Street view at Skaneateles, New York. Editorial credit: PQK / Shutterstock.com

10 Small Towns in New York With Big Charm

Also known as the “Empire State,” New York is the fourth most populous state in the United States. The Empire State is home to the “Big Apple” city, the most populous city in the country, and other big cities like Albany, the state capital. Embedded between these big cities are dainty towns that should not be overlooked!

Tourists and vacationers looking for a quiet vacation should consider spending time in any of these towns in New York, from breathtaking mountain towns to enchanting island towns. Whether travelers are slow-living, on a road trip, or exploring the state, these ten small towns will leave folks with fond memories of a lifetime.

Andes

View of the Pepacton Reservoir and Catskills Mountains at sunset from the Shaverton Trail overlook in Andes, New York.
View of the Pepacton Reservoir and Catskills Mountains at sunset from the Shaverton Trail overlook in Andes, New York.

The town of Andes is on the western edge of the Catskill Mountains in Delaware County. Approximately a three-hour drive from New York City, Andes is an excellent place for a family vacation, romantic getaway, and even corporate retreats. In this town, there are great swimming spots like Big Pond. It is also a great site for canoeing, fishing, and camping. Fans of hikes that aren't too stressful but are moderately tenuous will love hiking along the Shavertown Trail. On the hike, you get to enjoy a spectacular view of the Pepacton Reservoir and the mountains beyond. 

Skaneateles

The small upscale village of Skaneateles, New York in autumn. Editorial credit: debra millet / Shutterstock.com
The small upscale village of Skaneateles, New York, in autumn. Editorial credit: debra millet / Shutterstock.com

Southwest of Syracuse is a choice lake town called Skaneateles, after the Iroquois name for “Long Lake.” Located on the shores of one of the cleanest lakes in the United States, Skaneateles is a hub for many water sports. Kayaking or windsurfing at Skaneateles Lake are great ways to spend an afternoon. You can check out the picturesque shores of the Finger Lake from a boat’s deck on one of the Skaneateles boat cruises. Downtown Skaneateles is one of the most breathtaking and activity-filled Downtowns where you can go shopping and wine tasting. Also, dine at Joelles French Bistro or Rosalie's Cucina restaurants. There are lovely lodging options in town as well, such as the Mirbeau Inn & Spa.

Lake George

Aerial view of Lake George New York.
Aerial view of Lake George, New York.

Originally named ‘Caldwell' after James Caldwell, Lake George was formed in 1810 and is a small New York town with a charming ambiance. This beautiful town was renamed in 1962 after Lake George. With a population of around 3,500, this lakeside town is splendid for a staycation. 

This town is filled with many unique opportunities, especially for outdoor adventurers who love to explore the wild. Amazingly, there is an interest for both young and old. Enjoy the striking view of the water and mountains when you go parasailing or see Lake George from the sky with your friends and family in a hot air balloon.

If travelers are looking for activities that are a bit laid back, there are several renowned sites in town. Founded in 1903, Wiawaka is the oldest continuously operating retreat for Women in America. You can also spend time at the Lake George Battlefield Park Historic District to learn more about the French and Indian War. 

Cobleskill

Stewart's Shops in Cobleskill, New York. Editorial credit: a katz / Shutterstock.com
Stewart's Shops in Cobleskill, New York. Editorial credit: a katz / Shutterstock.com

Visit Cobleskill, a quaint town in Schoharie County that sits beside a lovely creek by the same name (Cobleskill Creek). Cobleskill is home to the State University of New York’s College of Agriculture and Technology. This college town has more to offer than meets the eye. Cobleskill has been hosting the Schoharie County Sunshine Fair in August since 1876. This fair attracts people from all over the country to witness and be part of the festivities, from livestock shows to demolition derbies. 

Outside the town, adventure awaits at two caverns, the Secret Caverns, formed during the last Ice Age, and the Howe Caverns. These caves are a great adventure to go on with friends. It is important to note that Secret Caverns is usually closed when the weather causes flooding in the cave. 

Shelter Island

Sunrise on the Mashomic Preserve on Shelter Island, NY.
Sunrise on the Mashomic Preserve on Shelter Island, NY.

Shelter Island is a beautiful Island in Suffolk County,  surrounded on three sides by the Shelter Island Sound and on the fourth side by the Gardiners Bay. The area was originally called Manhansack-aha-quash-awamock by the Manhanset Indians, meaning “an Island sheltered by Islands.”

Shelter Island can be accessed through a Ferry crossing. You can join a ferry ride from Greenport on the North Ferry, which lasts approximately 8 minutes, or a ferry ride from North Haven on the South Ferry, which lasts approximately 5 minutes. The town also has a nature preserve area known as the Mashomack Preserve. The preserve has trails for hiking and bird-watching alongside the barrier-free Braille trail for visually impaired people. 

Visitors can spend the day sunbathing on the pristine Wades Beach in this little island town. If you want to explore other regions, Shelter Island is perfectly positioned where visitors can explore the Hampton regions or the Wine Country.

Riverhead

An evening view of the Peconic riverfront park in Riverhead, NY. Editorial credit: Jay Gao / Shutterstock.com
An evening view of the Peconic Riverfront Park in Riverhead, NY. Editorial credit: Jay Gao / Shutterstock.com

Resting on the mouth of the Peconic River is a small town, with its name derived from its position near the river. Riverhead was founded in 1792 after the American Revolution as part of new jurisdictions. This town has been the county seat of Suffolk County for over two centuries. 

The town has a strong agricultural economy both historically and in the present day. Embedded in this town is a community of Polish immigrants known as “Polish Town," which was established at the turn of the century.

Downtown Riverhead is a hub of activities that keep tourists entertained throughout their stay. Walking on the Downtown Riverhead Historic Trail is an ideal way to start exploring. Along this trail, you can make stops and talk with town residents. A visit to the Long Island Aquarium is also an excellent way to learn about the wonders of the Ocean.

Saugerties

View of the Opus 40 outdoor sculpture park in Saugerties, New York. Editorial credit: quiggyt4 / Shutterstock.com
View of the Opus 40 outdoor sculpture park in Saugerties, New York. Editorial credit: quiggyt4 / Shutterstock.com

On the northeastern corner of Ulster County is the adorable town called Saugerties. Some part of this town is inside the Catskill Park. This town was the host of the Woodstock 1994 Music Festival, held to celebrate the 25th anniversary of the music festival.

Explore the terrains along the Hudson River if you choose to pay a visit to Falling Waters Preserve. The preserve was once home to the Mulford Ice House, and although the house is no longer standing, you can walk on the trails that once led to the house. Once done with the preserve, another great stop is the Hudson Valley Detours. The Hudson Valley Detours allow you to explore the scenic terrains of the Hudson Valley. Another great destination is Opus 40, a nonprofit sculpture park with 63 acres of meadows, bluestone quarries, and historic quarrying trails. 

Windham

Windham, NY is one of the most popular destination for scenic drives, bike trails, foliage and nature lovers.
Windham, NY, is one of the most popular destinations for scenic drives, bike trails, foliage, and nature lovers.

Nicknamed the “Gem of the Catskills,” Windham is a cute town in Greene County, possibly named after Windham, Connecticut, though not proven yet, as many early settlers came from that state and other parts of New England. Many towns in the county were created from what might be referred to as “Old Windham.” 

This town can be found in the Catskill Mountains. This mountain town is home to Windham Mountain Ski Resort, which is a major attraction for tourists in this town. The rugged terrain around this town makes it a hotspot for mountain bikers. Two miles east of Downtown Windham is Elm Ridge Trails, built specifically for bikers. 

New Paltz

Arched gate and watchtower at Mohonk Testimonial Gateway in New Paltz, New York.
Arched gate and watchtower at Mohonk Testimonial Gateway in New Paltz, New York.

Located in the southeastern part of Ulster County is an eye-catching town named after Pfalz-am-Rhein, a German State. New Paltz is a college town, home to the State University of New York. 

New Paltz is small with a lovely and pleasant ambiance. There is much to see and do in this town that will leave you breathless. History lovers will have fun at the Historic Huguenot Street. The street is 10 acres of well-preserved historic buildings that allow visitors to experience over three hundred years of history. 

People looking for unique landmarks will enjoy exploring the Mohonk Preserve Testimonial Gateway. The preserve provides tourists with the opportunity to explore the Testimonial Gateway Tower. This tower once served as the formal entrance to the Mohonk Mountain House. 

Woodstock

Legendary Woodstock village in Woodstock, New York.
The town of Woodstock, New York. 

Located in the foothills of the Catskills is an art-centric town called Woodstock, with a population of 6,263 people. The town is also the namesake for the famous Woodstock Music Festival. The town's art scene is very active today, as seen in the Woodstock School of Art or the all-encompassing Woodstock Playhouse, which hosts arts, theater, and music all year round.

Tinker Street is a great shopping experience in Woodstock, perfect for buying souvenirs or a postcard at any shop on the street. For those who are religious or interested in learning more about Tibetan Buddhism, a visit to the Karma Triyana Dharmachakra Tibetan Buddhist Monastery will not disappoint. This monastery hosts beautiful events and offers personal retreats for students interested in exploring Tibetan Buddhism.

New York is a state where many small towns have big charms that will blow your mind away. Sometimes, these towns may be overlooked because of the surrounding big cities. However, they are well worth a visit as you will have lots of fun and experience more of what New York has to offer. This is a call for you to pack your bags and go on that well-deserved vacation with your friends and family. 

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