Rumored as the inspiration for the setting of F. Scott Fitzgerald’s The Great Gatsby, Westport in real life is more subdued, though still wealthy, and without the scandals described in the novel. While Westport has grown into an affluent suburb of around 26,000, it has proudly maintained its New England charm and heritage. The town boasts excellent schools and an active community both committed to preserving its small-town feel and embracing modern conveniences that make Westport such an attractive home for families. Covering over 33 square miles, the town includes historic neighborhoods, a vibrant downtown area, as well as beautiful parks along the coast on Long Island Sound.
Two stops along the Metro North New Haven line, Green’s Farms and Westport, connect the town to Grand Central with a commuting time of a little over an hour. Nearby Amtrak stations 10 and 12 miles away provide additional connection to the Northeast Corridor. While many residents commute to work, a number of businesses in the financial services industry operate in town. The Merritt Parkway runs along the northside while I-95 crosses through the southern part of town. The Saugatuck River Bridge is the oldest surviving moveable bridge in the state, connecting the east and west sides of town along the Post Road, which runs through central Westport.
Westport CT Commute Times
Westport is served by a number of active community organizations, including a Neighbors and Newcomers Group that organizes frequent meetups and events. TEAM Westport also supports multiculturalism and diversity efforts in town. The Greens Farm neighborhood lies in the oldest part of town, and Revolutionary and Victorian-era homes can also be spotted in Old Hill, west of the Saugatuck River. Downtown Westport provides a central area for shopping, restaurants, and other businesses while in contrast Compo Beach, and the surrounding area known simply as Compo, retains its character as an early 20th century beach colony.
For more info see: Westport CT CITY-DATA
Westport CT Commute Times
Schools in Westport CT
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Top 10 Schools
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For the Kids
The facilities at Earthplace, a nature discovery center, make for an excellent destination for the whole family, with hiking trails, canoeing, as well as after school programming and an on-site preschool. The Connecticut birds of prey exhibit allows visitors to observe these majestic creatures up close, including Cerena the bald eagle and the aptly named raven, Edgar. The Wakeman Town Farm provides another way to connect with nature, with cooking classes, family workshops, and events like their Family Fun Day. In the summer, Compo Beach provides the tranquil setting for family-friendly movie screenings, as well the annual Point to Point Swim for ages 10 and up. The Parks and Recreation Department maintains two dozen fields around town and also organizes youth sports like basketball, water polo, and tennis from April to December. Rainy day? Head to Kidville for mommy-and-me classes and open gym for the town’s tinier residents.
AMENITIES & RECREATION
Compo Beach’s 29 acres provide for a beautiful, sandy retreat that is kept peaceful by limiting the number of pass holders admitted in the summer. Visitors can access the boardwalk or take advantage of the skate areas and athletic fields within the park. Burying Hill and Old Mill provide additional beaches in town, as well as the coastline within Sherwood Island State Park. The state park spans 235 acres within the Greens Farms area and also offers saltwater fishing, frisbee golf, and hiking trails. In cooler months, visit their Nature Center to enjoy the live animals and educational programming, or head over to Earthplace’s 62 acre sanctuary. The town maintains the public facilities at the 18-hole Longshore Golf Course and Longshore Pool, as well as both clay and all-weather tennis courts that can be conveniently reserved online. Westport also boasts two marinas for launching boats, as well as the Longshore Sailing Academy, which operates out of Longshore Club Park near the mouth of the Saugatuck River. On a clear night, visit the Rolnick Observatory to take advantage of the largest telescope available to the public in Connecticut.
Food & Drink
Westport CT & Surrounding Area
Top 10 Restaurants
$$ . Seafood
$$ . American (Traditional)
$$ . Juice Bars & Smoothies
$$ . Cheesesteaks
$$ . Coffee & Tea
$$ . Pizza
$ . Mexican
$$ . Asian Fusion
$$$ . Indian
$$ . Wine Bars
Downtown Westport offers a central location to browse shops from retail chains like J. Crew, Brooks Brothers, and Restoration Hardware, as well as smaller boutiques like She La La. Check out the eclectic accessories available at Local Soul, or peruse the fine jewelry at Lux Bond & Green. The Curio Cottage Thrift Shop, run by the Westport Women’s Club, rewards the patient shopper with unique home goods and other treasures. Mitchells, the popular family-run department store, also operates a luxury brands specialty store on the Post Road.
ARTS & ENTERTAINMENT
The Westport Arts Center organizes free, rotating exhibits to the public, as well as special educational programs for children and adults. The Westport Country Playhouse delights audiences with a range of shows from Romeo & Juliet to Man of La Mancha between April and November, and offers Family Festivities in the off-season. The Levitt Pavilion for the Performing Arts stages live performances of music, comedy, and more in its recently updated facilities, including 60 nights of free arts and entertainment during the summer. Local oenophiles unite at Westport Uncorked, an evening of 100 wines organized by The Westport Sunrise Rotary club. The local group also coordinates the decidedly different Great Duck Race, which launches up to 3,500 yellow ducks down the river. The Westport Fine Arts Festival returns to Main Street each summer, and has partnered with the Westport Library Annual Book Sale for a weekend in celebration of both art and the written word.
Records indicate that the Pequot tribe inhabited the land that would later become known as Westport, and the Paugussett names for regions like Compaug and Saugatuck remain today. The area was first settled by a group known as the Bankside Farmers in the mid-seventeenth century and eventually incorporated as Westport in 1835. During the Revolutionary War, British forces traveled to the area with the intent of destroying the Continental Army’s supplies but were met with a surprise attack by Minutemen. The town flag of Westport, created for its 150th birthday, bears the image of a Minutemen as a symbol of the town’s “independent spirit.” The nineteenth century saw a shift in industry from agriculture to shipping, and with the twentieth century came the arrival of artists and writers from New York seeking a quieter haven.
Chowdafest is just over a decade old, but has already solidified its reputation as a must-visit event for self-professed “chowda heads.” The festival ushers in the fall season, held on the first Sunday of October in Sherwood Island State Park. Entrants from 40 New England restaurants compete for excellence in classic chowder, traditional chowder, creative chowder, soup/bisque, and vegetarian categories. Visitors can eat with a conscience, as proceeds benefit charities like Food Rescue U.S. Those who miss out can still visit Westport’s own Dunville’s Restaurant & Bar, which has taken the lead in the traditional category with both their Manhattan and Rhode Island style chowders.