Aerial View of Rosendale, New York.

9 Quirkiest New York Towns You Didn't Know Existed

We are drawn to strange things, unusual places, and rule-breakers. You can call it “the Road Less Traveled,” like Robert Frost, or just admit that we are wired to seek out the unfamiliar. That's why we romanticise towns such as Slab City, California, an off-the-grid community that lives without laws, without water, without official electricity. Although you may not find these extremes in the Empire State, that does not mean New York does not have its intriguing versions of quirky towns. Starting with Chittenango, discover the 9 quirkiest New York towns you didn't know existed.

Chittenango

Chittenango in Upstate New York.
Rustic buildings in Chittenango in Upstate New York. By Idawriter, CC BY-SA 3.0, Wikimedia Commons.

Chittenango is the birthplace of the Wizard of Oz author L. Frank Baum, a connection it celebrates with one of the quirkiest festivals in the region: the Oz-Stravaganza. The annual event, which typically lights up the town the first weekend of June, is the largest and longest-running Wizard of Oz-themed festival in the world. You will find parades with costumed floats, a massive yellow brick road, and themed decor and murals, all of which transform the town into a fairytale fantasy land. The All Things Oz Museum is on Genesee Street and features fascinating memorabilia of the beloved film. But if you prefer to find joy in nature, the well-maintained Chittenango Lions Botanical Park & Creekwalk has a garden and several benches to sit on and enjoy the sound of the creek. Pass by DeMario's Eatery, one of the best burger restaurants in the Syracuse area.

Cold Spring

Independent stores and boutiques on a sunny day in Cold Spring, New York.
Independent stores and boutiques on a sunny day in Cold Spring, New York. Image credit James Kirkikis via Shutterstock

Cold Spring is nestled in the Hudson Highlands close to Breakneck Ridge, a fantastic outdoor space loved for its epic hiking views. It may strike you as just a beautiful and relaxing venue for a weekend of winding off, but Cold Spring features certain interesting quirky elements. You will find an unusual shrine containing Godzilla and an assortment of plastic dinosaurs on the corner of Main Street and Rock Street. It is dedicated to the memory of a teenager who died in a car accident in 1996. And in the woods north of town, you will find the Cornish Estate Ruins, a ruined mansion owned by a couple that died within two weeks of each other. There is the West Point Foundry Preserve, once the most important military supplier in America. One of its claims to fame is that it manufactured the first iron ship in the United States: the USS Spencer. Crown everything with a relaxing meal at Cozy Corner Cafe, a family-owned establishment that has mastered the craft of preparing insanely delicious burgers.

Phoenicia

New York, Phoenicia, Ulster County, Upstate New York, United States.
Caption

Phoenicia is a small Catskill Mountains town with a hipster edge. On the second floor of the town library, you will find the Jerry Bartlett Memorial Angling Collection, once the largest circulating collection of books about fishing in the Northeast. Although fire destroyed the initial collection in 2011, restoration work was done with skill and attention, and the site is still an awesome ode to Catskills fishing. You can tube down Esopus Creek, a critical tributary to the Hudson River Estuary, enjoy fresh seafood at the Phoenician Steakhouse on Main Street, an unpretentious eatery with a patio and a bar, or spend a quiet moment at the St. Francis Meditation Garden and Grotto, one of the most peaceful places in downtown Phoenicia.

Saugerties

Aerial view of the Esopus Creek Bridge in Saugerties, New York
Aerial view of the Esopus Creek Bridge in Saugerties, New York

Saugerties, the Dutch word for “sawmill,” boasts one of the most beautiful natural settings. The austere grandeur of the Catskill Mountains is in the backdrop, the tumbling beauty of the historic Hudson River, and the countryside allure of the Plattekill and Esopus creeks. You will find vintage shops, a beautiful 19th-century lighthouse, and lots of art. To touch on art, there is some surreal landscape art at Opus 40, a 6.5-acre stone-sculpture park in an abandoned quarry with trails, a museum, and a gift shop. Expect beautiful views of the Catskills and the Hudson, and a fantastic experience overall. To think that one man crafted all of this out of rock over the course of his life is simply mind-boggling. Spend some time at the Clermont State Historic Site, which has stone walls that have braved over 350 winters. A tranquil trail oasis also awaits at the Esopus Bend Nature Preserve, a picturesque locale with hiking trails and a creek to paddle.

Ticonderoga

Fort Ticonderoga, New York.
Fort Ticonderoga, New York.

History meets sci-fi at Ticonderoga, a peaceful location in the heart of the Champlain Valley in New York's Adirondack Mountains. You have probably heard of Fort Ticonderoga, the best-preserved fort from the 1700s in North America. This historic site, built in 1754, was the site of the first offensive victory for American forces in the Revolutionary War. A short drive from the history-defining fort, you can experience the Star Trek Original Series Set Tour, a full-scale recreation of the original USS Enterprise TV set from the Star Trek series of the 1960s. You will love immersing yourself in the 23rd-century vision of the future. To sate your hunger pangs, Burleigh's Luncheonette on Montcalm Street transports you back to the 50s with retro decor, neon lights, and interesting vintage photos. If the weather is friendly, the LaChute River Walk Trail is a must-do. It is a paved trail along the water with signs for learning all about the chute.

Narrowsburg

View of the Main Street in Narrowsburg, New York.
View of the Main Street in Narrowsburg, New York. Editorial credit: Alizada Studios / Shutterstock.com.

Narrowsburg is a small Delaware River town with lots of outdoor charm and artsy vibes. You will find galleries, indie shops, rustic bookstores, and stylish cafes. Considering how it looks and what it offers, you will think that Brooklyn has escaped into the woods. Delaware Valley Arts Alliance is an awesome spot with interesting exhibits, mostly focused on the Upper Delaware region. Across the street is One Grand Books, an unusual space in the sense that every shelf reflects the reading list of a celebrated person, whether Tilda Swinton or Bill Gates. You can sit down with a gripping read and occasionally see bald eagles soaring out in the sky. There is the iconic Tusten Theatre, where you can catch rib-cracking shows, and the Fort Delaware Museum, which feels like walking straight into the 1700s while surrounded by colonial reenactment.

Aurora

K / Shutterstock.com Caption: The Pettibone House at Wells College campus in Aurora, New York, USA
K / Shutterstock.com Caption: The Pettibone House at Wells College campus in Aurora, New York, USA

A mix of eye-catching 19th-century architecture, Ivy-covered buildings, and the rustic beauty of Cayuga Lake transform Aurora into something that any artist would want to paint on canvas. Aurora was once called “Deawendote,” translated as “the village of constant dawn.” Wells College, one of the town's most defining landmarks, was founded by businessman Henry Wells in 1868. Today, the Aurora Village-Wells College Historic District boasts more than 10 properties on the National Register of Historic Places. The Preservation League of New York State recently named the college, which is now closed, one of New York’s Seven to Save. Long Point State Park, a slice of paradise right on the water, is a short drive away. Don't skip the Spa at the Inns of Aurora, a magical location with a relaxing environment and top-tier spa facilities. As for food, Fargo Bar & Grill knows what it takes to whip up delicious chicken sandwiches.

Pultneyville

A lakeside view in Pultneyville, New York.
A lakeside view in Pultneyville, New York. Image credit: James H Dunning, Wikimedia Commons.

The quirky side of Pultneyville finds expression through its old homes, quaint theatre, and unique boating charm. To a first-time visitor, Pultneyville will appear like some long-forgotten New England coastal town. Gates Hall, a long-running cultural hub on the State and National Registers of Historic Places, has a history that goes back to 1825. It started as a worship venue. If you want to sniff some fresh, fragrant air, Cornwall Preserve is a short drive from town. It is on Lake Ontario and has scenic trails for hiking, grasslands for birdwatching, and a rocky beach for relaxing. It is as pure and pristine as any outdoor space can be. On the other side is B. Forman Park, a tranquil space to have headphones in their ears and just enjoy the incredible all-around scenery. The trick is to start at the Pizza Stop Pub and Bistro, especially if you have a thing for kick-ass garlic knots.

Rosendale

 Rosendale, New York.
Rosendale, New York. Editorial credit: yuriyt / Shutterstock.com

Rosendale is an offbeat, artsy mountain town that feels like a time warp. Almost every house here could be the set of an indie film. The Rosendale Trestle, a 940-foot continuous truss bridge that spans the Rondout Creek, was once the highest-span bridge in the United States. Views from the bridge capture the heart and character of the entire Hudson Valley. Places such as the Widow Jane Mine are as quirky as the imagination can grasp. It is a former cement mine that now serves as a 500-seat underground venue with a pond as the backdrop. Limestone from these caves helped to build the Brooklyn Bridge and countless other national landmarks in the country. Rosendale Theatre is quaint and intimate and serves some of the best popcorn in the world. The building that houses it started as a blacksmith's shop in the years before the Civil War, before becoming a casino, a fireman's house, and a full-time movie theatre. Across the street is the Well Nice Wine Bar, a sweet little find that serves delicious pierogis and carrot fritters.

The Takeaway

The Empire State has secrets, and they are anything but boring. They also don't care what you think of them. Imagine watching a performance in an underground theatre or finding a Godzilla shrine tucked behind boutique cafes. Think of yellow brick roads and unique Indie bookstores. Have you had enough of Anytown, America? Start exploring New York at its most unexpected. The best part? You will be spoilt for choice.

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