Tucked Away in Connecticut’s Coastal Corner: A Charming Town with Sandy Beaches and an Adorable Downtown

Tucked in the southwestern corner of the state of Connecticut is a coastal gem that offers old-world New England charm, along with a locale in short proximity to one of the most iconic cities in the world. The setting is Westport, Connecticut, a town of just over 25,000 residents that sits along the shores of the Long Island Sound. It’s one of the most affluent suburbs in the area, and it’s also rich in culture while preserving the land’s beauty. The waterside setting of Westport has brought settlers here for close to 400 years, dating back to the Native Americans, and today, it’s an idyllic town on the Connecticut coastline that is one of the most desired destinations in southern New England.

Situated on the waters that connect New England to the Atlantic, Westport is a picturesque community that is actually geographically closer to New York City than Connecticut’s bustling and underrated capital city of Hartford. The scenes of day-to-day life in Westport make it feel like a world away, making it an ideal town for New York City travelers who want to also experience an oceanside setting devoid of city noise. The Saugatuck River winds through the adorable town filled with cute restaurants and shops to explore, and the white sand beaches of Westport will have you forgetting where you are on the map. Westport invites you to unwind and take in your surroundings.

The origins of Westport date back to Native American settlements in the mid-17th century, but today’s residents who call Westport home range from creatives and entrepreneurs to New York City business commuters looking for leisure and a beachside setting when they’re not working. Westport’s convenience of having the Metro North Railroad and Interstate 95 minutes from the city also allows for it to be a great day trip in the Tri-state region. The train ride to Manhattan averages about 65-70 minutes to drop you off in Grand Central Station in the heart of the action, making it a great hack to help navigate New York City. In the heart of Westport, Main Street is a mix of old-world feel and new-school charm, featuring brick buildings with modernized shops that are functional while fitting the aesthetic of this coastal enclave. 

Instead of venturing into New York City to check out the Museum of Modern Art (MoMA), Westport’s Museum of Contemporary Art offers a convenient way to enjoy local creative culture. Sculptures, exhibits, live music, and performing arts are just a sampling of the showcases at MoCA, which sits just a few miles north of Westport’s downtown shopping district along the east bank of the Saugatuck River. It’s there where you can shop to your heart’s content in a lovely, old-school New England setting that has the mid-century wonderland vibe of a neighboring town. The red brick walkways and old-world architecture feature modernized shops for all tastes. Big brands, including Lululemon and Vineyard Vines, are popular, and visitors say the Anthropologie in Westport is more expansive than the NYC flagship store. There are also local boutiques such as Great Stuff and a plethora of cute eateries to stop in as you tour downtown.