1. Where to Stay
Hit the outdoors at the sprawling Winvian (from $650), a country estate and spa located next to the White Memorial Foundation Nature Preserve in Morris. Ask the staff to make arrangements for hiking, mountain biking, horseback riding, or hot air ballooning, and sleep in one of eighteen private, themed cottages (golf, music, maritime) spread over the property’s 113 acres.
Indulge in the Deep Blue Lavender Embrace ($245 for 90 minutes) at Washington’s Mayflower Inn & Spa (from $545), a five-star pampering haven. The treatment—a mix of buffing, steam, and massage—uses lavender, peppermint, rosemary, ginger grass, and fir scents to put you in a country state of mind. Rooms in the quaint Colonial Mayflower House boast four-poster canopy beds and eighteenth- and nineteenth-century art works.
Enjoy a mash-up of old and new at the Falls Village Inn (from $199), a stately three-story Victorian brought out of foreclosure and reopened in March by designer and local resident Bunny Williams. While the 1834 structure has been left intact, the interior has been thoroughly modernized, with formerly fusty décor replaced with contemporary touches like Moroccan tables and zebra prints.
2. Where to Eat
Dine in high locavore style at Community Table, a farm-to-table operation helmed by Chef Joel Viehland, formerly of Copenhagen’s famed Noma. The menu, which changes weekly, recently included slow-smoked suckling pig with roasted onions, peppers, peaches, and kale ($26), and a rabbit fricassée with an open ravioli of mushrooms and ramps ($23). There’s no liquor, but there are well-chosen local wines (a Sauvignon Blanc blend from Woodbury, $9 per glass) and beer.
Tuck into traditional country-inn favorites like French onion soup ($6.95) and peppercorn filet mignon ($32) at the cozy George Washington Tavern. Head there on a Saturday night when live jazz and blues attract a local crowd, and be sure to try the sticky toffee pudding ($6.75) for dessert.
Rub elbows with the army of regulars at Dottie’s Diner in Woodbury (740 Main Street South; 203-263-2545), where the signature dish is a hearty chicken pot pie ($13.95). The rib-sticking macaroni and cheese ($4.95) and meatloaf ($12.95) have earned a cult following; be sure to save room for the chocolate-covered cinnamon doughnuts (80 cents each), which are a local obsession.
3. What to Do
Ogle top-tier antiques at Buckley & Buckley (84 Main Street, Salisbury; 860-435-9919), where items like eighteenth-century Queen Anne tables and Dutch period accessories are for sale in a charming white Colonial home. Casual antiquers can hit Carey Sanford Antiques (469 Bantam Road, Litchfield; 860-567-4041) for artwork, home furnishings, and books. Native American jewelry is a specialty here; silver and turquoise bracelets are currently on sale from $75.
Hook eighteen-inch rainbow trout on the Housatonic River, a formerly PCB-chocked waterway that has been significantly restored in recent years to the renowned trout fishery it once was. The guides at Housatonic River Outfitters ($275 for full-day guided trips for two) can point beginners and experts alike to the thousands of replenished fish. If you’d rather just take in the scenery, Clarke Outdoors offers canoe, kayak, and rafting trips suitable for novices (from $24).
4. Insider’s Tip
Although wet summer weather led to flooded fields and diminished crops for many New England farms, Ellsworth Hill Orchard & Berry Farm in Sharon fared better than most due to its advantageous mountaintop location. Pick out a perfect pumpkin (60 cents per pound) or a bushel of apples, and wander through the winding corn maze (through November).
5. Oddball Day
Experience culture clash in the town of Kent, home to a quirky mix of wealthy New Yorkers with second homes (Oscar de la Renta, Henry Kissinger), prep schools, art galleries, and scruffy backpackers. Fuel up with sweet potato pancakes ($5.49) at the Villager Restaurant before spending a few hours on the Appalachian Trail. The best option is the Bull’s Bridge trail, which offers everything from a relatively easy walk across the namesake covered bridge past waterfalls and rapids along the Housatonic River, to a more strenuous uphill jaunt to a picture-postcard scenic overlook above the river. Reward yourself back in town with an espresso ($1) and Three Funkey Monkeys (a trio of white-, milk-, and dark-chocolate chimps; $7.95) at Kent Coffee & Chocolate Company. Spend the afternoon browsing the stacks at the pleasantly musty Richard Lindsey Bookseller (15 North Main Street, Kent; 860-927-3025), home to 7,000 titles. In the early evening, stroll Old Barn Road to view contemporary paintings at the Morrison Gallery and Ober Gallery. For dinner, try the roast half-duck flambé ($28), carved tableside, and a bottle of Silver Oak Cabernet ($130) at the old-school Continental dining haunt Fife ’n Drum.
Find weekly events listings and other local news at the Litchfield County Times.
Connecticut Magazine publishes in-depth travel, dining, and shopping information.
The Northwest Connecticut Chamber of Commerce offers a thorough guide to hotels, restaurants, and activities.