8 of the Most Charming Small Towns to Visit in Upstate New York
Crisp, clean, and playful air envelopes you in an incredibly gorgeous and lush countryside. Heart-melting lake views, especially around the Finger Lakes Region, are breathtaking. There's a reason Upstate New York is considered among America’s most beautiful regions. Inhabited by friendly, close-knit communities and dotted with quaint and charming small towns, this vast expanse of natural beauty is a delight to explore. For the best adventure experience, discover below eight of the most charming small towns to visit in Upstate New York.
New Paltz
Exuding a beauty that strikes the sweet spot between subtle and striking, New Paltz is one of Upstate New York’s most underrated gems. Stroll through the Water Street Market, where sparkling fountains, a sculpture garden, and gorgeous views of the Shawangunks — one of America's premier climbing areas — combine to set the heart purring. The one-of-a-kind Denizen Theatre is along this stretch. Like many black box theaters, it is devoid of cosmetic pretension but provides an unmatched intimate experience. Advocates of such a design believe it represents the purest form of theater, connecting the audience and the actors in an indescribable way.
Lining the street is an array of charming stores, most of which are small and family-owned. The Antiques Barn, for example, is perfect for those wanting to add a touch of yesteryear to a modern setting. Stroll through Historic Huguenot Street as well, and don't miss a stop at Krause's Chocolates, especially if you can’t resist the delicious, earthy flavor of chocolates. Also, the scenic Wallkill Valley Rail Trail meanders through the middle of town and is a must-see. Many consider this one of the best hikes in New York.
Lake Placid
Forget about the popular movie by the same name. While the movie is set on a fictional lake in Maine, this charming town is nestled between Mirror Lake and Lake Placid, at the foot of Whiteface Mountain in the Adirondacks. Lake Placid is renowned for its Olympic history, having hosted the Olympic Winter Games twice. For a heart-gripping glimpse of the town’s sports heritage, first-time visitors will want to explore the Lake Placid Olympic Museum, which houses the second-largest collection of Winter Olympic artifacts in North America. Alternatively, if you're eager to zipline at speeds of up to 30 mph or watch athletes training, the Olympic Jumping Complex is the place to be. On another note, even if history isn't your primary interest, a visit to the home and gravesite of the ardent abolitionist John Brown can be both evocative and enlightening. Historians believe John Brown’s raid on Harper’s Ferry was pivotal in American history. Needless to say, Lake Placid’s walkable downtown area is quite captivating, especially as it showcases hues of natural beauty that envelop the town in a rustic and enchanting allure.
Watkins Glen
For those who love good food — as we all do — Graft Wine + Cider Bar should be your first stop in Watkins Glen. The menu offers an abundance of choices, but their finely cooked and flavored strip steak comes highly recommended. Watkins Glen, affectionately known as “the Glen,” is nestled in the heart of the Finger Lakes, about 20 miles from Elmira. It graces the southern tip of Seneca Lake, celebrated as the lake trout capital of the world. A defining attraction of the town, Watkins Glen State Park, lies just a few steps from the main street. This spectacular gorge extends about 1.5 miles and features up to 19 sparkling cascades. Additionally, Watkins Glen is heralded as the Birthplace of American Road Racing. A first-time visitor will not want to miss the Watkins Glen Grand Prix Festival, which brings the town to life every September. For those seeking a pampered stay where luxury and refinement are paramount, the Watkins Glen Harbor Hotel, a Four-Diamond AAA-rated establishment, is an excellent choice. And being on the Seneca Lake Wine Trail, it would be remiss not to visit outstanding wine-tasting venues such as Lakewood Vineyards, arguably the area's most scenic winery.
Ithaca
In Greek legend, Ithaca is the homeland where the faithful Penelope awaits the return of her husband, Odysseus, from the Trojan War, symbolizing joy as the ultimate reward after a period of adversity. In the American context, however, Ithaca is a captivating town at the southern end of Cayuga Lake, renowned for its breathtaking natural beauty. An outdoor enthusiast’s paradise, the area boasts more than 100 waterfalls within 10 miles of downtown Ithaca. While many recognize Cornell University for its academic excellence, ranking among the world's best, fewer may know that it boasts one of the most picturesque campuses in America. Cornell University is home to several attractions open to the public, including The Herbert F. Johnson Museum of Art, Cornell Botanic Gardens, and the Cornell Lab of Ornithology. Notably, the top floor of The Herbert F. Johnson Museum of Art offers stunning views of Ithaca and the glistening waters of Cayuga Lake. Visitors can swim in an actual gorge at Robert Treman State Park or in a natural pool at the base of Buttermilk Falls. To fully appreciate Ithaca, however, requires more than an afternoon; give it enough time to truly do it justice.
Skaneateles
Pronounced “SKAN-ee-AT-ləs,” welcome to what many consider the “Jewel of the Finger Lakes region,” partly because it borders one of the area's cleanest lakes. The town is named after the Iroquois word for "Long Lake" and sits on the shores of the pristine lake that shares its name. It was ranked number one on Oprah Magazine's list of “60 Charming American Towns You Haven't Heard of But Should Visit ASAP.” Skaneateles Lake is known for its incredible cleanliness and serenity, making it the town's defining feature. Additionally, Anyela's Vineyards frequently receives rave reviews for its delicious wines, crisp air, picturesque vistas, and especially its blooming peonies in spring. For a plate of perfectly cooked fish, Doug's Fish Fry comes highly recommended. Be sure to bring a good camera and pack your sense of adventure.
Woodstock
Many associate Woodstock with arguably the most iconic music festival in America’s history, an event that entertained a crowd of half a million with performances by the music industry's luminaries, including Jimi Hendrix, Joe McDonald, and Ravi Shankar. However, while the festival bore the name Woodstock, it actually took place on a dairy farm in Bethel, about 60 miles from the town of Woodstock itself. Just outside the town is the Byrdcliffe Arts Colony, arguably the oldest operating arts and crafts colony in America. Founded in 1902 and listed on the National Register of Historic Places, it offers a step-back-in-time atmosphere and a glimpse into the lives of its founders, Ralph and Jane Whitehead. Nearby, the Woodstock Artists Cemetery stands as a testament to the town’s rich legacy in art, music, theater, and literature. For those interested in retail therapy, Tinker Street is the go-to destination. Shops like Three Turtle Doves offer a delightful array of vintage finds, some of which are rare. And when hunger strikes, the town’s many casual dining spots, including Tinker Taco, are ready to satisfy your appetite.
Saratoga Springs
Catapulted onto the global vacation scene as one of the first resort towns in America, Saratoga Springs continues to attract enchanted adventurers from across the country. The area was originally called “Sarahoga” by the Natives, meaning "place of swift water." The springs, renowned for their healing properties, are located in High Rock Park, just across Maple Avenue. Directly opposite is the historic Olde Bryan Inn, known for its ghost stories and impressive architecture. The healing properties of the spring waters attracted famous figures, including George Washington and Alexander Hamilton, to the area. While Saratoga Race Course is not the oldest racetrack in the country (a title held by Freehold Raceway in New Jersey), it is possibly the oldest organized sporting venue in the United States. The course's beauty was captured in the Hollywood movie Seabiscuit. Saratoga Springs boasts a higher density of restaurants per capita than any other place in America. To explore this culinary abundance, take a stroll down Broadway and enjoy the variety of classic eateries, including the highly-rated Wheatfields Restaurant and Bar.
Old Forge
Nestled on the shores of Fourth Lake, Old Forge is home to New York's largest waterpark. The Enchanted Forest Water Safari, which opened in 1956, has delighted visitors for nearly 70 years. With more than 50 rides and attractions, including 32 heated water rides, it offers a world of fun and adventure. To begin your exploration and truly feel the pulse of the town, an hour at Tony Harper's Pizza & Clam Shack is a must for sampling some perfectly crusted pizza. Art enthusiasts will find the View Arts Center an exceptional gallery showcasing local talent. Additionally, McCauley Mountain Ski Center, located just outside Old Forge, features 21 slopes and trails and offers breathtaking views that stretch to Whiteface and Mt. Marcy.
The Takeaway
Pack your camera and fasten your seatbelt, for Upstate New York promises an adventure unlike any other. Some vistas may remind you of Switzerland, while others bring to mind the charm of California, the lushness of Washington, or the grandeur of the Alps. Whether you start by strolling through the Water Street Market in New Paltz — soaking in the town’s serene charm — or exploring The Byrdcliffe Arts Colony in Woodstock, recognized as the oldest operating arts and crafts colony in America, there is a wealth of sights and experiences awaiting. Lake Placid, Watkins Glen, and Ithaca are equally enchanting, offering a surreal, fairytale-like experience that makes them truly worth exploring.
