8 Quirkiest Upstate New York Towns To Visit In 2026
It's one thing to drive to a small town, snap a selfie in front of a giant cow, a pink house, or some other spectacularly odd roadside attraction, and then turn around and head home. It's another thing entirely when the quirky landmark is just the start of the adventure. The best offbeat small towns give you a reason to stop, and then plenty of reasons to stick around. Mine for sparkling "diamonds" in Herkimer, hunt for UFOs in Pine Bush, or wander Lily Dale's famously spiritual streets. Here are eight of the quirkiest small towns in upstate New York, where the oddity is only the opening act. Come for the quirky landmark; stay for the museums, restaurants, railtrails, history, and other surprises waiting just beyond it.
Herkimer
What you see is not what you get in Herkimer, a small upstate New York village on the north side of the Mohawk River, first settled by Palatine German immigrants around 1723. Stop at the Mohawk Valley Center and enjoy a 90-minute cruise aboard the Lil' Diamond II with Erie Canal Cruises through the historic 1910s Lock 18. Explore downtown Herkimer and fuel up with an all-day breakfast at the retro Crazy Otto's Empire Diner.
After lunch, head over to Herkimer's signature attraction and spend a few hours mining for diamonds at the quirky above-ground Herkimer Diamond Mines. While the gems aren't real diamonds, you'll find incredibly clear quartz crystals that formed about 500 million years ago, with a distinctive double-terminated shape that gives them the look of a real diamond. Fun for kids of all ages, you can mine, dine, and even stay overnight in a glampsite at the Herkimer Diamond KOA Resort.
Lily Dale
For a supernatural turn, visit Lily Dale, a small hamlet on the east side of Cassadaga Lake, founded in 1879 as a retreat for spiritualists. During the summer season, Lily Dale offers 10 weeks of lectures and events on topics ranging from ghost hunting and ESP to astrology, tarot, and communicating with the spirit world. There's a small admission fee to visit the town during the summer, but admission is free the rest of the year.
Follow a trail through Leolyn Woods, surrounded by old-growth 100-foot-tall trees while channeling the dead, then stop for regularly scheduled spiritual reflections at the town's outdoor gathering spot, Inspiration Stump. Visit the famous Lily Dale Pet Cemetery, where the 275 or so full-time residents of town have created a solemn place to honor their four-legged friends. For a deeper dive into the town's spiritual beginnings, check out the Lily Dale Museum, an 1890 one-room school that houses vintage memorabilia and artifacts from the past.
Chittenango
Wizards and waterfalls are the draw in Chittenango, a small village about 15 miles east of Syracuse, famously known as the birthplace of L. Frank Baum, the author of "The Wonderful Wizard of Oz." The town celebrates its literary hero at the All Things Oz Museum, which rotates about 1,500 pieces of memorabilia in its showroom from a collection of over 16,000 artifacts, including original props from the movies and musicals. There's an annual Oz-Stravaganza festival which features fireworks, a costume contest, parade, food trucks, carnival rides, and more.
Established in 1812, Chittenango has a rich history rooted in the Erie Canal, where you can explore the historic canal site on walking paths past reconstructed dry docks, a blacksmith shop, mule stables, and a boat shop. Discover even more inside by visiting the exhibits at the Chittenango Landing Canal Boat Museum. Finish the day at the main attraction in nearby Chittenango Falls State Park by following the winding trails to the 167-foot waterfall and enjoying a picnic.
Pine Bush
From the magical world of Oz to mysterious lights in the sky at night, Pine Bush is renowned as the "UFO Capital of the East Coast." A small hamlet about 70 miles northwest of New York City, Pine Bush has long been associated with reports of unidentified flying objects and strange lights. But it was during the 1980s, when the community's reputation as a UFO hotspot began to grow, that Pine Bush started turning its unexplained visitors into a tourism attraction. Book a guided tour of the quirky Pine Bush UFO & Paranormal Museum, or coordinate a visit around the town's annual "UFO Fair," where you can don a tinfoil hat and mingle with cosplayers, extraterrestrials, and paranormal enthusiasts from all over the East Coast.
Take time to explore the beautiful Hudson Valley on horseback with a 45-minute trail ride with Juckas Stables, or book one of the themed rides like "Saddles and Slices," which includes a ride through the woods and meadows followed by pizza slices, beer, and s'mores by the fire. If you're into retro diners, be sure to check out the early bird specials at the Cup & Saucer Diner.
Saranac Lake
Once a destination for tuberculosis patients searching for a cure in the crisp Adirondack air, Saranac Lake has turned its medical past into one of its most unusual attractions. Historic cure cottages, like Ames Cottage, are a throwback to a time when patients came to the Adirondacks to rest on open-air porches, believing that fresh mountain air and a peaceful setting could restore their health. Learn all about the so-called "fresh air cure" at the Saranac Laboratory Museum and the Trudeau Building, the one-time home and medical office of Dr. Edward Trudeau.
Follow the doctor's order, and spend time in the great outdoors on a guided 4-hour paddling trip with Adirondack Outfitters, who'll provide a guide and all the gear you need to get on the lake right away. Listening to loons singing mournfully on the lake as you paddle along is the ultimate Adirondack experience. Wind down a busy day in Saranac Lake with soft-serve ice cream from Mountain Mist Ice Cream, an old drive-in restaurant that first opened in 1951.
Wilmington
Stick around the mountains a while longer, and head to the town of Wilmington, about 20 minutes northeast of Saranac Lake. You can take a drive along the Whiteface Veterans' Memorial Highway almost to the summit of Whiteface Mountain, ending at the Castle parking area around 4,600 feet. Enjoy the 360-degree panoramic views of Adirondack Park, fuel up with a snack at the so-called highest restaurant in New York, the 4610' Grill, and stop by the Castle Gift Shop for souvenirs before heading back down the mountain.
The mountaintop views aren't the only surprising feature of Wilmington; it is also home to North Pole (not that North Pole), a tiny hamlet where they've been celebrating Christmas since 1949. While the star attraction, Santa's Workshop, is closed for upgrades during the summer of 2026, explore the Christmas-themed street names, take a few photos for your Insta, and enjoy the novelty of visiting a real place called North Pole.
Phoenicia
Phoenicia is a laid-back mountain town that owes its quirky character to the era when the Catskills became one of New York's favorite summer haunts for escaping the heat and humidity of New York City in the late 19th century. Take a step back into the railroading past of the Catskills with a visit to the Empire State Railway Museum, where you can tour the historic 1899 Phoenicia Station, the Waiting Room, the Agent's Office, and the Freight Room.
Check out Rail Explorers for a guided outdoor adventure along a historic railroad with a choice of tours along the Esopus Creek to view the "scrapture" artwork at the Mount Tremper Station Sculpture Park or through the mountains at sunset. The 1962 Phoenicia Diner is legendary in this tiny town, so be sure to grab a table at the retro resto to enjoy all-day breakfast, then pick up a batch of their famous pancake mix to make at home.
New Paltz
New Paltz is a mashup of centuries-old Huguenot history, college-town energy, and pretty Hudson Valley scenery about 90 miles north of Manhattan. One minute you are wandering down the 17th-century stone house-lined Historic Huguenot Street, where you can see over three hundred years of history in seven stone-house museums, a 1717 French Church, or the community's original cemetery, and the next minute you're sipping sangria at the Main Street Bistro.
Hike beneath the cliffs of the Shawangunk Ridge (also known as "The Gunks") and enjoy amazing views of the Hudson Valley, or buy a day experience pass to enjoy the 85 miles of trails surrounding Mohonk Mountain House, a surprising Victorian castle resort on an alpine lake hidden in the mountains. The resort offers farm-to-table cuisine and activities like guided mountain bike rides, tomahawk throwing, and yoga.
Discover New York's Quirkiest Corners
These eight towns share a habit of building whole days around a single oddity. Herkimer sends visitors underground for quartz "diamonds," Lily Dale keeps a spiritualist tradition alive at Inspiration Stump, and Chittenango leans into its Wizard of Oz roots with yellow-brick sidewalks. Pine Bush counts UFO sightings, Saranac Lake preserves its cure cottages, and Wilmington runs a Christmas hamlet named North Pole year-round. Pick any one of them for a weekend, and the roadside curiosity turns out to be just the front door.
