Dating in Litchfield Hills
In shortThe Litchfield Hills are quiet, rural and beautiful, and people here often drive a fair way for a date. That makes a scenic drive with a lunch stop a natural plan. Fall is the busiest and most colorful time to go.
A first date idea
A western Connecticut foliage drive
CTvisit's foliage route starts in New Preston, loops Lake Waramaug, then follows Route 7 along the Housatonic River past the West Cornwall Covered Bridge. It finishes on the Litchfield Green, where you can stop for a meal. Go on a weekday if you can, as fall weekends are busy.
Source: CTvisit: The Ultimate Foliage Tour, Western Connecticut, checked 8 November 2026
Drive the back roads to the West Cornwall Covered Bridge.
For more ideas, read where Connecticut singles actually meet or fall dates in Connecticut.
