Storybook Southport


To drive through historic Southport village is to travel back in time. Fortunately, strict zoning laws ensure that the village’s rich history will remain intact indefinitely; Southport is listed on the National Register of Historic Places. The offerings in the commercial part of Pequot Avenue in this charming village are abundant. Along with boutiques, the Fairfield Women’s Exchange, an antique store, the Horseshoe Bar (known as the oldest tavern in CT), Southport Galleries, and Southport Pizza, locals can also stop here for provisions at Spic and Span Market and toiletries at Switzer’s Pharmacy. Just around the corner, the Delamar Hotel provides the perfect atmosphere for out of town guests, and Artisan Restaurant boasts both excellent food and a bar with an outside terrace. Across the street, Gray Goose offers more casual dining and a lively bar scene. The historic residential areas of the village, all within walking distance of the “downtown”, are arguably among the most scenic and picturesque in New England; architectural styles include Victorian, Federal, Colonial, and Greek Revival. But the village is really much more than this charming downtown and its coveted dwellings. Along with its own train station, coffee shop, and fire station, you’ll also find:

  • The harbor – located next to the Pequot Yacht Club (a private sailing club), Perry Green is the perfect spot for a picnic. In early June, Ye Yacht Yard, a public marina on the tip of Harbor Road, hosts the annual Blessing of the Fleets, a parade and ceremony to launch a bountiful and safe season on the water.
  • Churches – Locals walk to Southport Congregational Church, which hosts the annual design showcase “Rooms With a View, and Trinity Episcopal Church, built in 1856, this is a community symbol and landmark with its historic spire. Both churches, by the way, offer coveted preschools.
  • Southport Park – the recently opened 11-acre park provides walking trails for families, joggers, and dog-walkers. Map stands and interest stations are provided throughout the trails to provide people with information about the local flora and fauna. A natural playscape at the park’s opening is a perfect draw for children before heading out on a family hike.

  • Southport Beach – Just past the library along Pequot Avenue, many walkers and joggers take a break to take in the view at this quaint beach, also perfect for exploring during low tide. This is truly a hidden treasure of Southport
  • Wakeman Boys & Girls Club – this amazing nonprofit organization keeps on growing. Serving kids in Fairfield, Southport, and Bridgeport, this clubhouse offers tons of after-school and weekend activities, and includes a gym, computer center, art studio, weight room, and turf field.
  • A public library, Pequot Library, is located in a Romanesque building a few blocks down Pequot Avenue. Along with a vast collection of rare books, the library provides a myriad of programs, including lecturers, authors, performers, and events for children. Annual events include an egg roll at Easter, caroling during Christmas, a Kentucky Derby tailgate, and art show.

Walking along the bluestone sidewalks to marvel at the historic homes is a treat. During the summer months, the hydrangeas pop among the beautiful landscaping that abounds here. The best part about this time capsule? It’s also convenient. When life calls you outside of the village, you can still get to downtown Fairfield in five minutes. The best of both worlds.

About Cindy Raney

Riverside Realty Group
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