WESTPORT

Westport occupies Fairfield County's Gold Coast along Long Island Sound, about 48 miles northeast of New York City. The town splits its commercial activity between downtown Main Street and the waterfront Saugatuck neighborhood.

Levitt Pavilion has run free outdoor concerts every summer since 1973, hosting roughly 60 performances a season on its stage at 260 South Compo Road overlooking the Saugatuck River. Westport Country Playhouse, a nonprofit theater founded in 1931, produces a full season of professional plays and musicals.

Downtown Westport lines the Saugatuck River with independent shops, galleries, and seasonal outdoor dining. Greens Farms, the town's oldest neighborhood, has its own train station and post office south of the Post Road.

Tip: Levitt Pavilion concerts are free but a handful of annual fundraiser events are ticketed — confirm before showing up with a blanket.

Neighborhoods: Downtown • Saugatuck • Greens Farms