1. Long Island Sound
The town of Westport is located on Long Island Sound. It has three beaches and is known for boating, fishing, and idyllic shoreline views.
2. Westport Schools
Rated #1 in Connecticut,Westport’s public school system has over 5,000 students from Pre-K through 12th grade, with a student-teacher ration of 13 to 1. According to state test scores, 74% of students are at least proficient in math and 83% are proficient in reading.
3. Transportation
There are two commuter rail stations in Westport: Green’s Farms and Westport. Both train stations received award-winning renovations in the past 5 years. Metro-North provides a quick and easy commute to New York City. Norwalk Transit also operates the Westport Transit District buses and provides service throughout town. Easy access to Interstate-95 and the Merritt Parkway add to Westport’s commuting convenience.
4. Westport Library
Overlooking the Saugatuck River, the library has earned “Five-Star Library” status multiple years (only 1% of public libraries earn 5 stars). Recently modernized with extensive renovations, Westport’s library is a community hub.
5. Longshore Park
Longshore is a 169-acre park. It features a premier 18-hole golf course, nine tennis courts, paddle tennis, a picnic area, 3 swimming pools, a playscape, a pavilion, a marina, sa ailing school and an ice rink. There is also the Inn at Longshore by OnTheMarc, the only waterfront event space in Westport. The Pearl offers waterfront dining and entertainment all year long.
6. Westport Farmers’ Market
Westport Farmers’ Market provides its community with fresh, local, healthy and seasonal food all year round — not to mention live music by local performers.
7. Restaurant Week
In the past five years, Westport has been working hard to set the standard in gourmet dining. Once a year, more than 25 restaurants throughout Westport participate in a two-week special event that features special fixed-price lunch, brunch and dinner menus. Try some of the local favorites such as Spotted Horse Tavern, Terrain, Kawa Ni, and Tarantino.
8. Levitt Pavilion
The outdoor, open-air Levitt Pavilion hosts one of the largest and longest-running free outdoor summer festivals in the nation. The festival is open from late June through early September, producing almost 60 nights of free arts and entertainment. Past performers include Jose Feliciano, Huey Lewis & the News, and Palehound.
9. Westport Beaches
Westport has miles of coastline on the Long Island Sound and provides three town beaches: Compo, Burying Hill and Old Mill. All of Westport’s beaches are open with lifeguards on duty Memorial Day weekend through Labor Day weekend.
10. Westport Playhouse
Founded in 1931 by Lawrence Langer, the Westport Country Playhouse is a nationally recognized, not-for-profit, professional theater. The mission of WCP is to enrich, enlighten, and engage the community through the power of professionally produced theater worth talking about. In years past, Paul Newman could be seen performing at the WCP.
11. Sherwood State Park
Connecticut’s first state park is still one of its finest. Have a leisurely lunch in the shade of the picnic grove, swim in Long Island Sound, or view marsh life from the observation platform at Sherwood Island. You can also find at their nature center a wide variety of displays and exhibits and learn about the rich diversity of plant and animal life.
12. Historical Society
The society, founded in 1889, is an educational organization dedicated to preserving, presenting and celebrating the history of Westport and increase awareness of the importance of preserving the town’s heritage and its historic buildings and landmarks.
13. Astronomical Society
The Westport Astronomical Society (WAS) maintains and operates the Rolnick Observatory, which is open to the public on selected nights. It consists of a 40-foot tower and two auxiliary buildings at 182 Bayberry Lane in Westport. One of the adjacent buildings serves as the WAS office, containing a library of both books and videotapes. The other building is the Fred Bump Education Center.
15. Richardson Tree Farm
The Richardson Tree Farm is a cut-your-own Christmas tree farm located on 12-acre plantation in the 75-acre Audubon sanctuary. Its gift shop offers wreaths, roping, tree stands, swags and more.
16. Annual Dog Festival
The Westport Dog Festival is an annual summer event that takes place at Winslow Park. This event is fun for the whole family and dogs are (obviously) encouraged to attend! The Dog Festival includes: vendors, food trucks, face painting, caricature artist, photo board and training sessions. The event’s proceeds are donated to TAILS, Westport K9 unit, EARS, Fidelco, CT Humane Society and Adopt-a-dog.
17. Fine Arts Festival
Produced by The Westport Downtown Merchants Association, the festival is nationally recognized and features a premier roster of 170 national and international fine artists exhibiting in a variety of categories.
18. Community Band
The Westport Community Band, founded in 1977, is a 65-piece concert band which performs at community venues including the Levitt Pavilion, the Memorial Day parade, and various schools and nursing homes.
19. Earthplace
Earthplace is a natural history museum, nature center and wildlife sanctuary located at 10 Woodside Lane. It provides hands-on learning experiences and environmental education programs. It sits on 74 acres, with 2.5 miles of trails. (Pro tip: Try having a staring contest with one of its owls. Not easy.)
20. Merchants Association
Downtown Westport is a unique combination of quaint New England charm and sophisticated shopping and dining in a lovely riverside setting. Experience all that downtown Westport has to offer: mom-and-pop-shops, local chains and retailers, eateries, entertainment venues and galleries.
21. Community Theater
Westport Community Theatre (WCT) is located in Town Hall. WCT offers high-quality productions of classic and modern plays to showcase the talented members of our community, as well as newcomers, seasoned actors and directors.
22. Gilbertie’s Herb Gardens
Gilbertie’s is the largest herb plant grower on the East Coast, with greenhouses and gift shop surrounded by theme gardens providing an experience for both the casual gardener and serious botanist. The garden also offers: annuals, perennials, trees and shrubs, statuary, tropical plants, fish, pottery, fall pumpkin picking and hay rides, and more!
23. Annual Minute Man Race
This event consists of a USA Track and Field Race Certified 10K run, 5K run or walk and Kids Fun Run, taking place at Compo Beach. Race proceeds directly benefit charities with an emphasis in education located in lower Fairfield County.
24. Bedford Square
Bedford Square is an iconic mixed-use development: a retail, dining and residential destination that further elevates the exposure and draw of downtown Westport, Connecticut.
25. Food Truck Festivals
Foodies have a new avenue for food adventure! Spend the day outdoors, listen to some great music and enjoy your surroundings, all while you treat your taste buds to some titillating flavors.
26. Community Garden
The Westport Community Garden provides garden plots to Westport residents of all ages. Gardeners from school-age children to senior citizens can share the enjoyment of growing their own food or flowers, while exchanging gardening tips. This is a true community of gardeners.
27. Woman’s Club
The Westport Woman’s Club (WWC), organized in 1907, is a non-profit philanthropic organization dedicated to giving back and the raising of funds in support of the charitable, educational, cultural and public health services in Westport and surrounding towns.
28. Westport/Weston YMCA
The Westport/Weston Family YMCA enriches the community by developing and nurturing youth, promoting healthy living for all and fostering social responsibility. The Y is a nonprofit established in 1844, originally located in Bedford Square in downtown.
29. Sidewalk Sale
The much-anticipated annual Westport Sidewalk Sale allows savvy shoppers to find amazing sales throughout Main Street, the Post Road and other areas surrounding downtown. Shops bring merchandise to the sidewalks and offer incredible bargains. Times will vary by store, but shop early for the best selection!
30. Wakeman Town Farm
The Wakeman Town Farm Sustainability Center is an organic demonstration homestead dedicated to serving the Westport community. The farm is a model facility created to educate the community on local healthy food production and community service orientation. Activities include educational workshops, student internships, after-school environmental clubs, and children’s summer camp programs.
