Things to Do in Westport, Connecticut 

1. Earthplace is a 62-acre nature and wildlife sanctuary that houses over 50 animal ambassadors and offers educational programs to connect children to nature. There is also an outdoor amphitheater, walking trails, picnic grove, and a 22,000-square-foot learning center. Every weekday at 10:30am, parents can drop in with children under 5 for an animal-themed story and encounter with one of the Animal Hall residents! Earthplace blends science, conservation, and education into pathways for learning about nature and the environment.

2. Sherwood Island State Park is Connecticut’s first state park and still one of its best. Enjoy a leisurely lunch in the picnic grove and a swim in the Long Island Sound. There is also saltwater fishing, sports fields, and a nature center. A 9-11 Living Memorial is located in the exact place from where the twin towers of the World Trade Center were once visible from Sherwood Island Park.

3. Wakeman Town Farm is a favorite of many families. This organic homestead was created to educate the community about local healthy food production, responsible land stewardship, and community service. Wakeman Town Farm provides a place where kids can experience hands-on homesteading practices, encompassing time-honored and cutting-edge methods. The farm has educational workshops in animal husbandry, as well as growing fruits and vegetables. It also offers cooking classes, student internships, after-school environmental clubs, and summer camps.

Showing off original creations. Photo courtesy of MoCA Westport

4. Westport Museum of Contemporary Art (MOCA) is not your average community arts center. This is a proper contemporary museum offering a breadth of workshops and activities for children of all ages. After-school art and music classes, as well as camps and special events, fill this beautiful little museum's busy seasonal schedule. Exhibitions rotate frequently, so there’s always something fresh to see.

5. Located in the heart of downtown Westport and overlooking the Saugatuck River is the beautiful Westport Public Library. The library underwent a massive renovation that was completed in 2019, and the results are wonderful. There are daily events hosted both in-person and online, and there are programs for infants all the way to teens.

6. Connect with the cosmos and enjoy the wonders of the night sky with the Westport Astronomical Society (WAS). Free to the public, this nonprofit organization is open every Wednesday night from 8pm-10pm (clear skies permitting). The Observatory is located in one of the highest and darkest points in Westport (182 Bayberry Lane). WAS offers an important support system for the scientific community by creating a venue to explore the night skies.

Learn to sail! Photo courtesy of Longshore Sailing School

7. Learn to sail at Longshore Sailing School. Located at the mouth of the Saugatuck River and Long Island Sound, Longshore Sailing is a community of sailing that offers kayaks, sailboat, and paddleboard rentals as well. This is a public facility and is open to residents and also people who don't live in Westport. Children 5 and older can sign up for private or group sailing lessons, and kids over 8 can go it alone.

8. Launched in 2006 by Paul Newman, the Westport Farmers Market is open every Thursday from 10am-2pm during the summer months (May 13 to November 11) at 50 Imperial Ave, and during the winter months at Gilbert's Herb Garden (7 Sylvan Lane). This exceptional farmer’s market aspires to “increase awareness, knowledge, and support for local producers focused on sustainable and healthy growing practices.” Be sure to pick up one of Izzi B’s allergen-free goodies for the kids or some Kneads Bread other-worldly goodies!

9. Westport Country Play House is a non-profit theater. There are countless programs for kids and teens alike. While currently closed due to the pandemic, the playhouse hopes to soon bring-back the popular Together at the Table program, where kids and adults can enjoy dinner and a show for $10. They also offer the Conversation About the Show series, in which they invite families to a casual, communal dinner, followed by conversations about the show hosted by members of their artistic team.

10. Enjoy a day of sand and surf at Compo Beach. This beautiful 29-acre park includes long sandy beaches that hug the Long Island Sound and Saugatuck River. It is handicapped accessible and includes a boardwalk, pavilion, concession stand, two volleyball courts, bathrooms, lockers, a skate park, and is adjacent to the lovely Ned Dimes Marina. The beach is open year-round. From May 1 through September 30, a daily fee is charged to park from 4am-10pm.

11. Since its founding in 1889, the Westport Historical Society has been a cultural and educational organization “dedicated to preserving, presenting and celebrating the history of Westport.” Located in the Bradley-Wheeler House in downtown Westport, this ½ acre property houses an interactive museum that is free of charge and open to the public. Westport Museum hosts programs for children and adults, including history happy hours, walking tours, author talks, and film showings. The museum also oversees that Adams Academy, an authentic one-room schoolhouse that was used from 1837-1867. Young history buffs can join the team as volunteers or interns and get the opportunity to work with artifacts, and assist with exhibition and program creation!

12. Splatterbox is an adorable little art studio that offers so much more than just painted clay objects. From birthday parties to mini-camps, they have painting, beading, crafting, reading, games, and fun science experiments. For kids 5 and up, they have something called Morning & Afternoon CREATE. Create time includes arts & crafts (ex: painting, drawing, beading, experiments, Legos, ETC.). The flexible schedule makes it easy to drop in once a week or as many times as you’d like. Ready. Set. CREATE! 

Take in a concert for a lovely evening. Photo courtesy of Levitt Pavilion for the Performing Arts

13. The Levitt Pavilion reopening for 2021! With the beautiful Saugatuck River as the backdrop for this open-air theater, free concerts are offered all summer long. Scheduling for the 2021 summer season is still been worked out, but in years past the Melissa & Doug Children’s Series featured the best of children’s entertainment and even offered complementary face-painting for kids.

14. Re-opening Memorial Day weekend, the Westport Paddle Club offers paddleboard and kayak rentals right on the Saugatuck River. The club is open 9am-6pm, seven days a week during the summer season. This Westport gem offers summer camps for kids ages 7 and up. Classes are suitable for beginners. They also teach ocean safety, boating rules, equipment care, and much more.

15. No family day in Westport is complete without a trip to Saugatuck Sweets. This wondrous candy-land is located right on the Saugatuck River and is situated in a beautiful courtyard on Riverside Ave., right off of Bridge Street. Families can enjoy bags of candy and ice cream while kids work off their energy in this lovely outdoor space, all while enjoying the sunset on the river. It's the perfect cap to a perfect day.

Sweet treats at Saugatuck Sweets. Photo courtesy of Experience Fairfield

16. Longshore Ice Rink is a wintertime favorite for the residents of Westport. Sadly, the rink was closed this past season due to COVID, but the rink has every intention of reopening this upcoming winter. The outdoor ice rink is open from late November through early March and is located inside Longshore Club Park, right on the water. This lovely rink offers many popular programs for children and adults who are interested in learning and improving their skating abilities. There have private and group lessons (starting for kids as young as 3), along with private parties. All programs are designed the keep skaters enthusiastic about learning from the time they begin lessons until they reach their goals.

17. Sharkey’s Cuts for Kids is a family favorite. This incredible children’s hair salon is part arcade, part barber shop, and 100% a good time! Children can sit in a Dodge police cruiser, Barbie Jeep, Frozen Jeep, Lighting McQueen Race Car, Hummer, or Fire Engine. Older kids will love playing Xbox or PS4 on 40-inch screens or watching a favorite movie, sport, or concert event.