History’s Picks: 4 Historic Inns That Bring America’s Past to Life

The Traphanger Tavern was a rustic stop at a crossroads where travelers could water their horses and get a meal. The tavern’s location in Rhinebeck Village—about halfway between New York City and Albany on the Kings Highway and along an east-west thoroughfare that led to an active Hudson River ferry crossing—attracted a steady stream of travelers. By 1766, the tavern proved busy enough that an inn, called the Beekman Arms, was added.

The Beekman Arms is thought to be the oldest continuously operated inn in the country. Over time it hosted colonial-era bigwigs like George Washington and Alexander Hamilton, while Revolutionary War troops drilled on its front lawn. About 160 years later, local-boy-made-good President Franklin D. Roosevelt used its columned front porch as the backdrop to several key speeches.

The Beekman Arms’ lobby features well-worn wide-plank floors and oil paintings of its more famous guests—and is still warmed in winter by a fireplace. Guest rooms have been updated to modern standards but remain intimate in size. The Beekman Tavern benefits from the talent pool provided by the nearby Culinary Institute of America. The village of Rhinebeck, right outside the door, is walkable and illustrates why the picturesque Hudson Valley has been a tourist destination since George Washington slept here.

You might worry that a place marketing itself as a “historic inn” probably means low timber-beamed ceilings and dark rooms. But the handsome, upright John Rutledge House Inn dashes that preconception thanks to its airy rooms, windowed facade and vivid paint choices. So now you’re worried that maybe it’s not properly historical? Would scars from Civil War shelling, still visible on the upper stories, convince you? Or the fact that John Rutledge was a delegate to the First and Second Continental Congresses, served as South Carolina’s first president and later governor and signed the U.S. Constitution?

For further proof of the inn’s place in history, during the complimentary afternoon tea or evening brandy, sherry and wine gatherings in the library, guests are invited to flip through a scrapbook of clippings and vintage photos, peruse display cases of antique curios and stand on the wrought-iron balcony overlooking Charleston’s Broad Street and the surrounding mansions and townhouses.

The John Rutledge House Inn is unusual among historic city accommodations because its main house dates to before the American Revolution. As author Adrian Covert explains, “When the American economy started growing in the early 1800s, wealthier people decided they no longer wanted to share a room with someone else. The new institution, the French-sounding 'hotel'—where you got your own room, though still shared a bathroom—had taken hold. The old taverns and inns fell into disrepair and, if they were in a city, taking up valuable land, they were destroyed.”

As a result, there are few truly old accommodations in big cities like New York, Boston and Philadelphia, while many remaining historic inns have survived because they were located in quieter towns or along smaller roads that were bypassed by larger highways.

Envisioning the Homestead’s transition from the original 1766 wooden lodge to today’s stately resort hotel takes some serious squinting. Still, the original guests arrived for many of the same reasons as today’s guests: not just to access the Allegheny Mountains but to bathe in the local mineral-rich waters, thought to contain healing properties.

One early proponent of the treatment was Thomas Jefferson, who spent 22 days taking to the area's waters in 1818 to relieve his rheumatism. Jefferson was one of 24 U.S. presidents who have visited the Omni Homestead, but presidential visits are hardly the only history to unfold at this bucolic spot.

During the Civil War, the hotel was requisitioned for use as a Confederate hospital. Then in 1941, immediately after Pearl Harbor, 785 Japanese people—diplomats and their families—were held prisoner at the Homestead for seven months during negotiations for their repatriation to Japan. (The U.S. government hoped the comfortable lodgings and use of the resort’s facilities would result in gentle treatment for its own captured personnel.)

Today’s guests can play golf or tennis or partake in any number of diversions at the Homestead. Those with a mind for history can head to the iconic, restored wooden bathhouses down the road to soak in stone pools fed by 98- to 99-degree spring water. The Gentlemen’s Pool House is an octagonal wooden structure built around an octagonal pool; the Ladies’ Pool House is 22-sided. Both are lit and ventilated by large oculus openings in the roof. A good long soak, gazing up at a mountain sky framed by timbers, may feel like a cure indeed.

According to the legend passed down by a long line of innkeepers, the Red Lion Inn started out in 1773 as a general store, tavern and inn built by Silas and Anna Bingham along the stagecoach road between Boston and Albany, a welcome stop on a mountainous journey. The origin story goes that when Britain passed its repressive Intolerable Acts in 1774, the Red Lion was where the rebels gathered to protest and plan their resistance. 

Historians differ about whether the Red Lion predates the Declaration of Independence and suggest that the story about the Patriots and the inn’s role in the Revolution may have been embellished by later owners. Historical records indicate that the Binghams arrived in Stockbridge in 1775 and that Bingham’s Tavern didn’t begin operating until 1778.

The original building, greatly expanded over the years, burned down in 1896 and was quickly rebuilt in time for the following summer season. Perhaps this was the moment the owners felt the need to burnish the inn’s backstory with a little historic magic.

Even though it was tucked away in the Berkshires, the Red Lion has hosted a historic and international roster of guests. As the inn passed from owner to owner, its guest books recorded a far-flung clientele including Jane Goodall, Cicely Tyson and Ray Davies, as well as six U.S. presidents. Local celebrity Norman Rockwell was a regular in the inn’s dining room and left his mark with several casual sketches that are framed and displayed around the inn. The guest rooms, spread among several historic buildings, including a restored firehouse, are filled with antiques and art.