Drink Up History – Historic Tavern Trail

Iron Forge Inn, Warwick
Iron Forge Inn, Warwick

Orange County’s historic taverns continue to serve.

George Washington not only slept here, he drank here! Inspired by long ago cocktail-ers, the Historic Tavern Trail of the Hudson Valley has launched a popular last-Friday-night-of-the-month event series highlighting historic Orange County taverns. Their signature cocktail is the “Apple Jack Downing,” a tasty libation made with local hard cider from one of the eight cideries in the county. If you can’t make their events, explore Orange County’s charming historic taverns on your own. It’s a chance to be surrounded by the past with the best of today’s food and drink.

These establishments are participants in the Historic Tavern Trail program:

Iron Forge Inn

38 Iron Forge Road
Warwick  10990

Open Thurs-Sun.
Located in the quaint hamlet of Bellvale, the site of an historic forge destroyed by the British, the inn is set in a Revolutionary era home built circa 1760. The five intimate upstairs dining rooms contain antiques, original artwork, paintings, furniture, and carvings, adding to the warm colonial ambiance. Farm to table dishes are their specialty. The Tap Room features a pub menu and seating near a fireplace that was part of the original 1760 cooking kitchen. Iron works from this area made significant contributions to the chain that blocked the Hudson River at West Point during the American Revolution.


Painter’s Restaurant

266 Hudson Street
Cornwall-on-Hudson, 12520

Open 7 days.
When it was built in the late 1800’s, the building that houses Painter’s Restaurant was known as the Elm Park Hotel, a boarding house, restaurant, and bar popular with the steamboat visitors from New York City seeking Cornwall’s fresh mountain air and verdant forests. During its tenure as The Cornwall Inn from 1924 to 1994, it was damaged by fire in 1960, but was restored and re-opened. Painter’s operates there today as an inn, casual restaurant, and local art gallery. Go to https://orangetourism.org/themed-adventures/48-hours-in-cornwall for more on this beautiful Hudson Highlands village.


Chateau Hathorn

33 Hathorn Road
Warwick 10990

Closed Monday & Tuesday.

Late in the 19th century, noted Arts & Crafts architect E.G.W. Dietrich was hired to transform an early American farmhouse into the elaborate graceful mansion known today as Chateau Hathorn. The estate changed hands several times through the years and was operated as the Warwick Dude Ranch in the 1950’s. The Zueger family bought and restored the property in 1984, establishing the fine restaurant with historically accurate dining rooms, an award-winning wine cellar, and 7-suite B&B that they still operate today.


Schlesinger’s Steak House

475 Temple Hill Road
New Windsor  12553

Open 7 days.

Schlesinger’s, popular for its menu and its nightlife, grew from a simple fieldstone house built in 1762 to a unique space with dining rooms, a cigar bar, and even a “beach.” Its location near the New Windsor Cantonment, where George Washington’s Continental Army spent the last days of the Revolutionary War, made it useful for officer’s quarters. The original builder, Samuel Brewster, is remembered as the owner of the forge that made some of the famous chains that blocked the British from advancing up the Hudson River. Find lots more “Revolutionary” fun at: https://orangetourism.org/themed-adventures/a-revolutionary-tour.


Ward’s Bridge Inn

135 Ward Street
Montgomery 12549

Closed Monday.

This classic country inn near the Wallkill River occupies a restored 1820’s building also known as the Empire House. It’s located along the Newburgh-Cochecton Turnpike which served as the main road of commerce through the region between 1810 and the arrival of railroads in the 1840s. The Village of Montgomery was once called “Ward’s Bridge” for James Ward, an early settler who established a grist mill and built the first bridge across the Wallkill River there in the mid-18th century. The tavern lies within Montgomery’s “Bridge Street Historic District.”


Erie Hotel and Restaurant

9 Jersey Avenue
Port Jervis 12771

Open 7 days.

Built in 1890, the Erie Hotel is an original “railroad hotel” that once served weary Erie Lackawanna Railroad travelers visiting Port Jervis.  Historical features include an elaborate wood and mirror bar carved by German craftsmen and dozens of historical photographs of Port Jervis scenes. The Brink family purchased the Hotel in 1986 and restored it in 1994, including the upstairs hotel rooms for those who want to stay the night for an authentic experience!  Go to https://orangetourism.org/themed-adventures/48-hours-in-port-jervis  for more places to explore this city on the scenic Delaware River.


North Plank Road Tavern

30 Plank Road
Newburgh 12550

Closed Monday.

Within one of Newburgh’s oldest surviving buildings, the North Plank Road Tavern is an authentic early “roadhouse.”  In operation since the early 1800s, its historical features include an elaborate carved mahogany bar originally from Newburgh’s former United States Hotel, and hand-painted “Trompe l’oeil” walls mimicking wood, brick, and stone. Note the circa 1900 impressionist fresco of the scenic Hudson River entitled “Pecheur” in the middle dining room. Artifacts displayed from the tavern’s days as a Prohibition-era “speakeasy” include whiskey bottles, counterfeit labels, and trap doors that hid the liquor. No doubt about it, this tavern has a storied past! Go to https://orangetourism.org/themed-adventures/48-hours-in-newburgh/for more to do in this Hudson River city.

North Plank Road Tavern, Newburgh
North Plank Road Tavern, Newburgh

Just in case any of the historic tavern trail locations you visit are out of “Apple Jack Downings,” we know where you can get one ”“ the Orchard Hill Cider Mill located at Soons Orchards and Farm Market in New Hampton.  Their mixologist, Donnan Sutherland, created the drink made with locally-produced applejack brandy and apple cider with an apple slice garnish. It’s named for Andrew Jackson Downing, famous Newburgh, New York-born horticulturalist and architectural design tastemaker. For added fun, stop by during one of their “Speakeasy” events held Saturdays from 5 to 9 pm. Cheers! www.orchardhillnyc.com

The Tavern Trail events are held at on the last Friday of each month from April through October.  Each event is preceded by an “Early Bird Tour” at a nearby local historical museum or site. Then the tavern event kicks off at 5:30 p.m. with a “history happy hour.”  Guests can try the ”˜Apple Jack Downing’ a new signature cocktail featuring local ingredients.  At 6:00 p.m. each evening’s entertainment will include a short talk about the tavern and local community history by a local historian  Optional dinner follows at 7:00 p.m. Find the latest scheduled event at https://www.facebook.com/taverntrail or on the Orange County Tourism events calendar, https://orangetourism.org/events. 

Have an appetite for more flavorful history?  Here are more Orange County eateries with historic backgrounds that serve both food and spirits.

40 Park Place, Goshen 10924
Open 7 days.
Catch the action on the Goshen Historic Track from the dining room of this restaurant and sports bar. It’s located within the historic Goshen Inn built by Roland Harriman in 1912. The exterior of the building is an exact replica of an Elizabethan Inn in Melbourne, England. Hearty American fare is their specialty.

Glenmere Mansion, 634 Pine Hill Road, Chester
Dine at glamourous Glenmere, the Italianate mansion built in 1911 as the country retreat of industrialist Robert Goelet. Elegant, upscale dining is offered at 2 evening seatings from Thursday to Sunday in the opulent Supper Room. Frogs End, a cozy tavern, is open 7 days for light lunch, informal dinners and full bar service.

Lake View House, 343 Lakeside Road, Orange Lake, Newburgh
Closed Tuesdays
Known as O’Malleys when it opened in 1899, this is the first restaurant in Orange County to receive a liquor license. It started in Orange Lake’s heyday when the area was a popular summer resort and amusement park destination accessible by trolley. Eclectic lunch and dinner menus are served in the Victorian-style dining rooms and on the outdoor patio overlooking the lake.

Landmark Inn, 526 Route 94 North, Warwick  10990
Closed Mondays.
Enjoy the rustic, warm atmosphere at this casual country inn set within a Colonial period farmhouse. According to the historic marker just outside the restaurant, it was the 1778 homestead of Conrad Sly, a blacksmith who forged the Revolutionary War chain that crossed the Hudson River at West Point. Order hearty pub fare or elegant dishes from the fine dining menu prepared by CIA Chef/Owner Michael DiMartino.

Limoncello at the Orange Inn, 159 Main Street, Goshen 10924
Open 7 days.

This Goshen landmark, built on the foundation of an old prison, dates back to 1790. It was a haven for escaped slaves during the Civil War and a popular stop for patrons of the Goshen Historic Track. Some sensitive souls feel the presence of spirts in the old building which has been transformed into an Italian restaurant and bar with patio dining.

MacArthur’s Riverview Restaurant at The Thayer Hotel, 674 Thayer Road, West Point 10996
Open 7 days.
Gaze out at the Hudson River from the Gothic windows in this beautifully appointed fine dining room within the historic Thayer Hotel on the grounds of the United States Military Academy at West Point. Sip cocktails and catch magnificent views from the hotel’s rooftop Zulu Time Lounge in season. The hotel celebrated its 90th year in 2016.

Nina, 27 West Main Street, Middletown 10940
Open 7 days.
Brick walls and a burnished tin create a cozy atmosphere in this eatery located in a vintage 1800s storefront in downtown Middletown.  Zagat rated it one of the top 40 restaurants north of Manhattan. Enjoy the sounds of the city’s Friday night summer concert series when you dine at a table in the back courtyard.

Park Restaurant, 451 Main Street, Highland Falls 10928
845- 446-8709
Closed Monday.
Located across the street from the West Point Visitor’s Center, the building that houses the Park Restaurant was once a hotel and a bar. During Prohibition there was a soda fountain where the bar is now and a speakeasy in the back dining room. Find traditional American fare on the menu for breakfast, lunch, and dinner.

Restaurant 1915 and Roof Tapas Bar, Bear Mountain 10911
Restaurant open Thursday-Sunday. Tapas Bar open daily.
Within scenic Bear Mountain State Park, dine in the ambiance of the historic Bear Mountain Inn, built in 1915. Overlooking Hessian Lake, the panoramic park views and huge indoor fireplace are renowned at this landmark listed on the National Register of Historic Places. An eclectic mix of global farm to table cuisine is featured.

Rustic Wheelhouse, 39 Main Street, Chester 10918
Open 7 days.
This casual Italian dining spot occupies what served as an 1855 carriage factory, transformed into a Chevrolet dealership in 1926. Although the previous tenant used the name Bodles Opera House, the actual opera house was located across the street. The restaurant sits in the heart of historic downtown Chester.

Silvio’s Villa, 274 State Route 94 South, Warwick
Closed Monday
This 18th century inn began as a home built by Revolutionary War veteran Levi Ellis. Expanded in 1811, it was called Maple Glen Farm and added to again in the mid 1800’s. The property changed ownership several times before coming into the hands of Silvio who’s been showcasing Italian specialties on the menu for two decades. Paranormal activity detected at the site has earned it a place on the Haunted History Trail of New York.

Silvio's Villa, Warwick
Silvio’s Villa, Warwick

Vinum Cafe, Wine Bar & Restaurant
, 84 Brotherhood Plaza Drive, Washingtonville 10992
Open Wednesday-Sunday.
Continental French cuisine is the specialty at this charming dining establishment occupying the ground floor of the original winery building, circa 1839, on the grounds of Brotherhood, America’s Oldest Winery. Enjoy the unique ambiance of this charming venue in the dining rooms or the outdoor patio. Choose from restaurant or café menus accompanied by the full service bar/wine bar.

The Wherehouse, 119 Liberty Street, Newburgh 12550
Closed Monday.
Although it’s located in an 1860’s storefront building across the street from Washington’s Headquarters, this popular eatery has adopted a 1960’s psychedelic theme to promote its huge assortment of beers and burgers. The space started as a general store and evolved into a 1920’s upholstery warehouse. When the building was renovated in 2008, vintage photographs were used to restore the front to its original design and some of the original tin ceiling tiles were incorporated into the bar.

When searching events on this website, please contact the venue directly to confirm whether the event is still being held or not. For important information regarding Orange County services,please click here.