Storefront in Woodstock, New York, via solepsizm /

8 of the Quirkiest Towns in Upstate New York

Upstate New York is a land of mountain ranges, gentle rolling hills, vineyards, shimmering lakes, and dramatic waterfalls. Among the natural beauties are quaint towns and villages with unique histories, quirky festivals, and distinctive landmarks. Many are known for their celebration of the arts and their well-preserved, historic downtowns. Some have hosted world-famous music festivals, like Woodstock ’69. Others have earned a place in popular culture due to famous residents, such as the birthplace of Wizard of Oz author L. Frank Baum.

Join us on a walk through some of the quirkiest small towns in upstate New York and learn what sets them apart from New York’s Big Apple. There is so much to discover in these towns, from nearby state parks, nature hikes, and water activities. We hit all the must-see landmarks and commercial attractions that will make for an enjoyable weekend getaway, with something for everyone. 


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

Located along the Hudson River and at the base of the foothills of the Catskill Mountains, the small town of Saugerties is a funky, artistic village that plays host to music festivals throughout the year. Most notably, the Woodstock ’94 concert was held here on an 800-acre farm. One factor that makes the town quirky is its bohemian boutiques and cafes, such as Love Bites Cafe ( Landmarks include the historic Saugerties Lighthouse, which is located on the Hudson, Opus 40, a quarry and sculpture park, and Esopus Creek (with its nature sightseeing, kayaking, and fishing). The town even has a quaint local theater, The Orpheum, with its distinctive live performances. Saugerties offers verdant forests and hills and river views. The downtown is full of shoulder-to-shoulder Victorian-style homes. 


Pier and boats docked in the Skaneateles Lake, one of the Finger Lakes
Pier and boats docked in the Skaneateles Lake, one of the Finger Lakes, via PQK /

The town of Skaneateles is situated in the Finger Lakes region. The lakeside downtown with its Greek Revival and Victorian architecture, is enveloped by wooded hills. The town is probably best known for its lake, a glacial lake of the same name. Skaneateles Lake is one of the clearest lakes in the state due to its lack of algae. Other landmarks include the Sherwood Inn (an 1807 hotel) and the John D. Barrow Art Gallery. What makes the town quirky is its annual Dickens Christmas tradition, where it feels like the town time travels back to the 19th century. Another commercial attraction is the plush Mirbeau Inn and Spa with its French bistro. 


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

The Saw Kill River winds its way along the town of Woodstock, with its thick forests and streams. The downtown architecture offers colonial and artistic influences. One of its quirky qualities that put the town on the map in popular American culture was the 1969 music festival held here, known by the town’s name. The town has long celebrated the arts and continues that tradition with the annual Woodstock Film Festival. Some local historical landmarks are the Woodstock Playhouse, Overlook Mountain (with its hiking and abandoned hotel ruins), and the early 20th-century Byrdcliffe Arts Colony. The Woodstock Farm Sanctuary and Tinker Street, with their shops and galleries, are some commercial attractions. 


Chittenango, New York
Chittenango, New York, By Idawriter, CC BY-SA 3.0, Wikimedia Commons

The Erie Canal runs north of downtown Chittenango, providing scenic waterfront views. The rolling hills dotted by farmhouses and cottages provide a charming effect. The picturesque Chittenango Falls are not to be missed, when visiting this town. Chittenango is the birthplace of the now famous author of the novel, The Wonderful Wizard of Oz, L. Frank Baum. The town is full of Oz-themed memorabilia, adding to its quirkiness factor. Be sure to visit the All Things Oz Museum, for a deep dive into the fictional world created by Baum. Other landmarks include the Chittenango Falls State Park, where one can explore the falls up close. The Erie Canal is a historic walking path and waterway. Commercial attractions are the Yellow Brick Road Casino and The Wild Animal Park, with its exotic animals, likely featuring “lions, tigers and bears, oh my!”.


The buildings at the Wells College campus in Aurora, New York
The buildings at the Wells College campus in Aurora, New York. Image credit PQK via Shutterstock.

The architecture of Aurora’s downtown is lined with quaint 19th-century homes and the area is surrounded by lush hills and vineyards. Aurora is located in the Finger Lakes region, and the town lies along Cayuga Lake. Home to Wells College for Women, Aurora is a small (roughly a square mile) college town that has been described as a “dollhouse-worthy village” by Town and Country Magazine. The town’s preservation and beautification is largely thanks to efforts by Pleasant Rowland, founder of the American Girl brand, and former Wells attendee, who has poured money into restoring the town’s buildings. Vogue's headline was, “Aurora, New York: Brought to you by American Girl.” This recent history adds to the quirkiness of the town. Historical landmarks worth seeing are Wells College, MacKenzie-Childs (home goods and ceramics studio) and the 1833 lakeside Aurora Inn. One might also stop in at Faro Bar and Grill for a bite and consider a picnic at Long Point State Park, along the lake. 

Cold Spring

Sidewalk scene in Cold Spring, New York
Sidewalk scene in Cold Spring, New York, via Joe Tabacca /

Lying along the Hudson River and framed by the Hudson Highlands mountain range, the town of Cold Spring boasts wooded and hilly terrain. The downtown’s historic district has well-maintained 19th-century architecture. Hudson Valley Magazine described Cold Spring as “…an absolute wonderland. With cozy cafes, riverside views, and artisanal shops, the waterfront town delights day trippers and locals alike” ( One thing that makes the town unique is that it serves as a gateway to Breakneck Ridge, a challenging hiking spot. Other landmarks include Boscobel House and Gardens (Federal-style mansion) and Hudson River Front, for a walk with waterfront vistas. Cold Springs Depot is a historic train station that’s now a restaurant. Foundry Dock Park is another must-see, with walking trails along the water.  


Aerial view of Hammondsport, New York
Aerial view of Hammondsport, New York, via File:The Village of Hammondsport, NY.jpg - Wikimedia Commons

Located at the southern end of Keuka Lake is the little town of Hammondsport. The area is enveloped by hills and is full of European-style vineyards. Keuka Lake is one of the few Y-shaped lakes in the world, adding to the uniqueness of the town. The charming downtown has well-preserved 19th-century buildings. Must-see landmarks are the Glenn H. Curtiss Museum for Aviation, named after the local inventor, Keuka Lake Wine Trail and the Pleasant Valley Wine Company (one of the oldest in the area). Every September, the town hosts the Wings & Wheels event, with exotic cars and seaplanes. The area has been a resort destination since the mid-1800s and won’t disappoint.


View of downtown Cazenovia , New York , early morning, in wintertime
View of downtown Cazenovia, New York , early morning, in wintertime, via debra millet /

The town of Cazenovia lies along Cazenovia Lake and is surrounded by lush rolling hills. The downtown features Greek Revival and Victorian architecture. The style of the homes and buildings, in addition to the rural landscape, have kept the town set in time. The town’s founder, John Lincklaen, placed a high premium on preserving the natural beauty of the area, as well as the town’s history. As a result, the downtown has no telephone lines, which is one quirky feature. Landmarks worth checking out are Lorenzo State Historic Site (with its 19th century mansion), Cazenovia Lake, and the Stone Quarry Hill Art Park, with its blend of art and nature in an outdoor experience.  

Quirky Upstate Towns

When the world thinks of New York, the focus tends to be on the concrete jungle of Manhattan. An environment of skyscrapers, Wall Street titans, fashion icons, real-estate moguls and Broadway musicals. Yet, there is a whole other side to the state with small towns boasting of lakes, waterfalls, vineyards, and distinctive festivals, histories, attractions, and features that set them apart from the experience one will find in the Big Apple. Come explore the towns of Upstate!

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