9 Quirkiest New York Towns To Visit In 2025
New York can be serious, fun, dramatic, and quirky. The Empire is more than the Big Apple or its charming towns. Sure, like the boroughs, you can cluster New York into regions. Picture your perfect retreat. Is it steeped in history, a lakeside, or a mountain hiking adventure? There are plenty of ways to experience the Empire in 2025.
With a scene for each taste, some of the state's best beaches are at "The End" in Montauk. "It's a Wonderful Life" nostalgia mixes with women's rights monuments in Seneca Falls. Whatever your dreamscape entails, these charming New York towns meet and raise it with quirky attractions that offer a stark contrast to the life you know.
Babylon
While names can be misleading, Babylon, aka the “Jewel on the Bay,” aspires to leave lasting impressions even without the ancient ruins. Incorporated in 1893, it was a retreat for decades and home to famous people, like Thelma “Butterfly” McQueen, an actress from Gone with the Wind. Despite a lull following World War II, Babylon has resurged along the southern edge of Long Island. Just 10 minutes south of Islip, Babylon draws big-city dwellers with its calm vibes, marinas, and diverse geography to explore.
Once here, the mariners direct their sails deep into the Great South Bay, while the fishers find sanctuary at neighborhood parks. Argyle Lake Park is popular for fishing, dog-walking, and wedding photographs, with statues and benches erected in honor of famous people around its perimeter. Southards Pond Park centers on a teeming pond with perch, bluegill, pumpkinseed, carp, and trout stocked seasonally.
Chippewa Bay
This little fishing town was put on the map when the Chippewa Yacht Club won the Gold Cup in 1904. Ringing the eponymous water body, Chippewa Bay remains largely undiscovered along the St. Lawrence River across from Canada. Its rich history includes prominent figures like George Boldt, after whom the nearby Boldt Castle was named. He visited the area in 1896 along with Frederick Bourne, Charles Englis, and David Lyon. Bourne built his own massive stone castle offshore. It is a fascinating place to explore the beautiful area via canoe or on foot.
As a jet-setter to the Thousand Islands, visitors get enamored with its secluded lifestyle, along the few streets to its name, and the untouched trails through a local preserve. Drop by the local museum for fascinating tidbits of its past. Many are drawn to explore Dark Island, with its century-old Singer Castle, a 28-room chateau with secret passages, artifacts, and guided tours, accessible by a scenic boat ride and beautiful upon approach. There are a few accommodation options, such as a marina and a waterfront general store, which are straight from a picture book.
Corning
This crafty community at the southern edge of the Finger Lakes has big-time charm and a vibrancy unparalleled by any other. Poking around galleries, shops, and sculptures, every turn seeps inspiration. Take the "portal" of the Corning Museum of Glass through 3,500 years of glass art, from Egyptian artifacts to modern pieces, on a self-guided tour, plus on-demand demos and workshops. There's a new centerpiece, vintage wear, or unique ceramics to get your hands on, while Hands-On Glass Studio offers to bring your own creation home.
Take a sunny day stroll along the Chemung River through Corning's Gaffer District. The Rockwell Museum is a breathtaking building on the corner. It draws thousands into the art-filled space with a permanent collection of paintings that elicit meaning through emotions and regular exhibits. For more history, take a trip to the 187-foot-tall Little Joe Tower, which dates back to the early 20th century. It was erected by the company Corning Glass Works and used to draw glass for making thermometers.
Hammondsport
Tiny, like a hummingbird, this Hammondsport's big-time charm accentuates the southern tip of one of the most beautiful Finger Lakes, the Y-shaped Keuka Lake. The Depot Park is a great place to stretch your legs after the drive, along the waterfront area for a swim, with picnic tables and benches in pretty scenery. After a day of jet skiing or kayaking at Champlain Beach, which offers rentals and amenities, there is an idyllic collection of art galleries, charming shops, and B&Bs within walking distance from the public beach.
Just up the shore, Bully Hill Vineyards is one of the best in the entire region for strolls, tastings, and great pairings with unbeatable views on the restaurant's porch, plus an extensive gift shop. Drop by the Glenn H. Curtiss Museum because, like a hummingbird, it has history in flight. Here, in the "Cradle of Aviation," Glenn H. Curtiss made numerous advancements, celebrated at the local museum with 20th-century aircraft and motorcycles.
Montauk
While apt, "The End" is quirky in that it feels like the beginning of priceless memories, particularly if you've never been this far before. Montauk's reputation holds it as one of the state's best vacation beach towns in New York. The serene Ditch Plains Beach will hold you captive with unobscured views and ideal conditions for swimming and surfing, plus nearby restaurants and lodgings. The historic 1796 Montauk Point Lighthouse Museum is located within a dedicated state park. Tourists are invited to climb to the top for breathtaking views and to visit the museum within the oldest lighthouse in New York, which was authorized under President George Washington. The adjacent picnic area is great for soaking in the landmark against the stunning Atlantic, with nature trails and surf fishing around.
For something wilder, to justify days of basking on the beach, Hither Hills State Park offers a recreation area along the dunes with a large campground. Shadmoor State Park offers hiking trails, picnic areas, birdwatching platforms, and saltwater fishing.
Penn Yan
Named not after a man but for Pennsylvania, Yankee, Penn Yan rings the northern tip of the beautiful Keuka Lake, the only one in the US that flows both north and south. In addition to lakefront amenities, a marina, and watersports, Penn Yan is a top fall destination in the Finger Lakes Region. The area is particularly lovely against the changing leaves, with reflections in the placid waters to paddle a kayak. Many visit during harvest with persisting weather for beautiful foliage hikes that often end up at an acclaimed nearby winery.
Whether you're biking along the seven-mile Keuka Lake Outlet Trail to Dresden on Seneca Lake or for tastings along the Keuka Lake Wine Trail, this historic village is worth uncorking to. It is home to stunning views, Finger Lakes-grown and produced wines, and the first-ever farm and craft market in upstate New York. After exploring historic landmarks, waterfalls, and serene overlooks, catch the sunset over the lake at Red Jacket Park.
Salamanca
The Allegheny River traverses this charming town through Allegany State Park, New York's largest at 64,800 acres. Offering hundreds of campsites and cabins, it is an idyllic setup for a memorable family vacation with fishable lakes, sandy beaches, and kayaking. The hiking trails and bike paths fan out south and turn to cross-country skiing and snowshoeing, some of the state’s best in winter. Exploring further in the park, Stone Tower feels like an enchanting fortress after climbing the stairs to the top, with views along the parapet.
Those who enjoy comfort enjoy the local hospitality and prices coming from the city for the five-star service at the Seneca Allegany Casino. Whether you swim in the pool or enjoy luxury rooms and a full spa, it feels like a winning retreat either way. Afterward, the Salamanca Mall Antiques is an ever-popular stop to sift through treasures, including comic books, furniture, and paintings.
Seneca Falls
Minutes inland from Cayuga Lake State Park, Seneca Falls is known for two relatively unrelated things: primarily, the birthplace of women’s rights. Its strategic location near the Cayuga-Seneca Canal fueled the town's industrial growth and social reforms. The Women's Rights National Historical Park honors the first-ever US women's rights convention and those who fought for women's rights. Among preserved architecture from that time, the Wesleyan Chapel is where the 1848 convention took place.
The It’s A Wonderful Life Museum is a local "Bedford Falls" attraction with nostalgic displays and film memorabilia. Crossing the pedestrian "It's a Wonderful Life Bridge" is a must for movie fans, with scenic views and walking distance from other women's rights movement sites. Both shaped its quirky personality, with landmarks all along the Seneca River, which, for a heartbeat, turns into Van Cleef Lake in town. The lakeside is popular for shallow- and deep-water fishing, plus hilltop campgrounds to unwind at sunset.
Youngstown
Across the Niagara River from the charming Canadian town of Niagara-on-the-Lake, Youngstown is under 20 minutes north of Niagara Falls. But wait, there's plenty here, like historic character. Fort Niagara State Park features a nature center and Old Fort Niagara, the majestic structure steeped in history. You can explore willy-nilly or tour the soldiers' barracks and hear the captivating story of the fort commander's life that transports you to the bygone era in authentic views at the mouth of the beautiful Niagara River.
From lake/river boating and secluded hikes to a pool and waterslides, stick around for delicious restaurants and amazing sunsets, where it meets Lake Ontario. "Young in spirit, ageless in pride," the town's motto is reinforced by thrilling attractions like Skydive The Falls, a popular recreational pursuit for the young at heart. Why not explore the area like the townsfolk back in the day with the help of Lakeside Quarter Horses? A horse ride is all you need for a fun end to a day in Youngstown.
Concluding Thoughts
The Empire is a state of mind you have to experience with all five senses, like a puzzle of infinite pieces. It is too large to attempt to categorize, and every step off the beaten path is worth the journey. Each quirky town offers a captivating slice of local culture and nature for the peaceful side of New York life.
Even the toughest Yankees dream of escaping the crowd, heat, and traffic noise to unwind in the sounds of nature and relative stillness, the sparkling waterfalls, rushing rivers, and serene lakes. Like a living organism, the Empire is ever evolving, and these nine are the quirkiest towns to visit in 2025.
