It had been years since I last explored the winding, scenic roadways of western Connecticut, but I fondly recalled the joy of cruising alongside rivers, through covered bridges and forests, and among farms and waterfalls. It was time for a return trip, and this 113-mile loop route certainly qualifies as a favorite ride.
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I met two friends, Pathfinder Rich and Yamaha Joe, at the Putnam Diner in Patterson, New York, a few miles from the Connecticut border. Rich was riding his BMW K 1600 GTL, Joe was on his customized Yamaha Stryker 1300, and I rode my trusty Kawasaki Vulcan 900 Classic LT.
We crossed into Connecticut on a brilliant sunny day and began heading north on State Route 37 through forests and farms. We stopped at Great Hollow Nature Preserve, which encompasses 825 acres of wetlands, woods, and hiking trails, as well as a restored 18th century farmhouse used for environmental workshops.
Back on the road, we enjoyed the clean, clear air and the soothing warmth of the sun. At Sherman, we continued north on State Route 39, passing by more farms and country estates. We made a stop at Greener Pastures, a farmstand that sells vegetables and pasture-raised meat produced on-site at the idyllic, 100-year-old Happy Acres Farm.
Continuing our northward path, we turned east on State Route 55 for a few miles to Gaylordsville, then turned north on U.S. Route 7 and crossed the Housatonic River. We cruised alongside the river to Bulls Bridge Road, where we took a brief detour to ride through Bull’s Bridge, which was built in 1842 and is one of three historic covered bridges in Connecticut.
We cruised through the small riverside town of Kent, which has quaint shops, galleries, restaurants, and the authentic feel of 19th century New England.
Next, we stopped to stretch our legs and to admire the view at Kent Falls State Park, where the Kent Falls Brook cascades 250 feet as the cool, clear waters make their way to the Housatonic. Rather than climb the trail to the top of the falls, we turned our attention to two trikes in the parking lot: a silver Gold Wing and a bright orange Rewaco – one of the wildest machines we’d ever seen.
We continued our cruise up U.S. 7 along the Housatonic, crossing the river at the town of Cornwall Bridge. On the other side, I spotted a beautiful white clapboard country church. The St. Bridget Church, built in 1883, is typical of churches in rural western Connecticut. Its serene setting next to the river tempted us to stay longer, but we had to answer the call of the road.
A few miles farther north, we crossed the Housatonic again via State Route 128, riding through the 172-foot-long West Cornwall Bridge, another historic covered bridge that was built in 1864.
After riding back across the bridge, we followed U.S. 7 north again to North Canaan, where we had lunch. For our return route south, we made a counterclockwise loop via U.S. Route 44 and State Routes 41 and 4 back to the town of Cornwall Bridge. We enjoyed cruising through the quilted land of farms, lakes, forests, and villages, where there was something new to see around every corner and bend.
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South of Cornwall Bridge, we took State Route 45 to Lake Waramaug, which is surrounded by low-lying mountains and picturesque country homes. We circumnavigated the lake on a winding route that included North Shore Road, Lake Waramaug Road, and West Shore Road before returning to SR-45. Two state parks adjacent to the 656-acre lake offer plenty of recreation opportunities.
Since the day was growing late, we left the beautiful lake behind and started our journey home. Heading south on U.S. Route 202, we crossed the Housatonic again near New Milford and backtracked on U.S. 7 to SR-37 and New York.
Riding along the weaving roads, the cool, late afternoon air was invigorating. As the sun washed the landscape with color, I was glad I had made it to western Connecticut again. Its many beautiful sights and pleasant backroads make for an enjoyable and interesting ride.
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Western Connecticut Motorcycle Ride Resources
Kenneth W. Dahse is a writer and photographer from northern New Jersey and a regular contributor to Rider. Ken has been riding since he was a teenager, and his favorite rides are relaxed multiday excursions.
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