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The 20 Best Things to Do in Westport, CT

Explore a Christmas Tree Farm and Smith Richardson Wildlife Preserve

Westport is one of the most interesting towns in the United States. It is located 52 miles from New York City and 40 miles from Manhattan; Westport is centrally located, making it easily accessible by railway or road. There are plenty of fun activities you can try out during your stay in this beautiful city, such as going paddleboarding along the Saugatuck River, visiting the Westport Country Playhouse, being amazed by the natural beauty of its public beaches, going on a shopping spree at many local boutiques, enjoy the eclectic mix of contemporary and traditional art at the town's local museum. Here, we will take a closer look at some of the 20 best things to do in Westport, CT.

Downtown Westport

20. Take a walk in Downtown Westport

According to TripAdvisor, Downtown Westport is the town's central business district. It perfectly blends the charm and adorability of the New England coastal town with diverse dining and shopping centers. If you walk by the Saugatuck area, you will see the town's local chains, historic buildings, eateries, boutiques, and museums. Some of the town's most well-known retailers include; Urban Outfitters, South Moon Under, Banana Republic, and Tiffany & Co, among many others. There is also abundant parking and plenty of stunning views for you to enjoy.

Sherwood Island State Park

19. Explore marsh life at Sherwood Island State Park

Sherwood Island State Park is the first state park in Connecticut and is situated over 234 acres of natural woodlands, wetlands, and beaches along the shore of Long Island Sound in Westport. This park is a spectacular place for all nature lovers to enjoy nature strolls, bird-watching, recreational sports, swimming, picnicking, kite-flying, biking, and many other fun outdoor activities. Sherwood Island Nature Center is open to all guests from Wednesday to Sunday, while the Sherwood Island State Park is open all days of the week from 8 am to 8.30 pm. Entry is free for all Connecticut-licensed vehicles, $15 for out-of-state cars on weekdays, and $22 for weekends.

Black Duck

18. Enjoy the best-stuffed burger at Black Duck Café

Black Duck Café is located on the Saugatuck River and is popularly known for serving the most delicious cuisines on its diverse menu. Back in the 1920s, it was the fastest rum-runner boat, but it was later transformed into one of the locals' favorite restaurants. Their diverse menu includes classic American cuisines such as salads, appetizers, burgers, and sandwiches that are best enjoyed with their amazing selection of beers and wines. The Black Duck Café is open from Monday to Thursday from 11.30 am to 1.00 am, Friday to Saturday from 11.30 am to 2.00 am, and Sundays from 11.30 am to 11.00 pm.

Saugatuck River

17. Try paddleboarding on the Saugatuck River

The Saugatuck River is one of the main popular tourist attractions in the town, where friends and families gather to spend memorable moments together. Spanning a length of 38 kilometers, the Saugatuck River offers calming sky-blue water and stunning views surrounded by the town's natural beauty. You can also enjoy your favorite water activities such as swimming, paddleboarding, snorkeling, or fishing. It is the perfect place for all nature lovers with the beautiful view of the fish, rock pools, and sandy beach. You will get to walk across the legendary Saugatuck River Bridge, whose origin dates back to 1884. It is fully open to everyone 24 hours a day and is completely free.

Westport Farmers Market

16. Visit the Westport Farmers Market

According to Planetware, Paul Newman officially opened the Westport Farmers Market in 2006. Since its establishment, the market has grown rapidly and expanded its location to 50 Imperial Avenue. Over the past decade, the Westport Farmers Market has become a respected institution, working closely with local businesses and supervising most of the programs in the town. In 2019, more than forty traders at the Westport Farmer Market were selling fruits, flowers, prairie-raised meats, exotic sauces, cakes, herbs, pickles, fresh fish, and vegetables.

Museum of Earthplace

15. Explore the wildlife museum of Earthplace

To all the nature and science enthusiasts, Earthplace is the ideal location for your stay in Westport. Earthplace is a nature discovery center that is solely dedicated to creating a greener future for Earth and the generations to come. Inside this wildlife museum, you will be amazed by the animal hall, interactive nature displays, interesting animal documentaries, and a Connecticut birds of prey exhibit. Located on 25 hectares of open space, Earthplace is home to several creatures such as lizards, insects, birds, amphibians, ferrets, and other wild animals. You can stroll along the center's 2 miles of walking trails and explore the amazing ponds, streams, and forests. Earthplace is open from Monday to Sunday from 9 am to 5 pm and Sundays from 1 pm to 4 pm. Entry is completely free.

Le Rouge

14. Try out the hand-decorated desserts at Le Rouge Handmade Chocolates by Aarti

Are you a fan of sweet, mouthwatering desserts? Then, you should make your way to Le Rouge Handmade Chocolates by Aarti. This desserts shop has been voted the best chocolate shop in Westport for six years consecutively and was recently voted the town's best desserts shop. Le Rouge Handmade Chocolates are popularly known for their delicious hand-decorated desserts, chocolate cakes, fudge, hand-rolled chocolate truffles, and state-of-the-art packaging. Le Rouge Handmade chocolate shop is open from Tuesday to Sunday from 11 am to 5 pm but is closed on Mondays.

Rolnick Observatory

13. View the beautiful night sky at Rolnick Observatory

Rolnick Observatory, currently known as Westport Observatory, is an astronomical observatory situated at the highest point in the town. It was previously used as a Cold War radar site to spot oncoming enemies easily. Today, the Westport Observatory is a popular destination to get a clearer view of shooting stars, whizzing comets, and lunar eclipses. There is also a gift shop in the observatory packed with souvenirs for you. The Rolnick Observatory is open on Wednesday from 8.15 pm to 10 pm but closed from Thursday to Tuesday. Entry is completely free.

Gallagher House and Cranbury Park

12. Visit the Gallagher House and Cranbury Park

According to Thecrazytourist, Cranbury Park comprises 227 acres of gorgeous gardens and sculpture gardens within the Tudor Revival Gallaher Mansion. This residence was constructed for industrialist Edward Beach Gallaher in 1931 during the Great Depression and features cross gable, tempered window sills, hand-painted stained glass, and bay windows. This oak-paneled residence is usually rented out for special events. At the same time, the large carved garden is open to the public for picnics, dog walks, hiking, and enjoying your favorite outdoor activity.

Westport Country Playhouse

11. Watch a play at Westport Country Playhouse

Back in the late 1830s, the Westport Country Playhouse was used as a tannery. Later on, in 1932, Lawrence Langner converted it into a non-profit regional theater. This cultural landmark in Westport features the local's new and classic plays and serves as a venue for various arts that unite the town's theater enthusiasts. To date, the Westport Country Playhouse has produced more than seven hundred plays. The Westport Country Playhouse is open from Tuesday to Wednesday from 12 pm to 6 pm, from Thursday to Friday from 12 pm to 5 pm, and is closed on weekends.

Westport Historical Society

10. Learn about history at the Westport Historical Society

Westport Historical Society was established in 1889 to showcase the town's rich history through a holistic approach. Here, you will get to increase your knowledge about the town's historic landmarks and buildings. Westport Historical Society features a Bradley-Wheeler Barn museum, a cobblestone barn comprising historic house research, archives, and a unique shop. This museum is also used to host events and other programs.

MoCa Westport

9. Admire the fine art at MoCA Westport

The Museum of Contemporary Art (MoCA), previously known as Westport Arts Center, is an art museum dedicated to inspiring and showcasing visual and performing arts produced by the town. They hold several art performances and exhibitions appropriate for all ages in this museum throughout the year. MoCA Westport is open from Thursday to Friday from 4 pm to 6 pm and from 12 pm to 4 pm on the weekends.

Longshore Sailing School

8. Learn new skills at Longshore Sailing School

Are you looking for a fun destination to spend your summer? Then you should visit Longshore Sailing School. This school is popularly known for teaching sailing lessons and renting out watercraft. Longshore Sailing School is the most renowned and oldest sailing program in the United States of America. According to Travellens, this school was awarded the most prestigious sail training award in the state. They also provide lessons on kayaking, paddleboarding, and other water-based activities to people of all ages. Longshore Sailing School is open on Monday from 9 am-6 pm, Tuesday from 12 am-5 pm, and Wednesday to Friday from 9 am to 6 pm.

Hummock Island

7. Take a tour of Hummock Island Oyster Farm

Located near Compo Beach, Hummock Island Oyster Farm is best known for growing oysters using state-of-the-art technology. Your experience at the farm is further improved by booking a tour that begins with a short boat ride and learning more about ancient crafts of farming. Hummock Island Oyster Farm is open all days of the week, 24 hours a day.

Enjoy a stroll on the boardwalk at Compo Beach

6. Enjoy a stroll on the boardwalk at Compo Beach

Compo Beach is situated on a 29-acre green park with recreating facilities such as a softball field, a multi-purpose field, a skate park, and two lighted basketball courts. In addition to being a perfect destination for a walk, Compo Beach is handicapped-accessible, and you are allowed to tag your dog along at designated places. The beach is open all week, 24 hours a day, and entry is completely free.

Old Mill Beach

5. Enjoy the sunset view at Old Mill Beach

Located on a 1.8-acre park, Old Mill Beach is the perfect location to relax and savor the fresh sea breeze. Here, you will wake up to a splendid sunrise view and the spectacular sunset view in the evenings. This is the ideal getaway location for you and your family as a calm and serene environment surrounds it. Old Mill Beach is open all days of the week, 24 hours a day, and entry is free.

Visit the Westport Library

4. Visit the Westport Library

The Westport Library is one of the town's popular tourist attractions and one of the town's busiest locations. It is the perfect location to work on your job-related assignments, read your favorite book, or relax. There is also free Wi-Fi, laptop booths, a lively kid's read section, a quiet reading room, and a computer terminal. The library is used to host film screenings and public art exhibitions.

Levitt Pavillion

3. Visit the Levitt's Pavilion for the Performing Arts

The Levitt's Pavilion for the Performing Arts is one of the oldest and largest outdoor summer festivals in the United States. There is a special children's movie series on Wednesdays and dance lessons given by experts. From July to September, the Levitt's Pavilion holds 60 nights of entertainment and a live concert for pop, blues, rock, world music, folk, band, and dance performances.

Southport Beach

2. Southport Beach

Southport Beach is located on a 2.5-acres land open to all visitors in the summer and winter. Situated near Sherwood Island, this is the perfect location to get away from the noisy city. Southport Beach is popularly known for its calm and relaxed surroundings that help create an exceptional vacation experience.

Explore a Christmas Tree Farm and Smith Richardson Wildlife Preserve

1. Explore a Christmas Tree Farm and Smith Richardson Wildlife Preserve

The Christmas Tree farm is located on a 24-acre land, where you can easily pick and cut your centerpiece tree for the festive season. According to Mommypoppins, the Smith Richardson Wildlife Preserve is situated on a 14-acre wildlife habitat that is home to the town's native wildlife. This preserve is very popular among the locals and attracts a large number of tourists year-round.

Liz Flynn

Written by Liz Flynn

Liz Flynn has worked as a full-time writer since 2010 after leaving a career in education. She finds almost all topics she writes about interesting, but her favorite subjects are travel and food. Liz loves the process of researching information, learning new things, and putting into words what others who share her interests might like to read. Although she spends most of her time writing, she also enjoys spending time with her husband and four children, watching films, cooking, dining out, reading, motorsports, gaming, and walking along the beach next to her house with her dog.

Read more posts by Liz Flynn

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