Litchfield Hills Loop Drive Offers Unexpected Pleasures

Trees bloom in front of a home outside Woodbury, Connecticut, along the Litchfield Hills Loop.

Trees bloom in front of a home outside Woodbury, Connecticut, along the Litchfield Hills Loop.

Story by Kassondra Cloos; photos by Michael Ciaglo

Kassondra is a freelance writer from Rhode Island currently slow-traveling the world. Michael is a freelance photographer based in Denver, Colorado.

The northwest Connecticut road trip showcases scenery and shopping.

Postcard-worthy red barns sinking into rolling hills, an antique shop located in a former grist mill, farm-fresh food — all this and more characterizes the northwest corner of Connecticut, something of a well-kept secret. When a friend and I drove through the sparsely-populated Litchfield Hills, I found a Connecticut I never knew existed.

We began the roughly 75-mile-long Litchfield Hills Loop in Woodbury, Connecticut, about 90 miles north of New York City, and wound our way through West Cornwall, Warren, Litchfield and Kent. As we exited Interstate 84 and turned up Highway 6, we opened the sunroof of our rented Jeep, ready to immerse ourselves in classic New England.

One sunny but crisp morning, I hopped on an e-bike alongside Bob Ensign, owner of Covered Bridge Electric Bike in West Cornwall, and we zipped up and over the hills. I didn’t think I was into road cycling, especially not on an incline, but the bike did almost all the hard work, so I enjoyed the views of the rolling farmland.

On a rainy afternoon drive, the scenic landscape was saturated in deep shades of green, crafting a tunnel of leaves that cradled the road, branches laden with cherry blossoms on nearly every curve. It felt like traveling through a fairytale forest.

Warm Welcomes, Great Antiquing

At every stop on the trip, we found an easy friendliness not often associated with my native New England. At Good News Restaurant and Bar in Woodbury, the owner, Carole Peck, stopped to chat as we munched on sautéed fiddlehead ferns, a seasonal local delicacy foraged just for her customers.

We asked Carole where to go antiquing, and she called the George Champion Modern Shop to ask if George himself would show us around. His showroom is a midcentury modern paradise, teeming with Eames and Tecno chairs in such quantity, you’d think vintage picking was easy.

We also stopped at Mill House Antiques, a former gristmill along the Nonnewaug River. Moss-covered crabapple trees surround the building, and ivy cascades near the front door. I couldn’t help but open every single 18th-century European writing box and “traveling desk” and imagine what it might be like to write a letter with a quill while inside a carriage rumbling between palaces.

Around every curve, as we explored with little in the way of plans, I wished we’d allotted more than two days for the trip. Just a few minutes’ drive from the Hopkins Inn, where we stayed on the edge of Lake Waramaug in Warren, we hiked short trails around the Pinnacle, a panoramic overlook I'd have guessed was in the Shenandoah Valley if I’d not walked there myself. Indeed, the Appalachian Trail, which stretches 2,190 through forests from Maine to Georgia, crosses through these very hills.

As I peered over Lake Waramaug from a rocky overlook, enjoying the last few moments before dusk on our last day, I felt entirely at peace. The Litchfield Loop is far too pretty — and too easy a drive from New York — to be this quiet. But I must admit, I didn’t mind being part of the secret. 


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