13 Most Charming Towns in Upstate New York

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While many people associate New York with New York City, there’s so much more to this state. The Upstate region makes up the majority, including everything other than NYC, Long Island and the Lower Hudson Valley. It’s home to many charming towns that make for a relaxing escape and easy access to the great outdoors, with these destinations standing out as some of the best.

Cooperstown
Cooperstown, New York

Cooperstown

One of the most beautiful small towns in the United States, Cooperstown is only a small village, but most people have at least heard of it thanks to the National Baseball Hall of Fame & Museum. While that’s reason enough to come for baseball fans, it’s also rather charming and offers plenty of other things to do. Sometimes referred to as the Village of Museums, it’s also home to one of the country’s oldest living museums, the Farmer’s Museum, and the Fenimore Art Museum, which hosts one of the most impressive collections of folk and American Indian art in the U.S. Set along the shores of Otsego Lake, there are plenty of outdoor activities on offer too, including hiking in Glimmerglass State Park.

New Paltz
Lake Mohonk in New Paltz

New Paltz

New Paltz makes a great day trip or weekend getaway from the Big Apple, just 90 minutes away. It’s home to the 10-acre National Historic Landmark District, which has more than 300 years of history to explore across seven historic stone-house museums, a reconstructed 1717 French church, and more. The period-style rooms and exhibits reveal the stories of the French Huguenot settlement as well as the Indigenous and enslaved African peoples. There’s lots of nature to enjoy as well, including a hike on the Lemon Squeeze, one of the state’s top hiking trails. You’ll find many outstanding eateries to feed hunger pangs afterward, along with boutique shops to browse.

Lake Placid
Chairs alongside Lake Placid New York

Lake Placid

Nestled in the Adirondack Mountains, the village of Lake Placid is a popular destination for outdoor adventure enjoyed among spectacular scenery. It’s well-known for hosting the 1932 and 1980 Winter Olympic Games, and today visitors can enjoy a wealth of winter activities like skiing and snowboarding as well as watch everything from world-class ski jumping to luge, bobsled, and skeleton racing at the Olympic venues. During the warmer months, swimming, paddling, boating, and hiking can all be enjoyed. Fall is a popular time to be here too, with the oak, maple, birch, and beech trees bursting into fiery red, vivid orange, and yellow hues among the green of the deeply forested mountains that surround the lake.

Catskill
Catskill, New York

Catskill

The town of Catskill offers magnificent mountain views and a ton of history. Famed painter Thomas Cole made his home here, which is now a National Historic Site, while author Washington Irvington based his well-known short story Rip Van Winkle on the town. Beyond a trip into the past, visitors can enjoy one of the tallest waterfalls in the state nearby, Kaaterskill Falls, along with epic adventures into the mountains, including hiking, climbing, mountain biking, ziplining, and camping. After a day of play, there are plenty of tasty eats along Main Street, while shopping enthusiasts can give their wallets a workout in the many boutiques.

Saratoga Springs
Congress Park, Saratoga Springs, New York

Saratoga Springs

Tucked into the heart of the Hudson Valley, Saratoga Springs is famous for horse racing, but it offers plenty more, including over 20 public mineral springs, something that attracted many of the state’s elite during the Gilded Age. Spread throughout the city, free self-guided tours are available for sampling them. You’ll also find lush gardens and parks, including Saratoga Spa State Park, which hosts two public pools and a farmer’s market. Along Broadway downtown, there are many local shops and boutiques, galleries, bars, and restaurants.

Cold Spring
Cold Spring New York

Cold Spring

Cold Spring is listed on the National Register of Historic Places, serving as a popular weekend getaway for New York City residents. Its center is filled with 19th-century buildings that now house a unique collection of antique stores, independent shops, coffee houses, ice cream parlors, and restaurants with tables for alfresco dining. At the river’s edge park areas, you’ll find benches overlooking the Hudson. A variety of activities can be enjoyed during the warmer months, like biking, kayaking, and boating.

Beacon
charming Beacon, New York

Beacon

Beacon is just a 90-minute drive from New York City, set along the banks of the Hudson River, boasting serene beauty, small-town charms, a thriving art scene, tasty eateries, and even a castle. Many come to explore its modern art museum, which is housed in a former Nabisco box printing factory as the largest museum of contemporary art in the country. Main Street is filled with art galleries, including pop artist Ron English’s unique and cartoony gallery, Pop Mart. There are local craft breweries, bars serving craft cocktails and decadent sweets at Hudson Valley Marshmallow Co. too.

Alexandria Bay
Alexandria Bay, New York

Alexandria Bay

Located along the St. Lawrence River in the heart of the Thousand Islands, the small village of Alexandria Bay may not be doable as a day trip, just a stone’s throw from the border of Canada; it’s well worth the trip with its magnificent setting and wealth of activities that can be enjoyed on the water. One of the top attractions is Boldt Castle on Heart Island, looking as if it’s straight out of a fairytale, with public tours available. The Power House and Clock Tower are its most photographed structures, designed in the fashion of a Medieval Tower. A variety of boat tours can be enjoyed, or you can rent a pontoon boat and just relax as you float. You’ll also find plenty of shops and eateries, including menus featuring farm-to-table fare.

Lewiston
Frontier House, Lewiston, New York

Lewiston

Located just north of the town of Niagara Falls, most travelers seem to visit Lewiston simply for its proximity to the famous cascades, but it has plenty to offer of its own, including a charming downtown. Center Street is the main street that leads to the Niagara River and Canada across the way. It will also take you to the crown jewel of the historic district, Frontier House. Built in 1824, it faces the river and was considered America’s finest hotel in the early 19th century. It’s had many incarnations, serving as a private residence, a fine-dining restaurant, a museum, and even a McDonald’s at one point. It will soon feature short-term vacation rentals for those seeking a historic and possibly haunted stay near the falls. Another one of the top attractions here is the Whirlpool Jet Boat Tours, a thrilling 45-minute ride that will take you into the heart of the Niagara Gorge and through Devil’s Hole rapids.

Watkins Glen
Watkins Glen State Park waterfall in a canyon

Watkins Glen

Watkins Glen sits at the south end of Seneca Lake near Watkins Glen State Park, the most famous of the Finger Lakes Park, which includes 19 waterfalls along a stream framed by 200-foot cliffs. In the village itself, there are many locally owned, independent restaurants, cafes, bars, and shops. The town may best be known for its long auto racing tradition, but it’s also popular for its summer festivals, including the Finger Lakes Wine Festival and the Italian American Festival.

Woodstock
Newkirk House, Woodstock, New York

Woodstock

Woodstock is best known for the legendary 1969 music festival of the same name, although it actually took place in the town of Bethel, 60 miles away. The town was a leading site of the Hudson River School in the 19th century, followed by the Arts and Crafts Movement in the early 1900s, with the founding of the Byrdcliffe Arts Colony further defining the cultural influence of Woodstock. Today it’s known as a place that draws plenty of artists and freethinkers, but it also offers some fabulous vintage shops, organic cider farms, and destination restaurants serving farm-to-table cuisine. There are a number of historical landmarks to discover, like the Newkirk House with a historical marker that reads: “Newkirk House one of the earliest houses in Woodstock, occupied 1777 by Garret Newkirk, later by Jacobus Eltinge.”

Rhinebeck
East Market Street in Rhinebeck, New York

Rhinebeck

You can hop on the train from Penn Station and be in Rhinebeck in just two hours, enjoying its small-town charms, with galleries, performing arts venues, and historic architecture. It comes complete with a farmers market that’s considered one of the best in the state, and for those who like sweet streets, Samuel’s Sweet Shop, a classic candy store partially owned by actors Jeffrey Dean Morgan and Paul Rudd. If you’re here in August, don’t miss the Dutchess County Fair, which includes craft and antique shows, livestock shows, a popular wine and food festival, and a sheep and wool festival. Hiking, mountain biking, and fishing can all be enjoyed nearby.

Sleepy Hollow
Mill house in Sleepy Hollow

Sleepy Hollow

Sleepy Hollow, located less than an hour north of New York City, is a place most people are quite familiar with thanks to the 1820 horror classic penned by Washington Irving and the multiple subsequent films, including the 1999 version starting Johnny Depp. Steeped in history, there are many sites to explore, including Rockefeller Estate in Rockefeller State Park Preserve, the Old Dutch Church, and Philipsburg Manor. In the 1750s, the Philipsburg estate was run by a community of two dozen enslaved individuals of African descent and included a bustling trading complex and mill, something you can learn more about on a fascinating visit. It happens to be located near Sleepy Hollow Cemetery, where well-known historical figures like the author Irving himself, Elizabeth Arden, Brooke Astor, and Andrew Carnegie were all laid to rest. There’s even a headless horseman next to it.

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