Among the prettiest of New England towns, Litchfield, founded in 1719, is set in a landscape of rolling hills, endless woodlands, and early American houses. You can almost imagine arriving by stagecoach—especially as this was once an important stopover between Boston and New York. Many 18th- and 19th-century houses stand along the streets that radiate from the village green, in styles from Georgian and Saltbox to Greek Revival, along with later classics. Nearby towns in Litchfield County—Washington, Salisbury, Kent—figure in American history. Today the area is home to many well-known designers, artists, and actors.