Explore Fairfield County :: Westport


“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 NorwalkWiltonWeston, 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

Photo by Evan Messerli

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.
Photo by Evan Messerli

3. Top Outdoor Activities

Photo by Evan Messerli

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!
Photo by Evan Messerli

5. Top Health and Wellness Facilities (and Eateries)

6. Top Date Night or Moms’ Night (or Day) Out Activities

Photo by Evan Messerli

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.
Photo by Evan Messerli

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!
Photo by Evan Messerli

Have you visited Westport? Do you live here? What do you love about it?

Read all the posts in our Explore Fairfield County Series by clicking here.


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