You can still see the outlines of the historic villages that make up the Westport community as you drive from the Metro North station to a Zagat-rated restaurant or when you bike on the winding roads from Green’s Farms to the beach. Yet along with its historic charms and scenic coastline, Westport offers premier schools - both public and private - superbly crafted homes, beautiful countryside, and a vibrant downtown framed by the lazy curves of the Saugatuck River. Just 47 miles from Manhattan with easy access to major expressways and to LaGuardia and Westchester Airports, Westport is a bustling, eclectic community. When you consider Westport’s artistic legacy, home of The Westport Country Playhouse and to such luminaries as Bette Davis, J. D. Salinger, and Paul Newman, you begin to understand what makes Westport so special.
Westport is unpretentious yet sophisticated: rent a kayak or dock your yacht; discover a bargain at the Summer Street Fairs or purchase the perfect bracelet at Tiffany’s; grab a bagel at Gold’s or at Oscar’s or linger over fine French and Continental cuisine. Whatever your tastes, whatever your interests, Westport presents a tremendous range of pleasures and opportunities in its small-town environs. And whether you are Joanne Woodward or a PTA parent, Westporters are passionate about their community.
Community Involvement. Westporters get involved. Dream to build a state-of-the-art playground at Compo Beach and the community is there to fundraise and volunteer to build it. Rally the community to get out the vote at election time, and they vote in a higher percentage then any community in Connecticut. Get the kids together to march in the Memorial Day Parade that weaves through downtown and enjoy bands, the little league floats, the Fire Department and the Veterans’ groups. In July, residents gather annually for the Minute Man Race, the one-mile point-to-point open-water swimming race. In January, the downtown celebrates New Year’s Eve with First Night, a night of family fun and entertainment that ends with fireworks over the river. New Year’s Day; join the Polar Bears to take a plunge into the icy waters of the Long Island Sound to benefit Westport’s Save the Children. Volunteer as well as educational organizations are plenty and include: Wise men and Wise Women, Sunrise Rotary, Young Woman’s League and one of the states most active League of Women Voters.
Education. Westporters are passionate about their schools. In 2011, Staples High School was ranked No. 1 in Connecticut by Connecticut Magazine -- students regularly winning top math and science awards with eleven students selected as semi-finalists in 2011. Well-rounded, Staples students are perennial contenders for state athletic championships in at least eight varsity and club sports. The Staples Players are known for their stunning musical theatre and theatre performances year round, winning state and regional awards for excellence included the coveted Moss Hart Award. The school newspaper, Inklings, has won the Columbia Scholastic Press Association gold medal every year since 2000. Westport kids got game!
Recreation and culture. During the summer, Westporters have easy access to the sand and surf of Westport’s clean beautiful beaches at the Compo Beach and Marina is a 29-acre park Compo Beach-Longshore Complex; offering calm waters, extensive beach areas, a concession stand and, pavilion, bath houses with lockers, and picnic areas including grills on south beach. The park also features a huge wooden playscape, basketball courts, sand volleyball courts, open skate areas, and a softball field. And state of-the-art volunteer-built playground! Longshore also includes one of America’s best kept (and sometimes challenging) public golf courses, along with tennis, sailing, kayaking, swimming pools overlooking the Sound and bathing pavilion. Westport’s other beaches are Old Mill, Burying Hill, Cockenoe Island Beach and the 300-acre Sherwood Island Beach and State Park.
Westporters appreciate that this one-time artist’s colony has grown modern gracefully. The Landmark Westport Country Playhouse was recently renovated with Joanne Woodard at the lead. Downtown, your shopping is the “Rodeo Drive of Connecticut,” and unmatched public spaces include Westport Public Library, one of Connecticut’s best, concerts under the stars at the Levitt Pavilion for the Performing Arts and Toquet Hall, a teen center, where youngsters can check out bands or showcase their own musical talents, and the hills and acres of open space at Winslow Park, where residents meet for winter sledding and stroll 2.2 miles off-leash dog walking trails.
Whether you are building your dream home or looking for a beachside family residence, whether you are retiring to a comfortable condo or shopping for a capacious colonial, Westport is a community to be passionate about.