7 of the Quirkiest Towns in New York
New York is one of the most eclectic places to travel in the United States, and its small towns are where the state’s personality really shines. Beyond New York City’s skyscrapers you will find lakefront villages, river communities, and mountain hamlets that feel worlds away yet are easy weekend trips. If you enjoy artsy main streets, quirky museums, and character-filled inns, these destinations belong on your bucket list.
Each of the following small towns and villages offers its own twist on “quirky New York.” Expect vibrant arts and music scenes, indie shops instead of big chains, and local bars and cafes where you can end the day like a resident, not a tourist. Many are set on lakes or rivers with big views and four-season scenery. These eight towns all feel different, but each one stays true to its small-town roots while welcoming curious travelers.
Clayton
Clayton, in the Thousand Islands region, helped put this island-dotted stretch of the St. Lawrence River on the map. Today, it draws travelers for its walkable waterfront, historic brick buildings, and lively events calendar rather than castles alone. The star attraction is the Antique Boat Museum, one of the premier freshwater boat museums in the United States, with more than 300 classic wooden boats, sleek runabouts, and historic racing craft on display and on the water.
After the museum, you can sample Clayton’s farm-to-glass spirit scene. Clayton Distillery uses rye and barley grown on the family’s 400-acre farm to produce small-batch vodka, gin, and whiskey, while the St. Lawrence Downtown Tasting Room showcases award-winning local spirits in a cozy setting. The beautifully restored Clayton Opera House hosts concerts, comedy, and community performances, giving you an easy way to end a riverfront day with live entertainment. Set right on the St. Lawrence River, Clayton feels like a classic Upstate New York small town with a polished, creative edge.
Westfield
Westfield is a small village in Chautauqua County and the heart of the world’s largest Concord grape-growing region. Travelers come for Lake Erie views and a laid-back wine-country vibe, with easy access to fishing, sailing, and water sports on the lake. In summer, the nearby Chautauqua Institution buzzes with lectures, concerts, and classes, turning the whole area into a seasonal hub for arts, ideas, and culture.
Wine lovers can spend an afternoon tasting along this stretch of Lake Erie Wine Country. Wineries such as Noble Winery and Johnson Estate Winery, one of the oldest estate wineries in New York, offer year-round tastings and vineyard views. Before or after touring, stop by the Lake Erie Grape Discovery Center to learn how grapes shaped the region’s history and sample local products in one stop. With its walkable main street, farm markets, and lakeside sunsets, Westfield is ideal for a relaxed weekend that still feels distinctly “New York.”
Goshen
Perhaps the quirkiest thing about Goshen is that it is home to LEGOLAND New York Resort, the largest LEGOLAND theme park in the world. Set among rolling hills and orchards about 60 miles from New York City, the resort features seven themed lands, more than 50 rides and attractions, and a colorful on-site hotel built for families. For many visitors, it turns Goshen into an easy, kid-focused base for a playful Hudson Valley getaway.
Goshen still keeps one foot firmly in its small-town past. At the Harness Racing Museum and Hall of Fame, interactive exhibits and historic sulkies tell the story of the sport that once dominated the region. The nearby Historic Track is believed to be one of the oldest active harness racing tracks in the country. Salesian Park offers peaceful walking paths and ponds, while the Stagecoach Inn, a former 19th-century stagecoach stop, now welcomes guests with elevated farm-to-table dining and cozy rooms. Plan a visit around the Great American Weekend or other festivals to see Goshen at its most lively.
City Island
City Island is a 1.5-mile-long island off the coast of the Bronx that feels like a New England fishing village tucked inside New York City. From the shoreline you can catch views of Manhattan and the bridges of the East River while wandering past marinas, clapboard houses, and mom-and-pop shops. It is best known for its seafood restaurants lining City Island Avenue, where you can end a day trip with a plate of fried clams or lobster.
To understand how this tiny community helped build New York’s maritime past, stop at the City Island Nautical Museum, which showcases the island’s shipbuilding and sailing heritage. Throughout the year, local galleries and studios open their doors, and in fall the Arts and Crafts Fair brings handmade jewelry, art, and decor into the streets. With its relaxed sidewalks, coastal breeze, and easy access from the city, City Island is a classic “hidden gem” day trip for New Yorkers and visitors who want a slower pace without leaving the five boroughs.
Aurora
Aurora is a postcard-perfect village on the eastern shore of Cayuga Lake in the Finger Lakes Region. Known for its stately 19th-century homes and the historic Inns of Aurora, the village feels like a lakeside retreat frozen in time. Wells College gives Aurora a youthful energy, and the campus lawns and lakefront paths are open for quiet strolls with big-water views.
Downtown Aurora is small but memorable, with antique shops, galleries, and taverns that make it easy to spend an unhurried afternoon. The Fargo Bar and Grill is a local favorite that pairs pub fare with lake-town atmosphere and a reputedly excellent burger. Nearby wineries and cideries along Cayuga Lake offer tastings with views of vineyards rolling down to the water, making Aurora a smart base for exploring the broader Finger Lakes wine region. History fans can stop by sites connected to President Millard Fillmore and the Aurora Historical Society, which preserves the village’s stories in several small museums.
Rhinebeck
Rhinebeck is a cultural haven in the Hudson Valley, known for historic architecture, destination restaurants, and a strong farm-to-table scene. Stately homes such as the riverfront Wilderstein Historic Site offer tours and walking trails through 40 acres of lawns and woodlands overlooking the Hudson River. For a deeper dive into local stories, the Museum of Rhinebeck History showcases letters, journals, and artifacts that bring the town’s past to life.
Weekends in Rhinebeck often revolve around events. The Old Rhinebeck Aerodrome turns summer skies into a stage with vintage aircraft shows, and visitors can book bi-plane rides for a truly memorable view of the valley. Rhinebeck’s village center is packed with independent boutiques, bookshops, and cafes, plus a popular farmers’ market in season. For lunch or dinner, Amsterdam is a standout, serving refined farm-to-table dishes and stocking a market with artisanal cheeses, breads, and pantry staples you can take home.
Woodstock
Many people associate Woodstock with the iconic 1969 music festival, though the concert actually took place in nearby Bethel. Even so, the town has fully embraced its creative reputation. Tinker Street, Woodstock’s main road, is lined with brightly painted storefronts housing record shops, galleries, bookstores, and boutiques selling everything from handmade jewelry to vintage clothing. Street musicians and pop-up performances add to the bohemian energy on busy weekends.
Culture is a year-round draw here. The Woodstock Playhouse hosts plays, concerts, and festivals in a historic theater, while the Bearsville Theater presents live music beside a scenic stream, paired with on-site dining. When you need a break from browsing and shows, nearby Catskills trails offer hiking and waterfall views within a short drive of downtown. Woodstock manages to feel both lively and low-key, making it a great choice if you want a creative escape without a packed itinerary.
New York is often associated with sophistication, the Big Apple, and classic New York-style pizza, but its small towns reveal a more intimate side of the state. Stepping off the main highways into places like Clayton, Rhinebeck, or Woodstock leads to experiences that big cities simply cannot replicate: chatting with local artists in tiny galleries, learning niche pieces of history in small museums, or watching the sunset over a quiet lakefront.
Together, these quirky destinations showcase just how varied New York’s small-town scene can be. From a record-breaking LEGO theme park in Goshen to grape
