10 Oldest Founded Small Towns to Visit in Upstate New York

While some adventurers are moved by the terrifying beauty of a tumbling rapid, others will stop mid-step at the sight of a 500-year-old red brick. The latter will feel tiny, emotional, or just lost in time. To be reminded that there are people who came before you and left their footprints in the sands of time is among the most surreal and sobering experiences. Old — indeed — is gold. If you want to take the role of a time traveler and explore beautiful small towns that have seen it all, the following are the ten oldest-founded small towns to visit in Upstate New York.

Kingston

Although Kingston is in the Hudson River Valley, it is north of Poughkeepsie, a section of the valley typically considered upstate. Kingston was founded in 1652, just about 30 years after the landing of the Mayflower at Cape Cod. It served as the first capital of New York State. Subsequently, Poughkeepsie, Albany, and New York City all stepped into the role at various times.

Today, Kingston is renowned for its handsomely preserved 17th-century architecture in the nostalgic Stockade District. Visitors will enjoy exploring the Senate House State Historic Site. The house was built in 1676, making it one of the oldest in the nation. Ulster Performing Arts Center is a beautiful piece of history and a fantastic place for an afternoon of fun and laughter. It was built before the Great Depression and is the only unaltered pre-World War II theater now in Kingston. You can also feel history at the Old Dutch Church, a National Historic Landmark established in 1659.

Coxsackie

The story of Coxsackie beautifully dovetails with that of a Swedish sailor and his Dutch wife, who came into the area in the 1650s and first pitched camp in present-day Albany. Pieter Bronck later moved south and settled in Coxsackie, then known by the Indian name "Koixhackung". He built a small, simple stone house at the base of the Kalkberg Ridge in 1663 that is today recognized as the oldest surviving home in Upstate New York. The house is at the Bronx Museum, which is currently being redesigned to incorporate a world-class arts facility. Although the Museum’s North Wing remains open at regular hours—Wednesday through Sunday—with free admission, the south galleries are closed until the renovation is complete.

For a different experience, Riverside Park has benches where one can sit and enjoy beautiful views of one of the nation's most iconic waterways, the Hudson River. Meanwhile, the Little Bake Shop, a charming space on Mansion Street, serves delicious coffee cake with a hint of almond.

Oswego

Oswego is on the southeastern shores of Lake Ontario and boasts soft waterfront views that anyone will die for. The story of Oswego as a settlement begins in 1722, when the British and the Dutch established it to facilitate fur trade with the Indians. At the time, fur was hot cake because Europeans needed lots of stylish beaver hats while Indians wanted clothes and guns.

One of the town's best-known landmarks is Fort Ontario, one of the oldest garrisoned posts in the United States. It may not look extraordinary, but this historic fort influenced nations' destinies and shaped the New World's history. There is the West Pierhead Lighthouse, which predates the Second World War by about 5 years, and the Children's Museum of Oswego (CMOO), which can keep a little one entertained for hours. For more historic insight, the H. Lee White Maritime Museum displays historic boats and several other interesting nautical artifacts.

Kinderhook

Kinderhook is part of the upper Hudson Valley region, about 60 miles north of Poughkeepsie, widely considered to be the lower boundary of Upstate New York. It was chartered as a township in 1687, qualifying it as one of the oldest-founded towns in Upstate New York. The other thing that makes Kinderhook famous is that it is the hometown of Martin Van Buren, the eighth president of the United States.

Those interested in local history should visit Kinderhook Village, which has been on the National Register of Historic Places since 1974. Here, one can visit Martin Van Buren National Historic Site on Old Post Road, which provides insights into the life and accomplishments of the nation's eighth president. The house opens for the season in May, and the grounds are open for visitation from 7 am to dusk. Moreover, the School: Jack Shainman Gallery, an old high school converted to an art gallery, is among the most outstanding private indoor art spaces in Columbia County.

Germantown

Did you know that farmers from the Palatinate region of southwest Germany settled in the Hudson Valley more than three centuries ago? To a large extent, the story of Germantown is the story of this daring, enterprising ethnic group. Germantown is also in Columbia County, and is about 30 miles north of Poughkeepsie. With its old stone houses, it effortlessly transports the mind to slower, simpler times. Historians trace the town's settlement to October 1710 and identify the event as one of the largest single migrations in the Colonial era.

Central House, built in 1876, has operated as a hotel, restaurant, and a speakeasy. It is even whispered that it was once a brothel. It is right on Main Street and a fantastic place to pitch camp. Nearby, Ernest R. Lasher Memorial Park provides beautiful views of the Hudson River, and if you're lucky, you will see a couple of Amtrak Trains. You will want to swing by the Valley Harvest Ice Cream & Grill as well, and sample their tongue-tingling selection of salads and burgers.

Saugerties

The area around Saugerties was settled in the 1730s, way before the American Revolution and the Declaration of Independence. This beautiful Hudson River town is brushed with forests and wraps a charming village known for its shoulder-to-shoulder Victorians. The Orpheum, which was built in 1908, is a beautiful piece of history and a cozy venue for a mood-lifting show. Similarly, the Saugerties Lighthouse, built in the years after the Civil War, stands proudly as a living museum and a cherished Bed & Breakfast. The area around the lighthouse is among the most beautiful spots in all of New York. If you want beautiful trails or fresh, playful air, spend some time at the spellbinding Esopus Bend Nature Preserve. The trails here are fairly gentle and will suit almost any fitness level.

Salem

Salem was first settled in 1761. It remains an unspoilt rural community speckled with some eye-catching sculptures. The area lays claim to some of the best maple syrup in the state, the most succulent sweet corn, and the most colorful fall foliage. Salem is in Washington County, home to four covered bridges. Three of these bridges are in the town, including the Historic Rexleigh Covered Bridge, one of the few remaining covered bridges made using the Howe trusses. It was originally built in 1874.

On a similar note, Fort Salem Theater, whose captivating history goes back to 1774, was once among the premier summer stock theatres of the Northeast. It started as a church, then a fort, then a church once more, before the new owners repurposed its altar into a stage and redesigned it as a performance venue. End your trip by driving to Cary Hill and admiring all the awesome artwork on the way.

Johnstown

Johnstown is in Fulton County and beautifully nestled near the foothills of the Adirondacks, about 45 miles northwest of Albany. William Johnson, a quick-witted Irish immigrant who easily picked up Indian languages and culture, founded the town in 1760 and named it after his son. Johnson would go on to acquire (or be gifted) large tracts of land so that by the time he died, he had accumulated about 400,000 acres, making him one of the largest landowners in British America. The house he built in 1762 (some sources say 1763) survives today as the Johnson Hall State Historic Site. Drumm House, at the junction of Green and State streets, is also a relic of the Colonial era. For other things that turn back the clock, the Two Line Museum is worth every minute.

Hudson

Hudson has one of the most captivating downtowns in the Hudson River Valley. Warren Street, the town’s nerve centre, is like stepping straight into a Victorian fairy tale. The best part is that galleries and restaurants along the stretch retain their old-world facades, even if owners brush their interiors with a touch of modernity. Hudson was settled by New Englanders in 1783 and named for Henry Hudson, one of the explorers most credited with the public’s understanding of North America’s geography.

Olana State Historic Site, which Mark Twain called “an exalted hill of art,” has views that will electrify every fibre in your body. You can’t miss the Hudson-Athens Lighthouse as well. If you have visited several lighthouses, you know that it's uncommon to find one right in the middle of a river. The Hudson-Athens Lighthouse bucks the trend. Before leaving, spend some time at the FASNY Museum of Firefighting, a diamond in the rough with lots of antique fire apparatus.

Cooperstown

Cooperstown is mostly known as home to the National Baseball Hall of Fame, one of the most well-known sports shrines in the world. The idea that baseball was invented in Cooperstown in the years before the Civil War has been debunked. What has not been debunked is that Cooperstown is one of the oldest communities in Upstate New York. Cooperstown was founded in 1786 by William Cooper, a shrewd Quaker storekeeper described as “a good judge of land and an even better judge of men.”

The area, once a melancholy wilderness, is now a much sought-after summer resort. The best place to start? Possibly the Fenimore Farm and Country Village, a fun, nostalgic space that keeps a collection of historic buildings from other parts of the state. There is Otsego Lake, once described as a glimmerglass, and, of course, the nearby Glimmerglass State Park.

The Takeaway

From Victorian dreamscapes to Colonial theatres, few things are as charming as small, beautiful towns that echo with history, nostalgia, and timelessness. Think of streets lined with moss-draped oaks, an old, sombre building where a consequential treaty was signed, a hotel room that provided shelter to a tired general, or a tavern frequented by a notorious outlaw. Unfortunately, you will not find most of these in a newcomer of a town. You will have to explore some of the oldest-founded ones. The best part? Upstate New York has boatloads of them.