Ossining, NY Road Trips

The village of Ossining lies within the township of the same name. As one of the smaller towns within Westchester County, Ossining is well known for its humbling diverse character. The variety of cultures, ethnicities, and socioeconomics has created a town that offers a unique glimpse of America’s melting pot. Along the Hudson River (just north of the Tappan Zee Bridge) and 30 miles north of New York City, Ossining is a great destination for those looking for a taste of metropolitan life in a suburban setting.

1 Ossining Heritage Area, 95 Broadway. The Joseph G. Caputo Community Center of Ossining features wonderful exhibits for visitors to the historical area. Free. 2 Sing Sing Prison Museum, 127 Main St, ☏ +1 914-236-5407. he collection features a replica of the original electric chair and a collection of homemade knives confiscated from prisoners. (updated Aug 2020) 3 Ossining Arts Council Gallery, 117 Main St, ☏ +1 914-502-4157, [email protected]. For art lovers, be sure to check out the monthly exhibits displayed in various locations throughout the community. (updated Apr 2021)

With approx. 130 acres of land devoted to recreational use, there are a variety of beautiful parks for kids, and even adults, to enjoy. Ryder Park, Morningside Dr. Features a soccer/football, fitness trail, horseshoe pits, pavilions, tennis courts, basketball courts, ball fields, playground, picnic area, rest rooms. Gerlach Park, Old Albany Post Rd. Features horseshoe pits, pavilions, hiking/nature study, ball fields, playground, picnic area, rest rooms. Veteran's Park, Narragansett Ave. Features areas for soccer/football, horseshoe pits, fishing, bocce courts, basketball courts, ball fields, playground, picnic area, rest rooms, roller hockey rink. Louis Engel Waterfront Park. Located next to the Ossining railroad station, this riverside park features areas for fishing, playground, picnic area, a sunning beach, and rest rooms. Buck Johnson Park, Blue Lantern Rd. As one of the more quaint parks, Buck Johnson's has basketball courts and a playground. Cedar Lane Park, Cedar Ln. Features fitness trail, basketball courts, fishing, picnic area, restrooms, soccer field. Membership to an open-door swimming pool can also be purchased for the summer season. Old Croton Aqueduct. Go hiking or biking on the aqueduct's trailway. The original water supply to New York City is now a walking trail that runs from Croton-on-Hudson in the north to Yonkers in the south. Over the 180 years since it was built, portions have disappeared from the downtown areas of several river towns, including Ossining. Art Barn at 211 N. Highland Ave. sells maps of the trail.

There is an amazing variety of restaurants, with ethnic food geography ranging from Northern European (German and Swiss) to South American (Peruvian, Mexican) with stops at Portugal and Italy. Italian-American cuisine is particularly delightful. 1 Lucy's Pizzeria, 26 S Highland Ave, ☏ +1 914-762-0001. M–Sa 11AM–10PM, Su noon–10PM. Great pizza and Italian dishes make this small pizzeria a local favorite. Selling items from individual slices to entrees. $2-15. (updated Apr 2021) 2 Ossining Pizzeria & Restaurant, 181 Croton Ave, ☏ +1 914-762-1455. Su–Th 11AM–9PM, F Sa 11AM–10PM. Delivery, take-out, and sit-down Italian restaurant. Lunch and Dinner entrees $10-15. (updated Apr 2021) 3 New Yummy China Wok, 157 Main St, ☏ +1 914-941-1202. Tu–Th 10:30AM–10PM, F Sa 10:30AM–10:30PM, Su 11:30AM–10PM. Chinese cuisine. Take-out and delivery available. Under $10. 4 Los Abuelos, 197 S Highland Ave, ☏ +1 914-502-0220, [email protected]. Daily 11AM–10PM. Mexican cuisine. Lunch and dinner entrees $10-15. (updated Apr 2021) 5 Capri Pizza & Pasta, 228 S Highland Ave (Arcadian Shopping Center), ☏ +1 914-944-8000, [email protected]. Daily 10AM–10PM. Sit-down Italian restaurant. Child friendly. Lunch and dinner entrees $10-15. (updated Apr 2021) 6 The Boathouse, 46 Westerly Rd ( just N of the Ossining train station), ☏ +1 914-923-6466. W Th 4–9PM, F 4–10PM, Sa noon–10PM, Su noon–8PM. Located along the Ossining waterfront, the locals come here for great American and seafood cuisine. Outdoor dining available.

1 Karma Lounge, 175 Main St, ☏ +1 914-502-0360. Martini bar and grill with international cuisine. Daily happy hour specials. Features a live band and late hours on Friday and Saturday nights. Lunch and dinner entrees $10-15.

Westchester County Airport, 240 Airport Road, White Plains, +1 914 995-4860 (airlines). The closest airport, about a 30-minute drive. Rental cars are available. Stewart International Airport, 1180 First St, New Windsor, +1 845 564-2100. Another alternative to the congestion of the 3 major airports. Allegiant Air, American Eagle, and JetBlue operate flights from Florida and Philadelphia (Mar 2021). Newark Liberty International Airport, Newark, New Jersey, John F. Kennedy International Airport, and LaGuardia Airport: The three major international airports in the New York City area offer service to just about anywhere. Westchester-based taxi and livery cars offer regular service to and from the three internationals from most areas of the county. New York City yellow cabs will take to you Westchester in a pinch, but the fares can be exorbitant. If staying in Westchester, ask if your hotel offers shuttle service. Traveling by car is the most convenient way to get around the town, as it also makes traveling to nearby locations more efficient. If you don't bring your own car, renting a car during a short-term stay may be helpful. Enterprise Rent-A-Car. (updated Apr 2016) Whether you're going to the airport or coming home from a late-night dinner along the river, multiple taxi services are available for those who seek to travel distances unavailable by other means of transportation. Most taxi services charge $5 for intown destinations. Metro-North Railroad – Hudson Line.

Route 9 is called Highland Avenue in Ossining (in adjacent villages it is usually named Broadway). Cars are the most efficient way to get around town, although one can take advantage of the taxi and bus services.

Dial 911 from any telephone for emergency police, medical, and fire services.[2]