Things to Do with Grandkids in Port Chester & Mamaroneck, NY

Port Chester and Mamaroneck sit side by side on the Westchester Sound shoreline, close enough that combining them into one outing makes sense. Port Chester has The Capitol Theatre (one of the Northeast’s most beloved music venues, with family-friendly performances throughout the year) and Lyon Park on the waterfront. Mamaroneck has Harbor Island Park, a standout waterfront destination with a beach and marina, and Walter’s Hot Dogs, which has been feeding Westchester families since 1928.

Neither town requires a full day alone, but the two together do.

Quick Reference

Venue	Town	Category	Price	Rating	Best For
Harbor Island Park	Mamaroneck	Beach / Park	Paid	4.6 ★	All ages
Walter’s Hot Dogs	Mamaroneck	Restaurant	Paid	4.6 ★	All ages
The Capitol Theatre	Port Chester	Music / Events	Paid	4.7 ★	Ages 5+
Lyon Park	Port Chester	Park	Free	4.6 ★	All ages
Colony Grill	Port Chester	Restaurant	Paid	4.5 ★	All ages
Sal’s Pizza Mamaroneck	Mamaroneck	Restaurant	Paid	4.6 ★	All ages

Mamaroneck

Harbor Island Park

Mamaroneck’s crown jewel, a peninsula park with a beach on the Sound, a marina, kayak rentals (summer), and views of the harbor. The beach is sandy and lifeguard-staffed in summer. The park has playground equipment, picnic tables, and open lawn. Admission fee applies in summer; the park is free to walk year-round. Easy, well-organized parking in the adjacent lot.

Harbor Island Park | Mamaroneck | 4.6 ★, 1,906 reviews

Walter’s Hot Dogs

A Mamaroneck institution since 1928, a pagoda-shaped takeout stand that has been serving the same style of hot dog for nearly a century. The dogs are griddled in their own fat; the mustard is the house blend. It’s not a sit-down restaurant; you order at the window and eat outside. For grandparents who grew up in this area, Walter’s is a memory; for grandkids, it’s the experience of watching something made simply and well. Seasonal hours, generally open spring through fall.

Walter’s Hot Dogs | 937 Palmer Ave, Mamaroneck | 4.6 ★, 1,724 reviews

Sal’s Pizza Mamaroneck

A local pizza institution that works for a quick, reliable lunch. The thin-crust style is well-regarded and the portions are generous. Good pick if Walter’s isn’t your thing or if the weather pushes you indoors.

Sal’s Pizza Mamaroneck | Mamaroneck | 4.6 ★, 1,451 reviews

Port Chester

The Capitol Theatre

A legendary 1926 music venue that has hosted everyone from the Grateful Dead to current touring acts, and books family-friendly performances and children’s shows throughout the year. When the right show is on, it’s an exceptional outing: the hall is intimate (2,800 seats), acoustics are excellent, and the grandkid memory of a real concert in a real historic theater outlasts most ordinary outings. Check the calendar before planning around it.

The Capitol Theatre | 149 Westchester Ave, Port Chester | 4.7 ★, 2,755 reviews

Colony Grill

A Connecticut original that expanded to Port Chester, famous for thin-crust bar pizza, particularly the “hot oil” style. Casual, family-friendly, no reservations needed for parties under six. A reliable post-Capitol Theatre or mid-afternoon option.

Colony Grill | Port Chester | 4.5 ★, 1,051 reviews

Lyon Park

A waterfront park on the Port Chester harbor with a playground, picnic tables, and views of Greenwich Harbor. Small but well-maintained. Free. Good 30-minute stop if you’re in the area and the grandkids need to run.

Lyon Park | Port Chester | 4.6 ★, 588 reviews

Practical Notes

Combined day plan: Harbor Island Park (morning swim in summer) → Walter’s Hot Dogs (lunch) → drive to Port Chester → Capitol Theatre (if there’s a show) → Colony Grill (dinner).

Non-show day alternative: Harbor Island Park → Walter’s → Lyon Park walk → Colony Grill.

Parking: Harbor Island has a lot with seasonal fee. Port Chester downtown has street parking and a public garage on Adee Street.

Browse all Westchester venues at grandkidsguide.com/westchester-ny.