10 Most Eccentric Towns in New York
New York State is famous for New York City, but there’s so much more to explore beyond the skyscrapers. Scattered across the state are eccentric small towns and villages, each with unique vibes and stories.
From offbeat museums to lively festivals, there’s plenty to see and do. Historic landmarks, like grand estates and castles, bring the past to life, while waterfalls, mountains, and serene lakes make it a paradise for nature lovers.
What’s even better? These eccentric towns are easy to reach and perfect for a quick weekend trip or a longer adventure. With that, here are some of the most eccentric towns in New York.
Woodstock
Woodstock, a town with 6,195 residents, is a hub for art and culture tied to the 1960s counterculture movement, even though the famous 1969 festival happened in Bethel. The town celebrates its artistic roots with landmarks like the Byrdcliffe Art Colony, established in 1902, which offers workshops and exhibits local crafts.
The Woodstock Playhouse, a restored theater, features live performances ranging from folk music to contemporary plays. Outdoor activities include hiking the Overlook Mountain Trail, which leads to a fire tower with panoramic views, and exploring the Catskill Forest Preserve. Unique shops like The Golden Notebook (an independent bookstore) and nearby art galleries like Elena Zang Gallery highlight Woodstock's creative flair.
Rhinebeck
Rhinebeck, a Hudson Valley town with 7,468 residents, is home to galleries, museums, and performing arts. The Beekman Arms Inn, established in 1766, is a key historic landmark and a popular destination for history buffs. The town’s art scene thrives with galleries and furniture spaces like Albert Shahinian Fine Art and Hammertown Rhinebeck, which feature regional and contemporary works.
For shopping, The Country Living Fair attracts vintage enthusiasts, while Samuel’s Sweet Shop, co-owned by actor Paul Rudd, offers nostalgic candies and treats. Nature lovers can explore the nearby Poet’s Walk Park, a picturesque trail with views of the Hudson River.
Cooperstown
Cooperstown, with a population of about 1,831, is home to the National Baseball Hall of Fame and Museum. But this small village has much more to offer beyond baseball. For history lovers, the Fenimore Art Museum features a notable collection of American folk art and Native American artifacts. Nature enthusiasts can enjoy Otsego Lake, nicknamed "Glimmerglass" by James Fenimore Cooper.
The Glimmerglass State Park, just a short drive away, adds hiking and seasonal activities to the mix. For shopping, visit the Cooperstown Bookstore for rare and vintage titles or browse quirky local goods at Tin Bin Alley. Art lovers can explore The Smithy Gallery, a three-story space dedicated to regional artists.
Lake Placid
Lake Placid, a village of 2,276 residents in the Adirondack Mountains, is rich in Olympic history. It hosted the Winter Olympics in 1932 and 1980, leaving behind iconic landmarks like the Olympic Center and Museum, which celebrate winter sports history. In winter, visitors can enjoy unique experiences such as toboggan rides on the frozen Mirror Lake or skating at the Olympic Speed Skating Oval.
During summer, the village attracts outdoor enthusiasts through activities like hiking at Adirondack High Peaks or paddling on Mirror Lake. Lake Placid's Main Street features local gems such as The Bookstore Plus for book lovers and The Adirondack Store for handcrafted goods. For art enthusiasts, Gallery 46 hosts exhibitions of regional artwork.
Skaneateles
Skaneateles, located in the Finger Lakes region, has a population of around 7,041 and is known for its clear, pristine lake. The town features restored 19th-century storefronts and offers several unique attractions. Explore the John D. Barrow Art Gallery for 19th-century paintings, or visit Imagine for handcrafted jewelry and art.
The Skaneateles 300 is a favorite for vintage finds, while Skaneateles Bakery serves up classic baked goods and coffee. The annual Dickens Christmas festival transforms the town with Victorian-era costumed actors and live performances. The Antique and Classic Boat Show on Skaneateles Lake showcases vintage boats, while the Skaneateles Festival brings world-class chamber music each summer.
Ticonderoga
Ticonderoga, with a population of about 4,636, is a small town packed with history. The star of the town is Fort Ticonderoga, a Revolutionary War landmark where visitors can explore its restored fortifications. The fort plays a key role in U.S. history. For something more unexpected, check out the Star Trek Original Series Set Tour, where you can walk through a detailed replica of the USS Enterprise from the original 1960s series.
Ticonderoga also offers local events like the Ticonderoga Arts & Crafts Festival held every fall, showcasing regional artisans. The town has small, unique shops like Fox and Fern Adirondack Mercantile, a quirky gift store perfect for browsing local souvenirs, and Burleigh's Luncheonette, a retro spot for classic diner fare.
Narrowsburg
Narrowsburg, a small village with a population of 369, offers a mix of outdoor activities and artistic flair. Visitors can enjoy whitewater rafting on the Delaware River or go eagle-watching along its shores. The town’s art scene includes the River Gallery, showcasing local artists, and Maison Bergogne, which specializes in reclaimed antiques and vintage finds.
The Tusten Theatre hosts indie films and live performances. Pizza lovers can check out The Laundrette, which also offers views of the Delaware River. Key events include the Riverfest, featuring local and regional music, arts, and ecology.
Cold Spring
Cold Spring, with a population of 1,995, is a village full of history and nature. Visit the West Point Foundry Preserve to learn about the town's industrial history or take in the 19th-century architecture that lines the streets. Outdoor lovers can hike the nearby Hudson Highlands, including the challenging Breakneck Ridge, which offers breathtaking views.
For a quirky experience, stop by Cold Spring Antiques Center, known for its eclectic collection of vintage treasures. Don’t forget to check out the Cold Spring Farmer’s Market held every Saturday in Garrison, located 1.3 miles from Veterans Monument.
Sleepy Hollow
Sleepy Hollow, with a population of around 10,962, is best known as the setting of Washington Irving's The Legend of Sleepy Hollow. This small village offers visitors a deep dive into history, with notable sites like the Old Dutch Church and Sleepy Hollow Cemetery, where Irving is buried. The village is especially lively in October, hosting the famous headless horseman rides, a spooky, theatrical event.
The Great Jack O'Lantern Blaze, showcasing over 7,000 intricately carved, glowing pumpkins, is a must-see held at Van Cortlandt Manor. For nature lovers, the nearby Rockefeller State Park Preserve offers scenic hiking trails and views of Swan Lake.
Saugerties
Saugerties, a town of about 19,633 residents along the Hudson River, combines historical landmarks with an artistic vibe. The Saugerties Lighthouse, built in 1869, stands as a symbol of the town's maritime history. The downtown area is home to the Saugerties Antiques Center, The Local Center for Arts and Culture, a cultural center, and the Saugerties Farmers Market.
Visitors can stroll through Seamon Park or the Saugerties Village Beach, which offers stunning views of Esopus Creek. Another highlight is the Hudson Valley Garlic Festival, which is held every September. Visitors enjoy garlic-themed dishes and live music.
From the artistic vibes of Woodstock to the historic charm of Sleepy Hollow, these eccentric New York towns offer a refreshing escape with a unique touch. Whether you’re seeking adventure, history, or relaxation, these destinations promise a memorable experience.
