Portsmouth

A small but lively Colonial port across the river from Kittery, Maine, upscale Portsmouth buzzes with trendy restaurants, swank cocktails bars, contemporary art galleries and boutiques, and acclaimed cultural venues that host nationally recognized speakers and performers—the action is focused largely around downtown's Market Square. Settled in 1623 as Strawbery Banke, Portsmouth grew into a prosperous port before the Revolutionary War, during which it harbored many Tory sympathizers. These days, this city of 22,000 has many grand residences from the 18th to the early 20th century, some of them preserved within or—such as the Wentworth-Coolidge Mansion and Governor John Langdon House—on the blocks near the fascinating Strawbery Banke Museum, and others are close by, such as the Wentworth-Gardner House. For a scenic drive or bike ride, follow Rte. 1B east from downtown across the Piscataqua River, following it around leafy New Castle Island—where you'll pass Fort Constitution and the grand, historic Wentworth by the Sea Hotel.