6 Most Vibrant Towns in Upstate New York
From Niagara Falls to the mighty Catskill Mountains, Upstate New York is a hub of the state's best attractions. Drawing city dwellers from the Big Apple and visitors from all corners of the country, this region might surprise you with some of its charms, often found in its smaller communities. Offering tranquil lake days, colorful galleries, hundreds of waterfalls, and everything in between, these vibrant towns and their spirited locals know how to let loose, relax, and enjoy life’s finer pleasures. Whether you visit one of the Finger Lakes for a day of waterside wine tasting or journey through one of the region’s glorious state parks, Upstate New York beckons with something to excite any traveler this 2024.
Woodstock
The iconic 1969 Woodstock festival may not have taken place in the town that inspired its name, but a visit today will show you where the inspiration came from. Woodstock has always been a colorful town, and back in the day it was alive with hippies, artists, and musicians like Bob Dylan. Brightening the community with their artistry, a reputation was soon built, and present-day Woodstock still embraces this love of free spirits and wanderers. Live music is a core promise of the town, with venues like the Bearsville Theater offering a more intimate atmosphere while places like Levon Helm Studios are a bit more lively. Art lovers can also sample the area’s talents at one of the nearby museums, like the Elena Zang Gallery or the James Cox Gallery. For those looking to reconnect with nature, hiking paths like the Overlook Mountain Trail feature views that inspire and awe.
Penn Yan
In the heart of the Finger Lakes region, Penn Yan is another vibrant town in Update New York welcoming nature lovers. The village rests on the northern end of Keuka Lake, the only lake in the United States that flows both north and south. Along with this rare feature, the lake is one of the most popular Finger Lakes for swimming and boating due to its warm, shallow waters, and fishing for its abundant trout spawning. Aside from the gorgeous residential lakefront properties, you will also find incredible vineyards, like the Keuka Spring or Rooster Hill Vineyards, whose breathtaking backdrops make for the perfect day of sipping and sampling. And for a more family-focused lake experience, the 7 mile wooded Keuka Lake Outlet Trail follows the Keuka Outlet, along with the reward of a dazzling tiered waterfall.
Ithaca
If waterfalls intrigue you, anyone from Upstate New York will tell you there is a must-see town whose cascades will blow you out of the water. Ithaca, also located in the Finger Lakes region, sits on the southern tail of Cayuga Lake. Boat tours with companies like Discover Cayuga Lake are a beautiful way to cruise, or you can discover your own path by renting a kayak with Paddle-N-More at Stewart Park in the summertime. Yet, with more than 100 waterfalls within 10 miles of Ithaca’s downtown, it is no wonder so many recommend a visit here for the cascades. Near Stewart Park, Ithaca Falls and all 150 feet of its plummeting glory can be taken in from a bridge over Lake Street. Buttermilk Falls State Park is another popular spot, its namesake cascade flaunting a 165 foot drop. So whether you come to Itaca for a day on the lake, a day hiking for waterfall views, or both, the experiences and sights will not disappoint.
Watkins Glen
Around thirty minutes from Ithaca, Watkins Glen is another town with lake access and waterfalls galore, so many like to visit both during their time in the Finger Lakes region. Akin to Ithaca, this Upstate New York town is also right on the southern end of a Finger Lake, so water recreation and lakeside views are some of the town’s best features. Companies like Captain Bill’s Lake Cruises are set to reopen for the 2024 season in April, offering fabulous sightseeing tours and dinner cruises. Or, you can explore the waters by paddleboard or kayak, renting from Summit to Stream Adventures. By volume, Seneca Lake is the largest of the Finger Lakes, meaning there is plenty of room to share in the fun, even during the busier summer months.
But perhaps the most sought-after feature of this darling lake town is Watkins Glen State Park, an attraction luring nearly 800,000 people each year. The most popular of the Finger Lakes parks, its 200 foot cliffs are as dazzling as they are exciting, with 19 waterfalls descending their sides. The Gorge Trail takes you past all 19 of the cascades, and is set to reopen at the end of May 2024.
Skaneateles
Despite its name meaning “long lake" in the Iroquois language, Skaneateles is only the fifth largest of the Finger Lakes. It is, however, one of the most clean and clear due to lower rates of algae production, explaining its nickname, “the Jewel of the Finger Lakes Region.” Located in a village by the same name, the lake is the top attraction for obvious reasons, and accommodations like Mirbeau Inn & Spa grant direct access to its shimmering shores. The lakeside serenity extends to locations like Anyela's Vineyards, a year-round winery perched on a hillside above Skaneateles Lake, and to attractions like Cliff Park, whose lake view and garden paths enchant all who visit. Right across from the park you will find a different accommodation option, the historic Sherwood Inn, whose history stretches back to 1807. So, whether visiting for a day trip or weekend getaway, this Finger Lakes town delights all who pass through.
Kingston
Known for being New York’s first capital, Kingston’s historic charms are what bring this river town to life. Nested on the west bank of the grand Hudson, touring the waters with Hudson River Cruises is a must, passing historic mansions, lighthouses, and a serene, tree-lined shore. Back on land, the Hudson River Maritime Museum features a fascinating display of marine artifacts and interactive, informative displays that are great for kids. And if you are eager for more time on the river, their solar-powered Solaris Boat Tour takes you on a trip to the historic Rondout Lighthouse which is operated by the museum. But if you are someone who prefers land, there are tons of other historic attractions in town, like the Uptown Historic District, Old Dutch Church, and Senate House State Historic Site, the meeting place for New York’s first Senate.
Final Thoughts
For city dwellers, Upstate New York is a blissful escape from the stresses of everyday life. But even those living outside the state’s urban jungles find themselves allured by the region’s natural beauty and vibrant communities. From Woodstock’s bold art scene to Ithaca’s spectacular waterfalls and Kingston’s preserved maritime history, there is a town for any art, nature, or history lover. For the chance to slow down and enjoy life’s offerings, let Upstate New York mesmerize you this 2024.
