Westport & Weston

Explore each town and what makes each one wonderful and unique


Just 47 miles from Manhattan, Westport is located on the “Gold Coast” shoreline of the Long Island Sound in Fairfield County, Connecticut. 

Covering 22 square miles, with a population of approximately 27,000, Westport is a vital and colorful community, rich in culture and history, yet bustling with 21st Century quality of life. With easy access to The Connecticut Turnpike (Route i95), the scenic Merritt Parkway and Metro North Railroad, it is clear why Westport has long been the mecca for commuters to Manhattan and Westchester as well as local businesses owners alike.

Westport is home to Connecticut’s #1 Ranked Public Schools, and nationally recognized Blue Ribbon systems, leading the way in curriculum, athletics, special education, gifted programs, and extracurricular activities, while stressing academic excellence and individual growth. 

Sometimes called
the “Rodeo Drive of Connecticut”,

Westport’s sophisticated yet informal Main Street atmosphere has attracted chic boutiques, fine dining and farm to table restaurants, making the town a gourmet and shopping haven. The Farmer’s Market became so popular, that it now assembles twice weekly, offering local produce, baked goods, flowers and more!

In 1960, its residents, a forward thinking active group, purchased the 110 acre Longshore Country Club for $1 million, for use as a town facility. This private country club, of which all Westport residents are automatically members, offers an 18 hole golf course, paddle, pickle and tennis courts, swimming pools, a sailing school along with town docks and daily boat rentals, and an outdoor ice skating rink in the winter.

F. Scott Fitzgerald summered here, as did Bette Davis. It is still home to many business leaders, artists and celebrities, who have joined the community to promote civic growth.

The late resident Paul Newman ran his “Hole in the Wall” charity here, while wife Joanne Woodward was busy running the committee to rebuild the Westport Playhouse. Michael Bolton stepped in at the last minute for a town fundraiser when planned entertainer Ray Charles fell ill.

The warmth of the summer finds Westport’s residents heading for the sand and surf of one of Westport’s private beaches, Sherwood Island State Park or the free outdoor summer concerts, performed nightly at The Levitt Pavilion. Our summer open air Art Show closes off Main Street to traffic for one full weekend, for art connoisseurs and curious onlookers alike.

Whatever the season, Westport is a vital and exciting place offering an incredible quality of life. 


Just 50 miles northeast of Manhattan, Weston is directly adjacent to its sister town Westport. 

Covering 20 square miles with a population of approximately 10,000, Weston, rich in history, is a vital and colorful community reminiscent of yesteryear yet quite modern thinking. Easy access to the Connecticut Turnpike (i95), The Merritt Parkway and The Metro North Railroad, has long made Weston a haven for commuters to Manhattan, Westchester and nearby towns.

Weston’s top ranked elementary, intermediate, middle and high schools share a 113 acre campus. Connected by a common drive, the complex boasts eight athletic fields. A wide variety of programs are available, from drama, music, math and computers, to special education. The school system, small in size yet great in scope, is recognized nationally as a blue ribbon school for academic excellence. They are justifiably proud of their record, which sends nearly 100% of graduates on to higher education. 

A plethora of sports activities are available through Weston’s Town Recreation Department.

Although Weston is inland, its residents have full rights to use Westport’s private beaches.

To ensure the continuation of its rural charm and natural beauty, Weston adapted two acre residential zoning in 1953, thereby effectively limiting commercial development to a small but convenient area. Small retail shops, a gas station, post office, a bank and the very best local market around comprise what is known as Weston Center, a small hub in which villagers can meet and shop. 

Nearly one third of Weston’s 20 square miles have been preserved as open space and hiking trails, prohibiting development, but welcoming residents to enjoy its natural wonders.

Weston’s residents have created a small community filled with opportunity for people of all ages. Its roads and lanes, its historic district and antique homes, its stone walls and vintage fences, even its Memorial Day Country Fair, represent the peace and beauty of the area.


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