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

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.