Of all the scenic routes you can take through the US, driving through the New York Catskills must be in the top ten. If you’re looking to escape city life, fill your senses with green vistas, delicious food and drink, wild art and historic estates pack the car for a scenic ride through the Catskills.
(Hosted trip but all opinions as always are mine details below.*)
I’ve heard about the Catskills forever but usually, it was as the home to the old comedy circuit (now immortalized in Jamestown at the National Comedy Center near the Catskills), the World War II summer resorts (think the movie Dirty Dancing or the HBO series The Marvelous Mrs. Maisel) and the infamous Woodstock Festival (celebrating its fiftieth anniversary in 2019 – 2010.) I learned to set aside those preconceptions and suggest you do too because there’s so much more. The region is home to vast swaths of green, sweet villages, a lot of historical spots, all kinds of niche ‘trails’ (think ghost trails, foodie routes, art gallery hops,) and realms of adventures from lakeside boating to extreme sports.
A little geography
The Catskills Mountains stretch from the Appalachian range to rise up from the Hudson Valley in the north, but they’re not actually mountains at all. They’re a dissected plateau which is to say geologically so old that the peaks have been eroded by oceans, rivers, even pre-historic ice sheets. The giveaway is that the ‘mountains’ all have the same height. Slide Mountain in the eastern Ulster County is highest at 4,180 feet. It’s not easy to see the height unless by drone or airplane. For the purpose of driving know that you won’t be tackling immense shifts in altitude but you will be scooting along twisty, hilly roads. Take it slow. Allow yourself time between spots to pull over on a whim.
Once you’re driving around the peaks and valleys you’ll encounter breath-taking views with an abundance of green, colorful villages, tempting roadside attractions and much more. The region encompasses four counties and is open year-round with ski resorts in the winter months giving way to hiking trails and the world’s longest, highest zip line in the warmer seasons. The Catskills also lay claim to being the birthplace of fly fishing.
What follows is a highly eclectic itinerary for a scenic ride going from the town of Corning in the northwest Finger Lakes region. The route then goes south to Tarrytown in the Hudson Valley:
Beth Johnson one of the owners of the Parkview Inn in Oswego, NY
On the Haunted Trail – Parkview Restaurant and Inn
Oswego gained its name from the Algonquin Indian word, Awagha, which meant the “place where the valley widens.” The city deserves time for a good wander but if you’re only riding through stop in the Parkview Restaurant and Inn. The grub is great and if you’re there early, join the coffee club in the bar. They’ve been meeting for decades. The Inn is part of the Oswego Haunted History Trail with a hidden room, mysterious bells, and other ghostly occurrences. The newest owners are updating and renovating with a lot of love. The location is also perfect for views of the river from the upstairs galleries.
Bethel Woods – The Real Woodstock
Spend a few hours at the Bethel Woods Center for the Arts with their concert center and galleries. Then walk the hallowed field where the Woodstock Revolution began. The Woodstock Festival fiftieth anniversary is taking place here. Year-round take in other concerts, art shows and the best Woodstock museum on the planet.
Casinos and Yoga Retreats
Monticello village was named after the Thomas Jefferson estate and continues today as the seat of Sullivan County. On the outskirts, the Resorts World Casino and Resort rises high above the trees and caters to anyone looking to get their game on. The new resort has many restaurants (frosted malts infused with Kahlua anyone?) state-of-the-art slot machines, halls full of game tables and private spaces, a massive concert center, and luxurious suite rooms.
Yoga room at Yog1
Close by, the Yo1 Wellness Center opened in 2018 on 1,300 acres. The grand building sits next to a lake, which is fully visible from the Yoga rooms and dining terrace. Pamper your body and spirit with Ayurvedic treatments and diet plans in this sleek new setting.
A moment inside the world’s biggest kaleidoscope.
World’s Largest Kaleidoscope
This is definitely a ‘pull the car over and stay a while’ spot, there’s even a lovely inn adjacent to the main attraction. Enter the ‘World’s Largest Kaleidoscope’ shop and don’t miss the ten-minute film by Heady Productions. Watch while laying on the floor, and let yourself fall into the immersive experience of being inside a giant kaleidoscope. Different versions of the topic rotate in for the holidays. Let your inner kid loose in the gift shop full of cool kaleidoscopes including the smallest, toy ‘scopes and a large collection of high-end kaleidoscopes. The lady running the shop is an excellent guide explaining the different types and materials used in making the kaleidoscopes.
Woodstock village main street
This village is not the site of the famous festival but takes advantage of the name and has many claims to fame regardless. It’s artsy and cute – well worth a long stroll. Have a bite to eat, check out the shops and murals and take a breather in the Woodstock Waterfall Park. It’s right in the middle of town. This village was home to fabled recording studios (the Band and Bob Dylan,) and movie venues like Upstate Films, a regional art center, and the Byrdcliffe Woodstock Guild, founded in 1939, keep its independent, creative spirit flowing.
Tannersville – Jessies Harvest House
It began with a love story – a shared love of food, family (Grandma Jessie lent her name) and local ingredients. Phil DiFalco graduated from the Culinary Institute of America and worked at the famous farm-to-table establishment Blue Hill Restaurant before meeting Sarah Slutzky. The two married their passion for fine Italian-inspired recipes when they opened Jessies. Over the years their following grew locally and now the Inn and upscale road-house is full to overflowing most nights.
Dessert in Jessies House
Take your thrill-seeking friends to Hunter Mountain any time of year. The owners have a fondness for superlatives and today the four-season resort is renowned as the “snowmaking capital of the world” with machines pumping to provide snow to keep all of the mountain’s 240 skiable acres blanketed. It is also home to the New York Zipline Adventure Tour with the longest and highest zip line in North America, canopy rides and the Adventure Tower obstacle course. Here’s a video about how I overcame my fear of heights while zipping across wide valleys and down the mountain.
Inside the Rip Van Winkle Brewery Cafe
Rip Van Winkle Brewing Company
All that exercise is bound to work up your thirst and appetite. The Rip Van Winkle Brewery is clearly a labor of love. It was established by the LoBianco family who emigrated from Sicily decades ago and opened a series of restaurants in the region. After they installed a brewing system in the 30-year-old Angela’s restaurant, the Rip Van Winkle Brewing Company was born. Washington Irving’s fictional character was adapted from a short story set in the mountain range behind the restaurant. The story has Rip coming upon a pair of ghosts playing Nine Pin. He joined them in toasts of ale and then fell asleep for twenty years before waking into a different world. Today the brewery will fill you with delicious food and brews. You may take a nap after but won’t sleep through the rest of your scenic ride.
Inside the studio of Thomas Cole, founder of the Hudson School of Painting
The Hudson River School of Painting
Thomas Cole lived on a ridge overlooking the Hudson River and was alarmed by devastating logging practices in the area. Determined to document the natural beauty of the region with his painting, he went onto founding an environmental protection movement and the famous Hudson River School.
Take time to walk the grounds, admire the heritage garden and visit the gallery. It’s a beautiful spot to stretch your legs and imagine the early days that inspired Cole.
President Franklin Delano Roosevelt’s home inside Hyde Park
Hyde Park and FDR
Hyde Park is the historic estate where Franklin Delano Roosevelt grew up and returned to when he retired. Today the National Historic Park is maintained for visitors and houses America’s first Presidential Library. The museum, dedicated to the historical legacy of the only President elected four times is an inspiring and graphically exciting museum. The family home is open to tour groups and sculptures dot the grounds. Be prepared to walk (or hop on the Park tram) as the Vanderbilt Mansion, Top Cottage, and Eleanor Roosevelt’s Val-Kil cottage are included in the park’s attractions.
The historic village is a cultural mecca with all the artistic and culinary diversions a visitor could want. Before the Civil War, Beekman Arms & Delamater Inn welcomed guests and the original building still stands proudly in the center of town. The colonial edifice holds onto its architectural past with low beamed ceilings, hearthstone fireplaces, and narrow stairways. The dining room flickers with candlelight and features a menu inspired by current culinary trends with nods to the region’s historical roots. Behind the restaurant is a tempting multi-vendor Antique Market. How much will your car carry home?
A scenic ride along the Hudson River takes you to the town of Poughkeepsie. Stretch your legs on the Walkway over the Hudson, a new State Historic Park. It rises above the city and train station to reach across the river. In time, it will connect to over nineteen miles of trails for bicyclists and hikers. Eateries in downtown are blessed with creative chefs from the CIA. Fortify your tummy and senses at the Artist’s Palate. The restaurant/gallery treats food as art with new flavor combinations.
Enjoy wine tastings? Outside of town Millbrook Vineyard, you’ll find a gallery of artwork in the loft. The walls are adorned with winning artwork from the annual competition for new label designs. For the last 20 years, Millbrook has been voted the “Best Winery” in the Hudson Valley. The vineyards fill a sloping valley and harvests have led to award-winning Pinot Noir and Chardonnay as well as Tocai Fruilano, and Reisling.
Crab cake entree at the CIA Brewhouse
Culinary Institute of America
The Culinary Institute of America houses four student-staffed restaurants that are open to the public. Sign up for a student-led tour and it’s a good idea to make advanced reservations for a meal. Save room for exquisite pastries and cakes from the student bakery. The imposing building was once a monastery and the student dining room may remind you of Hogwart’s imaginary dining hall in the Harry Potter movies. However, the architecture predates the movie and may have been inspired by the Great Hall at Christ Church in Oxford, England.
Here’s a soothing video about the Catskills Buddhist Monastery
The Largest Buddha in the West
Ready to rest away from worldly cares? Walk the acres at Chuang Yen Monastery where the largest Buddha sits inside the main building. The lake and adjacent temples feature other inspiring artwork. Check the calendar as the public is welcomed to visit for special events.
Cold Spring Getaway
The village of Cold Spring is about an hour and a half by train from New York City but has little in common with the metropolis. The train stops in town and you can easily walk to the village as well as the waterfront. Dine at the Hudson Hils Cafe and Market for breakfast or lunch. They’ll happily pack a picnic for you to take to your next stop.
The Headless Horseman was born here (in the imagination of Washington Irving.) Noted as America’s first internationally famous author, Washington Irving created a whimsical home and simply lovely gardens. Train tracks run alongside the estate and there are costumed guides at the entrance. When Washington Irving lived here he would travel into New York City by waiting alongside the rails to be picked up! Walk the house and marvel at the small rooms, the windows looking over the Hudson, and the trim gables.
Wherever you stop on a scenic ride through the Catskills there’s something tempting to do and see. What would be your favorite stop?
Helpful Information for a scenic ride and experiences in the Catskills:
The trail planning site, All Trails, lists peak times to hike, difficulty and much more.
No car? No problem. Check this link for train, bus and rideshare options for a scenic ride into the Catskills.
*Many thanks to NY Tourism and the tourist boards of Sullivan County and the Finger Lakes Region for making this trip possible. As always these notes and opinions are my own.
New places and the kindness of strangers
January 20, 2018
Maui luxury at the Fairmont Kea Lani Resort
March 25, 2015
Tastiest Breakfast Food in the World – Delivering the award
August 7, 2016
Navigating the unknown
June 29, 2011
Elaine J. Masters
Once we overcome the virus, the world will be waiting. Travelers know one thing - how to pivot and we will. We'll travel again and whether it's a short road trip or across the planet, I'll be here to help putting my years of travel to work. The Tripwellgal mission remains: to help us connect with our beautiful planet and each other with care and wonder. Stay in touch and happy travels!
YouTube Channel – Over 100K Views!
SPJ Awards: Video, Investigative Reporting, & History
Necessary cookies are absolutely essential for the website to function properly. This category only includes cookies that ensures basic functionalities and security features of the website. These cookies do not store any personal information.
Any cookies that may not be particularly necessary for the website to function and is used specifically to collect user personal data via analytics, ads, other embedded contents are termed as non-necessary cookies. It is mandatory to procure user consent prior to running these cookies on your website.