Town Guide to Westport, Connecticut
Overview
Westport, located in Fairfield County, Connecticut, is a vibrant coastal town known for its cultural attractions, thriving arts scene, and beautiful shoreline along Long Island Sound. As one of the more affluent towns in the state, Westport offers a sophisticated lifestyle with upscale dining, boutique shopping, and a strong sense of community. Its picturesque scenery and proximity to New York City make it a popular destination for professionals and those seeking a refined living environment.
Getting There
Westport is conveniently located along Interstate 95 and the Merritt Parkway, making it easily accessible by car. The town is also serviced by the Metro-North Railroad, with direct trains to Grand Central Terminal in New York City, making it an ideal location for commuters. Westport is approximately 50 miles from Manhattan, and the nearest airport, Westchester County Airport, is just a 40-minute drive away.
Things to Do
Westport Country Playhouse
A cornerstone of Westport’s arts scene, the Westport Country Playhouse is one of the nation’s most renowned regional theaters. Founded in 1931, the Playhouse has hosted performances by many legendary actors and continues to offer top-tier productions of classic and contemporary plays. It’s a must-visit for theater enthusiasts seeking high-quality performances in an intimate, historic setting.
Compo Beach
One of Westport’s most beloved destinations, Compo Beach offers soft sand, calm waters, and stunning views of Long Island Sound. This 29-acre park features picnic areas, sports courts, a marina, and a playground, making it perfect for a relaxing day by the water. The beach is especially popular in the summer months, with many locals and visitors coming to swim, sunbathe, or enjoy a barbecue.
The Westport Library
The Westport Library is a community hub offering a wide range of programs, events, and activities. Recently renovated, the library features modern amenities, a maker space, and even a café. From author talks and tech workshops to art exhibits and concerts, the library is an essential part of Westport’s vibrant cultural scene.
Earthplace
For nature lovers, Earthplace is a nature discovery center that offers 62 acres of walking trails, an animal care center, and environmental education programs. Visitors can explore the beautiful grounds, which include meadows, woodlands, and a pond, or check out the indoor exhibits that focus on local wildlife and environmental conservation.
Westport Museum for History and Culture
Located in the historic Bradley-Wheeler House, the Westport Museum for History and Culture provides an in-depth look at the town’s history, from its early colonial days to its modern development. The museum offers exhibits, events, and walking tours that highlight Westport’s rich cultural heritage and its evolution into a thriving town.
Dining
The Whelk
The Whelk is a popular waterfront restaurant specializing in seafood with a focus on sustainability and locally sourced ingredients. The restaurant’s modern yet cozy atmosphere makes it a favorite for date nights or special occasions. Be sure to try their famous oysters, which are shucked fresh and served with house-made sauces.
Tarry Lodge
Located in downtown Westport, Tarry Lodge is an Italian restaurant offering wood-fired pizzas, house-made pasta, and an extensive wine list. The restaurant combines rustic charm with contemporary Italian cuisine, making it a go-to spot for both casual dinners and larger celebrations.
The Spotted Horse Tavern
For a more casual option, The Spotted Horse Tavern is a lively, pub-style restaurant located in a historic downtown building. The menu offers a variety of American comfort food, including burgers, salads, and sandwiches, along with a great selection of craft beers. The relaxed atmosphere and friendly service make it a favorite among locals.
Shopping
Main Street
Westport’s Main Street is a charming shopping district featuring a mix of high-end national retailers and locally owned boutiques. Stroll down this picturesque street and browse stores like Anthropologie, Lululemon, and J. Crew, or visit unique local shops such as Terrain, which offers home goods, plants, and gardening supplies in a beautifully designed space.
Saugatuck Sweets
A local favorite for sweets and treats, Saugatuck Sweets offers everything from gourmet ice cream to homemade candy. It’s a great stop for anyone with a sweet tooth looking to enjoy a treat while exploring the town.
Westport Farmers Market
Held seasonally, the Westport Farmers Market is a vibrant marketplace offering fresh produce, local meats, artisanal cheeses, and handcrafted goods. With live music and food trucks, it’s a fun and lively place to spend a Saturday morning, supporting local farmers and vendors.
Education
Westport offers a range of educational opportunities, with public schools and private institutions that are highly regarded for both academics and extracurricular programs. Staples High School is well-known for its programs in the arts and music. Additionally, there are several prestigious private schools in the area, each offering unique learning experiences.
Events and Festivals
Levitt Pavilion Summer Concert Series
The Levitt Pavilion for the Performing Arts is one of Westport’s cultural gems, offering free outdoor concerts throughout the summer. The concerts feature a variety of genres, including jazz, rock, classical, and folk, attracting both locals and visitors who come to enjoy live music under the stars by the Saugatuck River.
Westport Fine Arts Festival
Every summer, downtown Westport transforms into an open-air gallery for the Westport Fine Arts Festival. This juried event features artists from all over the country, showcasing a wide variety of media, including painting, sculpture, photography, and jewelry. With live music, food vendors, and family activities, the festival is a highlight of the summer season.
Westoberfest
Held in October, Westoberfest is Westport’s take on Oktoberfest, featuring craft beer tastings, live music, and food trucks. It’s a lively event with activities for all ages, making it a great way to celebrate the fall season while enjoying local brews and entertainment.
Parks and Outdoor Activities
Sherwood Island State Park
Sherwood Island State Park, Connecticut’s first state park, is located on the coast of Westport and offers stunning views of Long Island Sound. The park features walking trails, picnic areas, and a large, sandy beach, making it a perfect spot for swimming, sunbathing, and picnicking. The park also offers opportunities for birdwatching and fishing.
Longshore Club Park
Longshore Club Park is Westport’s premier recreational facility, offering a public golf course, tennis courts, a marina, and a swimming pool. Located along the coast, the park offers beautiful views and plenty of options for outdoor activities. Longshore is a favorite spot for locals looking to enjoy a round of golf or a day on the water.
Burying Hill Beach
For a quieter beach experience, Burying Hill Beach offers a more secluded spot with rocky shores, picnic areas, and stunning sunset views. It’s a peaceful alternative to the more popular Compo Beach and is a great spot for fishing or a relaxing afternoon by the water.
Real Estate and Living
Westport is known for its upscale real estate, featuring a mix of waterfront homes, historic colonial houses, and modern estates. Many homes are set on large, private lots with lush landscaping, and the town’s proximity to New York City makes it a desirable location for commuters. Westport’s scenic neighborhoods and vibrant downtown contribute to its reputation as one of Connecticut’s most sought-after places to live.
Conclusion
Westport, Connecticut, offers an ideal blend of coastal charm, cultural richness, and suburban luxury. Whether you're visiting to enjoy its beautiful beaches, explore its thriving arts scene, or simply relax in a welcoming community, Westport has something for everyone. With its upscale shopping and easy access to New York City, Westport remains one of the most desirable places to live and visit in Connecticut.