The Undiscovered Joys of Southport, Connecticut
Along the Connecticut coast, little south of, say, Branford can be thought of as “undiscovered.” There are a million fun things to see and do in Fairfield, for example, but it often feels like the known world. That’s why a true find in those parts is so unexpected.
Nestled right in the bustling town of Fairfield, not far from Westport, is just such a hidden treasure—Southport. Covering only about 3 ½ square miles, it’s more like a neighborhood than a town. On the Register of Historic Places since 1971, it’s a bit like being transported back in time. From the classical 1830s of Connecticut before the advent of the railroad to the nostalgic 1950s to the height of Victorian excess, and then back to 2015, Southport brims with charm and character.
Possessing some of the most charming historic homes in New England, the dwellings here are the historic legacy of Southport’s commercial surge in the late 18th and early 19th centuries, when the town was one of the most important trading ports between Bridgeport and New York.
Former successful merchants’ and sea captains’ homes dot the streets; some so reminiscent of the Deep South that you’d swear you were in a port imagined by Mark Twain. No surprise there—one of Southport’s most successful trading routes was between Savannah and Charleston, which clearly influenced the design of its many federal and classical homes. Later on, some of Fairfield’s most prominent industrialists owned Victorian-style homes that still dazzle with their romantic forms, dramatic porches, and bright colors.
Southport’s streets feature sidewalks bordered by manicured lawns, iron fences, and impressive gardens. A walking tour of the town can begin at the junction of Harbor and Rose Hill roads, which is set on a bluff overlooking the harbor.
As you make your way down the hill to the water’s edge, you’ll see a pleasant brick building—the members-only Pequot Yacht Club. Established in 1920, this sailing club continues to thrive today with members who are active cruisers and racers in the sport at regional, national, and international levels. On a stretch of lawn next door, you might catch sight of picnickers relaxing at Perry Green, a public space that commands a full view of Southport Harbor, where yachts and sailboats bob. Farther down on Harbor Road is one of Fairfield’s two public marinas—Ye Yacht Yard—that accommodates 60 small boats and provides boat launch services for residents.
Anchoring the village is the Pequot Library, a breathtaking Romanesque structure designed by the celebrated architect Robert H. Robertson in 1894. Although it has 30,000 volumes, it’s much more than a book repository. Pequot Library is a cultural institution, conceived by Southport’s 19th century elite as a place where residents and visitors could expand their knowledge of books, art, music, and more.
On one side of the building there are wood-paneled reading rooms with cozy fireplaces that complement the library’s stacks. The book collection expands over two levels, and the original Victorian ironwork, spiral staircases, glass floors, and dramatic Tiffany glass window are magnificent.
On the other side of the structure is one of New England’s finest and most “acoustically renowned” concert halls, designed long before electronic amplifiers were invented. On any given weekend, you might stumble onto a concert from the Music for Youth series, an author talk, or an exhibit in The Perkin Gallery.
Two annual events not to be missed include the Pequot Art Show featuring work from local painters and photographers, and the “Holiday Caroling Party” on December 18. Complete with horse-drawn carriage rides, school choirs, and Santa. It’s is a local favorite.
Standing tall over the village and close to Pequot Library is Trinity Episcopal Church, with its dramatic white painted spire evoking an image of a wedding cake. Built in 1856, the building and its congregants have been tested several times by nature. A tornado in 1862 brought the steeple down, crashing into the sanctuary roof. The community banded together to rebuild it.
Three years ago, when Hurricane Sandy hit, the normally calm waters of Horse Tavern Creek Marsh rose into Trinity’s courtyard, breaking through windows and devastating the nursery school. It has been since restored, and the quiet spectacle of the old church still casts a beautiful silhouette at sunset.
An overnight stay in Southport should start at the Delamar Hotel, with its designer-decorated rooms, and Artisan—its terrific farm-to-table restaurant presided over by French chef Frederic Kieffer. Dine indoors in the more casual tavern area with the vintage 1920s bar or in the fancier dining room adorned with murals of lilies.
Enjoy a pre-dinner craft cocktail outside on the expansive patio lined with colorful Adirondack chairs. There is even a small but well-staffed spa on the premises for a couples massage or facial.
If you have the luxury of a couple of days to explore, you can embark on a culinary tour of the area. On a crisp fall afternoon, start with a sandwich from the Spic and Span market (we recommend the Reuben or any of their home-made soups)—another Southport institution that has been around since 1928. Bring your picnic to Southport Park, a 10-acre nature preserve great for walking or resting—a result of a collaboration between Aspetuck Land Trust, the Sasquanaug Association, Southport Conservancy, and the Southport Area Association.
If you continue on a 10-minute walk down Pequot Avenue, you’ll land on the shores of Southport Beach, the perfect place to catch a breeze and take off your shoes. It’s open to the public (and dogs) from October to May.
Locals rave about the lobster bisque, craft cocktails, and steak tips at The Grey Goose, and Italian food lovers covet the northern Italian specialties at Paci, a stalwart located in the vaulted stone ceilings of the Southport train station. For more casual dining, there’s the Driftwood, where you can have a seat at a luncheonette that will transport you back to the 1960s. Or grab a slice from the recently renovated Sammy’s Southport Pizza.
Southport is also home to the oldest tavern in Connecticut—The Horseshoe Tavern—where you are as likely to meet a long-time resident as you are a young Wall-Streeter just off the train.
As varied as Southport’s dining options, so too are its shopping venues.
There’s J. McLaughlin with its chic but preppy New England wear, Mama Jane’s Global Boutique, selling funky tunics and accessories made in various countries, and Walin & Wolff, with its eclectic offering of high-fashion shoes and accessories.
The Women’s Exchange, a non-profit organization first started in 1892, is staffed by volunteers and filled with gourmet food products, vintage and antique treasures, and carefully curated gift items, many of which are handcrafted by local artisans.
Speaking of antiques, Runk Douglas specializes in period English furniture, paintings, and vintage chic garden treasures. Across the street is Kasson Jewelers, a family owned business featuring both modern and estate fine jewelry. A popular spot to buy a hostess gift is Barbara Barbara, which offers a funky selection of bits and baubles.
No matter how much modernity abounds, Southport villagers are determined to maintain its historical past. A longtime hardware store is now a successful art gallery—Southport Galleries. Owners Sissy and Kelsey Biggers maintained the integrity of the old storefront inside and out—right down to keeping the 1920s painted wood shelving in the gallery space.
Featuring art of some notable American painters as well as contemporary work from a varied group, the gallery always has a show or new art to view. You might just leave with a new piece for your mantle. There’s a decidedly 1950s feel next door at Switzer’s Pharmacy where, if you’re lucky, you might meet Paddy the parrot. Weather permitting, co-owner Jack Ringle loves to keep his late wife’s pet bird outside to greet the neighborhood. An old-world pharmacy, people love the personalized service, not to mention the fact that you can buy a bottle of wine there.
Most folks coming up or down Route 95 pass right by Exit 19, Southport, without knowing the historic charms and the slow pace awaiting them in Southport Village. It’s a gem hiding in plain sight, and definitely worth your time.