Boasts laid-back luxury and spotless beaches.
Laid-back luxury in a charming New England town
The small, artsy town of Westport, Connecticut, boasts laid-back luxury and spotless beaches. The area’s earliest inhabitants, the Indigenous Pequot tribe, called this land “Machamux,” translated by the colonists as “beautiful land.” Westport has been a growing natural landscape since the late 1600s when settlers first began to expand the area for farming. The scenic coastline and natural wonders of the surrounding forests make Westport a visually charming and bewitching place to call home.
F. Scott Fitzgerald moved to Westport during the early 1900s — a time of great cultural expansion for this small town. Westport was known as creative heaven back then, and it remains so today. Around the turn of the 20th century, the town’s reputation became synonymous with art, and New York City residents began to pine for the tranquil atmosphere of Westport. They moved to the area and turned the farming town into a more suburban development but brought their artistic ideas and creative passions with them. Today, Westport is a thriving and affluent neighborhood that promotes art, nature, and the spirit of community, all within a 20-mile radius.
• The 234-acre Sherwood Island State Park
• Idyllic shoreline views
• The award-winning Westport Library offers hundreds of free programs throughout the year and brings in world-famous authors for visits and book signings
Residents of Westport enjoy a leisurely lifestyle. From shopping along Bedford Square, attending the Yankee Doodle Fair with the kids, or enjoying an afternoon out on the water, citizens of Westport appreciate the relaxing, laid-back atmosphere of their small town. It’s also a commuter’s paradise — New York City is easily accessible by train, and most residents are younger families, retirees, entrepreneurs, and young professionals.
Actor Paul Newman famously was from Westport and started the Newman’s Own Foundation, which strives to support children, nutrition and encourage philanthropy for citizens in America and beyond. Residents of Westport continue his legacy by focusing on community and providing charitable opportunities to help people in need throughout the world.
A restaurant is bound to be delicious when they provide an accompanying Spotify playlist. Turn up the tunes and visit bartaco to satisfy your Mexican-American cravings and enjoy your meal in their sprawling dining room or elaborate outdoor patio. Their menu is extensive, and each dish is made with fresh, quality ingredients. Another great dining destination is Pink Sumo, Westport’s go-to spot for sushi. Offering a Japanese and Cuban mix of flavors, Pink Sumo is a hip spot to enjoy dishes like blacked tuna tataki, fried avocado spring rolls, and dozens of hand-rolled sushi options.
For an upscale dining experience, a visit to The Whelk is a must. They offer a seasonal and ever-changing menu full of dishes made with fresh, local ingredients. The design of the restaurant is visually appealing — the huge windows overlooking the Saugatuck River put you in the perfect mood to enjoy delicious seafood in a relaxed atmosphere. Their menu features dishes like roasted oysters, barbecued clams, and mouth-watering seasonal desserts.
For a “sophisticatedly casual menu” in a fun and unique atmosphere, visit Little Barn, a cozy, rustic-chic barn with an outdoor patio that’s open year-round. The barn features an extensive and varied menu (try the colossal pretzel, tuna tacos, or the Thai chicken Buddha bowl), monthly live music, and an atmosphere that makes you feel comfortable and welcomed. Little Barn received a Certificate of Excellence from Tripadvisor in 2018.
Bedford Square is the place to shop in Westport. This shopping district is located in the “Golden Triangle” of Westport that includes high-end retail and dining options. Shops like Anthropologie, Serena & Lily, Nic & Zoe, and Williams Sonoma are included in this upscale, open-air shopping district. The architecture of the retailers, residences, and restaurants is reminiscent of early Tudor London homes and makes for a beautiful backdrop on a fun shopping day.