6 Best Historic Restaurants in Ossining

6 restaurants available nearby

A photo of 3 Westerly Bar and Grill restaurant

1. 3 Westerly Bar and Grill

4.5

Price: Expensive

• American • Ossining

Booked 6 times 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 Crabtree's Kittle House restaurant

2. Crabtree's Kittle House

4.7

Exceptional(3186)

Price: Expensive

• Contemporary American • Chappaqua

Booked 8 times today

Built in 1790 as a barn and named for local farmer John Kittle, the farm to table connection that began back then continues today at Crabtree's Kittle House. Internationally renowned for its Wine Spectator Grand Award wine list, superlative hospitality and contemporary American cuisine, it is a sophisticated country dining experience located only 45 minutes from Manhattan. Whether stopping in for a casual meal in the Tap Room or planning a formal intimate celebration from 2 to 200 guests, you'll find something for everyone and every occasion at Crabtree's Kittle House. The culinary team focuses on the local bounty of the Hudson Valley, from salads, burgers, & fresh cold shellfish to more refined cuisine, available in both the Tap Room, Main Dining Room and Ivy Hill Room. And nowhere is there a greater selection of fine wines (5000!) and other libations. Also a Bed & Breakfast, there are 14 rooms for overnight accommodations.

3. Peter Pratt's Inn

4.7

Exceptional(189)

Price: Expensive

• American • Yorktown Heights

Booked 3 times today

PETER PRATT’S INN IS OPEN FOR OUTDOOR DINING ON OUR BEAUTIFULLY RESTORED DECK AND LAWN, AS WELL AS LIMITED-SEATING INDOOR DINING INSIDE OUR GORGEOUSLY RENOVATED 1700’S FARMHOUSE RESTAURANT - ALL FOLLOWING NEW YORK STATE’S PUBLIC HEALTH GUIDELINES, INCLUDING STAFF AND TABLE DISTANCING, MASK WEARING BY STAFF AND CUSTOMERS, LIMITED CAPACITY INDOOR DINING, AND CONTINUOUS SANITIZING OF STAFF AND RESTAURANT.

A photo of Two Spear Street New American Restaurant restaurant

4. Two Spear Street New American Restaurant

4.6

Exceptional(590)

Price: Moderate

• Contemporary American • Nyack

Booked 1 time today

Family owned and operated, Two Spear Street is Downtown Nyack's premier restaurant offering views of the historic Hudson River and Tappan Zee Bridge. Two Spear Street’s Dishes are an eclectic blend of New American Inspired Dishes with influences from around the world. Our experienced wait staff and bartenders are committed to delivering an outstanding dining experience. Two Spear Street offers a Bar/Patio Menu, Weekend Brunch and Dinner Menu. We hope you join us soon. The Rubino Family!

A photo of Freelance Cafe & Wine Bar restaurant

5. Freelance Cafe & Wine Bar

4.8

Exceptional(290)

Price: Moderate

• Contemporary French / American • Piermont

Booked 2 times today

The Freelance Café & Wine Bar is of the one of the founding restaurants of Piermont’s now bountiful selection of eclectic spots to wine and dine in this historic and charming village by the Hudson River.The Freelance menu offerings consist of Small Plates, Large Plates, and Daily Specials. The menu remains a touchstone for Modern American Cuisine as informed and inspired by the French Bistro, the Italian Trattoria, the Japanese Izakaya and ever more tastefully global inspiration. We offer a long list of favorite dishes whether that’s French Onion Soup, Thai Pasta, Braised Short Ribs or Classic Crème Brulee, as well as an inspiring selection of wines by the glass or bottle. Rated by Zaget as “ Another fabulous dining experience” the Freelance cafe is a consistent winner.

A photo of Division Street Grill restaurant

6. Division Street Grill

4.0

Excellent(282)

Price: Expensive

• American • Peekskill

Located in the heart of Historic Downtown Peekskill's Artist District, The Division Street Grill offers eclectic American and International Cuisine, with Live Jazz Entertainment Friday & Saturday, in a New York Style setting.

Best Historic Restaurants in Ossining

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6 restaurants available nearby

1. 3 Westerly Bar and Grill

2. Crabtree's Kittle House

3. Peter Pratt's Inn

4. Two Spear Street New American Restaurant

5. Freelance Cafe & Wine Bar

6. Division Street Grill

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