Best Parks and Playgrounds for Grandkids in Fairfield County, CT — Grandkids Guide

Not all parks are equal for grandparent-grandkid days. Some have playgrounds that are exhausting to navigate (equipment designed for 10-year-old acrobats, no shade, parking half a mile from the play area). Others are genuinely excellent — good benches in the right places, accessible paths, bathrooms that work, and enough variety that you can spend two hours without running out of things to do.

Here’s the honest Fairfield County breakdown.

Parks Worth Making the Trip

Waveny Park, New Canaan

Three hundred acres, mostly flat, a mix of open fields and wooded trails. The playground is near the parking lot — unusual and wonderful. There’s a dog park on a separate section, so no surprise encounters if your grandkids are nervous around dogs. The picnic area has shade. This is the park for a whole morning.

Best for: Ages 3–10. Easy walking. Year-round.

Sherwood Island State Park, Westport

The beach gets the headlines but the rest of the park is excellent too — wide paths, pavilions, a nature center, and fishing access on the other side of the parking lot. Before 9am in the off-season, parking is free and you’ll have stretches of beach to yourselves.

Best for: All ages. Better on weekdays. Best May–September.

Compo Beach Park, Westport

Technically a beach but the park infrastructure around it — bandshell, paths, playground — makes it a full outing. The playground equipment is relatively modern and well-shaded. The snack bar opens in warmer weather.

Best for: Ages 2–8. Resident parking required in summer after 8am.

Mianus River Park, Greenwich

Flat trails along the river, minimal hills, accessible for most mobility levels. Not as manicured as Waveny, but the natural setting is better. You’ll likely see great blue herons. Kids like throwing rocks in the water — budget for time.

Best for: Ages 4+. Year-round. Bring bug spray in summer.

Calf Pasture Beach Park, Norwalk

Connected to the water treatment facility (which sounds worse than it is). The park itself has good wide paths, a small playground, and picnic tables right at the water’s edge. The Sound views are genuinely beautiful in any season.

Best for: All ages. Parking can fill up on hot weekends — go before 10am.

Local Favorites Worth Knowing

Jennings Beach, Fairfield — Town beach with a playground. The concession stand is better than you’d expect.

Greenfield Hill, Fairfield — No formal playground, but the open field near the church is great for running and the dogwood trees in April are spectacular.

Bruder Nature Preserve, Westport — Quiet, wooded, shorter trails. Good if you want something less structured.

Longshore Park, Westport — Has a pool in summer (day passes available), golf course, and a small beach. Good for a longer morning.

What to Look For (and What to Ask)

Before you commit to any park for the day:

Bathrooms: Are they near the parking lot or a 10-minute walk away? This matters.
Shade: Open sun is tough by 11am in summer. Look for tree coverage near benches.
Parking: Many Westport beaches require resident permits in summer after 8am. Darien town beaches are resident-only. Check before you go.
Benches: You’re going to be sitting. Make sure there are places to sit near where the kids play.

The parks listed above check all four boxes.

Browse all parks in the guide: grandkidsguide.com/fairfield-county-ct/park/