Town center of Woodstock, New York. Image credit littlenySTOCK via Shutterstock.

7 of the Quirkiest Towns in New York

New York is one of the most eclectic places to travel to in the United States. There are big cities, isolated woods, and gorgeous seasonal changes. However, some quirky spots will quickly fill up your bucket list of destinations.

These small towns and villages have vibrant arts and music scenes, and funky dive shops and bars begin and end the day in style. Most of these quirky locations are located away from the big cities and include beautiful lake views. These eight towns each have something different to offer while remaining true to their small-town roots. 


Downtown Clayton, New York on an overcast, early spring morning
Downtown Clayton, New York on an overcast, early spring morning, via DebraMillet /

Clayton, in the Thousand Islands region, built the first castle that the Thousand Islands are known for. In the present time, Clayton is known for their Opera House, museums, and distilleries. The star attraction of the town is the Antique Boat Museum, considered the premier freshwater boat museum in the country with over 300 boats on display.

Clayton Distillery is a popular spot for locals and visitors. It is a farm-based distillery with a farm-to-glass philosophy with the rye and barley being grown on the 400-acre family farm. There is also the St. Lawrence Downtown Tasting Room, another farm-based distillery that has often been voted New York's distillery of the year. This gorgeous town on the St. Lawrence River has a great atmosphere and friendly locals who embrace the small-town charm of Upstate New York. 


Westfield, New York: Buildings on East Main Street on a sunny fall day
Westfield, New York: Buildings on East Main Street on a sunny fall day, via woodsnorthphoto /

Westfield is a small village in Chautauqua County in the heart of the world's largest Concord Grape region. Adventurous travelers can find fishing, sailing, and water skiing on Lake Eerie while art and culture lovers can get their fill downtown. The Chautauqua Institution comes alive in the summer where visitors can enjoy history courses, performing arts, and classes over nine weeks. 

Several wineries including Noble and Johnson Estate offer year-round tours and tastings, which is a reason to visit in itself. The Lake Eerie Grape Discovery Center should be the first stop in town to discover the region's legacy and history. 


Aerial view of Goshen, New York
Aerial view of Goshen, New York

Perhaps the quirkiest thing about Goshen is the new New York Legoland Resort but of course, this is not the only show in town. The resort is the largest in the rolls and is set against a backdrop of rolling hills and orchards and is a great family destination. 

Other popular attractions include the Harness Racing Museum and Hall of Fame, Salesian Park, and the Historic Track. The Stagecoach Inn is a former 19th-century stagecoach stop that completes the experience. There are several live events throughout the year like the Great American Weekend, which are premier times to plan a trip here. 

City Island

Fish restaurants on City Island at City Island Avenue
Fish restaurants on City Island at City Island Avenue, By Wusel007 - Own work, CC BY-SA 4.0, Wikimedia Commons

City Island is a 1.5 mile island just off of New York City that offers spectacular views of Manhatten and the Big Apple skyline. It is a small fishing village with a distinct New England feel and is home to a state landmark, the Schofield House. Summer is the most popular visitor season because of the abundance of boating, scuba diving, and fishing opportunities. 

The City Island Nautical Museum details the shipbuilding history that put City Island on the map. In the Fall, there is an Arts and Crafts Fair along City Island Avenue. The main drag also winds past Art by Marta Medina, a local artist who highlights cultural influences through her work. The island is perfect for a day trip if you want to get away from the Big Apple's busyness without traveling too far. 


The buildings at the Wells College campus in Aurora, New York
The buildings at the Wells College campus in Aurora, New York, via PQK /

Aurora is a small village in the Finger Lakes Region. A popular college town, Aurora also boasts several historic inns and homes and is one of the prettiest towns in the state. There are also several wineries, which are worthy of a day or weekend trip.

The Wells College Campus is gorgeous and visitors can stroll the lawns, hit the links, and enjoy the swimming pool. Downtown is a small affair with antique shops and taverns like the Fargo Bar and Grill who claim to have the best burger in the Finger Lakes. The Aurora Historical Society oversees several museums where you can explore the fascinating history of the village including the Millard Fillmore Presidential Site. 


East Market Street in Rhinebeck, New York
East Market Street in Rhinebeck, New York, via Ritu Manoj Jethani /

Rhinebeck is a cultural haven with a booming arts and culture scene in the Hudson Valley. There is a treasure trove of historic homes like the Wilderstein Historic Site to discover and the 40 acres of manicured lawn is open for people to explore. For the history buff, the Museum of Rhinebeck History offers letters, journals, and other historic artifacts that detail the town's history.

The best time to visit is over the weekend when the Old Rhinebeck Aerodrome hosts numerous airshows. Bi-plane rides are also available for guests before and after the aerial shows. For lunch, it is hard to beat Amsterdam, which offers farm-to-table fare. They also have a market offering artisinal food staples and fresh food.


Storefront in Woodstock, New York
Storefront in Woodstock, New York, via solepsizm /

Many correlate Woodstock with the iconic 1969 concert, but in reality, it was held in a different town, Bethel. Nevertheless, Woodstock is a quirky town with funky-colored buildings lining the main road through town, Tinker Street. The small town is a mecca for bohemian artists, musicians, and writers, and a lot of their work can be found at the boutiques on Tinker Street. 

Other cultural highlights are the two theaters. The Playhouse is a landmark performing arts theatre that hosts regular plays and festivals and is not to be missed. There is also the Bearsville Theater, a live music venue on the stream that also includes two restaurants. This small and charming town has a lot to offer guests without feeling overwhelmed by too many activities.

New York is known for sophistication, the Big Apple, and, of course, pizza. However, getting off the oft-traveled roads to major metropolises will often lead to unique and creative experiences that big cities cannot offer. These eight towns should be visited by anyone traveling through the state.

There is a unique mix of towns waiting to be explored. From Legoland to a town full of books, these towns leave an indelible impression on the traveler. Places like Woodstock offer a serene and artistic weekend getaway. Set against a backdrop of mountains or orchards, the scenery just adds to the charm of these quirky towns.

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