8 of the Most Charming Towns in Upstate New York

New York is a beautiful state with an enormous amount of countryside. The Adirondack, Catskill, and Appalachian mountains stretch through this northeastern region, while 24 National Parks and 180 state parks comprise part of the protected land. It's home to the Hudson River, one of the most critical watersheds in American history, and the Finger Lakes, a geological wonder that formed during the ice age. Beyond its sprawling landscape, the state has one of the highest populations in the country, a dense portion of which is in New York City. However, communities upstate hold their own merits, too, attracting visitors and transplants who choose to set down roots. The natural beauty and coziness of the historic towns let life slow down a bit. Discover the eight most charming towns to visit in Upstate New York.

Saratoga Springs

Saratoga Springs is an upstate spa town in the Hudson Valley known for its mineral springs, which are the only naturally carbonated springs east of the Rocky Mountains. There are over 21 pools visitors can soak in from Congress Spring to High Rock Spring. The town's rich heritage as a health resort stretches far back to when it was a gambling destination. Visitors can get a feel for what that time was like at the Canfield Casino, one of the town's most historic buildings. It used to be an illegal casino and now serves as a museum and event space.

Gamblers were also drawn to the iconic horse races here that began in the late 1800s. The Saratoga Race Course is one of the oldest racing tracks in the country and attracts more than a million visitors each year. At the National Museum of Racing and Hall of Fame, visitors can learn about the early era of horse racing and its transformation to the present day. The museum highlights the achievements of racehorses, jockeys, and trainers.

Woodstock

In the Catskill Mountains, Woodstock is a community that represents peace, love, and the arts. One of the most famous rock festivals in the 1960s was named after this groovy town, even though it had never occurred here. However, the name for the Woodstock Festival stuck around because of the inspiring musicians and creatives here. Further, the festival was initially supposed to take place in Woodstock, which visitors can learn about at Bethel Woods Center for the Arts.

Besides its legendary name, Woodstock has so much to explore. Tinker Street is an excellent place to start, with adorable storefronts and restaurants. The community is also home to Karma Triyana Dharmachakra, a Tibetan Buddhist monastery. Visitors can tour the main shrine room, library, and the monastery grounds. And for a quirky stop, Emerson Kaleidoscope, the largest kaleidoscope in the world, is only 10 miles outside of town. The attraction is in a refurbished farm silo at Emerson Resort, and people often lie down on the ground for the best view.

Beacon

On the eastern shore of the Hudson River with Mount Beacon as its backdrop, Beacon is a charming town upstate that's an easy train ride from New York City. It's known for its contemporary art scene and numerous historic sites that are close by. A popular one is Bannerman's Castle, an abandoned castle on Bannerman's Island that was once a fortress for weapons. A Scottsman built it in the early 1900s, and the fort could only be traveled by boat. About 10 miles from there is Washington's Headquarters State Historic Site. Visitors can explore the historic stone house that General George Washington used to end the Revolutionary War.

Beacon has become a magnet for new and established artists because of the town's commitment to supporting public arts. There are numerous galleries, museums, and installations to explore. Dia Beacon, one of the United States' largest contemporary art museums, has magnificent paintings, sculptures, and multi-media works. Meanwhile, Howland Cultural Center helps keep the art community vibrant in Beacon, showcasing local artists in theatre, music, and dance. It's housed in a historic building known as the "Jewel of Beacon."

Hudson

Hudson is a charming city along the Hudson River that's 45 miles from Albany and 160 miles west of Boston. The town is known for its excellent antiquing. A great place to find hidden treasures is along Warren Street, where only independent antique stores sell everything from vintage clothing to interesting collectibles and old furniture. Many owners swapped New York City for Hudson in the 90s because they saw the town's potential, which led to the area's revival. While shopping, it's hard not to notice the beautiful storefronts. Hudson is referred to as a "dictionary of architectural history" because of the variation from 18th-Century Nantucket townhouses to old Victorian mansions and Federal-style buildings around town.

Hudson is also near state parks and historic sites. The Olana State Historic Site was home to Hudson River School artist Frederic Edwin Church, who was iconic in the mid-19th Century. Visitors can walk around the 250-acre landscape and tour the Persian-style mansion, which still has original stencils and paintings. From there, Minneswaska State Park Preserve is about an hour away. You can hike to numerous waterfalls, such as Awosting Falls, and incredible vistas at Sam's Point Preserve, the highest point of the Shawangunk Mountains.

Cooperstown

In the central region of upstate New York, among rolling hills and at the southern tip of Otsego Lake, Cooperstown is a darling place with a rich heritage, particularly in baseball. The town is home to the National Baseball Hall of Fame and Museum, which illustrates the history of America's pastime and the impact the sport has had on society.

Besides baseball, there's also a rich farming heritage in Cooperstown. Visitors can explore tons of orchards and cedar mills, like Fly Creek Cider Mill and Orchard. The Farmers' Museum in town goes over the agricultural history and is one of the oldest rural life museums in the country. The land it's on has been part of a working farm since 1813 and includes a working farmstead and a Colonial Revival barn, listed on the National Register of Historic Places.

Glimmerglass State Park is an obvious choice for experiencing the area's natural beauty. It overlooks Otsego Lake and was named after the Glimmerglass from James Fenimore Cooper's Leatherstocking Tales. Visitors can camp, hike, or just enjoy a picnic here.

Rhinebeck

East of the Hudson River, Rhinebeck is described as a cultural mecca with galleries, museums, unique architecture, and historic sites. A great example of Victorian architecture is the Wilderstein Historic Site, once home to Margaret Suckley, a distant cousin of Franklin D. Roosevelt who traveled with FDR during his presidency. Another exciting attraction is the Old Rhinebeck Aerodrome, a flying museum that features a large collection of antique aircraft. It has early aviation and World War I era planes, and a popular air show takes place on the weekends in the summertime.

Besides its well-preserved history, Rhinebeck is known as a health-conscious community. People from around the world come to the Omega Institute, a non-profit education and retreat center that offers workshops and retreats that focus on holistic living practices like yoga and healthy eating. Many come for spiritual growth and wellness on the sprawling and forested campus.

Hyde Park

Bordering the Hudson River north of Poughkeepsie sits Hyde Park, a gorgeous historic town with scenic views, old mansions, and interesting museums. The community is the home to 32nd President Franklin D. Roosevelt. The Franklin D. Roosevelt Presidential Museum and Library tells the story of the Roosevelt era, from his boyhood to his presidency. Visitors can also explore Roosevelt’s Springwood estate in town. And the Eleanor Roosevelt National Historic Site is one town over in Haviland. The historic cottage called Val-Kill served as a retreat for the First Lady and her friends.

Another point of interest is the Vanderbilt Mansion National Historic Site, owned by one of the wealthiest families in America during the Gilded Age. The National Park Service operates the 54-room mansion. Visitors can tour the grounds and see how the dramatic interior and detailed architecture represent a country palace and aristocratic lifestyle.

Saugerties

Saugerties is a cute waterside town with a colorful history that tends to attract artists and creatives. It's home to Opus 40, a world-famous sculpture park created by artist Harvey Fite. The park has interesting earthwork sculptures among 63 acres of meadows and forest paths.

Saugerties has several historic landmarks, such as the Saugerties Lighthouse. Built in the late 1800s, it was a beacon of light for ships navigating the Hudson River. The property has been transformed into a bed and breakfast, so guests can stay overnight here. Another interesting site is the 1727 Kiersted House. It is a gorgeous historic stone house that was once a working farm and home to the town's first doctor. Now, it houses the Saugerties Historical Society.

Discover the Charm of Upstate New York

From the horse racing history in Saratoga Springs to the baseball heritage in Cooperstown, Upstate New York is adorned with towns with deep history. Many historic communities have a vibrant art culture, such as Hudson, which is known for its contemporary art scene. Others are teeming with character and have quite a backstory, like the town of Woodstock, which is named after the famous music festival. The Omega Institute in Rhinebeck might give you a new point of view, while historic sites such as Bannerman's Castle will take you back to another time. Whether you want to relax and unwind in nature or enjoy the neighborliness of a small town, Upstate New York has so much to offer.