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Best Restaurants for Outdoor Dining in Ossining

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24 restaurants available nearby

A photo of 3 Westerly Bar and Grill restaurant
1. 3 Westerly Bar and Grill
4.4
Awesome(1666)
Price: Expensive
• American • Ossining
Booked 1 time today
Located in Ossining’s luxurious Harbor Square, adjacent to the Metro North Station and the NY Waterway Terminal, 3 Westerly Bar and Grill is a Modern American Restaurant housed within a distinctive free-standing lighthouse that features a variety of indoor/outdoor dining options—all of which offer stunning views of the scenic Hudson River waterfront. **Outdoor seating is on a First Come First Serve Basis. We do not accept Outdoor Reservations. Reservations are for Indoor Only.
A photo of Basso56 restaurant
2. Basso56
4.6
Exceptional(1521)
Price: Expensive
• Italian • Chappaqua
Booked 34 times today
Basso by PXK offers a contemporary Italian dining experience with a deep respect for tradition. Located in the heart of Chappaqua at 11 King Street, the restaurant is now under the culinary direction of Chef Peter X. Kelly.Inspired by his extensive travels throughout Italy, from the Michelin-starred kitchens of Milan to the rustic trattorias of Tuscany, Chef Kelly brings a modern perspective to classic Italian dishes. He emphasizes the use of fresh, seasonal ingredients sourced from local farms and artisan producers within the Hudson Valley. Savor a menu that celebrates the comforting familiarity of Italian cuisine while embracing innovative techniques and presentations.Pots, Pans & Pasta Sunday BrunchSundays, 11:30 AM to 2:30 PMEnjoy a continuous feast of delicious dishes presented table side, including a bountiful selection of fresh pastas, seasonal fruits and salads, frittatas, a variety of meats and fishes, and flavorful grains and risottos.
A photo of 105-Twenty Bar & Grill restaurant
3. 105-Twenty Bar & Grill
4.5
Awesome(139)
Price: Expensive
• American • Croton Falls
Booked 3 times today
Opened in December of 2018, 105-Twenty Bar & Grill is located in the heart of the village of Croton-On-Hudson, NY. Featuring an array of starters, salads, flatbreads, burgers, sandwiches, entrees and much more. We also feature a separate bar area away from the dining room with a horseshoe shaped 12 seat bar. 12 rotating seasonal draughts, numerous wines by the glass, specialty cocktails and a full bar. 3 Large Screen TV's in the bar area to watch all the live sporting events of the day. Seasonal Outdoor Patio & Sidewalk Dining available.
A photo of 105-Ten Bar and Grill restaurant
4. 105-Ten Bar and Grill
4.7
Exceptional(111)
Price: Expensive
• American • Briarcliff Manor
Booked 3 times today
Opened in January of 2014, 105-Ten Bar & Grill has continued to be a popular destination for guests from all over Westchester County. Offering a wide array of starters, salads, flatbreads, burgers, sandwiches, entrees, and much more. Our 20 seat bar features four 65" large screen TV's for all the big live sporting events. 12 rotating beers on tap, numerous wines by the glass options, specialty cocktails and a full bar give all of our guests plenty of beverage options. We also have a fully heated outdoor dining tent that is available 7 days a week for lunch & dinner. Live Music on Thursday & Saturday Nights.
A photo of Chatterbox restaurant
5. Chatterbox
4.7
Exceptional(223)
Price: Very Expensive
• American • Pleasantville
Booked 2 times today
Traditional Italian-American Cuisine with a Modern Twist
A photo of Benjamin Steakhouse - Westchester restaurant
6. Benjamin Steakhouse - Westchester
4.7
Exceptional(4257)
Price: Very Expensive
• Steakhouse • White Plains
Booked 20 times today
Founded in 2006, the family owned and operated Benjamin Restaurant Group has grown to comprise some of the New York metro areas premier culinary destinations. Now, they bring the glory straight to the heart of Westchester County. Offering exceptional food and service in luxurious environments, owners Benjamin Prelvukaj and Benjamin Sinanaj make it their mission to treat each guest like a member of their family. Benjamin Steakhouse offers juicy cuts of dry-aged beef-from 36-ounce Porterhouses to juicy, tender Ribeyes and succulent Filet Mignon. White Plains' dècor may look familiar to those who have dined at their Manhattan location with their signature dark wood floors, banquette seating, and burgundy booths in tow. The main dining room will also feature an oversized fireplace-a signature of Benjamin Steakhouse from day one. Whether it's a romantic rendezvous or boisterous family dinner, Benjamin Steakhouse is sure to please.
A photo of Red Hat on the River restaurant
7. Red Hat on the River
4.6
Exceptional(2296)
Price: Expensive
• Contemporary French / American • Irvington
Booked 36 times today
Nestled on the waterfront in Irvington, New York, Red Hat on the River is an American modern bistro serving satisfied diners since 2003. There's hardly a seat in the house that does not offer a spectacular view of the Hudson river. Banquettes and a pewter bar accent the space while the walls of this 100-year old renovated factory building are adorned with WPA-era art evoking a feeling of a turn of the century Parisian bistro. Evolving from a humble bistro on main street to a bustling restaurant on the river with a rooftop bar, Red Hat's commitment to providing the very best experience for their guests has always remained the same. Try the classic menu standards of steak frites, moules frites, country terrine, and the Red Hat burger. Seasonal salads, sandwiches, and seafood entrees round out the menu. The bar offerings of creative craft cocktails, local draft beer, and old world style wines complete the experience. Private events range from corporate dinners to weddings.
A photo of Zero Otto Nove - Armonk restaurant
8. Zero Otto Nove - Armonk
4.7
Exceptional(1300)
Price: Moderate
• Italian • Armonk
Booked 7 times today
Roberto Paciullo’s hometown of Salerno is transported to the streets of Manhattan. Zero Otto Nove is the second outpost of his famous restaurants from Arthur Ave. in the Bronx. From the atmosphere to the food, stopping by Zero Otto Nove is taking a quick trip to Italy. The wood-burning brick oven is at the center turning out classics like the Margherita, and Roberto's originals, such as La Riccardo with butternut squash puree, smoked mozzarella, spicy pancetta, and basil. All the pastas are homemade, and all ingredients are brought in from New York's Real Little Italy, Arthur Avenue.
A photo of MP Taverna - Irvington restaurant
9. MP Taverna - Irvington
4.8
Exceptional(2836)
Price: Moderate
• Greek • Irvington
Booked 15 times today
Outdoor dining is open weather permitting. MP Taverna, Chef Michael Psilakis’s modern interpretation of a traditional Greek tavern, is an exciting staple in the Westchester dining scene, located steps from the Metro-North Railroad and a stone’s throw from the Hudson River. Open for lunch and dinner, MP Taverna’s accessible, Greek-inspired menu brings Psilakis’ Greek fare into the American culinary lexicon and is another step towards the chef’s goal of putting Greek cuisine on the culinary main stage.
A photo of Otto’s Full Service restaurant
10. Otto’s Full Service
4.8
Exceptional(475)
Price: Expensive
• American • Piermont
Booked 3 times today
Upscale casual cuisine by awarded Chef Phil Iannuccilli in a premier Hudson Valley setting. Handcrafted cocktails and locally sourced ingredients. Sprawling patio, welcoming bar, and a lounge to get cozy in.Please note, our Friday and Saturday nights are extremely busy and in high demand. We look forward to seeing you soon here at Otto's.

See what locals rave about

From verified diners like you
From verified diners like you
  • Eileen
    1 review
    5.0
    Dined 1 day ago
    Staff is very attentive Always a good time and great food.
    More info
    105-Ten Bar and GrillPrice: Expensive• American• Briarcliff Manor
    •
    4.7
  • Dakota
    New York City •1 review
    5.0
    Dined 3 days ago
    It was a great Valentine’s Day dinner, of course busy but all and all would definitely go back
    More info
    3 Westerly Bar and GrillPrice: Expensive• American• Ossining
    •
    4.4
  • KiranVIP
    New York City •158 reviews
    5.0
    Dined 4 days ago
    We don't usually do Valentine's Day dinner but we are longtime fans of Chef Peter Kelly's culinary skills, innovative menus, great cocktails, and fabulous service, and had been to Basso 56 before but have been wanting to try Chef Kelly's new location. So this seemed like a great excuse to check it and it did NOT disappoint. Great wine list, exciting cocktail menu, awesome service, and amazing and innovative menu but yet able to accommodate 2 dietary restrictions in our party of 4 without a problem or hesitation. And Chef Kelly made the rounds in the dining room twice during our meal and was as friendly and gracious as always. Sorry no pictures but everything was presented beautifully and absolutely delicious. Salads were fresh and light, grilled octopus was terrific, shrimp with truffle special appetizer was outstanding, branzino was cooked perfectly, all the pastas are made in-house and delicious, and while not on the menu, they made a cacio e pepe for one of our guests who had a dietary need and it was outstanding, especially since it was a very busy night. We will definitely be back soon!
    More info
    Basso56Price: Expensive• Italian• Chappaqua
    •
    4.6
  • Michael
    New York City •4 reviews
    5.0
    Dined 4 days ago
    Excellent food, great and attentive service, big food portions
    More info
    ChatterboxPrice: Very Expensive• American• Pleasantville
    •
    4.7
  • EdVIP
    New York City •25 reviews
    5.0
    Dined on Jan 30, 2025
    Everything was great service food and just what you wanted for a great pub! Was Trivia night and bummed we had to leave will come back!
    More info
    105-Twenty Bar & GrillPrice: Expensive• American• Croton Falls
    •
    4.5

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