Scenic Summer Drive in Connecticut

A drive through Connecticut’s Litchfield Hills takes you from one picturesque town to another on roads that wrap around hills, trace river valleys, and slice through woodlands. You will see shimmering waters, expansive views, tidy village centers, and green hillsides. As with any trip, there are side roads to explore, making this a jaunt that can often be repeated without becoming repetitious.

Start on Route 7 just south of the Massachusetts border, in North Canaan. Right off the bat, there’s something worth stopping for: the New England Accordion Connection & Museum Company, a one-of-a-kind attraction situated within the painstakingly restored Victorian-era Canaan Union Station.

Head south of town on Route 7, which eventually begins running along the Housatonic River and through a state forest that skirts the border of Sharon (where the Sharon Audubon Center is a worthy diversion) and Cornwall, billed as “the greenest town in Connecticut.” If you see an opportunity to outflank the fly fishermen and score a parking space in one of the roadside jug handles, seize it. Photo opportunities abound here, but space to pull over and admire them does not. Either way, don’t miss the pinnacle of all photo ops, the c. 1864 West Cornwall Covered Bridge.

Plan to linger for a while in Kent, home to Kent Falls State Park, the Kent Collection Inns, and, for indie bookstore lovers, the House of Books; covered-bridge aficionados may opt for a side excursion to nearby Bull’s Bridge. From Kent, you’ll leave Route 7 and head east on 341, toward Warren and beautiful Lake Waramaug, eventually connecting with Route 202 near Washington, the town that inspired the TV show Gilmore Girls.

Sitting right off 202, Mount Tom State Park presents an opportunity to stretch your legs, and a moderately challenging climb pays off with an extraordinary 360-degree view from the 34-foot stone tower at the summit. On the road east to Litchfield, a trio of Arethusa Farm eateries in Bantam create a tourist trap you will be happy to be ensnared in.

Litchfield’s Village Green serves up a bevy of restaurants and boutique shops to explore before you continue on 202 into the (relatively) big city of Torrington, where you’ll look for Route 272 north. That will carry you up to Norfolk, home of the Yale Summer School of Music, and beyond that the return to Canaan, where you’ll already be planning your next go-round.

Yankee‘s Favorite Places to Stop Along the Way

New England Accordion Connection & Museum Company, North Canaan: More than 500 accordions, each with a story, line the walls in a restored train station that is also home to the Connecticut Railroad Historical Association and Great Falls Brewing Company. newengland accordionconnectionand museumcompany.com

Music Mountain, Falls Village: Located on 120 acres and listed on the National Register of Historic Places, Music Mountain has been presenting concerts that span classical to jazz in Gordon Hall since 1930. The 2023 season opens June 4. musicmountain.org

Clarke Outdoors, Cornwall: If you prefer getting out on the water to admiring it from the riverbank, you can find kayak rentals here, as well as guided tours and drop-off services. clarkeoutdoors.com

RSVP French Kitchen, West Cornwall: Make sure you’ve obtained reservations well in advance to land one of the 20 seats at this acclaimed French eatery. The five-course prix fixe dinner is magnifique. Instagram

Eric Sloane Museum, Kent: Celebrate the world of author Eric Sloane through his paintings, books, illustrations, and antique hand tool collection. The museum grounds feature riverside walking trails, as well as the stone ruins of the Kent Iron Furnace. ericsloane.com

House of Books, Kent: There is absolutely no wasted space at this expertly curated little bookshop. Where else might you find a little book-length essay on the history of socks? houseofbooksct.com

Mount Tom State Park, Litchfield: This 231-acre outdoor playground offers one-stop recreation at its finest: Work up a sweat climbing to the peak, then hit the beach for a quick lake dip to cool off. portal.ct.gov/DEEP

Arethusa a Mano,Bantam: This bakery-café is among three worthy Arethusa offerings here, along with the restaurant Arethusa al Tavolo and the scoop shop Arethusa Farm Dairy. arethusafarm.com

Winvian Farm, Morris: Just a few miles south of Litchfield lies this 113-acre luxury hotel comprising the 1775 Seth Bird house, 18 themed cottages (including a treehouse and a beaver lodge), a AAA Five Diamond restaurant, and a spa. winvian.com

White Memorial Conservation Center, Litchfield: Surrounded by a 4,000-acre wildlife sanctuary and more than 35 miles of walking trails, this museum and education center offers a deep dive into the region’s natural history. whitememorialcc.org

Haystack Mountain State Park, Norfolk: The views of Norfolk and Canaan from the 1929 observation tower atop this 1,716-foot peak make the hike worthwhile (though you can opt to take the auto road halfway up). portal.ct.gov/DEEP

Infinity Music Hall, Norfolk: Built in 1883 as a combination opera house, barbershop, and saloon, this 300-seat village landmark still features its original wooden stage, and the on-site GoodWorks Smokehouse takes the dinner-and-a-show concept to glorious new levels. infinityhall.com

Norfolk Chamber Music Festival, Norfolk: One of the country’s oldest summer music festivals, NCMF brings together emerging musicians and experienced pros, with memorable results. music.yale.edu/Norfolk

Have you driven this route (or do you have another drive to recommend)? Let us know your favorite stops along the way in the comments below!