If the walls and floorboards of the Hudson Valley’s hundred-plus-year-old inns and restaurants could only talk, we’d have thus-far-unimagined versions of history to consider. And even though they can’t, there’s enough lore and myth to fill any history buff’s eager mind, especially when that person avails him- or herself of the chance to walk those floorboards: an opportunity now presented by Historic Tavern Trails meetups in both Dutchess and Orange Counties.
Typically, meetups take place once a month from May through October. Historians, museum professionals and members of the public are welcomed in to partake of free Happy Hour drinks (including signature cocktails designed especially for the occasion) and local pub foods (for which dinner reservations at each tavern are encouraged). And a healthy helping of anecdotal information about each location is always on the menu, in the form of brief talks presented by the current tavern-owners and local experts – about liquor hidden under the floor planks or secret goings-on taking place upstairs or other intriguing tidbits about the people who once frequented the tavern way back when.
In Dutchess County, a different historic tavern will provide the revelry on the second Friday of each month for the remainder of the season: August 12 at the Stissing House in Pine Plains, September 9 at the Old Drovers’ Inn in Dover Plains and October 14 at the Kimlin Cider Mill in Poughkeepsie. A special Halloween event on Friday, October 29 will feature a special Prohibition-themed party marking the grand opening of Dutch’s Spirits in Pine Plains.
Events in Orange County take place on the last Friday of the month: July 29 at Painter’s Restaurant in Cornwall, August 26 at Chateau Hathorn in Warwick, September 30 at Schlesinger’s Steak House in New Windsor and October 28 at the Ward’s Bridge Inn in Montgomery.
Historian Johanna Yaun, who organized the Tavern Trail in Orange County, is quoted as having referred to the meetups as heritage tourism. “It’s a program that is history, tourism and economic development,” she said. “Many historic buildings in Orange County have found new purposes while acknowledging their debt to the past.” In the present, it’s all about socializing, networking, imbibing and nibbling, meeting new folks and dabbling in history.
Join the next meetup on this summer’s journey to Orange County’s historic taverns at Painter’s Restaurant in Cornwall-on-Hudson this Friday evening at 5:30 p.m. Painter’s (located in what was formally the Cornwall Inn) is located at 266 Hudson Street. Local historian Colette Fulton will give a brief presentation about the history of Painter’s Restaurant. Check www.facebook.com/taverntrail and www.facebook.com/dutchesstaverntrail for more information on other 2016 Historic Tavern Trail meetups.
Join the family! 
