“Southport continues to lure world-class sailors and influential figures like GE CEO Jack Welch, along with Tina Weymouth and Chris Frantz of the Talking Heads.”
Tucked along the Long Island Sound, Southport, Connecticut is where time seems to have slowed down. Tiny—just about 3½ square miles—Southport is more neighborhood than town. Sandwiched between Westport and Fairfield, Southport may be small, but to those who live here, it’s the best-kept secret on the Connecticut coast. A former 19th-century shipping port, the village is a beautifully preserved storybook with waterfront Federal homes with white picket fences and hydrangeas spilling over stone walls, overlooking sailboats bobbing in the harbor near the Pequot Yacht Club.
Founded in 1639 as Mill River and renamed Southport in 1836 as shipping took off, the village hit its stride in the 19th century as a prosperous maritime hub. A small but very wealthy merchant class built elegant Federal, Greek Revival, and Victorian houses. Many remain intact today, thanks to Southport’s historical society and strict zoning—protections that earned Southport a place on the National Register of Historic Places in 1971.
One of America’s earliest cultural leaders, Jonathan Sturges, was born in Southport in 1802 and became a key patron of art and literature, supporting figures like Ralph Waldo Emerson, Herman Melville, and Hudson River School painter Frederic Edwin Church. Southport continues to lure world-class sailors and influential figures like GE CEO Jack Welch, along with Tina Weymouth and Chris Frantz of the Talking Heads.
“A longtime seasonal resident, Albert Hadley founded the designer show house “Rooms with a View,” supporting the missions of Southport Congregational Church.”
Preservation is central to Southport’s identity and great interior design is part of the village’s DNA. That reputation was cemented over 30 years ago through Albert Hadley, the legendary half of design team Parish-Hadley. A longtime seasonal resident, Hadley founded the designer show house “Rooms with a View,” supporting the missions of Southport Congregational Church. “Rooms with a View” has raised nearly $3 million for more than 19 local charities and attracts top talent like Bunny Williams and Victoria Hagan.
“The show reflects Southport’s respect for tradition and its commitment to giving back,” says interior designer Parker Rogers, who serves as design chair alongside his longtime partner and show director Christopher Phillip.
Another standout is the Pequot Library, built in 1894 by architect Robert H. Robertson, featuring wood-paneled reading rooms, fireplaces, spiral staircases, Victorian ironwork, and a striking Tiffany window. The library also houses a concert hall that hosts chamber music, author talks, and gallery exhibitions.
A short walk from the village is a 10-acre nature preserve created by the Aspetuck Land Trust and the Southport Conservancy, perfect for strolling or a picnic. Prefer sand to shade? Southport Beach is a few blocks away.
For an overnight stay, Delamar Southport has luxurious rooms and fine dining. Southport’s food scene stays refreshingly classic: locals swear by the lobster bisque and craft cocktails at The Gray Goose, while Paci serves Northern Italian specialties beneath the vaulted stone ceilings of the historic train station. And the Driftwood delivers retro charm—it’s a luncheonette happily stuck in the 1960s.
For those seeking a coastal lifestyle that feels relaxed, cultured, and charmingly timeless, Southport is one of Long Island Sound’s best-kept secrets. – TED HILDNER
