If I only had one afternoon to share with riders from out of town, I'd treat them to a ride along the Route 7 corridor between New York and Connecticut. Naturally, we'd have to do some tire kicking at Marcus Dairy (just off Route 84 in Danbury) first, though I'd caution them to tread lightly when ordering breakfast, especially if they're watching their cholesterol-care for some eggs with that grease? From there, we'd head north on the local roads I've been exploring for 30 years. These secondary routes wind among farms, small lakes and homesteads that were already old before the redcoats were chased out of New England.
After some back-road bending, we'd take a breather in the village of Gaylordsville, mainly so I could tell them the dark tale of the Pyramid. The huge cinderblock edifice isn't very pretty, and neither is its story. Its builder created it as a monument to a child born out of his incestuous relationship with his daughter.
Just up the road, we might stop at the Bulls Bridge Inn for a drink if it's a cold autumn day and a quick ride through the famous covered bridge before continuing north on Route 7 along the Housatonic River. Or perhaps we'd just carry through until we hit the town of Kent. It's a genteel village, typical of "old money" New England, though in recent years it's become somewhat of a tourist trap, especially on weekends.
But the farther north we go, the better it gets. The road winds along the river past several pristine state parks-with camping permitted-and some of the best fly-fishing territory in the country. This section of Route 7 is a designated scenic road, so be prepared to share it with leaf peepers and antique hunters, not to mention local farm equipment and truck traffic. But if we time our ride right (early morning on the weekends or midday during the workweek is best, especially in the fall, when the leaves are in full color), we should have most of the road to ourselves. If it's warm enough, a picnic at Housatonic Meadows State Park wouldn't be too difficult to arrange. We can get our vittles at the old general store and watch kayaks shoot the rapids while we eat.
The next 15 miles of road through Litchfield County are some of the best I've ever ridden. In the spring and summer, pine scent permeates the air, and in the winter, the naked beauty of the river can take your breath away, as can the chill coming off it. A short detour through another covered bridge at the hamlet of West Cornwall would get us over the water, and then it would be up the road, through Falls Village and Canaan, before heading past Lime Rock Raceway, one of my favorite motorcycle tracks.
The roads heading back are less traveled, and they can also be extremely entertaining. We'd loop back toward New York State, maybe heading south on Route 22 for a short spell, before cutting back along the fast downhill sweepers of Route 4 back in Connecticut. From there, it'd be a quick toot over to Route 45, which would take us past the abandoned, allegedly haunted ruins of Dudleytown, around Lake Waramaug, and through the towns of Washington Depot and Roxbury, Connecticut. All told, this short and sweet ride would cover about 150 miles, making it a decent day trip or providing the perfect starting point for an extended tour of New England.