Street view of Skaneateles. Image credit PQX via Shutterstock.

10 Small Towns in Upstate New York to Visit for a Weekend Getaway

There are plenty of ways for tourists to experience life to the fullest, especially when traveling to exciting or exotic locations for a weekend getaway. With various states worth considering for one's next excursion, New York is a testament to how historic or natural beauty and vacation enjoyment go hand-in-hand. While New York State is often overshadowed by visitors strictly wanting to go to the Big Apple, it is also home to an array of small towns that offer authentic and unique opportunities. These ten small towns in Upstate New York are designed for the perfect weekend getaway.


Streetscape of Warren Street in downtown Hudson
Streetscape of Warren Street in downtown Hudson.

A city with a population of 5,898 residents, Hudson is a worthwhile destination for travelers. It is known for its unparalleled charm because of evening ferry rides from Hudson to Athens. While in Hudson, visiting the New York Harbor provides a natural touch of history, as it has high bluffs reminiscent of The Proprietors and their early work in 1786. Warren Street illustrates painted realism within parks like Promenade Hill Park or High Falls Conservation Area, natural sights of wonder for mountain travelers. The Historic Robert Jenkins House has 1800s-era genealogical library text and research-guided tours, ideal for weekend visitors. The Thomas Cole National Historic Site, with its calm hillsides and painting exhibits, is worth every moment. Tourists may consider the Nautical Nest Hudson or Hudson Whaler for bookings and reservations, as both enable accessible lodging options.

Cold Spring

Sidewalk scene in Cold Springs, NY
Sidewalk scene in Cold Spring, NY.

A village town in Philipstown, Cold Spring is home to the West Point Foundry Reserve, an abandoned American Civil War site with artillery foundries and machinery. On the other hand, the Constitution Marsh is more commercialized and open to the public, with accessible hiking trails worth the boardwalk visit. Besides these historic and natural sites is the Chapel Restoration Church, adorned with Greek architectural history. The Chuang Yen Monastery stands as a Buddhist foundation, with in-house memorabilia representative of the Tang Dynasty. For nature lovers, the Boscobel House and Gardens is a 19th-century historical Georgian mansion with lovely interiors and exteriors. Boat ride lovers may sail from Cold Spring to Bannerman Castle. This small excursion grants a lifetime of photographic memories with the castle's high-rise structure overlooking the island. For lodging, tourists can look at the Inn on the Hudson, Bear Mountain Inn, or Hudson House River Inn. Touring through Cold Spring is enough to keep tourists happy for the weekend.


Crowds of visitors at the Dutchess County Fair in Rhinebeck.
Crowds of visitors at the Dutchess County Fair in Rhinebeck.

Rhinebeck is a small town full of pleasantries with a population of 7,548. It is home to furnishings, bookstores, gift shops, and Hudson Valley landscapes. Dubbed a "cultural mecca" for guests all around the world, travelers can stay at Baker House Bed and Breakfast, a romantic lodging option on the woodland outskirts of Rhineback, or the Beekman Arms and Delamater Inn, a tourism favorite for history in the Hudson Valley. Samuel's Sweet Shop, a classic candy store owned by Hollywood actors Jeffrey Dean Morgan and Paul Rudd, is an iconic tourist locale. The Dutchess County Fair also has many crafts and live events, keeping visitors preoccupied. Tourists hoping for history in their travels will enjoy the Wilderstein Historic Site, a classic yet exquisite take on Victorian mansion architecture. Travelers can visit Ferncliff Forest and Burger Hill Park, which include hiking and mountain biking routes to get a majestic view of the Catskill Mountains. Combining history and natural environments, Rhinebeck provides guaranteed satisfaction for a weekend getaway in Upstate New York.

Sleepy Hollow

New York State historic sign at the Old Dutch Church of Sleepy Hollow

A Dutch town in Upstate New York with 10,955 residents, Sleepy Hollow is home to the famous "The Legend of Sleepy Hollow," a favorite story about the Headless Horseman. It has pop-up cocktail experiences for travelers wanting to take on spooky thrills and fine dining. The Philipsburg Manor provides history as a mill and trading complex first implemented in 1750. The Headless Horseman Bridge is equally important, generating thrills for young adults. For other endeavors, tourists may enjoy Washington Irving's Sunnyside landscape. Being around Rockefeller State Park Preserve and the Sleepy Hollow Lighthouse enhances nature and adventure. Guests booking their stay in Sleepy Hollow may want to check in at the Tarrytown House Estate on the Hudson, the Castle Hotel & Spa luxury hotel near New York City, or the Sleepy Hollow Hotel itself.

Watkins Glen

Watkins Glen State Park waterfall canyon in upstate New York
Watkins Glen State Park waterfall canyon in upstate New York.

With 1,832 residents, Watkins Glen is a nature-driven escape for tourists in Upstate New York. For instance, the Finger Lakes National Forest and Watkins Glen State Park are worthwhile lakeside hiking and exploration destinations. A scenic road trip stop at Route 414 can entice tourists to enjoy lake-hugging beaches and downtown Greek, Gothic, and Romanesque Revival architecture. The Micro Diner in this town is deemed the "World's Smallest Diner," randomly cozied up against a hair salon. Tourists can visit the International Motor Racing Research Center, famous for its motorsports history collection and research on race drivers, race series, and race cars. While booking a stay at Watkins Glen Harbor Hotel, Idlwilde Inn, or Tioga Downs Casino Resort Hotel (among countless other options across the Finger Lakes), there is nothing better than staying near Watkins Glen for the weekend.

Saratoga Springs

A landscape view of downtown Saratoga Springs shopping district on Broadway
A landscape view of downtown Saratoga Springs shopping district on Broadway. Image credit Brian Logan Photography via Shutterstock.

A city in New York State famous for its horse racing activities and competitions, Saratoga Springs is a vibrant getaway spot for weekenders. The glory of visiting this small town of 28,301 residents lies in the ability to see the National Museum of Racing and Hall of Fame, known for its decorated horse paintings and trophies, as well as the Saratoga Spa State Park for mineral bathing and pool complexes to relax in. For arts and entertainment, the Performing Arts Center provides many ways to experience live shows and concerts in the capital district. History fans will appreciate the National Historical Park, which comprises ten-stop tours and audio-based education on the Battlefield Tour Road pertinent to the Battle of Saratoga. The Saratoga Springs History Museum strikes influence into the hearts and minds of guests who want to see and hear about what happened during the 1870s. While staying at lodges and resorts, like The Inn at Saratoga, Brentwood Hotel, or the Saratoga Casino Hotel, any traveler will find so much to do in so little time.

New Paltz

New Paltz tower in autumn
New Paltz Tower in autumn.

New Paltz is a town big on outdoor excursions. With a population of 7,503 inhabitants, it is tourism-worthy for its suburban quality of life. For hikers and cyclists, the views of the Hudson Valley are pretty spectacular in this small town, with the Shawangunk Wine Trail being one of many wineries worth the visit. Tourists can find their welcoming on Historic Huguenot Street, which pays homage to stone-compiled museums and indigenous French settlers. Another good spot worth checking out is the State University of New York (SUNY). New Paltz also provides wildlife preservation and sanctuaries, such as the Nyquist-Harcourt Wildlife Sanctuary and the Mohonk Preserve, encompassing natural landmark views through herbaceous plantlife and creatures in their usual habitats. Tourists can pick between Moondance Ridge Bed & Breakfast, Minnewaska Lodge, or Mohonk Mountain House for lodging with extraordinary neighborhood sights. This small town has many ways to experience natural, historical, and academic life on a simple weekend.


Hiker in the Catskill Mountains, Woodstock, NY
Hiker in the Catskill Mountains, Woodstock, NY. Image credit Dan Hanscom via Shutterstock.

Woodstock, with a population of 5,793 residents, is best known for its aptly named music festivals and big entertainment districts. As such, tourists may enjoy several theatrical and historical landmarks here, like the Bearsville Park Theater and the Woodstock Playhouse, featuring plays and shows that are common for weekend amusement. The Opus 40 is a sculpture park and museum that hosts more than 63 acres of meadows, forested paths, and bluestone quarries. Overlook Mountain is also a delightful appeal for hikers and mountain climbers. The Woodstock Way Hotel and the Woodstock Inn on the Millstream are idyllic and unforgettable hotel choices. Generational entertainment avenues are not a rare spectacle in this town, as travelers will typically have many options for live music and performances.


Street view of Skaneateles.
Street view of Skaneateles. Image credit PQX via Shutterstock.

Skaneateles is a quintessential lakefront town with 7,112 residents. It has a one-of-a-kind relaxation landscape that suits travelers of all backgrounds. While guests can choose to stay at hotels like the Hobbit Hollow House, the "Sunset Delight" cottage at Five Mile Point, or the Packwood House, there is plenty of room for tourism. The del Lago Resort & Casino, Schweinfurth Memorial Art Center, and the Seward House Museum all support a casual or leisurely stroll along artwork and antiques of ancient history. The lowkey sensations from Mirbeau Inn & Spa make the trip more meaningful for tourists who want to see Claude Monet's impressionist talent while staying comfortable indoors. Elderberry Pond and Clift Park instill incredible, picturesque restaurant ecosystems for fine wine and fresh cuisine picnics.


Corning Museum of Glass in Corning, NY
Corning Museum of Glass in Corning, NY. Image credit PQK via Shutterstock.

A city in the U.S. with a population of 10,738 residents, Corning encourages museum culture and urbanized tourism mainstays. Traveling parties can see the world-renowned Corning Museum of Glass, a modernized approach to glassmaking with contemporary technologies that improve on over 3,500 years of history. Another great locale for small-town visitors is the Rockwell Museum, unique for its Native American art collection. City folks and tourists with a drive for the symphony will appreciate St. Mary's Church in the town and Iron Flamingo Brewery for delicious beer tasting. Historic landmarks, such as Centerway Square and the Gaffer District, bring about decades of charm and citywide development for a weekend stay. There will always be a reasonable amount of joy expected in Corning, so tourists should check in at the Radisson Hotel, Staybridge Suites, or the Horseheads Hideaway for a memorable outing.

Upstate New York offers many activities to keep everyone engaged and content when traveling. No matter what type of itinerary one chooses, all of these small towns establish a connection to the tourist distinctly. This list can keep vacationers up-to-date with what is trending in small-town New York life!

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