The countrified hut urbane enclaves of Ridgefield and Westport, 15 miles apart in tony Fairfield County, have long enjoyed popularity among artists, actors, and writers. These two upscale towns are celebrated for their artistic attractions and downtowns abundant with galleries, fine restaurants, and elegant shops.
Despite its proximity to Manhattan, Ridgefield feels a bit like one of the grand colonial New England towns in northwestern Connecticut’s Litchfield Hills. Mature shade trees line Main Street, a wide showcase of storefront businesses and venerable mansions. Don’t miss the town’s seminal Aldrich Contemporary Art Museum, one of the first museums in the nation devoted exclusively to contemporary art. Its lack of a permanent collection is compensated for by provocative, changing exhibits that focus on emerging artists. Behind the museum is a fine 2-acre sculpture garden.
Downtown Ridgefield may be known for its snazzy restaurants, but the local legend is a modest hot-dog stand called Chez Lenard, which doles out such heavenly fare as Le Hot Dog Garniture Suisse (topped with cheese fondue blended with white wine and Kirsch). Later, dress up for dinner at Bernard’s, situated in one of the dignified clapboard houses that illustrate the town’s centuries-old roots. On Ridgefield’s border with the town of Wilton, you’ll find Connecticut’s only national park, the 153-acre Weir Farm National Historic Site, dedicated to Impressionist landscape artist J. Alden Weir.
It’s 12 miles southeast from the farm to Westport, perhaps best known to many as the longtime home of actors Paul Newman and Joanne Woodward, who are closely associated with the acclaimed Westport Country Playhouse, a supreme small-town theater (Elizabeth Taylor, Paul Robeson, and Bette Davis arc among the alums). Many of the first-rate dramas and comedies that originated in this converted barn moved on to greater fame on Broadway.
The perfect roost in this creative country outpost is one of the most whimsically decorated and sumptuous accommodations in New England. Westport’s Inn at National Hall occupies a three-story Italianate Victorian built in 1873 on the banks of the Saugatuck River. The eight rooms and eight suites have been designed by a cadre of talented local artisans and decorators with fancy and flair.