Truex, opened Privet House last spring (4 Cornwall Rd.; 860-868-1800), and word spread fast. It’s easy to see why. There are Santa Maria Novella creams and potions, scented candles from Versailles, Belgian handblown candlesticks. Next door is the gallerylike Vol 1. Antiques, curated by Lambertson’s business partner, Suzanne Cassano (12 Cornwall Rd.; vol1antiques.com).
Locals bemoan the arrival of CVS and Talbots, but they still come for house-cured salmon and braised short ribs at West Street Grill (43 West St.; weststreetgrill.net), the early Americana at Jeffrey Tillou Antiques (39 West St.; tillouantiques.com), and Lawrence Jeffrey Estate Jewelers’ vintage charm bracelets (33 West St.; lawrencejeffrey.com). To counter the consumption is the Charym wellness center, created by interior designer Alexandra Champalimaud. There are yoga classes, acupuncture, and a serious holistic medicine program headed by Dr. Malynn Utzinger, the Chopra Center for Wellbeing’s former director of women’s health, and David Williams, board-certified physician and expert in Ayurvedic medicine (by appointment only; 174 West St.; charym.com).
Michael Trapp antiques (7 River Rd.; michaeltrapp.com) is a landmark for 19th-century Dutch Colonial teak benches ($1,540) and 18th- and 19th-century terracotta tiles from Burgundy ($35 a square foot). At Ian Ingersoll’s workshop and gallery the furnituremaker handcrafts chairs and benches in the Shaker style (422 Sharon Goshen Tnpk.; ianingersoll.com).
Litchfield County covers 920 square miles, which means that it can take about an hour to travel from Bridgewater to Salisbury. Getting from one town to another requires at least a 15-minute drive (if driving is not an option, Carriage Limousine car service knows the area well, 800-782-0570). For shoppers: There may be an upswing in full-timers, but the area’s best-known antiques shops are usually open weekends only, or by appointment. And lastly, RuralIntelligence.com, a blog that covers all things Litchfield (as well as nearby Dutchess, Berkshire, and Columbia counties), is manned by former magazine editors Dan Shaw and Marilyn Bethany, who keep tabs on everything from small farms selling organic beef to the best place to catch Fourth of July fireworks.