Fast-Tracking Newcomers

Just moved to town? Welcome! Now, here’s your homework: visit the following five places in town as soon as possible. Not only will you enjoy your visit, you’ll fit right into your new hometown.


  1. Compo Beach: Half the reason you moved to town is the option in schooling; the other half is Compo Beach—or, at least, it seems that way. In the summer, most of your new neighbors and friends can be spotted down at Compo. In the morning, you’ll find people tossing the football around, walking the dog, or taking pictures of the sunrise. All day, it’s soaking in the sun, letting the kids loose on the playground, building sandcastles and getting a bite at Joey’s. By day’s end, folks are enjoying a casual picnic and toasting the sunset. 60 Compo Beach Road

    Photographer: Katie Conte


  1. Main Street + Post Road: Shoppers, meet up with friends at the new Bedford Square, which has shops and dining options. Then stroll down Main Street, where you’ll find lots of stores, including Theory, Lux, Bond & Green, Blue Mercury, and Vince. Buckets of others are found on or near the Post Road—Lucy’s, Allegre, WEST, South Moon Under and Soleil Toile—or tucked in stylish Sconset Square (like Bungalow, Swoon, White Birch and more). You’re within easy walking distance of cute boutiques, like JL Rocks in one direction, and Fred in the other. In between, you’ll enjoy a fine selection of restaurants and eateries.


  1. Winslow Park: Westport loves its dogs. Each weekend you’ll find lots of opportunities to make friends at this centrally located park. You can take a short tour near the parking area or pass to the far end of the park and head up the trail. You’ll know you’ve made it by the water station and pack of happy dogs and owners. The stroll is easy and pretty and offers great opportunity to socialize your pet (and you). North Compo Road and Post Road East

    Photographer: Andrew Sullivan


  1. Westport Country Playhouse: You’ll certainly find your way to Westport Library, the Westport Arts Center and the summer Arts Festival, but we want to make sure you don’t put off visiting the Westport Country Playhouse. Not only can you take in excellent plays, you can also find script-in-hand readings, fundraising events and family-friendly theater and programs. The stage has been graced with far too many huge stars to name; check out the wall posters, which looks like a Who’s Who in theater.

    Photographer: Melani Lust


  1. Levitt Pavilion: All summer long, take in free performances under the stars at the Levitt Pavilion. What a gem! The recently built stage, with the Saugatuck River in the background, is a handsome setting for the bands, dancers and other artists. You’ll want to check out the calendar of events to see which is best for you: family-friendly, jazz, rock, pop and more. Don’t miss the annual fundraising gala with a headliner. Bring a chair or blanket, a picnic dinner and your dancing shoes—it’s a fun night out for all ages.

    Photographer: Helen Klisser During
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