Crossing into Connecticut from the north on US-7, the first thing that will catch your eye is the stainless-steel siding of Collin’s Diner (53 Main St., 860/824-7040) in North Canaan. A classic 1940s prefab O’Mahony diner, Collin’s has all the usual diner standards, and its big parking lot (shared with the neighboring historic railroad depot) is frequently full of equally classic cars, whose owners congregate here on summer afternoons. The rest of North Canaan is anything but prissy, a refreshing change of pace from the overly tidy tourist towns that dominate the surrounding region.
From Canaan, US-44 winds east toward Hartford, stopping after 12 miles at another gem of a small town, Norfolk; if any town has capitalized on being far removed from trading floors and board meetings, it’s this one. With three public parks and the largest nonprofit-owned and operated forest in the state, Norfolk has considered its sheer scenic beauty a stock-in-trade for nearly a century. The town green is worth the drive so that you can see the folksy road sign that points the way with pictures of rabbits and other cute creatures.
After extensive touring around New England, you risk taking white columns, wide porches, picket fences, and the obligatory Congregational steeple for granted.