Explore Fairfield County :: Westport

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“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 because of this, it has a lot to offer families! To help you get the most out of Fairfield County, our contributors have shared the top 10 things they love about each local area. To read more in this series, click here.”Westport

Westport is located along the Long Island Sound, neighboring NorwalkWiltonWeston, and Fairfield. Westport is easily accessible by both the Merritt Parkway and I-95 and is desirable for the 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. School-aged children might attend one of five elementary schools (K-5), two middle schools (6-8), or one high school (9-12). There are also two private schools in Westport: Greens Farms Academy and Pierrepont School. There are so many wonderful things to share about this family-oriented, picturesque, and oceanside town that values community and physical well-being, so we’ve broken down into the Top Westport “To-Do’s!”

Top Activities for Families and Children:

Photo by Evan Messerli

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, but it’s too nice to be indoors at the mall. Shopping is available in both Downtown Westport (safe for teens to walk along) and all along Route 1. Whether you prefer popular retail chains or shopping local, the list of retailers seems endless.
Photo by Evan Messerli

Top Outdoor Activities:

Photo by Evan Messerli

Top Arts and Cultural Events and Activities:

  • Westport Fine Arts Festival – This 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. From November to March, Family Festivities are 1-hour family-friendly performances of favorite children’s stories, for just $20 per ticket.  
  • 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 – This theater is located at Westport Town Hall and has been around for 64 years! They pride themselves in being “a community within a community!” 
  • Craft Westport – this is the longest-running indoor craft event in Connecticut! Held at Staples High School, it features top crafters from across the country. 
Photo by Evan Messerli

Top Health and Wellness Facilities (and Eateries):

Top Date Night or Mom’s Night (or day) Out Activities:

Photo by Evan Messerli

Most Scenic Places to Visit:

  • There are three beautiful beaches to enjoy in town – Compo, Burying Hill, and Old Mill give this town its stunning ocean views.
  • Sherwood Island State Park, located on the Long Island Sound, offers a beach and swimming, as well as a Nature Center (open seasonally), hiking, and a disc golf course.
  • This little 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. This is a sight worth seeing!
Photo by Evan Messerli

Top Town-Wide Events and Activities:

  • Point to Point Swim is sponsored by the Westport Weston Family Y and is held at Compo beach. There is a kid’s swim, as well!
  • The Great Duck Race is a fun family event that is held at Parking Harding Plaza at the Saugatuck River and is hosted by Westport Sunrise Rotary.
  • Westport Sidewalk Sale is an annual event that takes place each summer and provides great discounts on many products from the stores around Main Street and the 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

*Please note that some of these amenities are open to the public, fees may vary. 

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

Be sure to read all the posts in our Explore Fairfield County Series by clicking here.


A native of Fairfield County, Evan Messerli came to the business from a career in photography, video, and television where he specialized in architectural design, home, hotel, and yacht projects. Having renovated homes himself, he has a vast knowledge of building techniques and what to look out for when purchasing a home.

With attention to detail and service, Evan’s past clients and friends refer him time and time again. His knowledge of the market, unflappable negotiating skill, and proven ability to deliver have propelled him into Berkshire Hathaway’s honor society – top 14% nationwide. Berkshire Hathaway with its worldwide presence and top rankings offers top-notch marketing tools and strategies to help you with the sale of your home or business.

Listening closely to his clients’ needs, Evan is always there to answer questions and any concerns his clients have. Following-through while remaining calm in these fast-paced and sometimes turbulent times is his strong suit. His clients count on him for no-nonsense advice and for first-rate referrals of other home professionals they may need.

If you are looking to buy, sell, or invest, please contact Evan today. With that call, you will get honesty, integrity, and a willingness to go the extra mile.

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