Over the summer I got a chance to ride through over 37 states in search of America’s “misunderstood locations” to find out what they really were all about. One of the places on the list was the Catskills. Up until my visit the only thing I knew about it was that it’s not too far north from New York City and I had tried a wine from there once. I went into this area blind and with no plan. Instead I used my never ending inquisitive nature to find out where to go and what to see.
Scene2 Bridge
Over 6,000 square miles of lush forest, mountains, reservoir, rivers, waterfalls and over 400,000 acres of farmland make up the Catskills so you know just from that that no matter which road you take it’s going to be a beautiful one. I grew up on the backroads in rural Kentucky and these roads reminded me a lot of home except more rural if that’s even possible. The only bit of caution I have when riding these roads is to do it during the day. This pavement is for the locals, meaning that the locals know where each blind turn, rolling hill into a sudden stop sign and crossroads are. Aside from the extreme backroad way of travel there’s also a lot of wildlife that roam these areas as well and the lack of / nonexistence street lights makes for a dangerous combination when the sun goes down.
Below is a list of my three favorite rides in the area. These routes are meant to be used as a guide or a starting point. I give lots of tips of places to stop along the way and I choose them for their local appeal, hospitality and just plain ol’ fun. My hope is at each place you become more familiar with the local culture and find new places to go and make your own map. I think it’s the best way to experience all the area has to offer and a great way to make this your own ride.

The Emerald Isle 58 miles / 1 hour, 42 mins:

Emerald Isle
This route travels through Greene County’s Irish-settled countryside and offers breathtaking scenery and smooth roads. Follow the shamrocks on Route 145 to the Irish land of East Durham. The route offers riders the chanced to experience Cunningham Road, one of the most scenic roads in Greene County with a few gas stops along the way so those of you with smaller tanks don’t have to worry about running out. Prattsville Road runs along the reservoir and has some nice twist and curves as well as County Route 10 and Cunningham Road. Overall though this trip is for any level rider and the roads are unpopulated so you can focus more on the environment around you and your own ride.
While on this route make sure you stop by Pratt Rock, also known as “America’s First Mount Rushmore”. Don’t let the hype fool you though, Pratt rock isn’t near as grand as Rushmore and teeters more on the “Weird Roadside Attractions” list with its lack of symmetry and random carvings but it is something unique all the same and once you hike up to see it closer you get an amazing view of the Schoharie River below and a perfect time to catch up breath or take a selfie.

If you want to get fancy on your trip, then dust off your leathers and stop in for a tasting at the Windham Vineyards and Winery. This small family owned business has eight different varietals (that means type of grapes for us unsophisticated folk) to choose from and the land is the perfect place to kick back, unwind and enjoy the rolling hills and lush vineyard before starting your journey back home.

If you’re craving more than cheese, crackers and liquid grapes then make sure and stop at The Saloon Steakhouse & Pub for typical but very well cooked bar food, steaks and stiff cocktails. It’s a local biker hangout so you can usually run into others that share the same passion for the open road as you do.

The Grand Tour 144 miles / 3 hours, 44 minutes

Grand tour catskills
If you want to get the full Catskills experience and love to ride through mountains and wide open sweeping valleys, then this route is for you. Elevated twisty roads that go up around 3,500 feet and around crystal clear streams and brooks. Along this route you can expect to see rolling farmlands, high peaks and quaint country towns. The ride is for moderate to experienced riders and offers something for those who crave a more thrilling ride. Just travel along Platte Clove Road, the steepest road in the Catskills to get your kicks. It’s a lot of miles and there are quite a few places to stop along the way including five towns that have gas so you don’t have to worry about running on E. Some of the best sightseeing are on this route as well and the ones I would include on my list would be Bastion Falls, Kaaterskill Falls and the Mountain Top Visitors Center. You will have to do a little hiking to get the full experience but I think that make this trip unique. In fact, the day I did this trip I got my first official Iron Butt and stopped to hike 2 miles of Kaaterskill Falls during it. It was a nice way to break up the day and get the feeling back into my numb butt before heading back out on the road.
Trail sign
Since this route is a long one and if you add in some sightseeing stops then you are for sure going to get hungry. There’s a lot of unusual quirky saloons, cafes and restaurants in the Catskills but on this route, American Glory is by far my favorite. It’s the best Barbecue you can get north of the Dixie line and the atmosphere is hard to beat too. Rustic, traditional and quaint, it’s a struggle not to want to spend half of the afternoon in its wooden and brick décor.

Just a little north of where this trip begins is the Dewitt Oak Hill Guesthouse The Dewitt Oak Hill. I had the pleasure of staying here on my trip and it was by far the highlight of my summer. The place is steeped in history and walking into the huge red French doors is like walking back in time a couple hundred years.
Red Doors
This historic home is ran by a French chick and an English one, as their Instagram description puts it, and is perfect for anyone who wants to be surrounded by beautiful things but also kick back and relax. I was afraid at first that my loud pipes and dirty jeans wouldn’t fit in at such a place but I was instead treated like royalty. They made me cocktails while I hung out with their dogs and the breakfast in the morning was something that I wish there was a real-life Pinterest button for. The owners are the coolest and the people who stay there are just as eclectic. And even though I’m sure there was a ghost lurking around on that creaky stairway I still didn’t want to leave the next morning. The owners even signed and vouched for my Iron Butt paperwork, mailed my postcards out for me and gave me a high five before I left. So, if you want to get a real and true experience of the Catskills and have a good time while doing it I highly suggest you stay here.
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Mountain Clove Run 74 miles / 1 hour, 44 minutes

Mountain Clove RUn
If the mountains are calling to you then this route is a must. This twisty ride will test your skills on the rail and have you begging for more. It’s hard not to want to stop every other minute on this route since the scenery is so breathtaking but the curves and sweepers keep you wanting more miles of this route. There’s a lot of the same places on this route as in the Emerald Isle Map but this would be for more experienced riders or for riders who want a more scenic ride. It has all the falls, rock and mountains as listed in the routes before so I suggest stopping by the Greene County Visitor Center to personalize this trip to your liking.
This route has the most stops for places to grab a bite but I would choose the Red Roosters Roadhouse to get your grub on before finishing up the journey. It’s a total biker hangout and with a lot of colorful locals that can give you more tips on places to see along the way. There’s a lot of antique shops as well and if you have the room on your bike I suggest stopping in to do a little “peeking and picking” or shopping and dealing for you less county folk.

Even though I lived in NYC for five years I never had a reason to visit the Catskills before and that’s simply because I didn’t know much about it but now that I’ve been you can bet I will be going back for many years to come. From Howe Caverns, Kaaterskill Falls, farmland for days, untraveled roads and smooth pavement, this place is a biker’s dream. After riding just one of these route I have a feeling you will feel the same way.

Photo Credit: Dalton Dobson

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