This town of 18,600 overlooking Long Island Sound is so New England picturesque that former president Bill Clinton singled it out in his memoir, My Life, as an "especially old and beautiful" favorite during his time at Yale. But at a mere 36 square miles along the Connecticut shoreline, Madison is easy to miss—and residents happen to like it that way.
Almost exactly halfway between New York City and Boston, Madison attracts a sophisticated mix of professionals—lawyers, accountants, architects—as well as a growing community of artists. They frequent the town's independent boutiques and family-owned restaurants, most of which are housed in the two-story shingled and redbrick buildings (many dating from the 1930s) that line Main Street. In the summer, a scenic green in the heart of downtown hosts outdoor concerts and a farmers' market.
Left: R.J. Julia Booksellers, a Publisher's Weekly Bookseller of the Year and the crown jewel of downtown
Locals mostly know Madison as a quintessential laid-back beach town with a best-kept-secret feel. But word has gotten out: The community is drawing more and more second-home owners from neighboring metropolises. And although the majority of houses here are Colonial and Cape-style, averaging just below $500,000, the spectacular cedar-shingled waterfront homes—tucked among the hydrangeas of Middle Beach Road and Middle Beach West, and dotting the small streets off Liberty Road—go for millions.
"Often, buyers start out as summer folks," says native Kirsten Adams, who returned five years ago after a stint in San Francisco, "but then they fall in love with the town and realize that Madison is a wonderful place to live year-round. My husband and I made the decision to come back for family and a simpler way of life. It's a great town."
Left: Beautiful homes facing Long Island Sound
- The History: Old New England history is evident in Madison's many remaining antique buildings, such as the 1690 Meigs-Bishop House. Henry Bacon, the architect of the town library, went on to create the Lincoln Memorial.
- The Unspoiled Shore: Hammonasset State Park—Connecticut's largest shoreline park—has two miles of beach for shelling. And don't forget the binoculars: Some 300 species of birds, from loons and ospreys to the lesser-known marbled godwit, call this slice of coast home.
- The Deals: Cozy condos near downtown start around $250,000—and you're just a few minutes drive to the beach. And while prices for most single-family residences average right around $500,000, large fixer-uppers can go for $200,000 and less.
- The Convenience: Although it feels worlds away, Madison is just a quarter mile from major Connecticut thoroughfare Interstate 95. Positioned 20 minutes from New Haven, the town is both an off-the-grid escape and an easy commute to Boston and New York.
Left: Fun for all ages on the beach at Hammonasset State Park
Beach: The purple sands of the town's smaller East Wharf Beach are ideal for reading a book without interruption. Surf Club Beach is a favorite with families, thanks to lifeguard-protected swimming and courts for playing basketball and volleyball.
Main Street: Down Boston Post Road, dozens of locally owned shops line the street for unique finds: stationery in Two Ems, artisan jewels at Bella Perlina, and avian items at the Audubon Shop, a destination for birders from all over the Northeast.
Left: birdhouses at the Audubon Shop
Restaurants: Elizabeth's Café has inspired takes on comfort food, including a panko-crusted crab cake and rigatoni with Maine lobster. The Wharf Restaurant's seaside deck is the spot for an evening of fresh-shucked oysters and a bottle of rosé.
Activities: The ancient, rocky hills and gray cliffs of Rockland Preserve provide access to paths lined with rare flowers and hulking oak trees. Sustainable family farm Barberry Hill hosts popular farm dinners throughout the summer, and also sells its produce.
Left: A sandy path from The Wharf Restaurant to the sea