The northwestern corner of Connecticut is rural New England distilled, refined into a pure essence of covered bridges, small villages changed little since the 19th century, dignified historic homes, and innumerable trees that turn lush green in summer, change brilliantly in fall, and sparkle with ice crystals in winter. It is only a portion of what Connecticut has to offer, but it’s what many people instinctively imagine when Connecticut comes to mind.
Knowing how much there is to take in here, and how deceptively far apart Litchfield County towns can be, I wanted to map out a little road trip showcasing some of this area’s most scenic spots. This loop takes you past a few Instagram-famous highlights and many more underappreciated gems as it winds through a region where industry and agriculture have long coexisted with natural beauty. Along the way you’ll find quirky small businesses, wineries, old barns, farms spread out across hillsides, sweet little post offices and venerable town halls, and blue bridges spanning lively rivers.
You’ll also be tempted by nearly constant opportunities to turn down different roads, peek around more corners, and create your own route through this captivating place.
Start in Collinsville, a village located in the town of Canton. The centerpiece of this 19th-century factory town is the visually striking complex of red buildings where the Collins Company once manufactured axes and other edged tools and weapons. (This is where Connecticut native John Brown bought the pikes he used in his 1859 raid on Harpers Ferry.) To get a good look at the old Axe Factory, walk along Bridge Street (Route 179) where it crosses the Farmington River.
If you have time, tour the fascinating collections of the Canton Historical Museum, and browse around the sprawling Antiques on the Farmington. Or, walk along Main Street and its short side streets to explore Collinsville’s lovely architecture and independent shops. Stop for food at LaSalle Market & Deli on Main Street.
From Bridge Street, turn left on River Road (Route 179N), then left again on Route 44 W.
Look out for the charming (and very small) Pine Meadow Historic District in New Hartford.
Turn right on Reservoir Road (Route 219), or continue on Route 44 to explore New Hartford’s charming Main Street before doubling back to turn onto Reservoir Road.
Turn left on Saville Dam Road (Route 318 W) to get to the Saville Dam and Barkhamsted Reservoir in Barkhamsted. If you stop to photograph the fairy-tale gatehouse, don’t miss the map of Connecticut on the opposite side of the road, below the flag.
Continue on Saville Dam Road (Route 318), which becomes Route 318/Route 181/Pleasant Valley Road in the Pleasant Valley section of Barkhamsted.
Turn right on East River Road, or continue straight to see one of the area’s prettiest small bridges, which crosses the Farmington River. From here, double back to turn onto East River Road or turn right on West River Road instead. East River Road runs through Peoples State Forest, and West River Road runs through American Legion State Forest. These roads are parallel to one another, and both will take you to your next destination. If you want to further explore the trails and other activities that Peoples State Forest and American Legion State Forest have to offer, pick your route based on which side appeals to you more.
From East River Road, turn left on Riverton Road, or from West River Road, turn right on Riverton Road to reach the picturesque historic district of Riverton, where you can’t miss the local inn, built in 1811, and the general store that dates from 1889.
Head west on Robertsville Road, then turn left on Old Forge Road, then right on Robertsville Road again. (Yes, this part is confusing.) Continue onto Deer Hill Road, which becomes Smith Hill Road, Old North Road, Old Colebrook Road, and Stillman Hill Road (Route 182 W.) Follow Route 182 until it meets Route 44, then turn right onto Route 44 W.
This will lead you to the relatively lively center of Norfolk, where lovers of eclectic historic buildings will appreciate the architecture on display around the town green and along Greenwoods Road (Route 44), the town’s main thoroughfare. The green Infinity Hall concert venue, built in 1883, is especially eye-catching.
Turn left on Lower Road in the East Canaan section of the town of North Canaan. Look out for the beautiful North Canaan Congregational Church, an opportunity to take a classic New England snapshot, then continue to the Beckley Iron Furnace Industrial Monument, worth a stop for its historical significance as well as its serene setting on the Blackberry River. (This also makes a nice picnic spot.)
Continue on Lower Road, then turn left on Route 7 S, then left on Sharon/Goshen Turnpike (Route 128) towards the West Cornwall section of Cornwall. You’ll cross the Housatonic River via the postcard-perfect West Cornwall Covered Bridge, one of Connecticut’s three remaining historic covered bridges.
Continue on Route 128, then continue straight onto on Bunker Hill Road/Sharon Turnpike (Route 4.) Turn right on Old Middle Street (Route 63) at the traffic circle in rural Goshen. Continue straight on Route 63/Goshen Road/North Street until you reach the town green at the center of Litchfield.
Litchfield’s downtown is famously pretty, and home to upscale shops and restaurants in a walkable area full of grand old homes and buildings. Walk along the green to take advantage of the more commercial side of town, then stroll down South Street for more beauty and history.
Drive further down South Street (Route 63), then turn left on Webster Road to find Arethusa Farm Gardens, the dairy farm and seasonal produce stand which, along with its associated restaurant and coffee shop in the nearby Bantam section of Litchfield, have probably brought more tourists to Litchfield in the past few years than any other single attraction.
If you have time, continue on Webster Road and Whites Wood Road, then turn left onto Bissell Road and left onto Whitehall Road to the White Memorial Conservation Center, where you can follow 40 miles of trails, some of which consist of wooden boardwalks elevated above wetlands, through some of the most beautiful scenery in the area.
From Litchfield, complete the road trip by returning to Collinsville via Routes 118, 4, and 179. Or continue on, to wherever piques your interest, to wherever the winding roads of the Litchfield Hills take you.
To drive this route takes roughly two hours without any stops. Plan for one full day to drive it all with stops at most of the places mentioned here, and two days (at least) if you want to add in extra time at a few of these spots or leave time for your own detours.
Cell service can be spotty or nonexistent in some areas, especially in and around Riverton.