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 (860/824-7040) in the heart of 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—a couple of clothing stores and an old movie theater—is anything but prissy, a refreshing change of pace from the overly tidy tourist towns that dominate the surrounding region.
From North Canaan, US-44 winds east toward Hartford, stopping after 15 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 private 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 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. Even then, prim little Salisbury, a half-dozen miles west of US-7 at the junction of Route 41 and US-44, still may elicit reveries about what small-town America would look like if strip malls ceased to exist. Spend an afternoon sipping cardamom-scented tea in tiny Chaiwalla, on US-44 at 1 Main Street, or step over to Academy Street to nosh on a stylish lunch at the Harvest Bakery, while regulars banter with the owner as they stock up on the delicious breads and desserts, and see if you don’t conclude that franchising of fast food should be declared a misdemeanor.