Culturally inclined and upscale in its overall atmosphere, the desirable community of Westport covers 33 square miles, including the Saugatuck River and Long Island Sound. With its sandy beaches, scenic shoreline, and inland woods, Westport is a former summer resort town that remained a center for artists while it evolved into a bedroom community for leading New York executives. Westport is unique, with its two business centers and a commercial corridor down its center. Main Street Downtown is renowned for its upscale shopping and a wide variety of unique shops. Along the Post Road, anything can be found, from antiques to hardware and lumber. The people make Westport unique. It is a diverse town made up of many nationalities, religions and all walks of life. As an environmentally aware community, it was one of the first to ban plastic bags.
One of the major reasons for the town's cosmopolitan nature is that Westporters have a real sense of place. All of the town's agencies – from the Office of the First Selectman to the Planning and Zoning Commission, the Recreation and Conservation Commissions, to the Representative Town Meeting (the town's grassroots democratic representatives) – collectively work together in the town's best interests. People are often outspoken and they publicly differ, but when a decision is made they come together as a whole for the good of the community. The spirit and care with which people tend to this town, whether as elected officials or as volunteers, is what gives Westport its very heart and soul.
Westport has become one of the most affluent suburbs in America, culturally rich, filled with a blend of old Yankee farmers, academics, and professionals from all fields, reflecting its international flavor. Yet, it still retains the old New England small-town charm on many of its streets.
Recently renovated, the Westport Library is a full-service community hub on the Saugatuck River with the latest technology, including the MakerSpace – a place for creation, collaboration, innovation, and entrepreneurship, plus space to record your own podcasts, have a meeting or quietly study. The main hall is has hosted lecturers, artists, authors and concerts. There is even a good cafe on site with a riverside deck for coffee and snacks. A well-stocked children's library is a vibrant spot, with loads of events and even a toy lending library.
Westport boasts three town beaches, over twenty town parks, and Connecticut’s first state park, Sherwood Island State Park. Westport’s Compo Beach includes a sandy beach, skate park, playground, picnic area, ballfields, and marina. The Longshore Club Park and Golf Course includes a private sailing school, community pool, and skating rink. Westport is also home to a rich cultural scene with the Westport Country Playhouse, Levitt Pavilion for the Performing Arts, and many other active cultural organizations.
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