Things to Do in Westport with Grandkids — Grandkids Guide

Westport is one of the better grandkid towns in Fairfield County — good parks, an excellent beach, a walkable downtown, and enough variety that you can come back in a different season and have a different day. The parking situation requires some navigation in summer, but outside of peak months it’s genuinely easy.

Here’s what to do there.

Sherwood Island State Park

Connecticut’s first state park and still its best beach for a full grandkid day. The parking lot is large and flat, the walk to the beach is manageable, and there are covered pavilions for shade and lunch. The park includes a nature center on the eastern end that’s worth a stop if you have curious grandkids.

Parking: Free outside of Memorial Day to Labor Day. In summer, $15–$22 depending on CT plate vs. out-of-state. Arrive by 9am on peak summer days to avoid a full lot.

Best for: All ages. Year-round, though the beach is best May–September.

What to bring: Blanket, snacks, sunscreen. The concession stand is seasonal and unreliable — don’t count on it.

Compo Beach

Westport’s town beach is smaller than Sherwood Island but the surrounding park infrastructure — bandshell, picnic area, updated playground equipment — makes it a good choice for younger grandkids who want more variety than open beach.

Parking note: Westport resident permit required after 8am in summer. If you’re not a Westport resident, go to Sherwood Island instead — it’s a state park and open to all.

Off-season advantage: Spring and fall mornings are walk-in, free parking, almost no one there.

Westport Downtown — Strolling and Coffee

The stretch of Main Street and Post Road near downtown Westport is genuinely walkable. There are several coffee shops, a few bookstores, and enough visual interest to hold a grandkid’s attention for an hour. This works best as a warm-up before or cool-down after a bigger activity.

If it’s raining: Restoration Hardware’s Westport location is unexpectedly grand and kid-tolerant (the furniture is mostly too large to damage). Next door, there are typically a few options for lunch.

Longshore Park

A lesser-known option: Longshore Park is a Westport town property on Long Island Sound with a swimming pool (day passes available in summer), a small beach, tennis courts, and a sailing center. The café overlooks the water.

Best for: Families where some grandkids want to swim and others want to walk the waterfront.

Earthplace (Westport Nature Center)

Sixty-two acres of trails and a small nature center with live animals. It’s not as large as New Canaan Nature Center but it’s close to downtown and works well as a morning activity before lunch in town.

Admission: Small fee. Members free. Call to confirm hours — they vary seasonally.

Westport Timing Guide

Activity	Best Time
Sherwood Island (summer)	Before 9am or after 4pm to avoid parking crunch
Sherwood Island (spring/fall)	Any time — it’s yours
Compo Beach	Resident parking only in summer — skip if not a resident
Downtown stroll	10am on a weekday
Longshore Park pool	Weekday mornings — least crowded

Browse all Westport venues: grandkidsguide.com/fairfield-county-ct/westport/