The architecture and pleasing cultural offerings of Westport reflect a well-established history as a desirable summer resort, and the affluent lifestyles of residents. Impressive waterfront properties grace the coastline while magnificent estates, country-houses and streamlined contemporaries dot the countryside. Westport is very family-oriented and is not a community which "wears its affluence on its sleeve". In the summer, Levitt Pavilion, on the Saugatuck River, features a variety of family concerts and performances, and the Westport Playhouse hosts professional touring companies. Soothing chamber music concerts are performed by the Westport Friends of Music in the autumn and winter, and the Green Farms Center for the Arts offers theater, music and art exhibits throughout the year.

Education in Westport also benefits from the generous support and involvement of residents. From elementary education through high school graduation, the public schools emphasize a strong academic curriculum with an ever-widening spectrum of enriching programs as students progress. Modern equipment and facilities allow students to pursue such special interests as music, drama, visual arts, foreign language studies, advanced English and mathematics and student government. Both college preparatory and vocational paths are offered, and a special agenda is provided for disabled students.

Westport's superb natural setting inspires a wealth of recreational activity and outdoor pleasure. Residents take advantage of the pristine beaches and sparkling waters of Long Island Sound for many exciting water sports. Boating enthusiasts, in particular, appreciate the fine marinas and private yachting clubs of town. Town-owned Long Shore Country Club and numerous private country and hunt clubs offer golf, tennis, swimming and social events for all ages. An active recreation commission oversees activities and facilities on over 200 acres of preserved land. Sherwood Island State Park features additional shoreline fun and excellent trails for hiking and nature study.