'America's Oldest Restaurant' Is In A New York Village With Taverns, Historic Structures, And Trails

It's probably not surprising, but New York was the most-visited state by international tourists in 2024. There are near-innumerable reasons to pencil a trip to New York into your diary, with some of the most iconic attractions in the world scattered throughout iconic Manhattan and many smaller towns landing on travelers' radars, like this charming village for book lovers in the Catskill Mountains. The state embodies modern America; it's a glittering hub of capitalism and larger-than-life braggadocio, a kind of physical manifestation of the American dream. But New York also has a storied — and by American standards, ancient — history. For proof, look no further than the village of Tappan.

Located 12 miles north of New York City, Tappan was settled in the late 17th century by Dutch farmers and emancipated Black families. Around a century later, the handsome DeWint House, built with Dutch brick and native red sandstone, was the HQ of General George Washington during the Revolutionary War. The Orangetown Resolutions, protesting laws passed by British Parliament, were also signed here on July 4, 1774, exactly two years before the Declaration of Independence. 

Tappan is home to the '76 House, which was built in 1668 and famously served food to travelers, patriots, and army generals in the late 1700s. Considered "America's Oldest Restaurant," the '76 House remains open for business today and is Tappan's Number 1 ranked restaurant on TripAdvisor. If you want to skip New York's tourist traps (like Times Square), a day trip to Tappan and its historic tavern is a great alternative. 

After some shoddy, piecemeal renovations, the '76 House was lovingly restored, ensuring both the spirit and style of the original were maintained — the restoration team wanted it to evoke the days when taverns served as a focal point of a town's social life. You can eat in the centuries-old dining room, which is warmed by a beautiful delft fireplace and upheld by huge timber beams from trees that were deemed a capital offense to cut down. The menu features a who's who of American pub classics: chicken pot pie, meatloaf, crab cakes, a reuben sandwich, and a Thanksgiving spring roll. The tavern also serves an ale that so enamored George Washington, the owner gave America's soon-to-be first president the recipe. Washington supposedly reproduced the brew at his Mount Vernon estate.

The '76 House is arguably the most historic building in Tappan: Major John Andre, a British spy and notorious figure from the revolutionary years, was imprisoned here as he awaited his execution (at a time when Alexander Hamilton was also a resident of the house). But you should also visit the DeWint House, the oldest extant building in Rockland County. It was in this building, which has been restored to capture the essence of its 18th-century heyday, that Washington signed Andre's death warrant. There are more colonial-era homes and landmarks in the town's Historic District — download a scavenger hunt map from the local library's website and see if you can find them all.

Because the Big Apple is the beating heart of New York, it's easy to forget it's also one of America's best hiking states. There are popular, pristine trails webbing the Adirondacks and forest-shrouded valleys hidden among the Catskills. You'll also find some lovely hikes around Tappan village, running through the scenic Hudson River Valley.

The Joseph B. Clarke Rail Trail, starting at Tappan's southern end, travels for 4 miles along paved roads, cutting through hardwood forest and the hamlets of Sparkill, Orangeburg, and Blauvelt. For the best views, join the Old Eerie Path at Depot Square. A 3-mile, mostly dirt and gravel trail, it rubs shoulders with the western banks of the Hudson River and follows the old Northern Railroad of New Jersey corridor. Further north of Tappan you'll find the Hook Mountain and Nyack Beach Loop. A moderately challenging route, it overlooks a broad section of the Hudson from the Palisades Cliffs; keep an eye out for birds of prey whirling in the skies around here.