At anytime during riding season, the Cheshire County Loop offers an excellent day's ride for any motorcyclist. In the spring, when life is bursting forth, the earthy smells awaken a sense of adventure. On a quiet summer day, the tree-canopied roadways tease with dappled sunshine, and the ponds and lakes glint and reflect the sky above. And then autumn is perhaps the best, with New England's stunning palette of reds and golds painting the hillsides.
Start at the Irving Station on Route 101 at the Milford/Wilton line where you can fill the tank, have one last coffee, or purchase a few snacks for the road. Then head out on Route 31 north. Don't blink passing through Wilton or else you'll miss the town hall, a magnificent structure that dominates Main Street. On the approach into Greenfield, there's a big surprise: a large trebuchet aimed at a mock castle facade. In the fall the trebuchet is pressed into action and loaded with gourds that are hurled toward the fortress at the annual Pumkin' Chunkin' event.
From the town center of Greenfield, follow the signs for Greenfield State Park, continue on Forest Road, and soon, at the Hancock/Greenfield line, you'll cross the stream spilling from the Powder Mill Pond on the first of two picturesque covered bridges in the day's loop.