Connecticut's Old-School Town Near New York City Is A New England Charmer With Excellent Eats

Situated a little over an hour away from New York City, Southport, Connecticut, feels worlds away from the Big Apple's hustle and bustle. This scenic seaside village in Fairfield County offers a peaceful, upscale retreat replete with New England charm. Whether you're planning a weekend escape or an extended stay, Southport is highly accessible and endlessly inviting.

The shopping experience here, whether you're browsing for coastal-inspired fashion or one-of-a-kind antiques, is at once relaxed and refined. To connect with the outdoors, walk the dog, or give the kids time to play, be sure to visit the 10-acre Southport Park. And, small though it may be, Southport Beach offers a peaceful stretch of sand ideal for kayaking, sunbathing, or watching the sailboats drift by. Southport also features numerous cultural spots, including a theater, library, and history museum. 

Westchester County Airport in White Plains, New York, is located around a 40-minute drive from Southport. This regional airport is served by major carriers such as American Airlines and Delta, making it a convenient entry point for travelers flying in from across the U.S. For lodging, you can stay at the popular Delamar Southport, a European-style boutique hotel infused with timeless elegance. Have some time to venture a little further afield? Southport echoes nearby Milford, a scenic city with New England charm, lively arts, and delectable eats. Located just 15 miles away, it makes a great addition to any itinerary when traveling around Connecticut.

Great news for history buffs: Southport is nothing less than a living time capsule. Originally known as Mill River Village, Southport was established in 1639 as part of the Fairfield settlement, but it didn't come to be recognized as a local historic district until 1967. The coastal hamlet managed to preserve its colonial roots while evolving into one of Connecticut's most picturesque and historically rich communities. By the 1890s, it was supplying a whopping 100,000 barrels of onions annually to other cities throughout the country, cementing its reputation as a major shipping center. 

Southport's transformation from a modest riverside settlement to a bustling 19th-century shipping port is still reflected in its harbor, historic buildings, and cultural landmarks. Strolling through the Southport Historic District feels like stepping into a curated museum of American architecture. The elegant homes showcase varying styles, including the Victorian Gothic Moses Bulkley House and the Greek Revival Austin Perry House. Many of these homes are lovingly preserved and still privately owned, giving the village a lived-in authenticity.

Founded in 1889 and listed on the National Register of Historic Places, the Pequot Library is a cultural treasure. With its community events and rare book collection, it's more than just a library — it's a gathering place that reflects Southport's artistic and intellectual spirit. Though perhaps not as grand as Baltimore's George Peabody Library, an underrated treasure trove with grand architecture, the fact that its special collections number over 30,000 objects further testifies that this is no run-of-the-mill library. 

No visit to Southport is complete without making the rounds at its outstanding eateries. The village may be small, but its culinary scene looms large. From classic New England seafood to upscale farm-to-table dining and cozy cafes, this town is a haven for even the pickiest foodies. 

Inside the Delamar Southport is Artisan, an elegant restaurant that serves signature seasonal dishes. If available, ask to be seated in the garden patio, a phenomenal setting for brunch or dinner. What's more, the delicious continental breakfast includes fresh eggs and pastries to fuel you up before sightseeing. For a more casual vibe, The Gray Goose Cafe delivers with its eclectic New American menu and rustic-chic interior. Stop by for a delicious lunch or a laid-back dinner, with choices ranging from truffle fries to fresh seafood specials.

Seafood diehards should also make the 15-minute drive to the waterfront La Plage Restaurant & Oyster Bar in Westport. Meanwhile, meat lovers should not skip out on the inviting Blackstones Steakhouse. Looking for something more low-key? The Horseshoe Cafe, open daily, delights patrons with hearty burgers, live music, and a welcoming atmosphere. If you simply want an afternoon pick-me-up, head to the G Cafe Bakery, where the smell of fresh croissants and rich and roasty espresso alone will lift your spirits before you've even placed an order. And, if you have a hankering for pizza, you can always make the half-hour drive to New Haven, the pizza capital of the U.S. Needless to say, if you're going to be in the Constitution State, it's strongly recommended that you come hungry!