Route 7 through Connecticut's Litchfield Hills is, by any measure, one of the finest antique drives in the United States. The road follows the Housatonic River north through a succession of perfectly preserved New England villages, each with its own constellation of dealers — some tucked into old barns, others installed in Federal-style storefronts that have been selling antiques since before World War II.
What distinguishes this corridor is the quality ceiling. The dealers here are serious professionals who buy at auction, travel to England and France, and expect their clients to know the difference between a Chippendale chair and a Hepplewhite one. Bargain hunters will find richer hunting elsewhere, but serious collectors seeking authenticated 18th- and 19th-century American pieces will find few places in the country to rival it.
Plan for a full day, start early at New Milford, and work your way north. Lunch in Kent. Linger in West Cornwall. End with the remarkable cluster of high-end dealers in Salisbury before the afternoon light fades over the Berkshire foothills.