Tavern Trail

Take a journey to Orange County’s most historic taverns, restaurants and inns on the Historic Tavern Trail of the Hudson Valley! The Tavern Trail stops feature fascinating history, authentic surroundings, and great local food. Trail travelers will meet friends old and new, learn more about Orange County’s historic places, and can try the special Tavern Trail signature cocktail, the “Apple Jack Downing,” featuring local ingredients. The Tavern Trail provides the perfect social night out for those who love history to learn about Orange County’s greatest landmark taverns and their place in our County’s history, from the Revolutionary War to Prohibition and beyond.

The Historic Tavern Trail of the Hudson Valley is a recipient of the American Association for State and Local History’s “Leadership in History” award.


293 Main Street Highland Falls, New York (845) 446-3290

​Benny Havens Pub & Restaurant is a friendly neighborhood bar with roots in West Point Military Academy history. It is named for War of 1812 soldier Benny Havens, who ran an eatery on the academy grounds known for its buckwheat cakes, oysters, and a “hot flip” drink of rum, egg, sugar, and spices. Cadets were banned from drinking anything stronger than coffee or cider, and in 1832 Havens and his wife were caught serving stronger stuff and became the only Americans banned from West Point for life. Havens relocated, and his establishment remained a popular illicit destination for cadets and future generals. Patrons included George Custer, Jefferson Davis, Ulysses S. Grant, and William Tecumseh Sherman. Cadet Edgar Allan Poe called Mr. Havens the “sole congenial soul in the entire Godforsaken place.” Havens was memorialized in the tavern’s anthem, “Benny Havens Oh!” composed in 1838 and sung to the tune of “The Wearing of the Green.” Each graduating West Point class added a verse, and it became a popular Civil War marching song. Today’s Main Street incarnation of Benny Havens is renowned for its burgers and chicken wings. Historical features include stained-glass windows and the original “Havens Landing” sign over the pool room.

33 Hathorn Road Warwick, New York (845) 986-6099

​ Visitors to Chateau Hathorn will enjoy fine dining in an 1890s mansion reminiscent of the great chateaus of Europe. The Chateau was built on land owned a hundred years earlier by farmer Benjamin Burt, next door to the home of Revolutionary War militia general John Hathorn. Burt’s son inherited his father’s farm in 1796 and married General Hathorn’s daughter. In 1891, Civil War veteran and successful businessman Colonel Victor Audubon Wilder bought the property from the Burt family and hired noted Arts and Crafts–style architect E. G. W. Dietrich to expand the early farmhouse into an elaborate Tudor mansion. The Wilders sold the estate to James M. Fuller around 1900. Fuller died in 1932, and the estate became the Warwick Dude Ranch equestrian center in the 1940s. The estate was vacant in 1984 when Dolph and Helene Zueger were apple picking in Warwick and spotted the neglected mansion. The Zuegers bought the property and returned it to its former glory, restoring fireplaces, ceilings, and its staircases of oak, rosewood, and mahogany. The Zueger family have made Chateau Hathorn a special place for fine dining, with a menu offering a variety of appetizers, soups, salads, meat and fish entrées, and homemade desserts, many featuring local ingredients.

​9 Jersey Avenue Port Jervis, New York (845) 858-4100

​ The Erie Hotel & Restaurant offers hearty fare in an authentic 1890s “railroad hotel,” one of several built around the Erie Depot for passengers on the busy New York–to–Buffalo and Chicago main line. Railroad hotels offered overnight accommodations, full restaurant service, and quick meals during brief train stopovers. The hotel occupies the Padgen Building, built in 1890 for Bauer’s Hotel. Called “one of the neatest and brightest little hotels along the Erie line,” it slept forty guests and served meals twenty-four hours a day. Modern conveniences included steam heat, hot and cold running water, electricity, and gas lights. The hotel included a “sample room” where traveling salesmen displayed their wares to customers. In 1901 owner Hunt Brock renamed it the Hotel Erie, featuring a 150-seat restaurant touted as “the finest appointed dining room in the city.” Ownership later shifted to the Carroll family, who ran it as the Hotel Carroll for over thirty years. The Brink family bought the hotel in 1986 and restored it in 1994. Historical features include a carved-wood and mirror bar and old photos of Port Jervis scenes. The Erie is still a functioning hotel, offering original rooms for those who want to stay the night for an authentic experience.

​38 Iron Forge Road Warwick, New York (845) 986-3411

​E-mail: ironforgeinn@gmail.com Website: http://www.ironforgeinn.com Menu: http://www.ironforgeinn.com/Menus.html The Iron Forge Inn hosts diners in a circa 1760 house in Warwick’s former industrial hamlet of Bellvale. The inn is named for Crawley’s former iron forge on nearby Longhouse Creek. The forge was destroyed in 1750 under the British Iron Act to limit colonial iron making, one of the grievances leading up to the Revolutionary War. Longhouse Creek’s waterpower attracted settlers like Daniel Burt, who came here in 1760 to build grist and saw mills. In 1808, the Bellvale-Monroe Turnpike was established, and Bellvale grew into a busy mill village supporting carpet, chair, cider, grain, pipe organ, saw, and woolen factories. Now-sleepy Bellvale once had four hundred residents, two stores, a church, a school, and post and telegraph offices. Iron Forge Inn property owners included Stephen Hall Sr., a Revolutionary War soldier in Colonel John Hathorn’s Fourth Orange County Regiment, who was captured and imprisoned by the British. Another important owner was Augustus Burt, grandson of Daniel Burt and a local postmaster, justice of the peace, and founder of the Warwick Savings Bank. In 1950, the Peck family opened the Iron Forge Inn, later purchased by the Johansen family in 1998. Chef/owner Erik Johansen, a graduate of the Culinary Institute of America, offers an ever-changing modern American menu featuring seasonal local ingredients.

343 Lakeside Road Newburgh, New York (845) 566-7100 ​​

​ Lakeview House offers diners a picturesque view of 440-acre Orange Lake. Its waters, once surrounded by dairy farms, powered early mills, including Thomas Machin’s coin mint. The lake was a popular swimming and fishing spot until 1895, when former New York governor Benjamin Odell built the Orange Lake Park amusement park. Odell’s Central Hudson Steamship Company brought visitors to Newburgh, where they boarded Orange Lake Traction Company trolleys to the lake. The thirty-acre park became “the Playground of the Hudson Valley” and offered rides, boating, and bandstand acts like Tommy Dorsey and Benny Goodman. The park hosted twenty thousand weekend visitors by 1908, but automobile travel and the Depression affected attendance, and the park closed and was demolished in 1941. Hotels once clustered around the park included the Orange Lake Hotel and Pine Point Resort. Lakeview House opened in 1866 as a boardinghouse. By 1899 it was a popular watering hole called O’Malley’s, named for redhead proprietor Belle O’Malley, who owned it until 1934. Today’s owners James and Tori Carter renovated and reopened the Lakeview House in 1991. Historic items on display include the original sign, amusement park picture postcards, and the first-issued New York State liquor license, which still hangs over the bar.

​550 County Road 50 (Golf Links Road) New Hampton, New York (845) 374-2590

​Mason’s Marketplace welcomes visitors to an authentic country store in the former Talmadge House, an 1860s “railroad hotel.” New Hampton, located on the Wallkill River at the north end of the “Black Dirt” farming area, was originally called Hampton, after the estate of local mill owner Gabriel Phillips. Hampton was a scene of unrest in the local “Beaver-Muskrat Wars,” which pitted millers against farmers over water-control rights for much of the nineteenth century. Golf Links Road was a busy Goshen–Port Jervis road, and after the Erie Railroad arrived in 1843, Hampton became a small commercial hamlet. In 1866 Nathaniel Talmadge built Talmadge House, a stagecoach inn and railroad hotel. In 1917, New York City carpenter John Mason bought the inn, and his wife Margaret ran the store, which became a neighborhood landmark famous for its penny candy. The store closed in 2004, and in 2013 the Turi-Wright family purchased it and restored original details including wood floors, tin ceilings and glass cupboards. Mason’s breakfast, lunch and dinner menu offers locally-sourced products seven days a week. The taproom offers local craft beers served on furniture made from tall pine trees that once stood outside. The market features items from area farms and a “Beer Cave” featuring popular local breweries.

30 Plank Road Newburgh, New York (845) 562-5031

​ The North Plank Road Tavern offers fine food and drink in an authentic 1800s “roadhouse.” Located in one of Newburgh’s oldest surviving buildings, the tavern was once a stagecoach hotel for travelers on the Newburgh-Shawangunk Turnpike, also known as North Plank Road. The turnpike, established in 1801, connected Wallkill Valley farms to Hudson River shipping. New York led the early 1800s “plank road” movement, lining three thousand miles of roads with wood to keep wagon wheels out of the mud and compete with early canals. Augusta Sauer ran a rooming house and tavern here for years. Despite the advent of Prohibition in 1920, she continued serving alcohol, establishing the first “speakeasy” on the premises. In 1928, Anthony “Mitch” Nixon bought the tavern, introduced slot machines and gambling, and hid a bootleg distillery on the third floor. Prohibition-era artifacts found in the tavern and now on display include whiskey bottles, counterfeit labels, and even a pistol. Surviving historic features include a mahogany bar saved from Newburgh’s United States Hotel and painted walls mimicking wood, brick, and stone. Owned by the Costa family since 1979, North Plank Road Tavern works with local producers of the freshest quality ingredients to produce the finest food.

​ 266 Hudson Street Cornwall-on-Hudson, New York (845) 534-2109

​Painter’s Restaurant offers an ever-changing seasonal menu served in an 1870 Hudson River resort hotel. After the Civil War, Cornwall, with commanding views of Newburgh Bay and Fishkill Ridge just fifty miles from New York City, became a summer resort destination. Smaller than Niagara or Saratoga, Cornwall catered to families with children and offered recreation in the mountains and on the Hudson River. Painter’s was built in 1870 as the Elm Park Hotel, one of many Cornwall lodging “houses,” the largest of which, the Glen Ridge, accommodated 350 guests. A period local newspaper said “Cornwall has many fine hotels, but for location, pleasant drives, beautiful lawns and shade trees, spacious rooms and a table filled with all the latest delicacies of the season, none can excel the Elm Park Hotel.” In 1924, Elm Park reopened as the Cornwall Inn, offering Halloween, Thanksgiving, and New Year’s Eve parties, movies, dance bands, and winter sleighing. Painter’s Restaurant took over the Cornwall Inn in 1994 and is still a functioning inn, with seven rooms, restaurant, art gallery, and Art Deco–style wood bar. Painter’s offers an eclectic mix of American, Italian, Mexican, and Japanese fare, blending local seafood, meat, and produce to please every palate.

475 Temple Hill Road New Windsor, New York (845) 561-1762

​ Schlesinger’s Steak House features great porterhouse and T-bone steaks served in the Deacon Samuel Brewster House, a stone dwelling built in the 1760s. Sam Brewster, a local Presbyterian church elder, descended from William Brewster, who came to America on the Mayflower in 1620. Sam was an important local Revolutionary War patriot and member of New Windsor’s Committee of Safety, and ran an iron forge on nearby Moodna Creek. In 1775 the Continental Congress planned an iron chain across the Hudson River at Fort Montgomery to stop British ships. Brewster made parts of that chain, but the British attacked by land in October 1777, bypassing the river obstacle. In 1782, George Washington established the nearby New Windsor Cantonment, and Brewster made wagon parts, tools, and utensils for the eight thousand Continental army soldiers camped there. The Brewster House hosted important guests, including patriot John Adams, who dined at Brewster’s in November 1777 and enjoyed “a decent Grace before and after Meat—fine Pork and Beef and Cabbage and Turnip.” In 1994 Glynn and Neil Schlesinger turned the Brewster House into a restaurant featuring original exposed wood beams and stone walls and fireplaces, and offering delicious food, including USDA Prime steaks, fresh seafood, delicious pasta, and legendary barbecued ribs.

​ 135 Ward Street Montgomery, New York (845) 457-1300

​Ward’s Bridge Inn is a popular tavern and restaurant located in the former Empire House, a nineteenth-century turnpike hotel. German farmers settled nearby on the Wallkill River in the early 1700s, attracted to rich farmland and waterfalls to power mills. The village at the falls was first called Ward’s Bridge, for miller James Ward’s timber bridge over the river. Townspeople changed the name in 1789 to honor Revolutionary War general Richard Montgomery, killed in 1775 at the battle of Quebec. In 1801, Montgomery was a scene of scientific wonder when Charles Wilson Peale excavated an ice age mastodon. After the village was incorporated in 1810, industrialists dammed the Wallkill for paper and woolen mills. The Newburgh–Cochecton and Minisink turnpikes crossed near Ward’s Bridge, and after the Civil War, railroads connected Montgomery to New York City. Innkeepers established guesthouses here, including Ward’s Bridge Inn, started by Irish immigrants William and Katherine Lodge in 1871 and then known as the Empire House. The Lodges’ distillery made award-winning “William Lodge’s Apple Brandy,” enjoyed as far away as New York City. The Pskowski family took over the restaurant in 2005 and offer top-quality steaks, poultry, fresh seafood, local produce, salads, sandwiches, soups, and an extensive wine and beer list.