The 8 Can't-Miss Towns In New York
Beyond the glitz of the Big Apple, New York’s small towns appeal to the curious to discover the whole other side of the Empire. Some demand time to explore the waterfalls and wilderness on a camping trip to Watkins Glen or Ithaca, sampling vintages from award-winning wineries along the Finger Lakes.
Pick a slice to journey through the scenic, cultural, and quiet corners housing can't-miss sites, like historic estates near Rhinebeck, Olana south of Hudson, or one of the tallest and oldest waterfalls in the eastern US, the tiered 260-foot-tall Kaaterskill Falls near Hunter.
Annandale-on-Hudson
This town's effortless charm and collegiate spirit make for a chill retreat far from the city’s chaos. Its beautiful campus embraces nature with formal architecture and informal outdoor spaces to explore gardens, waterfalls, art, and historic mansions in a peaceful setting. Check out the impressive collection at the Hessel Museum of Art, plus regular events. Beyond the intellectual flair, the slower summer pace is ideal for traffic-free paddling down the river and crowdless sites.
Zabriskie's Waterfall is a voluptuous and purely magical adventure with a trail along the stream to the Hudson River through marshlands with blue herons and maybe a red-shouldered hawk. It is five minutes south of Tivoli to launch off in a kayak from Tivoli Landing or Tivoli Bays, via the trail behind dePeyster Hall. Meanwhile, Bard College Montgomery Place Historic Estate is a vestigial 380-acre estate with a seasonal botanic garden, woodlands, and views of the Hudson River.
Cold Spring
This charming village in the Hudson Valley is a popular day trip or weekend escape to charge up on good vibes. The retro appeal, candy-colored houses, and striking views of the Hudson set the bar high for your future escapes. If the mountains are calling, Hudson Highlands State Park is over 8,000 riverfront acres with all-level fitness trails and vistas like the abandoned military warehouse turned Bannerman Castle on a Hudson River island, catering to seasonal walking tours.
Some 60 miles north of NYC, or about an hour via Metro-North, you can have a late breakfast and head for a hike along a plethora of trails or a stroll along the Hudson to a scenic picnic. Back on the bustling, walkable Main Street, browse unique shops, eateries, and boutiques, alongside 19th-century architecture all the way to the waterfront promenade. Boscobel House and Gardens is a 19th-century Georgian mansion with gardens, orchards, and water views, plus regular cultural events.
Hudson
Perhaps NY's most lovable small town dates back to the Revolutionary War era. Perched above the Hudson, the hub of the valley morphed into a trendsetter, with fresh food, art, and live music scenes. Drawing scores with its historic facade, lively feel, and picturesque surroundings, artists and entrepreneurs continue to give Hudson its creative edge. Hudson Athens Lighthouse is a rustic beacon with a green light and fog bell.
Boasting a remarkable collection of preserved architecture dating to the 18th century, the walkable town is like a free tour of American architectural styles, posing as an incredible backdrop. From decor and books to artisanal bakeries, artwork, and antiques of all wares and eras, take a breather from Warren Street along Promenade Hill Park. The stunning Olana State Historic Site offers tours and exhibits of the painter Frederic Edwin Church's estate and studio with sweeping views.
Hunter
Contrary to the higher, more challenging, rugged Adirondacks, the Catskills' dome-shaped peaks, shorter, less strenuous trails, and drier climate are ideal for a wider dynamic. Catskill towns offer easier access and a stronger cultural identity with a food scene of former summer resorts, which makes being dependent on tourism easier. Settled in the early 1800s among the region’s highest peaks, Hunter is a true mountain town in the Northern Catskills, with a beer hall and an array of lodgings.
The rocky, mountainous terrain framing the town has drawn artists, poets, writers, and wealthy travelers to escape life into inspiring nature. Hunter Mountain Resort is a family-friendly, premier skiing destination atop 3,200-foot Hunter Mountain, with a scenic sky ride to the top and spectacular foliage views. Minutes east, the tiered 260-foot-tall Kaaterskill Falls is among the tallest in the eastern US, with a trail approach and lookout amidst a rustic woodland with year-round activities.
Ithaca
Home to Cornell University, Ithaca College, and wineries along the Finger Lakes Wine Trail, this witty and naturally "gorgeous" town exudes infectious energy with a mix of cultures and natural attractions on the southern tip of the longest of NY's glacial Finger Lakes. Starting along the Lake Cayuga waterfront, it dawns on you rather quickly that Ithaca is not a pit stop. Jampacked with over 150 waterfalls within a 10-mile radius, gorges, and miles of hiking trails, Ithaca is a scenic showstopper.
Ithaca Falls cascades next to the Ivy League campus, minutes from Cascadilla Gorge Trail leading to another waterfall in the heart of town. From the iconic Buttermilk Falls to the expansive Robert H. Treman State Park, water cascades through the gorges, with a stream-fed swimming hole, ringed by hiking trails and camping areas.
Rhinebeck
This historic Hudson Valley town is ideal to exchange the weekend traffic and tourist crawl of NYC for historic estates, inns with a local twist, and a thriving farmers’ market. In addition to the Old Rhinebeck Aerodrome with vintage planes, Paul Rudd and Hilarie Burton own the local Samuel's Sweet Shop. Home to a picturesque downtown, high-end restaurants, and unique boutiques, Rhinebeck's art and cultural scene is off the charts.
Visitors can explore the scenic Hudson Valley, local farms, and nearby sites, like the Wilderstein Historic Site, an ornate, 19th-century Queen Anne mansion on 40 acres with river views, plus a Gilded Age mansion south of there. Natural beauty rules through Ferncliff Forest, a 200-acre forest preserve with trails for hiking and biking, campsites, and a fishing pond. Finally, it is minutes to the shores or just 20 minutes by bike to catch the sunset over the Hudson River.
Saugerties
Dutch for "sawmill," this town in the Catskills foothills boasts varied terrain like the 160-acre forever-wild Esopus Bend Nature Preserve. Many enjoy kayaking and paddleboarding on the extensive frontage on Esopus Creek and its tributary, Plattekill Creek. Sourcing from the southern slopes of Kaaterskill High Peak, they flow into the Hudson. Saugerties Lighthouse is a remote landmark turned serene bed-and-breakfast, accessible via a driftwood/flora-laden walk along the sandy shore.
Noted as one of America's 10 best by Budget Travel, Saugerties' revitalized village center features an eclectic mix of antique stores, vintage shops, and restaurants. Most businesses stay open late every first Friday of the month with special activities and discounts. In addition to the magnificent Diamond Mills Resort and Spa next to a German chocolate shop, the awe-inspiring Opus 40, a 6.5-acre stone-sculpture park in an abandoned quarry with trails and a museum, is one of the state's hidden gems.
Watkins Glen
This upstate gem in New York offers a world of excitement on Lake Seneca's southern tip, the deepest of New York’s 11 Finger Lakes. Most known for its high-octane motorsports and wilderness, Watkins Glen rewards the adventurers with a spectacular waterfall, farm-to-fork fare, and legendary local wineries along the Seneca Wine Trail, alongside artisan goods at local farms. No less delightful is the town's Pier House, while Clute Memorial Park and Recreation draws beach crowds in the summer.
Watkins Glen State Park encompasses dramatic waterfalls over jagged rock formations with unique trails and nearby camping sites. Watkins Glen Gorge Walk is a short stroll from the visitor center, a precarious hike along a striking gorge to several waterfalls, like the iconic Rainbow Falls, with a set of stairs. The highest of the 19 waterfalls in the state park, this 60-foot tiered waterfall cascades, like the others, into the 400-foot-deep gorge.
You will discover that the state of New York is full of surprises. Did you know that the Catskills' enduring artistic mountain hamlets inspired the Hudson River School artists, the mid-19th-century movement with Thomas Cole as a key founder?
The Hudson Valley towns promise a smooth trip for every taste of small-town charm. Between Hudson, Rhinebeck, and Cold Spring, there is no excuse not to make a great escape or plan a fall-time getaway in these can't-miss New York towns.
