The Best Things to Do in Southport, CT

Southport, CT

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

Pequot BeachSouthport 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 public beach by the Sealodge Beach Club, 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.

Along Harbor Road, stately mansions front the harbor and the private Pequot Yacht Club. (Sadly, you’ll have to enjoy the boats from the shore unless you already know a member.) Don’t miss the art in front of trader Andrew J. Hall’s place on Harbor Road across from Perry’s Green: The millionaire still has a few pieces on his front lawn, even though one was loaned to MassMoCA after a spat with the town that reached the Supreme Court.

Southport Center is the crossroads of the historic village. Southport Galleries is worth a quick stop to see what’s on view; Switzer’s Pharmacy is 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

ArtisanAt the Delamar Southport hotel, Artisan is a polished new 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 really want a burger, head a mile up Post Road to the Westfield outpost of Shake Shack. At lunchtime on a Sunday, there was nary a person waiting in line.

Where to stay

Delamar SouthportThe 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. 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 environmentally friendly changes that integrate biodegradable cleaning products and energy-efficient lighting have gotten a nod of approval from the Connecticut State Department of Energy and Environmental Protection.

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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