10 Of The Best Small Town Road Trips You Can Take In New York State

New York State is so much more than the dense Metropolitans that it is commonly associated with. There are mountain ranges in the Northeast, endless lakes scattered throughout (plus their corresponding parks and beaches), long stretches of colorful countryside, and, of course, the North Atlantic Ocean. The best way to get an overview of the land is to take a road trip through the character-rich small towns. There are many to choose from, but here is a suggested, systematic itinerary to help you save on gas and stock up on highlights.  

Lake Placid

Lake Placid new york
The Lake Placid Ski Lift in autumn.

What better place to start a New York road trip than at the top of the state, in the fresh, energizing mountain air of Lake Placid? Relive the glory of the two-time host of the Winter Olympic Games, complete with inspiring views, endless outdoor recreation, and a friendly mountain-town feel to set a great tone for the journey. 

Lake George

Lake George, New york
Water sports in Lake George.

Next, head South on Interstate-87 to the small town of Lake George, in Warren county. Here, the soul-soothing pairing of the Adirondack Mountains and a crisp blue lake continues. Make sure to cruise the vintage downtown core, get out on the water, and if camping is your thing, maybe even pitch a tent on your own private island. 

Skaneateles

Skaneateles
Beautiful scenery on the Skaneateles Lake in Skaneateles. Editorial credit: PQK / Shutterstock.com

From Lake George, continue down I-87 before making a solid haul West on I-90, past Syracuse, and another adorable laketown, Skaneateles. This Onondaga Country hamlet offers a relaxing atmosphere to recharge after a long drive. Unwind for a couple of nights in one of the many cute B&Bs or old-timey Inns, and enjoy the rocking-chair-pace of life before getting back on the road. 

Aurora 

aurora new york
The buildings at the Wells College campus of Aurora. Editorial credit: PQK / Shutterstock.com

Ease back in with a short drive Southwest to the college-town of Aurora, in Cayuga County. With a population of around 700 residents, Aurora is the smallest of the small towns featured on this list. More specifically, it is a village within Ledyard. Take the opportunity to appreciate the close-knit community and historic infrastructure dating back as far as the 1790s. 

Canandaigua

canandaigua
Main Street in downtown Canandaigua, New York. Editorial credit: Ritu Manoj Jethani / Shutterstock.com

Continue West along the scenic Northshore of the Finger Lakes until reaching Canandaigua in Ontario County. Canandaigua, referred to as "The Chosen Spot," offers more of an up-scale laketown experience. 

Penn Yan

Keuka lake in Penn Yan
Summer scene at the harbor on Keuka Lake in Penn Yan. Editorial credit: PQK / Shutterstock.com

Backtrack East to Geneva and then head South to Penn Yan, in Yates County - yet another idyllic, laketown. Located just North of the East arm of the tuning-fork-shaped Keuka Lake, Penn Yan makes for a great swimming hole and picnic spot. Make sure to take a stroll to the Seneca Mills Falls to check out the pretty, 40-foot waterfalls that used to power the mill - the ruins of which are still standing. 

Ithaca

Ithaca new york
Students at Libe Slope watching sunset on campus of Cornell University in Ithaca.

From Penn Yan, dip further South and take the Eastward journey along the bottom of the finger lakes. You will soon arrive at Ithaca, which is this journey's second stop on Cayuga Lake. This Ivy League town boasts historic buildings all throughout Cornell's campus. The charm continues into the downtown Ithaca Commons and out into the lush natural surroundings.  

Woodstock

Woodstock new york
Town center at Woodstock in the Catskill Mountains. Editorial credit: littlenySTOCK / Shutterstock.com

How could one not be curious about the famed festival site that catalyzed the hippie revolution? Well…technically, that took place in the town of Bethel, but the name and the theme live on in modern-day Woodstock. This Ulster County town features live music, tie-dye, and vegan culture all along Tinker Street. Since you have a vehicle on hand, consider making a side trip up to the picturesque Kaaterskill Falls. 

Sleepy Hollow

Sleepy hollow
Philipsburg Mannor in Sleepy Hollow.

Add a little American Folklore to your adventure by visiting the spooky village of Sleepy Hollow. About 90 miles south of Woodstock, this Westchester County site is part of the ironically and eerily-named town of Mount Pleasant. The infamous setting of Washington Irving's, The Legend of Sleepy Hollow, is nestled on the East shore of the Hudson River. This quaint and colorful village is surprisingly close to the concrete jungle of Manhattan. 

Montauk

Aerial view of the Montauk Lighthouse and beach in Long Island, New York.

Finally, cap off your journey with a final leg out to Montauk, a hamlet on the tip of Long Island. Reenact a bit of magic from the movie, Eternal Sunshine of the Spotless Mind, and appreciate the romance of a small-town road trip that comes to an end on the North Atlantic Coast. Peer out into the ocean and count the highlights of this trip while pondering what is next. Then stretch your road-weary legs with walks on the pristine beaches and welcoming parks that beckon the nearby Metropolitan crowds. 

Those are just ten of the endless charming small towns to visit in New York State. The beauty of a road trip is the flexible itinerary. Be the captain of your own ship and go where the alluring landscape and quirky communities call you. Happy travels. 

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