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Westport

Boasts laid-back luxury and spotless beaches.

Welcome to Westport


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.

What to Love


 • 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

Local Lifestyle


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.

Dining, Entertainment, and Shopping


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.

Things To Do


The ultimate outdoor community destination is the Levitt Pavilion, an entertainment space that provides free access to the performing arts and brings nationally recognized artists to the Westport area. Their mission is to cultivate an outdoor community center for people of all ages and backgrounds to enjoy the arts and nature. The summer concert series has been named “the most ambitious and entertaining free summer festival in the Northeast” by The New York Times and offers free concerts every night over the summer.

The Westport Women’s Club hosts the Yankee Doodle Fair, a “Westport Institution” and family-favorite event. Attended by residents and non-residents alike, the Yankee Doodle Fair runs for four days in June and brings a huge carnival to the community. The fair is run by Women’s Club volunteers, and proceeds from the event go to help local service organizations. The fair features a bake sale, carnival rides and games, an International Food Court, and raffle prizes.

Westport Fine Arts Festival
has been a Westport tradition for 48 years. Held over Memorial Day weekend, the festival brings thousands of collectors and residents from the tri-state area to showcase their unique talents. The festival is free, though the artwork is available for purchase, and local food vendors, live music, and a vast array of mediums are represented during this nationally recognized celebration of art.

Schools


Westport has several high-achieving public and private schools in the area. Some include:

 • Coleytown Elementary School, a public school for grades K-5
 • Greens Farms Academy, an independent school for grades PreK-12
 • Staples High School, a public school for grades 9-12
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