An Introduction to Westport
Westport, Connecticut, has long been a coveted suburb—and for good reason. The picturesque town located along the Long Island Sound is known for its vibrant community, top-ranked public school system, stunning coastline, and rich cultural heritage.
Nearly 50 miles north of New York City, Westport draws families and professionals looking for the best of Connecticut’s Gold Coast while staying within striking distance of the city. If you’re considering this Fairfield County gem, you’ll find it offers an ideal blend of suburban charm, coastal beauty, and urban convenience. Here, we look at the myriad reasons people keep Westport high on their lists.
History of Westport, CT
European settlers first arrived in Westport in the late 17th century by following the King’s Highway—an inland route established to connect New York and Boston and establish small communities between the two cities. Westport was originally called Bankside to commemorate a district in London of the same name, a place where many of the early colonists came from. The town would officially be incorporated as Westport in 1835.
In the 19th century, Westport was one of the most prosperous markets for onion growing in the United States and was home to a robust shipping center. By the early 20th century, Westport was becoming a cultural haven for artists and writers—including F. Scott Fitzgerald—who had grown tired of city living.
By the 1920s, suburban living was taking hold in Westport, and the community would see rapid population growth brought on by automobile travel along U.S. Route 1—the northeast’s first real highway. Interstate 95 reached Westport by 1956, which brought even more residents to the area and ushered the town into the modern area.
Westport Community Overview
Today, Westport is home to 27,000 residents and is one of Connecticut’s most upscale towns, particularly because the financial services industry plays a large role in the town’s economy. Westport is home to several distinct neighborhoods including Coleytown, Compo Beach, Compo South, Green Farms, Downtown (Westport Village), Long Lots, Old Hill, Saugatuck, and Saugatuck Shores.
Westport is served by two commercial centers, one Downtown along Main Street and another near the water in Saugatuck. While Saugatuck offers luxurious residences alongside the namesake river and Long Island Sound, Compo is also a top pick for those seeking coastal estates. Those who want to be close to restaurants and shops—and have access to a variety of building styles—should seek out the Old Hill and Downtown areas.
Lifestyle and Culture of Westport
As in the early 20th century, today’s residents are attracted to the town’s artistic heritage and culture. Many residents in Westport take advantage of cultural resources like the Levitt Pavilion for the Performing Arts, which provides free outdoor access to music and art, and the Westport Country Playhouse, a historic theatre established in 1930.
To indulge in Westport’s contemporary art scene, residents can visit the Museum of Contemporary Arts (MoCA), a facility that offers art classes and workshops for all ages. There are countless cultural events on the calendar throughout the year in Westport, including comedy shows, children concerts, and the Westport Farmers Market which serves as a central food hub in the community.
The Yankee Doodle Fair, an annual fundraising event that has been sponsored by the Westport Women’s Club since 1907, comes to life every summer in Westport and is one of the most beloved events in the community.
Schools and Education of Westport, CT
Westport’s renowned school district makes the town an ideal community for families. In fact, Westport Public Schools—which operates one preschool, five elementary schools, two middle schools, and one high school—is ranked number two in the state, according to Niche.
Staples High School in particular is consistently ranked as one of the top public schools in the state of Connecticut and among the best in the country. Staples offers dozens of Advanced Placement and Honors classes, STEAM classes and various extracurricular activities where students can explore their passions in a safe and team-building environment.
Greens Farms Academy, which is Westport’s only private school, is a K-12 preparatory school and has been serving the community for 100 years.
Parks and Recreation of Westport, Connecticut
Known as the town with the most river and oceanfront in Connecticut, Westport offers miles of sandy beaches and scenic walks along the Saugatuck River shores. Westport has three town beaches that residents and visitors can enjoy along the town’s shoreline: Compo Beach, Old Mill, and Burying Hill Beach.
Both Compo Beach and Burying Hill Beach are open to the public in the summer and require a fee to enter. At Compo Beach, a 29-acre park, residents can find pickleball courts, volleyball courts, a boardwalk, and a concession stand. Another community favorite, Longshore Pool in Longshore Club Park,, offers two swimming pools, a wading pool, and a concession stand from May through September.
Sherwood State Park, the first in Connecticut, is one of most visited outdoor attractions in town. Westport residents can swim in the Long Island Sound, play a round of disc golf, collect seashells, or visit a 9/11 Memorial. Other parks throughout town offer relaxing nature strolls and memorable views along riverside walkways. Overlooking the Long Island Sound, many residents enjoy playing a round at the Longshore Golf Course, an 18-hole course operated by the Town of Westport.
Dining and Shopping
Westport has an array of high-end shops and restaurants that has made it a Fairfield County destination. Foodies can’t go wrong at Westport Bartaco, located at the seaside serving tasty tacos and vibrant hand-crafted margaritas. For a memorable weekend brunch residents can indulge in sustainable seafood and a menu filled with local produce at The Whelk.
And if you’re looking for a vegetable-forward meal, you can swing by Green and Tonic, a plant-based kitchen that serves nutritious and vibrant dishes. With more than 70 restaurants in town, there is something for everyone.
Residents can stroll Main Street, the primary commercial district, where they will find a variety of boutiques. For clothes from rising brands and designers, South Moon Under sells on-trend soft-florals and airy texture. For unique furniture finds from Europe, Bungalow Dècor offers high-end options for customers looking to furnish a new home. Another favorite small business in Westport is Kerri Rosenthal where the vibrant design style radiates through its art and clothing products.
Transportation
Westport’s proximity to New York City and efficient transportation system provides access to business districts in both CT and NYC.. There are two train stations in Westport along the Metro-North Railroad: Green’s Farm Station and Westport Train Station.
By train, Westport residents can reach New York City in about an hour and twenty minutes, while by car (Westport is located along Interstate 95) the trip varies based on traffic, but is often similar to riding the train. Going north, residents can reach New Haven in under 40 minutes.
Thinking of Moving to Westport, CT?
Westport, Connecticut, is a vibrant and welcoming community that offers a high quality of life, excellent schools, and a rich array of recreational and cultural opportunities. Whether you’re looking to live along the coast, you’re attracted to the dining scene, or you’re trying to escape the demands of city life in favor of suburban charm, Westport is an attractive option. If you’re ready to make the move, why wait? For personalized insights and to explore your options further, contact a local expert strategist.
