Litchfield Hills
Old New England in Its Sunday Best
The northwest corner of Connecticut is where New England keeps its 18th century polished and lived-in: white-clapboard villages around shaded greens, stone walls running through sugar maples, and a river valley strung with covered bridges, all within two hours of Manhattan. This ramble crosses the region west to east's mirror: from patrician Farmington, with its Impressionist-filled Hill-Stead Museum, to Litchfield, whose green and grand residential streets Sinclair Lewis judged the most beautiful in America, and where the Tapping Reeve house schooled the young republic's lawyers as America's first law school (Aaron Burr and John C. Calhoun among the alumni). The second act turns pastoral and then riverine: the 4,000-acre wilds of White Memorial, the vineyard shores of Lake Waramaug, and the art-and-antiques village of Kent, where the Appalachian Trail slips across Main Street. Route 7 then follows the Housatonic north past Connecticut's tallest cascade at Kent Falls, fly fishermen mid-river at Housatonic Meadows, and the barn-red 1841 covered bridge at West Cornwall, whose truss design bridge builders copied across the country. In early October, when the hardwoods turn, this is as concentrated a dose of classic New England as any drive on the continent.
Key Stops
Farmington. The gateway: an old-money river town where the Stanley-Whitman House preserves the 1720s in overhanging-gabled oak, and the Hill-Stead Museum, a 1898 country house designed by pioneering female architect Theodate Pope Riddle, hangs Monets and Degas in its original domestic rooms. Provision here or in Litchfield; the villages ahead run to cafes and general stores.
Topsmead State Forest. A short signed detour off Route 118: the Tudor-style summer estate that Edith Chase left to the people of Connecticut, its lawns, wildflower meadow, and stone-walled woods free to wander as if you owned them. The house opens on alternate summer weekends; the grounds are the point.
Litchfield. The centerpiece: one of New England's most perfect greens, overlooked by the steepled 1828 Congregational church, with North and South Streets' colonial mansions fanning out from it. Harriet Beecher Stowe was born here, and the Tapping Reeve House and Litchfield Law School tells how a small-town lawyer's classroom trained two vice presidents and shaped American law. A few minutes south on Route 63, White Flower Farm's display gardens bloom all season.
White Memorial Foundation. Southwest on Route 202, Connecticut's largest nature preserve: 4,000 acres of woods, wetlands, and Bantam Lake shoreline threaded with level trails and boardwalks, plus a family-friendly nature museum. Bantam Lake once shipped 75,000 tons of winter ice a year to New York; the conservation center still demonstrates the harvest.
Mt. Tom State Park. A compact classic: a short, steep trail to a bluestone lookout tower with views to the Catskills, and a spring-fed pond below for a bracing summer swim. One of the state's oldest parks and an easy hour.
Lake Waramaug and New Preston. Routes 202 and 45 deliver the drive's loveliest water: a 680-acre lake curling among green hills, with a state park beach and campground at its head and Hopkins Vineyard pouring tastings above the shore. Tiny New Preston, at the lake's outlet, packs design shops and cafes into a former mill hamlet.
Kent. West on Route 341 through Warren to the Housatonic, where Kent stacks galleries, bookshops, and eateries along Main Street while Appalachian Trail thru-hikers resupply among the browsers. South of town, Bulls Bridge, one of Connecticut's two drivable covered bridges, crosses the river beside churning cataracts; north of town, the Eric Sloane Museum honors early American tools and craftsmanship.
Kent Falls State Park. Connecticut's showpiece waterfall: a series of cascades dropping 250 feet through the woods to a meadow made for picnics, with a stair-and-platform trail climbing beside the water. Spring snowmelt and October color are its two peak performances.
Housatonic Meadows State Park. Route 7 rides the river through a corridor of pines where fly fishermen work the trout water and paddlers slide past riverside campsites. Pull-offs invite you to simply watch the river for a while.
West Cornwall. A turn onto Route 128 funnels you through the drive's icon: the one-lane, barn-red covered bridge of 1841, 242 feet across the Housatonic, its lattice-and-truss engineering so sound it was imitated nationwide. The hamlet beyond keeps a pottery, a general store, and absolute quiet.
Falls Village, Lime Rock, and Canaan. The final leg offers summer diversions: chamber music at Music Mountain above Falls Village (among America's oldest summer chamber festivals), vintage sports cars at Lime Rock Park, the storied circuit Paul Newman called home, and a finish among the cafes of Canaan, with the Berkshires beckoning north or a looping return to Litchfield.
Driving Tips
Book October like a holiday. Peak foliage (usually the first two weeks of October) fills every inn and B&B weeks ahead and slows Route 7 to a leaf-peeper procession on weekends. Midweek color trips get the same trees and half the traffic.
Expect deer at every dusk. The wooded two-lanes between villages carry constant deer traffic in low light, the region's one genuine driving hazard; the winding Routes 341 and 45 deserve particular care.
Know the state-park fee rules. Connecticut-registered vehicles enter state parks free under the Passport to Parks program, while out-of-state vehicles pay seasonal entry fees at the popular parks like Kent Falls and Mt. Tom; carry a card, and arrive early on summer and foliage weekends when lots close at capacity.
Mind the covered-bridge etiquette. West Cornwall's bridge is one lane with alternating traffic and a posted height limit; yield graciously, cross slowly, and photograph from the banks, not the roadway.
Time the villages' hours. Galleries, antiques shops, and small museums here often close Tuesday and Wednesday and keep gentle hours generally; Kent and Litchfield are liveliest Thursday through Sunday.
Check the Lime Rock calendar both ways. Race weekends bring crowds and paddock buzz worth planning around (in either direction), while the track's famous local agreement keeps it quiet on Sundays.
For more information visit: CTvisit, Connecticut's Official Tourism Site