“Explore Fairfield County” is an informational series that provides a glimpse into the wonderful towns and cities in Fairfield County. Fairfield County is diverse, including big cities, small suburbs, beaches, farms, and busy highways. It covers a large geographic area and has much 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. It 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. Its attractions include animals, the Natureplace museum room, a playground, and hiking trails. Additionally, Earthplace has a preschool and summer camp.
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, outdoor ice skating is available at the Westport P.A.L. Rink at Longshore. You can bring your skates or rent them! Westport-Weston Family YMCA offers many programs for the whole family, including indoor and outdoor pools and an outdoor splash pad.
The 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, which sells used books to raise funds for the library while employing adults with disabilities.
If you love taking the family out to dinner, try Little Barn, Sherwood Diner, The Black Duck Cafe, Bartaco, or Shake Shack. And be sure to try one of the local ice cream shops, including Gofer or Sunny Daes.
Local storefronts offer fun outings: Splatterbox for art projects, Le Rouge Handmade Chocolates for chocolate making, and Michaels for crafting.
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.
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.”
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 locally, the list of retailers seems endless.
The Longshore Sailing School offers rentals and programs for youth and adults. Rentals include paddleboards and kayaks.
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.
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 have been serving Westport since 1975. They are a non-profit, volunteer-run organization open to the public. The observatory has a dome, and the lawn regularly hosts the largest telescope in Connecticut!
If you are a golfer, Longshore Club Park Golf Course is an 18-hole course overlooking the Long Island Sound.
4. Top Arts and Cultural Events and Activities
Westport Fine Arts Festival is highly anticipated by people from Westport and surrounding towns! Here, 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!
There are many spots for entertainment. 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, it hosts “50+ Free Nights Under the Stars,” which features 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. It prides itself on being “a community within a community!”
Westport also has many museums and classes for kits! 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. 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. My favorites are Bare, New Luxx, Dream Spa and Salon, and New Beauty and Wellness.
Fitness and wellness providers are plentiful! 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 in 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 traditional and hot yoga. Kaia Yoga, Abbey Chase Yoga, and Child’s Pose are 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.
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, and Viva Zapata. Terrain is an elevated garden and home décor shop. This shop will wow you! It’s the perfect date to shop and dine in their café. Or walk along the Saugatuck River and dine at any local restaurants, including dessert at Momu Ice Cream!
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 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 within walking distance of the Westport train station and has 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 occurs each summer and offers great discounts on products from stores on Main Street and Post Road. The Holiday Extravaganza in Westport is a highly anticipated event! Shops have sales and fun activities in their stores, holiday strolling music fills downtown, tree lighting takes place, and pop-up events happen over a weekend in December!
During the summer, Westport Town Fireworks. Locals look forward to this event every year! This highly anticipated event at Compo Beach is fun for all!
