Westport

About Westport

Tucked along the Saugatuck River and the Long Island Sound shoreline in Fairfield County, Westport is one of Connecticut's most celebrated towns — a place where creative energy meets New England charm. Known for its thriving arts scene, walkable downtown, and a strong sense of community pride, it strikes a rare balance between cosmopolitan sophistication and small-town warmth. Whether you're browsing galleries, kayaking the river, or catching a show, there's always something going on in "WePo."

What to Know

• Sherwood Island State Park — Connecticut's oldest state park, offering miles of beachfront on the Long Island Sound, right in Westport's backyard.
• Westport Country Playhouse — A beloved regional theater founded in 1931 that has launched Broadway careers and continues to draw top-tier productions.
• Arts & culture hub — Westport has long attracted artists, writers, and entertainers; notable past residents include Paul Newman, Martha Stewart, and F. Scott Fitzgerald.
• Downtown Westport — Main Street and the Post Road corridor offer a curated mix of boutiques, acclaimed restaurants, and the beloved Westport Library, which has reinvented itself as a modern community innovation hub.
• Top-rated schools — Westport's public school system consistently ranks among Connecticut's finest, with Staples High School particularly known for its exceptional arts programs.

History

Incorporated on May 28, 1835, Westport was founded by Bankside Farmers who recognized the strategic value of its river and coastal access for trade. Through the 19th century it thrived as a port town, and by the mid-20th century it had transformed into a haven for New York City creatives drawn by its beauty and proximity to Manhattan.

Community & Living

Westport residents tend to be deeply engaged — in local theater, conservation efforts, school boards, and community events — giving the town an unusually active civic heartbeat. It's the kind of place where neighbors actually know each other, and where weekend farmers markets and beach days feel like a natural part of life.