If your goal is to ride Yankee Country with its rural roads, quaint colonial villages and charming churches, there’s no place better than western Connecticut and Massachusetts. On this interesting trip, I had the additional benefit of riding some of the scenic roads of northern New Jersey and southern New York as part of my motorcycling adventure. The roads of this four-state, multi-day excursion weave and roll through forests and mountains, alongside lakes and waterfalls, through small towns, parks and covered bridges, all of which ensure an excellent motorcycle getaway.
I began my tour in West Milford, New Jersey, cruising on Greenwood Lake Turnpike (State Route 511) beside the shimmering blue waters of the 560-acre Monksville Reservoir. From there, Sloatsburg Road passes historic Ringwood Manor Mansion, where General Washington slept and the mines supplied the Continental Army with the iron ore needed for its cannons. In Sloatsburg, New York, I turned onto the recently repaved Seven Lakes Drive and cruised through the lush 46,613-acre Harriman State Park. There’s nothing more soothing than rolling along on fresh, smooth asphalt while riding through forests alongside glistening lakes.
At the east end of the park, Perkins Memorial Drive takes you to the summit of Bear Mountain with its panoramic views of mountains, the New York City skyline (40 miles south) and mighty Hudson River. On weekends, Perkins is a rider and tourist mecca, and you never know what interesting sights await you.
After crossing the Bear Mountain Bridge hundreds of feet above the colossal Hudson River, I took State Route 9D to the Cold Springs area, which has 19th-century architecture, restaurants and impressive views of mountains, the river and West Point Military Academy from its riverside park. From there, State Route 301 took the Nomad and me east until we were enveloped by forest. The 1,600cc Kawasaki ate up the twisties on this rolling serpentine road like a ravenous child eating greasy fries, but when a statue of Buddha appeared marking the entrance to the Chuang Yen Monastery I decided to stop. I’m not a religious person in the traditional sense, but find that when visiting places of worship, an enjoyable sense of serenity washes over me like a warm wave.
Route 301 weaves through Fahnestock Memorial State Park and skirts by several reservoirs before it ends in Carmel. From there, I headed north on State Routes 52 to 311 and 22, then finally rumbled into Yankee Country on State Route 55. At Gaylordsville, we sailed north on the snaky and scenic U.S. Highway 7, which parallels the 142-mile-long Housatonic River.
Bulls Bridge was built in the 19th century and is one of the last three covered bridges in Connecticut. After stretching my legs with a short hike across it and along the river, enjoying both the woods and the thundering cascade, I fired up my Nomad and headed toward Kent. This is the quintessential small Yankee village: neat, quaint and charming with several restaurants, shops (including an independent book store) and galleries. A few miles north of town is Kent Falls State Park, which has picnicking, hiking trails and stream wading. The park features a series of falls that plunge over 250 feet. A short, steep hike leads you to the series in its entirety, or you can stroll to the base and view the last three falls dancing down the mountainside.
A few miles north of the park is the West Cornwall Covered Bridge. Built in 1864, it spans the Housatonic River and is 172 feet long. A small park on the other side of the bridge is a great place for a break, as is the Wandering Moose Café across the street.
From the bridge, I continued riding northward on U.S. Highway 7, my Nomad humming sweetly in my ear while the warm sun caressed my face and the fresh-scented air cleansed my lungs. Tall trees and lush greenery hug the roadway here. Although I stayed mostly on Highway 7 north through Connecticut and Massachusetts, you can deviate from it and explore other nearby roads, as well. Highway 7 in Connecticut is a superior ride over Highway 7 in Massachusetts because it is more rural. In Massachusetts, towns appear in greater frequency and most are deserving of a brief stop and walkabout.
Another quintessential Yankee town is Stockbridge, Massachusetts. If it looks like something out of a Norman Rockwell painting, that’s because it is. His painting of this “most famous Main Street in America” has been popular for decades. Rockwell lived and worked in Stockbridge for many years and there’s a museum devoted to him on the outskirts of town, with paintings depicting the idealized wholesome qualities of the Yankee spirit and lifestyle.
Stockbridge is also known for its legendary eatery. Now Theresa’s Stockbridge Café, it was formerly the Alice’s Restaurant made famous by Arlo Guthrie in his 1967 antiwar song/album/film of the same name. Arlo is the son of the famous Depression-era troubadour Woody Guthrie, who inspired a young Bob Dylan. One of Arlo’s most memorable lines in the song is, “You can get anything you want at Alice’s Restaurant—excepting Alice.” The restaurant is small, with a 19th-century style and much Arlo memorabilia. In fact, he still stops by from time to time. Deciding to have a late lunch there, I wolfed down a delicious and healthy turkey wrap with sprouts, lettuce and tomato.
By the time I arrived at the southern entrance/visitor center of the 12,500-acre Mount Greylock State Reservation, the highest mountain in Massachusetts, I was drained and the day had grown late so I rumbled on to Williamstown and my motel. The 1896 House complex encompasses two motels, luxury suites, a pool, restaurant and pub. The rooms are clean, the grounds attractive and the food excellent.
After a refreshing swim and a hot shower, I went to the pub for what must be the biggest, juiciest and tastiest bison burger on earth. Afterward, I spoke with the barkeep about the area and my next day’s ride. He suggested I head east on scenic State Route 2, but only as far as Greenfield, because after that Route 2 becomes congested. Route 2 is known as the Mohawk Trail, as it was a Native American trade route before the Europeans arrived. This additional stretch would add hours to the ride and require some backtracking. But that’s the beauty of being solo on the road, as I can go where the spirit moves me.
The next morning, from the southern entrance, I meandered easily through the forest, passing hiking trails and stopping at several scenic overlooks on the eight-mile ride up the serpentine road to the summit. On a clear day, mountains ranges in five states can be seen 60-90 miles away. On this day, the viewing conditions were good but not optimum. At the summit are the rustic Bascom Lodge and the 92-foot granite tower that commemorates all the brave American soldiers who were casualties in our wars. From its observation area, an unrestricted 360-degree panorama unfolds before your eyes.
After savoring the views, I remounted the bike and rode down the mountain, heading east on the Mohawk Trail (Route 2). Starting with the hairpin turn at the beginning of the climb into the mountains above Williamstown, I was rewarded with several impressive vistas while cruising over the mountains. After riding through several state forests, I stopped at Charlemont to see the Hail to the Sunrise statue. Erected in 1932, it honors the people of the Mohawk Nations.
In Shelburne Falls, the largest, politically incorrect cigar-store Indian I have ever seen soars 20 feet above your head. Eileen Rauch, the manager of the Native Views Mohawk Tepee store, said local Mohawks were originally upset with it, but after much discussion all had agreed that placing a statement at the base of the statue identifying it as a stereotype of a Plains Indian, and not representative of the eastern woodland Indians, would alleviate the slight. Peace in our time.
A little beyond Shelburne Falls, it was time to begin the trek home, so I U-turned and rolled west on Route 2, with a plan to explore State Route 8A south. The road was rough at first where it traverses parts of the Mohawk Trail State Forest, through some backwoods communities and the Kenneth M. Dubuque Memorial Forest. Stopping to stretch my legs, a black bear meandered across a yard. With my heart pounding, I reached for my camera and managed to get a few shots off before the bear melted into the forest.
Continuing on 8A, I connected with U.S. Highway 8 and rode the tree-lined, rolling and twisting two-lane road to Connecticut. At Winsted, Route 8 turns into a four-lane highway but is still scenic. My original plan was to take Route 8 to Litchfield and return via two-lane roads back to Gaylordsville, doing the last legs of my journey on the same routes on which I began. However, once I hit the highway on my Nomad and took it to the limit, there was no turning off the superslab. I stayed on Route 8 to Interstate 84 and blasted my way home.
Cruising to and through Yankee Country offers the rider quite a variety of mountains, lakes, rivers, waterfalls, covered bridges, quaint towns and fine roads. It’s a trip through gorgeous scenery and our country’s history that I already want to do again.
(This article Cruising Yankee Country was published in the August 2013 issue of Rider magazine.)