“Explore Fairfield County” is an informational series that provides a glimpse into the wonderful towns and cities in Fairfield County. Fairfield County is diverse in that it includes big cities, small suburbs, beaches, farms, and busy highways. It covers a large geographic area, and it has a lot to offer families! To help you get the most out of Fairfield County, our contributors have shared the top things they love about each local area. To read more in this series, click here.
Westport is located along the Long Island Sound, neighboring Norwalk, Wilton, Weston, and Fairfield. Westport is easily accessible by the Merritt Parkway and I-95 and is desirable for its proximity to New York City (there are two train stations on Metro-North’s New Haven Line). This family-friendly town is known for its highly rated public schools. There are so many wonderful things to share about this family-oriented, picturesque town that values community and physical well-being, so I’ve broken down my favorite Westport spots and activities.
1. Top Activities for Families and Children
- Earthplace is a nature center that offers both indoor and outdoor fun. There are animals, the Natureplace museum room, a playground, and hiking trails. Additionally, Earthplace has a preschool and summer camp.
- The Yankee Doodle Fair is one of Westport’s oldest and most beloved family events. You can enjoy carnival rides, international foods, face painting, bake sales, and more. Westport Women’s Club sponsors this event; all profits benefit local charities and college scholarships.
- There are two town pools to enjoy. Longshore Pool is an outdoor pool open in the summer, and Staples Community Pool is indoors and opens from November through May.
- During the winter, there is an outdoor ice skating at the Westport P.A.L. Rink at Longshore. You can bring your skates or rent them!
- Local storefronts offer fun outings: Splatterbox for art projects, Le Rouge Handmade Chocolates for chocolate making, and Michaels for crafting.
- Westport Library hosts events for children, teens, and adults, and many programs such as Camp Explore, Story Fest, and WestportREADs. Across the green is Westport Book Shop, selling used books to raise funds for Westport Library while employing adults with disabilities.
- If you love taking the family out to dinner, places like Little Barn, Sherwood Diner, The Black Duck Cafe, bartaco, and Shake Shack.
- Westport Weston Family YMCA offers many programs for the whole family, including indoor and outdoor pools and an outdoor splash pad.
- Try one of the local ice cream shops, including Gofer or Sunny Daes.
- My kids’ favorite toy store is The Toy Post.
- For back-to-school shoes, check out the new store Naturino.
2. Top Activities for Teens
- Toquet Hall opened in 1998 as a response to the need for a safe place for teens to hang out with one another. The hall is a “supervised drug/alcohol-free place where middle and high school-aged children can participate in social, cultural, recreational, and educational activities.”
- The Longshore Sailing School offers rentals and programs for youth and adults. Rentals include paddleboards and kayaks.
- Westport is a go-to place when there’s shopping to be done. Shopping downtown Westport is safe for teens to walk around and socialize. Whether you prefer popular retail chains or shopping local, the list of retailers seems endless.
3. Top Outdoor Activities
- The Aspetuck Land Trust maintains 40 preserves in Easton, Fairfield, Weston, and Westport. The Leonard Schine Preserve was their first preserve and includes a natural playground (approx. 10,000 sq. ft.) and a family nature trail.
- If you are a golfer, Longshore Club Park Golf Course is an 18-hole course overlooking the Long Island Sound.
- Wakeman Town Farm is “Westport’s Community Farm” with programming for all ages; there are farm/gardening workshops, farm classes and camps for kids, cooking classes for adults and kids, and much more.
- Westport Observatory and The Westport Astronomical Society has been serving Westport since 1975 and is a non-profit and volunteer-run organization that is open to the public. There is a dome observatory, and the lawn regularly hosts the largest telescope in Connecticut!
4. Top Arts and Cultural Events and Activities
- Westport Fine Arts Festival is a highly anticipated event by people from Westport and surrounding towns! You can find original works in painting, watercolor, jewelry, fiber, ceramics, photography, sculpture, drawing, printmaking, mixed media, glass, wood, and digital art. This festival takes place along the Saugatuck River in downtown Westport and includes live music, performances, and children’s activities!
- The Westport Country Playhouse offers live theater and other special events year-round.
- The Levitt Pavilion is an outdoor theater in Westport. During the summer, they host “50+ Free Nights Under the Stars,” with a wide range of performing arts, including the Melissa & Doug Children’s Series every Wednesday at 7 p.m.
- Westport Community Theater is located at Westport Town Hall and has been around for 64 years! They pride themselves on being “a community within a community!”
- Craft Westport is the longest-running indoor craft event in Connecticut! Held at Staples High School, it features top crafters from across the country.
- MoCA Westport is a beautiful art museum with changing exhibitions, musical performances, and kids’ classes.
- One River is an art school with classes for kids, teens, and adults. Then stop next door for a great cup of coffee at Shearwater Coffee Bar.
- If your little ones love music, try a Music Together class!
5. Top Health and Wellness Facilities (and Eateries)
- Spa services are very popular in Westport. A few of my favorites are Bare, New Luxx, Dream Spa and Salon, and New Beauty and Wellness.
- Fitness Centers are in no shortage! Orange Theory Fitness, F45 Training Westport, Westport Tennis Club, and Saugatuck Rowing Club are available for all your physical needs.
- Cryotherapy is used to treat pain with extremely cold temperatures. Greenwich Medical Spa and Restore offer these services.
- Sun Reflexology and Apex Foot Relax offer popular reflexology foot massage services.
- Multiple studios offer yoga – both traditional and hot. Kaia Yoga, Abbey Chase Yoga, and Child’s Pose are a few popular spots in Westport.
- After your gym sessions or visit a wellness facility, head to The Granola Bar, Aux Delices, Organic Market, Winfield Street Coffee, and GG and Joe to grab a smoothie, juice, or light meal.
- The Westport Farmer’s Market is one of the best around! Every Thursday from May-November.
6. Top Date Night or Moms’ Night (or Day) Out Activities
- There are plenty of delicious restaurants to choose from! Some top spots include The Whelk, The Cottage, OKO, The Boathouse, Spotted Horse Tavern, Pane e Bene, and Viva Zapata.
- Terrain is an elevated garden and home décor shop. This shop will wow you! It’s the perfect date to shop around and then dine in their café.
- Walk along the Saugatuck River and dine at any local restaurants, including dessert at Saugatuck Sweets!
6. Most Scenic Places to Visit
- There are three beautiful beaches in town; Compo (with an awesome playground), Burying Hill, and Old Mill. If you go to Compo, check out the new market, Old Mill Grocery & Deli.
- Sherwood Island State Park, located on the Long Island Sound, offers a beach, swimming, a nature center (open seasonally), hiking, and a disc golf course.
- “Saugatuck,” the neighborhood along the Saugatuck River, is walking distance from the Westport train station and is home to even more dining options.
- The Ruth Steinkraus Cohon Bridge can be found in downtown Westport. The bridge runs over the Saugatuck River and is often decorated with flags or lights.
7. Top Town-Wide Events and Activities
- Point to Point Swim is sponsored by the Westport Weston Family YMCA and is held at Compo beach. There is a kid’s swim, as well!
- The Great Duck Race is a fun family event held at Parking Harding Plaza at the Saugatuck River and hosted by Westport Sunrise Rotary.
- Westport Sidewalk Sale is an annual event that takes place each summer and provides great discounts on products from stores around Main Street and Post Road.
- Holiday Extravaganza in Westport! Shops have sales and fun activities in their stores, holiday strolling music fills downtown, a tree lighting takes place, and pop-up events happen over a weekend in December!
- Westport Town Fireworks. Locals look forward to this event every year! This highly anticipated event is held at Compo Beach and fun for all!