A Local’s Guide to Historic Southport, CT

About Southport

Settled in 1639, Southport, CT, is a small coastal village within the town of Fairfield, featuring quintessential New England charm on every street.

The layout of Southport is shaped by four different landscapes in the village—Southport Harbor, the Southport Historic District and downtown area, Southport Park, and Southport Beach.

The Southport Historic District has been on the National Register of Historic Places since 1971 to commemorate and preserve its history as a center of commerce and culture during the New Nation period and the National Expansion and Reform period. As you walk or drive along Pequot Avenue through Harbor Road, you’ll notice the historic buildings and traditional gardens overlooking the Long Island Sound.

This home featured in Architectural Digest captures Southport residents’ attitude towards blending tradition and modernity today—residents enjoy the charm and space of their Connecticut home while also taking advantage of the close proximity to New York City by train or car.

Compared to other coastal villages in Fairfield County, Southport benefits from its convenient location in Fairfield, a beautiful, established town itself that always has a full community calendar of activities year-round.

If you want to learn more about the history of Southport, listen to audio tours led by Jason Robards, who goes into detail about key historic homes and monuments in the Southport Historic District.

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Points of Interest in Southport, CT

Southport Harbor

Take in the waterfront views from Perry’s Green next to Pequot Yacht Club—watch the sailboats go by in the summer and the sun set behind the Country Club of Fairfield. If you prefer more activity, many runners and cyclists also take the scenic routes along Harbor Road and Pequot Avenue.

Note: If you belong to a reciprocal club of the Pequot Yacht Club, plan your visit in accordance with both your home club’s dock office and the Pequot Yacht Club’s dock office to secure a mooring reservation.

Address: 701 Harbor Road, Southport, CT 06890

Southport Park

Under the care of The Sasquanaug Conservancy for Southport, the 12-acre nature preserve is open to the public from dawn to dusk. There is a designated area for those walking with dogs, as well as picnic and playscape areas for families and children.

Address: 170 Old Post Road, Southport, CT 06890

Southport Beach

Southport Beach is one of the four beaches in Fairfield—it’s the second smallest beach, so it’s typically occupied by Southport residents who live nearby, while most Fairfield residents go to Jennings or Penfield. A resident permit through the Town of Fairfield is required for parking; the beach is open to the public.

Address: 1505 Pequot Avenue, Southport, CT 06890

Pequot Library

Founded in 1889, the Pequot Library continues to serve as a beacon of culture and community engagement over seven generations. The Pequot Library is a hidden gem for quiet study or small meetings—in partnership with the Fairfield Public Library, a Fairfield Public Library card grants members access to both the Pequot Library and the Fairfield Public Library.

Address: 720 Pequot Avenue, Southport, CT 06890

Shop and Stroll on Pequot Avenue

The village center of Southport has several locally owned restaurants and shops. For home goods and décor, Foxtrot Home and Lattice House are well worth a visit after an early coffee or brunch nearby.

Visit nearby Fairfield, Westport, Easton, or Redding

If you want to expand your horizons and explore beyond Southport, there’s a lot to see within a 20-minute drive. Fairfield is down the street; downtown Westport has plenty of stores, restaurants, and other attractions; and Easton and Redding offer more rural views of the area.

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Cafés and Restaurants in Southport Historic District

Gray Goose

The cozy American restaurant knows how to make the obligatory staples—juicy burgers, fresh salads, and mean martinis.

Address: 246 Old Post Road, Southport, CT 06890

Artisan at Delamar Southport

Located inside Delamar Southport, Artisan is a beloved fixture for Southport and Fairfield residents who want to celebrate a special occasion or simply enjoy a bright and sophisticated atmosphere. Guests can expect a diverse and elegant wine list to pair with the farm-to-table dishes.

Address: 275 Old Post Road, Southport, CT 06890

Sammy’s Southport Pizza & Grill

Not sure where to order your Friday night pizza in Southport? Sammy’s may be the only place to choose from in the village, but thankfully, it’s also a great pizzeria that makes a variety of pizzas, including Sicilian-style, thin-crust, and specialty gourmet pizzas.

Address: 295 Pequot Avenue, Southport, CT 06890

Horseshoe Tavern & Café

Referred to as “The Shoe” by locals, the Horseshoe Tavern was originally a blacksmith shop from 1916 until 1934, when it became a family-run restaurant. Horseshoe Tavern is proud to be run by the Fraser family for five generations and to continue the legacy of bringing the Southport and Fairfield community together.

Address: 355 Pequot Avenue, Southport, CT 06890

G Bakery

The “G” stands for gentilezza, which means “gentleness” in Italian, and is present at all G Bakery locations throughout Connecticut, including Southport. Fresh sourdough breads are baked daily, and baked goods and coffee are also available.

Address: 353 Pequot Avenue, Southport, CT 06890

Paci

A culinary gem tucked inside one of Southport’s outbuildings for the train station, the modern Italian restaurant has an intimate atmosphere in the main dining room and bar.

Address: 96 Station Street, Southport, CT 06890

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Additional Café and Restaurant Options in Southport

Southport Diner

Address: 3350 Post Rd, Southport, CT 06890

Hotaru

Address: 3363 Post Road, Southport, CT 06890

Mama Chow

Address: 3381 Post Road, Southport, CT 06890

Organika Kitchen

Address: 3456 Post Road, Southport, CT 06890

Garelick and Herbs Southport

Address: 3611 Post Rd, Southport, CT 06890

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