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The 12 Best Small Towns in New York

Here's what you need to know...
  • New York is a gorgeous, fascinating state to explore with a fun road trip
  • While the big city is a major draw, consider learning more about New York’s small towns to get to know all that the state offers
  • Before beginning a road trip, review your insurance coverage to verify that you are fully insured

Since the first Dutch settlers arrived along the banks of the Hudson River in 1624, New York has been a coveted destination to explore as well as to live in.

This state played critical roles in the formation of the country as well as in the fight for independence from Great Britain. It also was the original point of reception for millions of immigrants who later settled in other areas of the country.

More than that, New York plays a vital role in the country’s overall economy, and it is known as a cultural hub for music, theater, and more.

The natural landscape is robust, featuring everything from mountains and rolling hills to massive waterfalls, mighty rivers, historic bays and more. With all four seasons equally well-represented throughout the year, there is no bad time to visit New York.

Exploring this exciting state is a wonderful way to spend a few days, a few weeks, or longer.

From Niagara Falls in the north to New York City in the south, you can find numerous parks, beaches, festivals, museums and cultural sites to explore. Lake Placid, Ellis Island, and others beckon you to explore the nooks and crannies of the state.

When you are driving through New York, be sure to spend time at some of the state’s best small towns to get to know all that the area offers.

Are you wanting to roadtrip and visit New York? Enter your ZIP code above first and compare at least three to four auto insurance policies today to ensure you are fully covered on the road!

The 12 Best Small Towns in New York

#1 – Aurora

Population: 724
Must See: Cayuga Lake, Main Street, MacKenzie-Childs, the Aurora Inn

Situated on the shores of beautiful Cayuga Lake, this little town has recently been revitalized to captivate locals and visitors alike with its charm.

The renovation is the result of a large financial contribution from the American Doll founder, and the result is a town that draws visitors in droves to enjoy all that it offers.

While you are visiting Aurora, you can stroll down Main Street and enjoy an old-fashioned dining experience at the local pizza parlor. Be sure to tour the ceramics factory to learn more about the city’s primary economic contributor.

#2 — Cold Spring

Population: 1,983
Must See: Hudson River, Cold Spring Historic District, Hudson Highlands State Park

Cold Spring is a tiny village that sits on the Hudson River shore across from West Point. This town has a long history of being a high-end retreat for visitors from New York City. As a result, many historic, grand mansions have been built in the town over the years.

The village is known for its beautifully-preserved architecture in the Historic District downtown as well as throughout the residential areas.

Other notable attractions that you may want to visit while you are passing through Cold Spring include the Hudson Highlands State Park, Stonecrop Gardens, and the Julia L. Butterfield Memorial Library.

#3 — Saranac Lake

Population: 5,406
Must See: Saranac Lake, Adirondack Park, Lake Flower

Saranac Lake is located in northern New York in the heart of the Adirondack mountains. It boasts proximity to all three of the lakes that the town is named after as well as to Lake Flower and Adirondack Park.

Notably, the town is home to more than 185 historically-recognized buildings that have been well-preserve and was also named as an All-American City by the National Civic League in 1998.

Because of the city’s unique location, it is a favorite winter and summer vacation spot. Saranac Lake also is a prime artists’ community and hosts the Plein Art Festival each year.

#4 — Cooperstown

Population: 1,852
Must See: National Baseball Hall of Fame, Farmers’ Museum, Cooperstown Historic District

Cooperstown is one of the most recognizable geographic locations for baseball fans, because the famous National Baseball Hall of Fame is located here. However, Cooperstown offers much for visitors to enjoy beyond its baseball history.

The primary downtown area was built before 1900, and the Historic District has been revitalized to make it a charming place to explore.

The Farmer’s Museum has been a tourist attraction since 1944 as well. In addition, you can also explore the Fenimore Art Museum and the Glimmerglass Opera while in Cooperstown.

#5 — Skaneateles

Population: 2,450
Must See: Finger Lakes, The Creamery, Skaneateles Historic District

Skaneateles was originally settled in the 1790s because of the area’s desirable location close to one of the Finger Lakes. The town has not grown substantially in size over the years and has, therefore, retained its considerable small town charm.

You can enjoy amazing natural views of the lake from many locations, and you can also spend time touring The Creamery, which is a historical museum. Boat tours are available on Skaneateles Lake.

You can stroll through the Skaneateles Historic District and stop by the Skaneateles Library and John D. Barrow Art Gallery. There are also numerous buildings in the city that are on the National Register of Historic Places.

#6 — Greenport

Population: 4,165
Must See: Olana State Historic Site, Rogers Island, San Salsbergen House

If your exploration of New York takes you through the eastern region of the state, spend time exploring the small town of Greenport.

Greenport was originally explored by the legendary Henry Hudson, but the town was not founded until 1837 when it broke away from the town of Hudson, which surrounds the town’s limits on three sides.

History abounds throughout this town, and you can tour the Van Salsbergen House as well as the Turtle House and the Columbia Turnpike- West Tollhouse while you are in the Greenport area.

#7 — Lake Placid

Population: 2,521
Must See: Mount Von Hoevenberg Olympic Bobsled Run, Alpine Mountain, Whiteface Mountain

Lake Placid was originally founded as an iron ore mining town, but it is most notably the site of the 1932 and 1980 Winter Olympics.

It continues to host regular sporting events, such as pond hockey and lacrosse tournaments.

While some individuals travel to Lake Placid to learn about history or to take in a sporting event as a spectator, many others take advantage of Lake Placid’s location for both summer and winter outdoor recreational activities.

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#8 — Woodstock

Population: 5,884
Must See: Artists’ Cemetery, Ashokan Reservoir

Woodstock is situated in Catskill Park not far from New York City. It was founded in 1770, but Woodstock did not reach popularity as a vibrant arts community until 1902.

While the town is known for the famous Woodstock Festival musical event, the town’s founders did not approve the event permit. Therefore, the Woodstock Festival was held approximately 60 miles away.

You can walk through the Artists’ Cemetery to tour the final resting place of many famous artists’ graves. Another idea is to visit the Ashokan Reservoir. At the bottom of this body of water, nine flooded villages can be found.

#9 — Saratoga Springs

Population: 26,586
Must See: Saratoga Race Course, Saratoga Performing Arts Center, Saratoga Spa State Park

From its earliest days, Saratoga Springs has been a popular vacation spot because of its natural springs. Many people enjoy soaking in these waters at the Saratoga Spa State Park.

With so many people visiting Saratoga Springs each year, gambling and racing also became commonplace. The Saratoga Race Course is just one of several venues in the town dedicated to this activity.

The town is also the home of the New York City Ballet and the Philadelphia Orchestra, which both perform at the Saratoga Performing Arts Center regularly.

#10 — Ellicottville

Population: 1,598
Must See: Holimont Ski Resort, Holiday Valley Ski Resort

Ellicottville is located in the far western section of the state and was originally founded in 1815. It remained a sleepy town until two ski resorts opened nearby, and these resorts bring numerous visitors to the area each year.

The town is also home to annual celebrations, such as the Ellicottville Championship Rodeo that occurs each summer.

Several historical attractions may also be toured while you are in the beautiful Ellicottville area, and these include the John J. Aiken House and the Bryant Hill Cemetery.

#11 — Ithaca

Population: 30,014
Must See: Cayuga Lake, Cornell University

Ithaca was originally settled by Jesuit missionaries from Quebec in 1657. It grew slowly over the years because of the desirable location on Cayuga Lake.

In the early 1900s, the town gained fame because of early motion picture filming that took place in Ithaca. It also grew when Cornell University opened its doors in 1865.

Today, many people visit Ithaca to enjoy the natural beauty, to tour the college, or to enjoy the historical attractions, museums, and shopping experiences in the area.

#12 — Sleepy Hollow

Population: 9,870
Must See: Sleepy Hollow Cemetery, Old Dutch Church, Philipsburg Manor House

Sleepy Hollow is located close to the New York City metropolitan area and enjoys a desirable location close to several rivers.

The town is most well-known as being the location of the legendary event involving a headless horseman, which was made infamous by Washington Irving.

This horseman is buried in the Sleepy Hollow Cemetery, and the legend is only one of the reasons why people many purport that this town is among the most haunted places in the state.

Numerous notable historical sites are located in Sleepy Hollow, and these include the Old Dutch Church, Philipsburg Manor House, Tarrytown Light, and others. You can also visit the Rockefeller State Preserve and other natural areas while you are in Sleepy Hollow.

Driving in New York


These fascinating and beautiful small towns are located in all corners of the state, and this means that you may travel a great distance exploring all that the area offers.

It is important that you understand what the state’s insurance laws are and update your coverage as necessary before you embark on your road trip.

— Car Insurance Laws in New York

In New York, drivers are required by law to purchase and maintain a minimum amount of car insurance coverage at all times. This requirement pertains to liability insurance, such as:

  • $25,000 for bodily injury per person and $50,000 per accident
  • $10,000 for property damage per accident
  • $50,000 for personal injury property
  • Uninsured motorist coverage for bodily injury for these same amounts

— Choosing the Right Car Insurance Coverage


As you review your existing policy, it is important to note that these minimum coverages may not be sufficient for your needs. After all, they only include coverage for others’ expenses that are related to liability, and they do not pay for any of your own expenses.

Because New York is a no-fault state, it may be advisable to purchase a collision or comprehensive policy as well.

Car insurance rates can be expensive, so you need to find the best deal possible on your coverage. A smart idea is to get quotes from at least three or four reputable insurance companies before you make a final buying decision.

By comparison shopping, you can get the coverage you need at an affordable rate.

— Safe Driving in New York


You can also take steps to reduce the risk of an accident by following a few helpful tips:

  • Always obey posted speed limit and road signs
  • Inspect your tire tread and air pressure before driving down the road
  • Avoid driving during inclement weather conditions
  • Ensure that you are emotionally calm before getting behind the wheel
  • Keep your vehicle well-maintained at all times

Wanting to increase your coverage before a roadtrip to New York? Enter your ZIP code below and start comparison shopping today for better auto insurance!


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