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, 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 Norwalk, Wilton, Weston, and Fairfield. Westport is easily accessible by both the Merritt Parkway and I-95, and has 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.

1. Downtown Westport

Westport’s Main Street and connecting streets are easily walkable and full of many shopping and dining options. Free parking is an added bonus. The Westport Downtown Merchants Association hosts special events and festivals throughout the year, including the Sidewalk Sale, Westport Fine Arts Festival, and holiday happenings.

2. Parks & Recreation Amenities

Westport residents have access to many Parks & Recreation amenities and facilities in town. There are three beaches: Compo, Burying Hill, and Old Mill, and two pools: Longshore Pool (summer) and Staples Community Pool (November – June). The Longshore Club Park Golf Course is an 18-hole course overlooking the Long Island Sound. The Longshore Sailing School offers rentals and programs for youth and adults. In the winter months there is outdoor ice skating at the Westport P.A.L. Rink at Longshore. *Please note that some of these amenities are open to the public, fees may vary. 

Compo Beach in Westport

3. Sherwood Island State Park

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.

4. Westport Country Playhouse

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. Their regular season runs from April to November; take a look at what will be on stage for their 2020 season

Westport Country Playhouse (left) and The Levitt Pavilion (right)

5. Levitt Pavilion

Every summer, The Levitt Pavilion hosts “50+ Free Nights Under the Stars”, with a wide range of performing arts, including the Melissa & Doug Children’s Series every Wednesday night at 7 p.m.

6. Earthplace

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.

7. Leonard Schine Preserve

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.), as well as a family nature trail.

8. Wakeman Town Farm

Wakeman Town Farm is “Westport’s Community Farm” with programming for all ages. See what’s coming up soon; there are farm/gardening workshops, farm classes and camps, cooking classes for adults and kids, and much more.

9. Saugatuck

This little neighborhood along the Saugatuck River is walking distance from the Westport train station and is home to even more dining options, including two popular Fairfield County destinations: The Whelk Restaurant & Seafood Bar and Saugatuck Sweets

10. Shopping

Westport is our go-to town 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 and all along Route 1. Whether you prefer popular retail chains or shopping local, the list of retailers seems endless. I must suggest that you visit both Anthropologie & Co. and Terrain (including their café). 

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.


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