Last weekend, I hit the road for one of the most soul-refreshing trips I’ve taken in years – a scenic drive through the rolling mountains of the Catskills in New York. The Catskills region offers the perfect escape with its stunning waterfalls, quirky small towns, and outdoor adventures that will make even the most dedicated city-dweller consider country living.
As I wound my way along the Catskill Mountains Scenic Byway on Route 28, the stress of everyday life melted away with each mile.
My journey took me through four charming towns connected by the byway – Andes, Middletown, Shandaken, and Olive – each with its own unique character.
Between hiking trails that led to hidden waterfalls and stopping at local eateries serving food so delicious I was planning my next meal before finishing the first, every moment felt like a discovery. The Esopus Creek became my constant companion as I explored the 7,600 acres of natural beauty in the Kaaterskill Wild Forest.
Mapping Out the Perfect Catskills Route
Planning a route through the Catskills means balancing must-see destinations with those magical hidden spots that make road trips unforgettable. I’ve discovered that the most memorable journeys blend scenic byways with detours to charming small towns.
Starting Your Journey: Essential Tips
Before hitting the road, I always make sure my car is road-trip ready with a full tank of gas. Cell service can be spotty in the mountains, so I download offline maps and bring a paper map as backup.
The best time to visit is fall for the stunning foliage, but spring wildflowers and summer swimming holes are equally magical. I pack layers regardless of season—mountain weather changes quickly!
Plan to spend at least 3-4 days exploring. This gives enough time to enjoy both drives and stops without rushing. I’ve found starting early mornings helps beat the crowds at popular spots like Kaaterskill Falls.
Don’t forget a good camera and binoculars for wildlife spotting. The Catskills are home to deer, black bears, and countless bird species.
Driving the Catskill Mountains Scenic Byway
The 52-mile Catskill Mountain Scenic Byway along NY-28 is the backbone of any great Catskills road trip. This stunning route takes you from Phoenicia to Andes through the heart of the mountains.
My favorite section runs through the Esopus Creek valley with mountains rising dramatically on both sides. The drive between Phoenicia and Big Indian offers especially breathtaking views.
Don’t miss Route 23A’s hairpin turns as it descends into Kaaterskill Clove. This stretch, known as the Mountain Cloves Scenic Byway, passes near North-South Lake and several impressive waterfalls.
Other scenic routes worth exploring:
- Route 214: Connects Phoenicia and Hunter through a gorgeous mountain pass
- Platte Clove Road (County Road 16): Steep and spectacular (closed in winter)
- Route 42: Access to West Kill mountain and hiking trails
Navigating Small Towns and Backroads
The magic of a Catskills road trip happens in the small towns dotting these mountain roads. I always build in time to wander Woodstock’s artistic shops and grab coffee at a local café in Tannersville.
Phoenicia offers a perfect lunch stop with its famous diner and tubing on the Esopus in summer. Further west, Andes and Margaretville showcase the quintessential Upstate New York charm with antique shops and farm-to-table eateries.
When navigating backroads, I keep these tips handy:
- Gas up whenever possible—stations can be sparse
- Allow extra time for unexpected finds like farmstands and covered bridges
- Be prepared for narrower roads without guardrails in some areas
I’ve discovered some of my favorite spots by turning down unmarked roads. The drive along Spruceton Road (County Road 6) led me to a hidden swimming hole that became the highlight of my summer trip.
Cultural Stops: Art, History, and the Woodstock Vibe
The Catskills region pulses with rich cultural heritage that extends far beyond its natural beauty. Throughout my journey, I discovered how deeply art, music, and history are woven into the landscape of these mountains.
Bethel Woods Center for the Arts and Woodstock Festival
Despite common confusion, the legendary 1969 Woodstock Festival actually took place in Bethel, not Woodstock. I spent a fascinating afternoon at the Bethel Woods Center for the Arts, built on the original festival grounds. The museum offers an immersive experience with original footage, artifacts, and interactive exhibits that transport you back to that transformative moment in music history.
Walking the rolling hills where 400,000 people gathered for “three days of peace and music” gave me goosebumps. The preserved concert field features a monument marking the stage location.
The center also hosts contemporary concerts and events, keeping the spirit of Woodstock alive. Don’t miss the special exhibits that rotate seasonally, showcasing different aspects of 1960s counterculture and its lasting impact.
Hudson River School and Thomas Cole National Historic Site
My appreciation for the Catskills’ landscapes deepened after visiting the Thomas Cole National Historic Site in Catskill, NY. As founder of America’s first major art movement, the Hudson River School, Cole’s home and studio remain largely as he left them.
I marveled at the sweeping views that inspired his dramatic landscape paintings. The site offers guided tours where you can see his original artwork and painting materials.
Nearby, I visited Olana State Historic Site, home of Frederic Church, Cole’s famous student. The Persian-inspired architecture and 360-degree views of the Hudson Valley are breathtaking.
These artists didn’t just paint landscapes—they helped Americans see the spiritual value in nature conservation, shaping our national identity.
Exploring the Charm of Woodstock and Phoenicia
The actual town of Woodstock embraces its artistic reputation with open arms. I wandered through numerous galleries, craft shops, and boutiques that showcase local artists’ work. The Woodstock Artists Association & Museum houses an impressive collection of regional art spanning decades.
The town’s streets buzz with musicians, from casual jam sessions on the village green to scheduled performances at the Bearsville Theater. I caught an impromptu drum circle one evening that felt like stepping back in time.
Just down the road, tiny Phoenicia offers its own cultural charm. This hamlet hosts the annual Phoenicia Festival of the Voice, drawing opera and classical music lovers.
The Phoenicia Diner, housed in a restored 1962 building, serves up local cuisine with a side of nostalgia. I loved browsing the eclectic shops that blend vintage treasures with contemporary crafts by local artisans.
Outdoor Adventures: From Summits to Streams
The Catskills offer incredible outdoor activities year-round, from challenging mountain hikes to refreshing water experiences. My adventures through this natural playground connected me with both the towering peaks and gentle streams that define this remarkable region.
Hiking to the Peaks: Hunter Mountain and Overlook Mountain
I started my Catskills hiking adventure on Hunter Mountain, the second-highest peak in the region at 4,040 feet. The trail was moderately challenging but rewarding, with spectacular views from the fire tower at the summit.
On clear days, you can see five states from up there! I recommend starting early to avoid crowds and afternoon thunderstorms.
Overlook Mountain near Woodstock offered a different experience. The 5-mile round trip hike took me past fascinating ruins of the old Overlook Mountain House.
The trail is relatively steep but on a well-maintained path. At the top, I was treated to panoramic views of the Hudson Valley stretching to the Berkshires. Don’t miss the fire tower here either – it’s worth the extra climb!
Discovering Waterfalls: Kaaterskill Falls and Plattekill Falls
Kaaterskill Falls was definitely the highlight of my waterfall explorations. This two-tiered cascade drops a dramatic 260 feet, making it one of New York’s tallest waterfalls.
The newly constructed viewing platform provides a safe way to take in the majesty of the falls. I visited in early spring when the water volume was at its peak after the winter melt.
For a less crowded experience, I ventured to Plattekill Falls. This hidden gem required a short but somewhat steep hike to reach. The seclusion made it perfect for photography and peaceful reflection.
Diamond Notch Falls was another wonderful discovery. Located near the town of Hunter, this waterfall features a lovely swimming hole at its base – perfect for cooling off on hot summer days.
Activities on the Water: Fishing, Tubing, and Swimming Holes
The Catskills’ pristine streams provided me with some of the best trout fishing I’ve experienced. Esopus Creek and Willowemoc Creek are particularly renowned for fly fishing.
I rented gear in Phoenicia and received helpful tips from local outfitters about seasonal hotspots. Early mornings proved most productive for catching brown and rainbow trout.
Tubing down Esopus Creek became an unexpected favorite activity. The gentle rapids provided just enough excitement without being intimidating for a novice like me.
For swimming, I discovered several natural pools. The bluestone quarry near Woodstock offers crystal-clear waters for swimming. Another favorite was the deep pool beneath Peekamoose Blue Hole, though it now requires a permit during peak season.
The Mountain Top Arboretum near Tannersville also provided lovely walks along streams before or after water activities – a perfect way to appreciate the region’s diverse ecosystems.
Epicurean Delights: Breweries, Cideries, and Farm-to-Table Finds
The Catskills region offers an amazing food and drink scene that became the highlight of my road trip. From craft beverages to farm-fresh cuisine, the area’s culinary landscape perfectly complements its natural beauty.
Sampling Local Brews and Awestruck Cider
Roscoe, nicknamed “Trout Town USA,” surprised me with its impressive craft beverage scene. The Roscoe Beer Company became my favorite stop with their Trout Town American Amber Ale that paired perfectly with their beer cheese pretzel.
During my exploration, I discovered Awestruck Cider in Delaware County. Their tasting room offers flights of innovative hard ciders made from local apples. The Hibiscus Ginger cider was refreshingly unique with just the right balance of sweetness and spice.
Many breweries in the region use locally sourced ingredients. I loved chatting with brewmasters who explained how the pure Catskill water enhances their beer’s flavor profiles. Most places offer outdoor seating with spectacular mountain views.
Savoring Farm-to-Table Fare in Delaware County
Delaware County’s farm-to-table restaurants exceeded my expectations. The area’s rich agricultural heritage translates into some incredible dining experiences.
I found Table on Ten in Bloomville absolutely charming. This café serves wood-fired pizzas topped with seasonal ingredients from farms just miles away. Their sourdough bread, baked daily, was worth the drive alone.
The Bull & Garland in Hobart serves hearty British-inspired pub food with a locavore twist. Their burger uses beef from nearby Hill and Valley Farm, topped with cheese from Brovetto Dairy.
Farm stands dot the countryside roads, offering everything from heirloom tomatoes to artisanal cheeses. Many have honor system payment boxes, showing the trusting community spirit that made me fall in love with this region.
Unique Eats in Tannersville and Margaretville
Tannersville surprised me with its colorful storefronts and diverse food options. Twin Peaks Coffee & Donuts serves small-batch coffee and homemade donuts in flavors like maple bacon and lavender lemon that I still dream about.
The Phoenicia Diner near Tannersville offers elevated diner classics. Their skillet breakfast with local eggs and house-cured bacon fueled my morning hikes. The vintage atmosphere adds to its charm.
In Margaretville, I discovered Bun & Cone, a retro ice cream shop serving incredible grass-fed beef burgers. Their homemade ice cream comes in unique flavors like wild blueberry basil.
The Roxbury Motel houses The Public Restaurant, where I enjoyed farm-to-fork cuisine in a whimsical setting. Their seasonal menu features dishes like maple-glazed duck from nearby farms and foraged mushroom risotto.
Hidden Gems and Unique Finds of the Catskills
The Catskills hold secret treasures that many travelers miss. These special spots offer everything from artistic wonders to peaceful mountain towns and breathtaking natural landscapes.
Artistic Wonders: Opus 40 and Mountain Fire Tower
Opus 40 took my breath away when I first visited. This massive bluestone sculpture garden in Saugerties was created by one man, Harvey Fite, over 37 years. Walking through the ramps, platforms, and pools carved from an abandoned quarry feels like exploring an ancient monument.
Mount Utsayantha’s fire tower offers some of the most spectacular views in the Catskills. I climbed the tower on a clear autumn day and was rewarded with a full 360-degree panorama of the mountains. The vibrant fall colors stretched for miles in every direction.
Both sites provide perfect photo opportunities. Opus 40 is best visited in morning light when shadows create dramatic effects on the stonework. The fire tower is most magical at sunset, when golden light bathes the mountains.
Quaint Retreats: Windham and Roxbury
Windham charmed me instantly with its historic Main Street and friendly locals. This small mountain town offers excellent dining without the crowds of more popular Catskills destinations.
I stumbled upon the Windham Fine Arts gallery and spent hours admiring local artists’ work.
Roxbury holds its own unique appeal with the stunning Roxbury Motel. This isn’t your typical accommodation! Each room features wildly different themes from sci-fi to retro glamour.
The town’s historic district features beautifully preserved buildings from the 1800s. Don’t miss breakfast at the local bakery where they serve homemade pastries that rival any big-city establishment.
The slower pace and genuine small-town atmosphere make these villages perfect for those seeking authentic Catskills experiences.
Venturing to the Kaaterskill Wild Forest
Kaaterskill Wild Forest hides some of the most dramatic scenery in the entire region. The two-tiered Kaaterskill Falls drops over 260 feet, making it one of New York’s tallest waterfalls. I hiked there during spring runoff when the water volume turns it into a thundering spectacle.
The forest contains numerous trails suited for different experience levels:
- Easy: Kaaterskill Rail Trail (1.5 miles)
- Moderate: North-South Lake Loop (4 miles)
- Challenging: Black Dome Trail (6.5 miles)
Early mornings provide the best wildlife viewing opportunities. I spotted deer, wild turkeys, and even a black bear at a safe distance. The Artist’s Rock viewpoint offers the same vista that inspired the Hudson River School painters.
Some trails have steep sections with loose rocks, so pack plenty of water and wear proper footwear.
