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.
- 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, but at present offers few direct flights.
- 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.
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. Express service between Ossining station and New York City's Grand Central Terminal is about 50 minutes. A one-way ticket costs $11.25 off-peak and $14.75 peak. Local service is available between other Metro-North commuter stations. Full weekday and weekend schedules are available online. Local taxis are usually on hand, and Zipcars are available at this station. On-board fares are subject to a stiff surcharge, so buy your tickets online or at the vending machines in the overpass across from the station building.
- Amtrak. Long distance connections are available in New York City's Penn Station and at Metro-North's Croton-Harmon station.
- Haverstraw–Ossining Ferry. 15 minute ferry trip across the Hudson River between Ossining and Haverstraw, NY, operating during weekday rush hours only. The one-way fare is $4.25 for adults and $2 for children (6-11) and seniors. Children 5 and under ride free. Operated by NY Waterway.
- Bee-Line System. Westchester County's bus service provides access to White Plains and other locations in the county. Schedules and route maps are available online and at the Ossining train station.
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.
- Ossining Heritage Area, 95 Broadway. The Joseph G. Caputo Community Center of Ossining features wonderful exhibits for visitors to the historical area. Free.
- Sing Sing Prison Exhibit. Housed in the Joseph G. Caputo Community Center. The collection features a replica of the original electric chair and a collection of homemade knives confiscated from prisoners. 95 Broadway (off Highland Ave), +1 914 941-3189.
- Ossining Arts Council Gallery, ☏ . For art lovers, be sure to check out the monthly exhibits displayed in various locations throughout the community.
Parks and Gardens
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.
While one can find a variety of entertainment held throughout the year there are a few major annual events beloved by community members 
- Ossining Village Fair, Main St. Ever summer, the town closes down Main Street (located in the heart of Ossining) for must-attend festivities. For a small fee, businesses and organizations in Ossining can purchase booth spots along Main Street to promote their cause. They offer a variety of services for the public, from food to keychains to activities for kids. It's a perfect way to spend a summer day with friends and neighbors.
- St. Anne’s [dead link] & St. Augustine’s Fairs Two of the largest Catholic Churches in the town hosts a carnival every June and August, respectively. The St. Anne's Fair and the St. Augustine's fair are great events for all ages, particularly families. Rides and games for kids (or those young at heart), great food, and even gambling for the adults bring together all members of the Ossining community.
- Farmers' market. Corner of Main St and Spring St. Sa 8:30AM-2PM, June to mid December. Wonderful produce and naturally-made products for you to guiltlessly enjoy!
- Arcadian Shopping Center.
Stores include Stop-n-Shop supermarket, DSW Shoes, Verizon Store, and CV S pharmacy. Dining includes an Italian restaurant, a hibachi steakhouse, an ice cream parlour, McDonald's, and Subway.
- Chilmark Shopping Center.
Stores include A&P supermarket, a hair salon, pharmacy/boutique store, wine & liquor store, and Chase bank. Dining includes a pizzeria, Carvel, Subway, Baskin Robins, Dunkin' Donuts, and a Japanese restaurant.
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.
- Cidada Cafe, 123 Main St, ☏ . Bakery, sandwich, subs, Portuguese cuisine Breakfast, Lunch, Dinner available $5-$15.
- Purple Monkey, 238 South Highland Avenue/Arcadian Shopping Center, ☏ . Desserts/Ice Cream. Under $10.
- Golden Krust, 132 Spring St, ☏ . Caribbean cuisine, well-known among locals for their delicious beef patties. Call for price listings..
- Lucy's Pizzeria, 26 S Highland Ave, ☏ . Great pizza and Italian dishes make this small pizzeria a local favorite. Selling items from individual slices to entrees, prices range from $2- $15.
- Ossining Pizzeria & Restaurant, 181 Croton Ave., ☏ . Delivery, take-out, and sit-down Italian restaurant. Lunch and Dinner entrees $10-15.
- China Wok, 157 Main St., ☏ . Chinese cuisine. Take-out and delivery available. Under $10.
- Wobble Cafe, 21 Campwoods Rd, ☏ . Breakfast, brunch and lunch. Child friendly. Vegetarian selections. Voted best breakfast by Westchester Magazine.
- Yama Fuji, 1914 Pleasantville Road/Chilmark Shopping Center, ☏ . Great Japanese cuisine and sushi restaurant. Lunch and Dinner entrees $7-$20.
- Los Abuelos, 38 N Highland Ave, ☏ . Mexican cuisine. Lunch and Dinner entrees $10-$15.
- Capri Pizza & Pasta, 228 South Highland Avenue/Arcadian Shopping Center, ☏ . Sit-down Italian restaurant. Child friendly. Lunch and Dinner entrees $10-$15.
- Isabella's Brick Oven Pizza and Ristorante, 107 Main St, ☏ . Great Italian cuisine located in the heart of Ossining. Lunch and Dinner entrees $10-$15.
- Highland Diner, 191 N Highland Ave, ☏ . American and Greek cuisine. Child friendly. Breakfast, Lunch, and Dinner entrees $10-$15.
- The Olympic Diner, 265 S Highland Ave, ☏ . American, Italian, and Mediterranean cuisine. Breakfast, Lunch, Dinner entrees $10-$15.
- Pon Di Riva Caribbean Restauarant, 1 Station Plz, ☏ . Caribbean cuisine restaurant located along Ossining's waterfront, Breakfast, Lunch and Dinner entrees $10-$15.
- Goldfish, 6 Rockledge Ave, ☏ . American and Seafood cuisine. Lunch and Dinner entrees $15-$25.
- The Boathouse, 46 Westerly Road ( just north of the Ossining train station), ☏ . Located along the Ossining waterfront, the locals come here for great American and seafood cuisine. Outdoor dining available. Lunch and Dinner entrees $15-$25.
- Karma Lounge / Martini Bar and Grille, 175 Main St, ☏ . International ecuisine. Daily happy hour specials. Features a live band and late hours on Friday and Saturday nights. Lunch and Dinner entrees $10-$15.
- Starbucks, Arcadian Shopping Center.
- Dunkin Donuts. Two locations
- Alexander Hamilton House, 49 Van Wyck St, ☏ . Croton-on-Hudson. Bed and breakfast with river view from grounds. Air conditioned, high-speed internet access.
- Courtyard by Marriott, 475 White Plains Rd, ☏ . Tarrytown.
- Doubletree Hotel, ☏ . 455 S Broadway, Tarrytown.
- SpringHill Suites by Marriott, 480 White Plains Rd, ☏ . Tarrytown.
- Castle on the Hudson, 400 Benedict Ave, toll-free: . Tarrytown.
- Marriott, 670 White Plains Rd, ☏ . Tarrytown.
Dial 911 from any telephone for emergency police, medical, and fire services.
For those seeking adventure outside of Ossining, the surrounding NY area features numerous destination spots suitable for all.
- New York City. Ossining is only 30 miles north of Manhattan, which makes it easy for anyone to travel to and from the Big Apple. For those not looking to splurge on a week-long urban adventure, day trips or even a special dinner excursion are simple and absolutely worth it! If you're worried about driving in the busy city, the MetroNorth train is a short 45-minute ride along the Hudson River.
- Woodbury Common Outlets. Located right across the Tappan Zee Bridge in Central Valley, NY, this incredible outlet center is a popular shopping haven for both New Yorkers and tourists from around the world. Stores range from casual to designer, such as Gap, Burberry, Polo, Disney, and many more. A food court and restaurants are also provided to keep shoppers on the move.
- Palisades Center Mall. Also located right across the Tappan Zee Bridge in West Nyack, NY is a massive 4-level shopping mall. A variety of retail stores for shoppers to explore, as well as an ice skating rink, movie theater, and fun zone for kids.
- Greater Westchester Area. Activities such as ice skating, miniature golf, concerts, theatrical performances and historical tours are all within driving distance in the county.
|Routes through Ossining|
|Albany ← Croton-on-Hudson ←||N S||→ Briarcliff Manor → New York City|
|Poughkeepsie ← Croton-on-Hudson ←||N S||→ Briarcliff Manor → New York City|