New Milford

If you're approaching the Litchfield Hills from the south, New Milford is a practical starting point to begin a visit. It was also a starting point for a young cobbler named Roger Sherman, who, in 1743, opened his shop where Main and Church streets meet. A Declaration of Independence signatory, Sherman also helped draft the Articles of Confederation and the Constitution. You'll find old shops, galleries, and eateries all within a short stroll of New Milford green—one of the longest in New England.