Top 15 Charming Small Towns to Explore in New York | Go Travel Daily

Top 15 Charming Small Towns to Explore in New York

The state of New York is often overshadowed by the city of New York. Nevertheless, its small towns offer a wealth of experiences, including stunning mountains, delightful wineries, rustic allure, outdoor pursuits, and engaging historical narratives. The captivating scenery and rich culture merit exploration.

Here are our selections for some of the finest small towns in New York:

1. Cold Spring

Cold Spring – New York

With a population of approximately 2,000 and recognized on the National Register of Historic Places, Cold Spring serves as a favored destination for weekend getaways. Many buildings in the downtown area date back to the 19th century, and the community takes pride in its majority of independently-owned shops.

For those who enjoy leisurely strolls without a specific destination, Cold Spring provides charm, tranquility, and comfort. If outdoor activities are your preference, the Hudson River flows nearby, offering opportunities for boating and kayaking. Additional activities include golfing, biking, and hiking. Be sure to visit the historic West Point Foundry and Moo Moo’s Creamery.

2. Aurora

Waterfront Italianate Inn in Aurora

When we refer to small, we mean Aurora. Also known as Aurora-On-Cayuga, this village has a population of less than 1,000 residents. It is primarily recognized for Wells College, originally established for women. The combined village and college historic district comprises roughly 50 homes and buildings.

In 2001, Pleasant Rowland, a Wells College alumna and founder of the American Girl historic dolls and books series, initiated a revitalization effort for the town. Consequently, it now offers an ideal ambiance for those desiring to experience a rural setting, far removed from daily stressors.

3. Ithaca

Winter Trees Near Cayuga Lake

Ithaca is renowned for its cultural offerings, which are among the finest in New York. It boasts an array of unique and exceptional restaurants, remarkable art galleries, and captivating live music events.

Moreover, it is celebrated for its breathtaking natural landscapes. Visitors often find solace along the gorges that envelop the shores of Cayuga Lake. Explore the 28,000 acres of state forest and discover over 150 waterfalls that contribute to the area’s stunning beauty. Ithaca also hosts Cornell University, infusing the town with a vibrant and dynamic atmosphere.

4. Raquette Lake

Raquette Lake

For those seeking a camping retreat, Raquette Lake is the ideal destination. This town, situated on the western shore of the lake, is surrounded by breathtaking wilderness.

The pace of life here is leisurely, and with 99 miles of shoreline, exploring the largest natural lake in the Adirondack Mountains is a delight. The state of New York has designated the area ‘Forever Wild,’ adding to the charm of the stunning scenery and outdoor activities like hiking, camping, fishing, and boating.

Don’t forget to visit Pine Knot, Uncas, and Sagamore to appreciate the luxurious and rustic estates in the area.

5. Cooperstown

Cooperstown, NY

Most Americans can identify Cooperstown as the home of the Baseball Hall of Fame. However, the town encompasses much more. With no chain stores, abundant outdoor activities, and a rich cultural scene, this small town has a lot to offer.

Visitors typically start at the Hall of Fame, followed by a trip to The Fenimore Art Museum, showcasing 20th-century American art and Native American pieces. Additionally, The Farmer’s Museum allows guests to step back in time and experience life at the Lippitt Farmstead, enchanting individuals of all ages.

Brewery Ommegana is a preferred destination for unique craft brews, while The Glimmerglass Festival, held each summer, presents opera performances on the lake.

6. Lake Placid

Lake Placid, NY

Founded in 1900, Lake Placid is nestled in the Adirondack Mountains and was featured by U.S. News & World Report as one of the ‘Six Forgotten Vacation Spots of North America.’ It gained fame as the host of the Winter Olympics in 1932 and 1980, and it is remembered for the ‘Miracle on Ice’ when the U.S. men’s hockey team secured gold against the USSR. Here, one can marvel at New York’s highest peak, Mt. Marcy, and indulge in skiing on popular slopes like Olympic Mountain, Whiteface, and others.

Visitors enjoy a plethora of activities such as hiking, cross-country skiing, ice climbing, canoeing, swimming, and snowmobiling. The numerous resorts in the town offer superb dining, and each season brings delightful festivals.

7. Chittenango

Chittenango

For those enamored with The Wizard of Oz, Chittenango will undoubtedly delight. It is the birthplace of L. Frank Baum, the renowned author of the books, and locals are justifiably proud of their distinguished heritage.

Chittenango is a village within the town of Sullivan, housing fewer than 6,000 residents. Every summer, a three-day festival known as Oz-Stravaganza celebrates the author and the beloved story, featuring parades and performances from various community groups.

8. New Paltz

New Paltz

As a vibrant college town, New Paltz continually buzzes with activity. Its student population, favorable year-round climate, close proximity to both New York City and Albany, along with its historic district, has solidified New Paltz’s status as a cultural hub within the state.

In the 17th century, twelve Huguenots settled on 40,000 acres near the Wallkill River, establishing what is now the Huguenot Street Historic District, which is recognized on the National Historic Registry. It’s no wonder why the original settlers chose this location—New Paltz boasts some of the most stunning views of the Hudson River.

Visitors can relish in fine dining, boutique shopping, exquisite wines, and a lively local scene.

9. Greenport

Greenport

Designated by Forbes as one of the most picturesque towns in the U.S. (2011) and once a fishing village, Greenport is now famed for its vineyards. With a population hovering around 2,000, the combination of wine and fresh seafood makes Greenport a culinary destination.

Recognized as one of the Top 10 Wine Destinations in the United States, the town also remembers its fishing heritage. Historically a significant whaling port in the 18th and 19th centuries, it served as an oyster center for many years. Interestingly, it is said that Walt Whitman taught a semester of high school English here.

10. Saratoga Springs

Saratoga Springs

Located just north of Albany, Saratoga Springs ranks among the best places to live in New York, as reported by its residents. Established in the 17th century by English colonists, the area played a pivotal role during the American Revolution.

Today, the town is well-known for horse racing and cultural events. It hosts summer residencies for both the Philadelphia Orchestra and the New York City Ballet. Over its 200-year history, countless visitors have flocked to the famous mineral springs that bestowed the town with its name.

11. Pawling

Pawling

Situated in the foothills of the Berkshire Mountains, Pawling is an optimal location for nature enthusiasts. With access to the Appalachian Trail and Pawling Preserve, many weekend adventurers frequent this area.

Residents take pride in their community involvement, fostering an environment of generosity and abundance. Pawling exudes charm and serves as a serene retreat from urban life.

12. Geneva

Geneva, NY

Situated on Seneca Lake, the largest of the Finger Lakes, Geneva stands out as a central town within New York’s burgeoning wine scene.

The town prides itself on its ‘uniquely urban’ character, suggesting it combines the intimacy of a small town—where greetings are ubiquitous—with a diverse offering of cuisine, arts, shopping, and educational opportunities that capture visitors’ interest time and again.

13. Skaneateles

Skaneateles Mansion

If you are an enthusiast of bed and breakfasts, consider visiting Skaneateles (pronounced ‘skinny-atlas’). Featuring a historic downtown, charming inns, and excellent dining options, this town attracts many travelers.

The historic district, dating back to the 18th century, comprises the contemporary commercial center, situated directly on the lake, and it features three lakeside parks ideal for hiking and picnicking. During summer, you can join the town’s 7,000 residents in the Skaneateles music festival and the Antique and Classic Boat Show.

Each winter, the town celebrates a Dickens Christmas, where actors perform in period attire on the streets.

14. Westfield

Westfield, NY

Situated on the shores of Lake Erie, Westfield is another favorite within wine country and also a major producer of Concord Grape Juice. This town serves as a fantastic summer destination, where one can engage in fishing, sailing, and golfing, while enjoying music festivals, galleries, and theater performances.

The numerous wineries offering tastings will surely impress visitors. Additionally, Barcelona Harbor provides rolling green hills and a picturesque beach ideal for swimming!

15. Sleepy Hollow

Philipsburg Manor in Sleepy Hollow

This town occupies a unique place in American folklore. Sleepy Hollow became legendary through Washington Irving’s tale bearing its name. Thanks to the enduring popularity of the story, the township has preserved much of its history and rustic charm.

Additionally, many visitors are drawn here due to its reputation as one of the most haunted places in the world! While in town, be sure to explore the Old Dutch Church, Philipsburg Manor House, and the Sleepy Hollow Cemetery, where notable figures such as Elizabeth Arden, Brooke Astor, and Andrew Carnegie are interred.

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