Best 51 things to do in Pleasant Valley, NY

Try four watersports or relax aboard a private, instructor-led lake charter

Try five watersports with coaching, gear, and time to relax on the lake

Switch between five watersports with captain-led instruction

Try five watersports with coaching and gear included on Lake Lillinonah

Private 4-hour pontoon charter with captain and tubing on Lake Lillinonah

Private 1-hour pontoon charter with captain and tubing on Lake Lillinonah

Cruise to Petra Island and step inside two Frank Lloyd Wright-designed homes

Trace West Point history among notable resting places and an 1837 chapel

Walk through West Point history with Hudson River and Highlands views

Explore Russel Wright’s house, studio, and quarry landscape

Taste street food across the Lower East Side, Chinatown, and Little Italy on a Hebrew-guided tour

Walk Central Park with a Hebrew-speaking guide and photo tips

Explore Lenape lifeways aboard a solar-powered Hudson River boat

Meditate to live gong sound aboard a solar-powered Hudson River boat

Cruise the Hudson River at night with a live band on board

An evening cruise, island history, and a movie at Bannerman Castle

Cruise the Hudson and explore Bannerman Castle, gardens, and the newly unveiled Grotto

Pair Bannerman Island's historic scenery with a live music performance

Two-day kids waterski clinic with coached lake time

Fish Lake Lillinonah with a private guide on a comfortable pontoon

Private 2-hour pontoon cruise for up to 12 on Lake Lillinonah

Cruise Lake Lillinonah on a private pontoon with your group

Two-day kids wakeboard clinic (ages 8–14) with small groups

Cruise Lake Lillinonah for fall foliage and shoreline views