Tiny towns and city slickers make strange bedfellows – unless they’re in the Catskill Mountains. In the rolling plateaus perched northwest of New York City, you'll find the epicenter of upstate “cool”.
Spend a day summiting verdant peaks, touring trendy boutiques or drinking at a microbrewery, and one thing becomes clear: the Catskills are in the midst of a resurgence. The region's newfound hype comes with historic roots. Writer Washington Irving waxed poetic about these mountains in the early 19th century and artist Thomas Cole preserved them in paint soon after that.
Jewish families spent summers at grand Catskills resorts in the mid-20th century, as depicted in the TV show The Marvelous Mrs. Maisel, and hippies turned local farmland into a fun-loving mud pit at Woodstock music festival in 1969.
Although the tourists started thinning out after the 1970s, the topography that attracted centuries of travelers never changed. Today, the region is becoming the next "it" spot for NYC weekenders as a new generation discovers its artsy enclaves and natural beauty. Plan a trip around these experiences to see what all the fuss is about.
Explore Hunter Mountain in every season
Hunter Mountain might be the second-highest point in the Catskills, but when it comes to seasonal adventures, this peak earns first place. Thrill-seeking snow bunnies ski, snowboard or snow tube on over 50 trails descending the mountaintop every winter.
Aside from Lake Placid's Whiteface Mountain, these are some of the most well-maintained slopes in New York State – a fact that translates to large weekend crowds and long lines at the ski lift.
Fly through Hunter's canopy of trees by zooming along North America's tallest and longest zip line. Adrenaline junkies can enjoy the course year-round, but May's pastel buds and October's auburn hue make the experience particularly magical. Summer is best for hiking.
A strenuous four-mile climb through meandering woods leads to the state's highest fire tower. Make it to the top of the 4040-ft lookout on a clear day, and you'll see as far as Vermont's Green Mountains. For those who'd prefer an effortless ascent, ride the Kaatskill Flyer – a six-person chairlift – to the 3200-ft summit.
March in Livingston Manor's Trout Parade
If you take Coney Island's eccentric Mermaid Parade and marry it with small-town style, you get the Trout Parade: a fishy street fair that floods Livingston Manor on the second Saturday of June.
Locals dressed in trout drag strut alongside kooky brass bands and pick-up truck floats as the parade streams down Main Street. Visitors are free to join in the fun – just wear a funky costume and march to the beat of your own drum.
It may seem silly to celebrate foot-long river swimmers, but trout play an important role in this hamlet's history. Long before Livingston Manor became the go-to retreat for ex-urbanites, it was known as one of the Northeast's best spots for fly fishing.
Cast a line along Willowemoc Creek, which runs parallel to Main Street, and it won't be long before you tow in the town mascot. The Catskill Fly Fishing Center and Museum presents exhibits and events honoring the town's time-honored fishing tradition.
For anyone unenthused by fish frippery, pop into stylish boutiques along the parade route. Stores like Nest and Homestedt sell a mix of fashionable home goods and outdoor gear.
Hunt for unique antiques
If one person's trash is another's person's treasure, the Catskills are a veritable gold mine. Quirky antique stores abound, and unlike the neighboring Hudson Valley, they're actually affordable. Scour these vintage shops, and you'll wind up with mid-century modern furnishings, classic records and kitschy decor you didn't know you needed.
Plan your antique adventure around a few well-known destinations. Homer and Langley's Mystery Spot, located in Phoenicia, pays homage to the infamous Collyer Brothers (Homer and Langley), who made headlines in the 1940s after passing away in their Harlem apartment surrounded by mountains of sundries. Take a spin around this very odd establishment and you'll likely find something you like.
The Antiques Barn in New Paltz is known for great deals on quality goods. Livingston Manor's Taylor + Ace sells a well-curated collection of hip vintage housewares. Wherever you wind up, bring cash and try to haggle: you'll never get the deal if you don't ask.
Sample craft beer at a microbrewery
Thanks to a revitalization of craft beer brewing in the Catskills, suds connoisseurs are never too far from a free-flowing tap. Order a flight at one of the region's microbreweries to taste floral IPAs, earthy lagers and honey-sweet pilsners made with local ingredients.
Take a self-made beer tour by sticking to Sullivan County's western side. At Upward Brewing Company in Livingston Manor, visitors can whet their whistle while hiking around 120 acres of meadows and forests. Catskill Brewing Company is just over a mile away and Roscoe Beer Company pours pints in the neighboring town.
Travelers close to Hunter can imbibe at West Kill Brewing – a hip-hoppy paradise built on a historic dairy farm with mountain views. Russian Mule Brewery, which operates on a sleepy street in Claryville, is perfect for drinkers without a designated driver. Guests can spend the night at Blue Hill Lodge, a boutique motel conveniently located on-site.
Stay overnight at a trendy hotel
The Catskills are having a Dirty Dancing resort revival, and while today's retreats skew more hipster Millennial than big-family mitzvah, the effect is largely the same. Many sites serve as one-stop-shops where guests can sleep, eat and play without leaving the property.
Even if you don't stay overnight, check out the on-site restaurants, trendy bars and stylish lobbies central to this hotel resurgence.
Urban Cowboy, tucked away on 68 acres in the Big Indian Wilderness, appears like a real-life Pendleton ad. Colorful patterns adorn almost every surface and a two-person clawfoot tub awaits in every room. Head to the bark-lined bar for craft cocktails after exploring the surrounding nature preserve.
At the DeBruce in Livingston Manor, guests can fly fish on the Willowemoc Creek or hike around five miles of private trails. Dinner is the highlight of a stay; non-guests should consider reserving a table to enjoy the weekend tasting menu.
For those who want to get pampered, check into the suites at Kenoza Hall. The hotel, which overlooks its namesake lake, doubles as a wellness center with offerings like yoga, meditation, and a sauna.
Camp under starry skies
Light a bonfire and hunt for shooting stars. Doze off to a cricket symphony and wake up with the sun. Spending a summer night on one of the area's thousand-plus camp or glamp sites is an easy, cost-effective way to connect with the natural landscape.
Tent-pitching pros will appreciate Devil's Tombstone, one of the Catskill Forest Preserve's oldest campgrounds. Early Dutch colonizers believed Satan lived in the surrounding peaks, but today's intrepid visitors shirk their ominous tales by braving nearby trails heading into the mountains.
If you prefer heat, air conditioning and a door to keep out critters, check out Gather Greene – a collection of wood cabins huddled together on 100 acres of a former dairy farm. Tent-shaped picture windows framing each cabin make these free-standing hotel rooms feel like they're practically outside.
For an epic night of stargazing, plan your sleepover around the annual Perseid meteor shower, which takes place between late July and late August. On clear nights with little light pollution, it's possible to see between 30 and 100 meteors blazing across the sky every hour.
Admire art at the Thomas Cole National Historic Site
Soak up the sylvan views outside Thomas Cole's house and you'll understand why this 19th-century artist settled down in the town of Catskill. Cole, father of American landscape painting and founder of the Hudson River School, often depicted the region's thick forests and panoramic vistas on canvas to encourage environmental preservation. His work was a form of activism against industrialization – a message that feels increasingly urgent in modern times.
Today, the artist's abode is a museum celebrating Hudson River School masters. Step inside the Federal-style digs to see the collection before trekking to destinations that inspired the paintings. Check out itineraries offered by the Hudson River School Art Trail, which pairs landmarks like Kaaterskill Falls with works created in their image.
Find a hike or climb that matches your fitness level
The Catskill Mountains cater to all kinds of hikers, with roughly 100 peaks stretching from low-lying plateaus to rugged expanses. Wheelchair users can roll along the paved Ashokan Reservoir Promenade to gawp at views of Slide Mountain; rock climbers can try their hand at quartz cliffs along the Shawangunk Ridge.
For dynamic terrain that reaches commanding vistas, a thundering cascade, and chilly ice caves, visit Sam's Point. This day-long adventure is adjustable for both nature newbies and outdoor enthusiasts.
Mountain mavericks with a knack for the extreme can prove their prowess by joining the Catskill 3500 Club, which is open to hikers who summit 33 Catskills peaks above 3500ft in elevation. Put in the mileage and you'll be able to rhapsodize about crystal-clear watering holes, old-growth forests, and animals like cherubic chipmunks and elusive black bears.
Ogle unusually large roadside attractions
Small towns pack big surprises if you know where to look. Drive along Route 209 in Kerhonkson and you'll spot Gnome Chomsky, the original World's Largest Gnome. Since his unveiling in 2006, rosy-cheeked Chomsky fell to fourth place in the tallest gnome race (his adversaries live in Iowa, Poland and British Columbia).
Still, the 13-ft-and-six-inch art installation is no less whimsical. After paying your respects to the jolly giant, explore his home on Kelder's Farm. The kid-friendly agro center features a petting zoo, mini-golf, and seasonal pick-your-own produce.
If Chomsky isn't trippy enough, head to Emerson Resort and Spa in Mount Tremper to see the world's largest kaleidoscope in action. The polychromatic spectacle takes place inside a 60-ft-tall converted grain silo. Lay back on slanted boards and gaze toward the heavens to take the hallucinogenic journey.
Step back in time at Bethel Woods
Ask a long-time resident in Bethel about the summer of ‘69, and they'll tell you about the time 400,000 hippies descended upon a local farm for Woodstock. This star-studded concert – not to be confused with the actual town of Woodstock – put their pastoral town on the map and continues to be a source of local pride.
The site, now called Bethel Woods Center for the Arts, welcomes guests to the hallowed grounds throughout the year. In summer, the rolling hills are alive with the sound of music thanks to a popular concert series. Autumn brings leaf-peeping locals to the weekend Harvest Festival featuring local artisans and food purveyors.
History buffs will appreciate the Museum at Bethel Woods, which explores the tumultuous history of the 1960s. Play some Grateful Dead while standing by the Woodstock monument to bring the mythical festival's spirit back to life.
Cool off in a watering hole
When summer gets a little too hot, chill out in one of many freshwater lakes and rivers sprinkled between the Hudson and the Delaware. Lake Awosting – one of the Shawangunks' five mountaintop sky lakes – is a remote swimming destination at the end of a three-mile trail. Those willing to hike will be rewarded with solitude while sunning on the rock slab leading into the water.
If there’s a heatwave in the weather forecast, get a park permit to visit the Peekamoose Blue Hole. This clear turquoise pool is ice-cold throughout summer, providing a welcome shock on sweltering days. Beat the crowds by heading one mile upstream to a roadside waterfall where visitors rarely venture.
Lake Superior State Park is an excellent option for families. Pack a picnic and spend a few hours hanging out on the sandy beach. Rowboat and paddleboat rentals are available throughout summer.
Marvel at Opus 40's masterful masonry
Self-taught sculptor Harvey Fite spent 37 years hand-crafting Opus 40 – a 6.5-acre sculpture made of locally-quarried bluestone. It's like the Stonehenge of the Catskills – a seemingly impossible rock configuration that serves as a monument to human ingenuity.
Wind your way around the serpentine earthwork's ramps, pools, ledges and stairs before frolicking through the park's 50 acres of forests and fields. An indoor gallery shows rotating exhibits, but the real treat is what you'll find outside.
Picnic tables around the property make the site ideal for an afternoon meal. Plan your trip around autumn, when Mother Nature's annual art show gives Opus 40 a run for its money.
Eat food from local farms
Drive through the Catskills, and you'll see a checkerboard of apple orchards, cattle farms and corn stalks higher than the top of a car. Snack on the region's earth-grown grub to experience local life on your taste buds.
Get a feel for farming by picking fruit at Jenkins-Lueken Orchard. The family-owned business near New Paltz invites guests to pick their own berries, apples and pumpkins throughout summer and fall. On Sunday mornings, the Callicoon Farmers' Market is the place to go for locally-grown meat, veggies, wine, and fresh-baked pastries.
If farm visits and market stands are out of the question, there are other ways to support local businesses serving Catskills fare. Main Street Farm, Livingston Manor's boutique grocer, sells trout, eggs and goodies like honey and hard cider from nearby farms and microbreweries.
When cooking seems like a chore, treat yourself to dinner at Peekamoose, a former farmhouse where NYC-trained chefs craft seasonal dishes with local ingredients.
See performances at the Forestburgh Playhouse
Head to the Forestburgh Playhouse for its Judy Garland-in-Summer Stock (1950) vibes. Between June and Labor Day, Broadway-caliber thespians from NYC join a rag-tag mix of promising college-aged performers to put on a series of stage shows inside a converted barn. The playhouse, founded in 1947, is the oldest continually operating professional summer theater in New York.
Enjoy a roster of splashy musicals, children's shows, and contemporary plays on the theater's cozy main stage; a connected tavern serves cabarets and concerts with pre-show dinners or late-night drinks. Check the tavern's schedule to see who's performing. Local bands, Broadway legends, and quirky drag queens provide some of the best live entertainment in the Catskills.
Float down the Delaware River
The Delaware River, which cuts between New York's Catskills and Pennsylvania's Poconos, is a nature-made water park. Every summer, crowds cruise with the current in kayaks, rafts and canoes – but nothing is as popular on a sunny afternoon as floating downstream on an inner tube.
Companies like Lander's River Trips rent tubes for leisurely day-long excursions, short jaunts and guided tours through gentle rapids. For a successful all-day outing, apply plenty of sunscreen and don footwear to handle the rocky river bed. Pack a cooler with food and drinks – several of the companies will allow you to bring refreshments along for the ride.
As you snake along the riverbank, stay alert for signs of wildlife. There's no doubt you'll spot a family of white-tailed deer walking through the woods, and if you’re lucky, you might spot a bald eagle. The upper Delaware is a popular nesting ground for this regal ruler of the skies.
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