Main Content

Living in Westport CT and the Vibrant Downtown Westport Neighborhood

A quintessential New England village, the Westport Center neighborhood is an ideal place to live for those looking to enjoy all it has to offer – community events, upscale shopping, restaurants, concerts, and walkability on a fabulous riverfront location. Living in Westport CT and close to the downtown scene is the hot spot in this town. The neighborhood itself consists of beautiful three-to-five+ bedroom single-family homes and small apartment buildings. Many of the residences were built between 1940 and 1969 including some older historic homes built before 1940.

Living in Westport Center allows you to readily partake in many of its yearly events. Some of the most anticipated events in Westport Center are the Westport Fine Arts Festival, Halloween Family PumpkinFest, Westport Sidewalk Sale, and the Westoberfest, to name a few. Check out Westport Downtown Association for a complete list of their events. Great for families is The Great Duck Race, sponsored by Westport Sunrise Rotary, held at Parker Harding Plaza on the Saugatuck River.


Downtown Westport is the best place in town for food lovers. The neighborhood is home to local favorites such as 190 Main Bar & Restaurant, Spotted Horse Tavern, Little Kitchen, Sakura, and Terrain Café. These are just a few of the wonderful dining options, plus charming local eateries and nightlife venues. One of the best shopping destinations in Fairfield County, the downtown stores include many well-known brands, including J. Crew, Anthropologie, Eileen Fisher, Theory, Pottery Barn, West Elm, Lulu Lemon, and many more, along with upscale boutique shops.

For residents who love the outdoors, Winslow Park is the perfect spot to explore. This public space is a 28-acre park with beautiful fields and dense woods in the heart of town located next to the Westport Playhouse. In addition to walking and biking trails, it has a picnic area, a large off-leash area for dogs, fields, and gardens.

The Westport Public Library, situated in the heart of the downtown center overlooking the Saugatuck River, offers programs for kids, teens, and adults along with the popular STEAM Camp Explore for grades 4-10. Since 1886, the Westport Library has been devoted to enriching the intellectual and creative lives of the community. The library is a vibrant community hub where people of all ages come to seek information, gain knowledge, exchange ideas, and share experiences. The library offers many programs, series, and special events throughout the year.

Westport Center neighborhood is rich in culture and the arts. The Westport Country Playhouse is a non-profit theatre founded in 1931 by Lawrence Langner, a New York theater producer. The mission of Westport Country Playhouse is to enrich, enlighten, and engage the community through the power of professionally produced theater of the highest caliber and the welcoming experience of the Playhouse campus. Many notable performers have graced the stage, including Paul Newman, Joanne Woodward and Liza Minnelli. Today, the Playhouse produces five shows per season and provides theater experiences such as staged readings to free community events for kids and families.

Downtown is also host to the Westport Community Theatre; a 130-seat thrust-style stage located in Westport’s Town Hall since 1979. Five main stage plays are produced each season, and staged readings.

Located on the bank of the Saugatuck River, The Levitt Pavilion for the Performing Arts is a non-profit outdoor amphitheater. The Levitt Pavilion is an open-air summer festival that offers 50 free Nights of Music, Arts & Entertainment under the Stars! It’s one of the longest-running free outdoor festivals in the Nation. Performances run June thru August.

The Westport Historical Society, founded in 1889, is an educational organization dedicated to preserving, presenting, and celebrating the history of Westport. The museum holds monthly events, including live author talks, walking tours, Tuesday Treasure, and Chats on the Past.

The Westport Center neighborhood is bordered by the Saugatuck River to the West and Roseville Avenue to the east, with the Merritt Parkway and Route 1 serving as its north and south borders. Westport Center offers easy access to the Westport train station, I95, and the Merritt Parkway. Children in this neighborhood attend Saugatuck Elementary (grades K-6), Bedford Middle School (grades 6-8), and top-rated Staples High School (grades 9-12).

Westport Center is a vibrant and bustling neighborhood. Whether you are looking for convenience to town, community events, the arts, restaurants or shopping, there is something for everyone in the Westport Center neighborhood.

Are you thinking of moving to Westport? Discover one of the most sought after neighborhoods in Westport CT with Westport CT realtor Jennifer Lockwood. There are many other options in Westport Neighborhoods, make sure you research them all and see which one works best for you!
Westport Neighborhoods

Contact Jennifer is you are in need of real estate assistance buying or selling (203) 650-6870 or email at!

Check out the Pros and Cons of Living in Westport CT

Prev 1 of 1 Next
Prev 1 of 1 Next

Looking to buy a home? Check out the buyer’s guide to help you along the way!
Buyer’s Guide

What Is Your Home Worth?