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Kingston fits two very different eras into a single day. Up on the hill, stone houses remember the American Revolution. Two miles south, old warehouses recall the coal barges that once crowded Rondout Creek. Start uphill with a slow wander through Uptown Kingston, where colonial houses and an old church lead to lunch at a tavern.
Back in 1658, Peter Stuyvesant ordered settlers into a fortified village called Wiltwyck, surrounded by a fourteen-foot log wall. The wall has long since disappeared, but its footprint still guides the streets you can walk today in the Stockade District, Kingston, NY. Twenty-one colonial houses remain standing along them.
You’ll find four of the oldest buildings where Crown and John streets meet, at an intersection known as the Four Corners. Dating from the 1660s to the 1770s, the stone buildings occupy all four corners, something Kingston claims no other American intersection can match. Rooflines and additions tell their own stories, since a few centuries tend to bring some renovations.
A short walk away, the Senate House State Historic Site tells the political side of the Revolution. New York’s first Senate met here in 1777, renting a room from merchant Abraham Van Gaasbeek. British troops damaged the house when they burned Kingston that October, but it survived. After a $2.5 million restoration, the site reopened with two new museum exhibits.
A few streets away, the Old Dutch Church adds another chapter to Kingston’s history. Architect Minard Lafever built the 1852 church, though a Christmas Eve windstorm in 1853 destroyed its original steeple. Its replacement went up in 1861 and still rises above the neighboring rooftops.
While the steeple draws your eye upward, the churchyard holds a historical connection worth seeking out. George Clinton, New York’s first governor, died in Washington in 1812 while serving as vice president. His remains didn’t return to Kingston until 1908, nearly a century later, and a large obelisk now marks his grave.
Kingston’s story doesn’t end when you leave the historic sites, and lunch gives you a chance to experience another piece of it. Hoffman House Tavern on North Front Street occupies a seventeenth-century stone house that has seen more than its share of history. The tavern opens at 11:30 a.m. Tuesday through Saturday.
Inside, the restoration preserved original mantels, moldings, and door paneling, while even the old nails found their way back into the building. Rather than replace damaged floorboards, crews turned them over. After you eat, the shops along North Front and Wall streets give you a good excuse to explore more of Uptown.
The two historic districts sit about two miles apart, with Broadway connecting them through Midtown. Walking takes about 40 minutes each way, and UCAT’s Blue and Yellow bus circulators also run along Broadway Monday through Saturday.
Uptown has city parking lots with pay stations on North Front, Cornell, and Prince streets, so you can leave your car while exploring the Stockade. If you’re visiting both districts, consider transportation between Uptown and Rondout before deciding where to park.
Once you reach Rondout, the waterfront sights sit close enough to explore on foot. The neighborhood was once a separate village, only joining Kingston and Wilbur to form the city in 1872.
By the time you reach the bottom of Broadway, Kingston’s colonial houses have given way to buildings from its industrial years. The Rondout Historic District grew around the Delaware and Hudson Canal, which opened in 1828 and connected Pennsylvania’s coalfields with the Hudson River.
With coal, bluestone, cement, and bricks passing through, the waterfront became the third-largest port on the Hudson. The Cornell Steamboat Company grew into the river’s largest towing business and employed hundreds of workers along the creek.
Some of that prosperity is still visible along West Strand, where seven Italianate buildings feature arched windows and cast-iron storefront columns. These days, restaurants and small shops fill many of the old storefronts. That gives the former shipping district a new kind of trade and makes it a lively corner of Rondout.
The Hudson River Maritime Museum on Rondout Landing brings the waterfront’s past a little closer. The 1898 steam tug Mathilda sits in its courtyard, while exhibits explore the river’s working life. From May through October, the solar-powered Solaris also sails river cruises.
Just nearby, the Trolley Museum of New York takes the story from water to rails. Its historic trolley rolls along a former railway corridor on weekends during the operating season.
By evening, there’s little reason to head back uphill, especially with dinner waiting along West Strand. Ship to Shore serves seafood, steaks, pasta, and other American dishes in a nineteenth-century building near the water.
The storefront dates to the 1870s and even housed a speakeasy, giving the restaurant its own character. In warmer weather, outdoor seating brings the harbor views closer.
A day split between the Stockade and Rondout leaves little reason to rush. Give a few stops real time and treat the rest as a bonus. Together, the two districts offer colonial history, canal sights, waterfront dining, and plenty of other things to do in Kingston, NY. Hours vary by venue and season, so check each one before you go. A larger group can cover both districts and still leave room for an unexpected museum stop, another look inside an old shop, or a longer dinner by the creek.
