There are no lobster shacks in Southport, Connecticut. But considering that the tiny hamlet is so close to Manhattan, it’s about as New England as you can get just 70 minutes from Grand Central.
Set on a small inlet on Long Island Sound, the village is full of good restaurants, small but lovely beaches and perfectly manicured yards literally hemmed in by whitewashed picket fences. The main hub of activity in Southport is a historic library that hosts one of the region’s best book sales.
Conveniently served by Metro-North, Southport has flown under the radar of most weekenders, dwarfed by larger Connecticut towns like Bridgeport, Greenwich and New Haven. Tiny though Southport may be—population in 2010: 1,585—it has plenty to do on a weekend overnight, particularly if you bring your bike: quiet streets, rolling hills and short distances make Southport an ideal place for a pedal.
What to do
Southport is full of stately homes, quiet streets and fresh breezes off Long Island Sound, so the main thing to do is simply slow down, relax and breathe the fresh air. (On my visit over a steamy weekend in Manhattan, it felt mercifully and markedly cooler in town.) For ideal relaxation, head to the small Southport Beach, where kids build sand castles and parents dip into frothy reads while the very gentle waves lap the shore. You won’t mistake it for the Caribbean, but watching sailboats cruise by in the distance as you bronze offers its own sort of zen.
The Pequot Library is a social hub of the village, and the Summer Book Sale is one of the banner events, drawing vendors from around the country who deal in everything from current fiction to antiques as well as collectible vinyl and 45s. Other events fill the calendar, and the building itself is an architectural gem.
Southport Center is the crossroads of the historic village. Southport Galleries is worth a quick stop to see what’s on view. Afterwards, head to Switzer’s Pharmacy for a trip back in time. There are a few quick bites, here too, if you want to grab a snack before catching the train home.
In neighboring Fairfield, the Carl Dickman par-three course offers a great, easy game, with club and pull-cart rental available.
Where to eat
At the Delamar Southport hotel, Artisan is a polished American restaurant that leans heavily on seafood. Chef Frederic Kieffer dresses up traditional presentations—crab cakes, seafood chowder, sea bass—with welcome and creative flourishes. The contemporary cool of the dining room is tempered by hand-painted murals and bird’s nest-inspired chandeliers. An outdoor terrace and bar is less formal and just as good.
Set in the former eastbound station house, Paci is a fine-dining Italian restaurant with a tremendous wine list. The open kitchen adds some action to the relatively snug space that gets high marks for romance. The menu, which changes daily, leans heavily on the seasons, as all the best Italian food does.
Southport Brewing Company won’t win any culinary awards for the pub grub, but microbrew fanatics might want to try a couple of the house-made pours. If you want a classic meal, head to local diner The S&S Dugout Lunchonette for cheap food, dive vibes, and a basic meat and potatoes menu.
Where to stay
The only hotel in the village proper is the Delamar Southport, a converted apartment complex that has just 44 huge rooms, a thoughtfully curated house art collection and a killer restaurant. The in-room decor is a touch traditional and a touch nautical; elegant four-poster beds and big bathrooms come standard. While there’s no full-service spa, some treatments are available on property. During the spring and summer, bikes are available to guests. It’s a five-minute walk from Southport Station. Book the Metro-North package, which includes two roundtrip train tickets, champagne, deluxe accommodations, breakfast at Artisan Restaurant.
Further down Post Road from the Delamar, the Westport Inn is another small, modern boutique. A recently completed renovation borrows a beachy color palette from the nearby Sound, and free bikes for use along with a free shuttle to anywhere within 5 miles of the inn.
Directions: Southport is served by the New Haven line of the Metro-North Railroad, which you can catch in Manhattan at Grand Central Terminal or 125th Street. It’s about 70 minutes between Grand Central and Southport, and almost everything is within walking distance of the station. Before you take your bike, read this information on bicycles on Metro-North.
Photos: Delamar Southport, WalkingGeek, Paul Brady
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