The Mud Club, Woodstock, New York.

2024's 10 Most Adorable Small Towns in New York

Most people assume that New York is all about the Big Apple and one of the biggest cities in the world. But the hidden gems in the state of New York—particularly 2024’s most adorable small towns in New York are a far cry from New York City. Within the serene domiciles and quaint microcosms of New York’s rural side are some of the best attractions you will find beyond New York City. Between the fingers of the Finger Lakes are a handful of adorable small towns that embody the beauty and simplicity of this industrious New England state. This 2024, seek out the most adorable small towns in New York for both their cute atmosphere and their cultural and bucolic relevance.

Ithaca

Downtown Ithaca, New York.
Downtown Ithaca, New York. Image credit Spiroview Inc via Shutterstock

Near the waters of Cayuga Lake, one of the eleven Finger Lakes in the state of New York, you will come upon the cute small town of Ithaca. Although far from being the mythic-historic island where Odysseus lived, this small town in New York offers a cornucopia of suitable attractions for you to enjoy. Delve into the many gorges of the Robert Treman State Park or traverse the ancient stone walkways at the Cascadilla Gorge Trail. Head over to some of the many beautiful and luxuriating falls around Ithaca such as Taughannock Falls, Lick Brook Falls, Buttermilk Falls, and Triphammer Falls. Then, once your adventures and explorations leave you weary and worn, end your odyssey by sleeping peacefully at either the Canopy by Hilton Downtown or The Hotel Ithaca.

Watkins Glen

Franklin Street in Watkins Glen, New York
Franklin Street in Watkins Glen, New York. Image credit: Andre Carrotflower via Wikimedia Commons.

On the shores of Seneca Lake, the longest of the Finger Lakes, you will find the beautiful small town of Watkins Glen. Over 20 or more waterfalls can be found near Watkins Glen, accessible via scenic trails and routes like the Southern Rim Trail, the Gorge Trail, and the Indian Trail. Within the confines of the Watkins Glen State Park, Connecticut Hill Wildlife Management Area, and Sugar Hill State Forest, you will find a number of humble species and organisms living plentifully in New York’s wilderness. There are also plenty of fishes to see in Seneca Lake.

Definitely the highlight of Watkins Glen is the Watkins Glen International race track, known locally as "The Glen.” It was there that the NASCAR Cup Series, the Formula One United States Grand Prix, the IndyCar Series, and the IMSA SportsCar Championship races often transpired. Only about 24 miles from Ithaca, let the accommodations of the Watkins Glen Harbor Hotel, Lakeside Resort, and The Hotel Laurel at Seneca convince you to stay longer in Watkins Glen.

Skaneateles

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

Skaneateles derives its name from the Iroquois word for “long lake.” This is mainly an allusion to the nearby Skaneateles Lakes, another finger in the Finger Lakes that is often called “the Roof Garden of the Finger Lakes” for its impressive 863-feet elevation above sea level. Skaneateles Lake is also the second cleanest lake of the Finger Lakes, and as such serves as one of six natural water sources in the US.

The town of Skaneateles gives visitors access to the Bahar Nature Preserve, a habitat for many of New York’s biodiverse organisms. There is also Carpenter Falls, a great place to chill out or take pictures. On Genesee Street, you will find an abundance of Revolutionary Era edifices that have retained much of their original aspects. Additionally, you can learn all about Skaneateles’ involvement in the Revolutionary War at the Skaneateles Historical Society & Research Center. You will not feel down when staying in resplendent abodes like the Finger Lakes Lodging, Hobbit Hollow House, or Sherwood Inn.

Bethel

The Museum at Bethel Woods Center for the Arts in Bethel, New York
The Museum at Bethel Woods Center for the Arts in Bethel, New York, via Alizada Studios / Shutterstock.com

Most people assumed that the Woodstock Festival occurred in Woodstock, which is about 46 miles from Bethel. In actuality, the festival which called for the end of the Vietnam War occurred in Bethel, specifically in Max Yasgur’s 600-acre dairy farm. Now called the Bethel Woods Center for the Arts, this plot of land was where Janis Joplin, the Who, the Grateful Dead, Bob Dylan, Jimi Hendrix, and 30 renowned musicians promoted both the hippy culture and advocated for the cessation of the Vietnam War. The Museum at Bethel Woods offers more insight into that particular period, and at the end of May, you can attend the spiritual successor of the Woodstock Festival in the form of the Mountain Jam. If you are interested in seeing Bethel, then book a room at the Resorts World Catskills, The Gedney House, or Kenoza Hall.

Woodstock

Storefront in Woodstock, New York
Storefront in Woodstock, New York, via solepsizm / Shutterstock.com

Woodstock might not have been the venue for the oddly named Woodstock Festival, but this small town in the Catskill Mountains is nonetheless dedicated to the hippy cause with its Karma Triyana Dharmachakra Tibetan Buddhist Monastery. From such an illustrious and enlightening spot, you can appreciate the virtues of meditation and Buddhism akin to hippy culture. A more direct and natural appreciation of the world might be gleaned when walking the Catskill Park Trails or ascending Overlook Mountain. You might also want to head over to the Kaaterskill Falls for a deeper means of meditation. If you prefer more ordinary means of tranquility, then lodgings like the Hotel Dylan, The Inn on the Millstream, and Woodstock Way will provide the proper modes by which you can rest easily in Woodstock.

Cold Spring

Sidewalk scene in Cold Spring, New York, on a crisp fall day
Sidewalk scene in Cold Spring, New York, on a crisp fall day

Approximately 60 miles north of New York City, the alluring abodes of Cold Spring will leave you renewed and restored amidst the hectic heat in the daytime. Go sightseeing along the Hudson River towards magnificent wilderness destinations like Breakneck Ridge. At the Hudson Highlands State Park Preserve, there are over 7,400 acres of woodlands and pastures replete with some of New York’s amazing wildlife. Those with more urbane tastes can tour the Magazzino Italian Art Museum, home to dozens of abstract artworks. Learn all about ammunition production during the American Civil War at the West Point Foundry. Afterwards, enjoy the lackadaisical accommodations of Cold Spring’s lodgings like the Fat Hudson House River Inn and Pig Hill Inn.

Saratoga Springs

People walking on sidewalk in downtown Saratoga Springs, New York
People walking on sidewalk in downtown Saratoga Springs, New York, via aimintang / iStock.com

The past comes to life—and perhaps quite literally—in the historic town of Saratoga Springs. It was here that the Battle of Saratoga took place in the American Revolutionary War, a pivotal point of conflict which can be learned at the Saratoga Springs History Museum. But it is also in Saratoga Springs that the most haunted spot in New York can be found—the Canfield Casino. Formerly a gathering spot for New York’s elites in the late 1800s, the Canfield Casino has been featured in the hit TV series Ghost Hunters and is rumored to remain haunted to this day. Not everything in Saratoga Springs is so focused with the living and dead past, for travelers can enjoy the present with explorations at Saratoga Spa State Park and the Adironbacks’ mineral springs. Should you wish to stay a lot longer in Saratoga Springs, you need only book a room in fine hostels like the Adelphi Hotel or Embassy Suites.

Canandaigua

Main Street in downtown Canandaigua, New York.
Main Street in downtown Canandaigua, New York. Editorial credit: Ritu Manoj Jethani / Shutterstock.com.

For your vacation plan in the state of New York, choose Canandaigua, originally called Ganandogan by the Seneca people which is also a Tuscarora word for “The Chosen Spot.” At the Sonnenberg Gardens and Mansion, you will be traipsing through verdant vestibules and lively grounds from antebellum times. Close at hand, the Ontario County Historical Society Museum chronicles much of the indigenous cultures that have inhabited the state of New York. Meanwhile, over 100 antique carriages can be found at the Granger Homestead and Carriage Museum. There are many pleasant and adorable delights to be cherished in Canandaigua, so you should definitely plan a long stay in one of many excellent establishments like the Bella Ella Bed and Breakfast.

Sleepy Hollow

Downtown Sleepy Hollow, New York.
Downtown Sleepy Hollow, New York. Image credit Andrew F. Kazmierski via Shutterstock

Sleepy Hollow, located halfway between Cold Spring and New York City, is definitely not a place for the fainthearted. Many will recognize this eerie town thanks to “The Legend of Sleepy Hollow” by Washington Irving. Fortunately for visitors, Sleepy Hollow is a rather pleasant and amicable community despite the 18-foot-tall sculpture of the Headless Horseman and Ichabod Crane in the town square.

Outside the myths and folklores that haunt Sleepy Hollow, the town happens to be the former residence of David Rockefeller and his family, particularly at the hilltop dwelllings of Kykuit. There are even several notable attractions honoring Rockefeller, such as the Rockefeller State Park Preserve and the David Rockefeller Creative Arts Center, the latter being an excellent venue for local performances. You will definitely rethink your opinion about Sleepy Hollow once you spend a safe and comfortable evening at the Hotel Nyack, Sheraton Tarrytown Hotel, or Sleepy Hollow Hotel & Conference Center.

Auburn

Historical buildings in Auburn, New York
Historical buildings in Auburn, New York. Editorial credit: PQK / Shutterstock.com.

The poet Oliver Goldsmith once wrote in “The Deserted Village”—“the loveliest village in the plain, where health and plenty cheered the laboring swain.” He was, in essence, describing the town of Auburn on the banks of Owasco Lake. From this adorable small town, one can visit the home of the American heroine who freed over 700 slaves in the American Civil War, Harriet Tubman. The Harriet Tubman National Historical Park highlights Tubman’s role in the Combahee Ferry Raid, and how she was the first recorded American woman to organize an armed force in the Civil War.

Auburn was also the home of William Seward, Abraham Lincoln’s Secretary of State; his life and works can be best seen at the Seward House Museum. Finally, there is Theodore Case, the man who created sound film in the Case Research Lab which greatly improved the film industry and created 20th-century Fox. Do not worry about accommodations, because the Holiday Inn Auburn-Finger Lakes Region, Inn at the Finger Lakes, and Hilton Garden Inn Auburn have you covered.

From era-defining destinations like Woodstock and Saratoga Springs to towns reminiscent of classic literature like Ithaca and Sleepy Hollow, New York’s small towns have an air of adorability that promote much of New York’s rural outdoors. Feel active and curious in places like Watkins Glen and Woodstock which preserve much of New York’s lush, vibrant, and soothing woodlands and pastures. Savor the microscopic festivities and celebrations in engaging towns like Auburn, Skaneateles, and Canandaigua. Finally, allow the other adorable small towns near the Finger Lakes take your exhaustion and worries away and give you a tour to a kind of New York you never knew existed. So this year, make merry memories in New York’s most adorable small towns.

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