Ossining -- Activities
Hospital -- Phelps Memorial - 701 N. Broadway (Route 9 at Route 117), Sleepy Hollow
Activities on the Hudson
The Hudson isn't a typical river, carrying water downhill to the sea. Rather the Hudson is a tidal estuary, with fresh water flowing downhill to the sea and saltwater from the sea flowing and ebbing upstream on a regular schedule.
Most days, the water is clean enough for swimming. Ever day, its clean enough for boating. Water Quality.
In good conditions, moderately experienced paddlers with the right gear can reach parks and towns up and down and across the river.
Ossining Community Sailing club - a volunteer community-based organization with the goal of promoting recreational sailing by making it more accessible, affordable and convenient. With donated sailing vessels and experienced sailors sharing their knowledge, the club offers hands-on sailing experience without the expense and commitment of owning your own boat.
Ice Boats -- weather permitting
Caputo Community Center - pool with kid features, gym, ping pong, wifi, museum of Sing Sing prison. Closed Sunday. 95 Broadway,Ossining, NY 10562. (1.4 miles away)
Ossining Library (1.6 miles away)
Golf Simulator thebacknineindoorgolf.com (Cortland Manor)
Bocce, Shuffleboard, Laser tag, Arcade (and indoor/outdoor ropes course) -- SpinsHudson
Table tennis - serious club
Legoland -- (Yonkers)
- Westchester Skating Academy in Elmsford (20 minutes)
- Ice Time Sports in Newburgh (1 hour)
- McCann Ice Arena in Poughkeepsie (1 hour)
Dia Beacon - Contemporary sculpture museum (accessible by train)
Mt. Gulian Historic Site (Fishkill)
Frances Lehman Loeb Art Center -- Free art museum at Vassar College in Poughkeepsie
Neuberger Museum of Art (Purchase, NY)
Art Along the Hudson -- Guide
Mid-Hudson Childrens' Museum -- Poughkeepsie (1 hour)
Thompson's Cider Mill (Fall only)
Music, film, theater
Jacob Burns Film Center (Pleassantville)
Picture House (Pelham - 40 minutes SE)
Mid-Hudson Civic Center -- Events -- Poughkeepsie (1 hour)
Paramount Hudson Valley Theater (Peekskill)
Untermyer Gardens (Yonkers)
Lasdon Park & Arboretum (Katonah)
Wethersfield garden (Dutchess County)
Hammond (eastern) Museum and Japanese Stroll Garden (N. Salem) (summer only)
Larchmont Manor Park - private park on Long Island Sound (Larchmont)
Caramoor Garden with performances (Katonah)
John Jay Historic Site (Katonah)
Thunder Mountain Trap and Skeet (Shooting)
Renaissance Faire (August)
Downtown Ossining -- Historic buildings. Some stores and restaurants, but not a developed tourist area.
Hiking - there are a lot of hiking opportunities in the area, from the nearly flat Old Croton Aqueduct Trail (unpaved. Guide to the northern section. Start by taking Spring St. north to Maple.) and the Briarcliff-Peekskill Trailway (unpaved) to the challenging Breakneck Ridge. Lots of hikes at Teatown Lake Reservation and Blue Mountain Reservation (Peekskill). Many hikes offer river vistas or history (e.g. Crawbuckie Nature Preserve -- Rt. 9 to Beach Rd OR via the Old Croton Aqueduct Trail., Croton Dam). County trails. I have a book, Hiking and biking trails from Westchester County.
Biking - The North County Trailway is a 22 mile paved former railroad, which runs north from Ossining Detailed map. One can also bike on the unpaved Old Croton Aqueduct Trail (start by taking Spring St. North to Maple.)
To the north, Dutchess county's Harlem Valley Rail Trail looks nice.
To the north and across the river, the Walkill Valley Rail Trail looks great, though its not paved
Waterpark -- Splashdown in Fishkill (50 minutes)
Rye Playland (Amusement Park)
Big Bear Ziplines (Hyde Park) - closed?
Bear Mountain - Zoo, Merry-go-round, pool, skating.
The Clearwater (a sloop (old-style sail boat))
Walkway Over the Hudson - pedestrian bridge at Poughkeepsie
Storm King Art Center -- outdoor Modern sculptures (New Windsor, NY)
Opus 40 -- outdoor sculpture garden Harvey Fite (Saugerties, NY)
Pepsico Sculpture Garden -- outdoor sculpture garden (Purchase, NY)
Old Rhinebeck Aerodrome Museum --air show, fly in an open-air bi-plane. Summer weekends.
Farmers' Market - Saturday mornings, in season
Great Jack O'Lantern Blaze at Van Cortand Manor (Halloween)
Campgaw -- 45 minutes away. Small skiing hill and tubing. 270' vertical drop. Top is steep.
Victor Constant Ski Area @ West Point. Open to public Monday-Friday, I think. 36 minutes away. 487' vertical drop.
Mt. Peter -- 1 hour away. 450' vertical drop
Mt. Creek in Vernon, NJ -- 1 hour and 15 minutes away. 1,000' vertical drop
Hunter Mountain -- 2 hours away. 1,500' vertical drop
Blue Mountain Reservation in Peekskill (20 minutes)
Bear Mountain Ice Rink at Bear Mountain State Park (30 minutes)
Sledding Croton Gorge Park, Route 129 (Cortland)
Peekskill Attic Treasures (Sundays, 8:00-4:00. Bank Street, Peekskill)