Catskill Scenic Line
New Yorkers have been escaping to the Catskills for as long as New Yorkers have existed, and with good reason: the Catskills are epically beautiful. Now what was once dubbed the “Most Scenic Rail Line in the East” is one of the most scenic bike trails you’ll find anywhere.
Ride Details
75 miles
2 day ride
Depart: Drive
NYC >> Roxbury
Return: Drive
Roxbury >> NYC
Mix of crushed stone, dirt, grass, and grave
Stay in Roxbury
In days gone by, the Ulster & Delaware Railroad carried vacationers off steamboats from the Roundout in Kingston up to the resorts of the Catskills. Later absorbed into the New York Central railroad, the line was renamed the Catskill Mountain Branch. You can find more history about it here.
The two disconnected rides of this trip actually follow the same original right of way of this storied rail line, part of which is still in use for tourist trains run by the Catskill Mountain Railroad. That’s the reason these two rides don’t connect to each other or run all the way to Kingston.
I hope someday they do, so that bike trippers can follow dedicated trails from NYC straight up into the Catskills. For now, however, you’ll need a car to access them. Sigh…
Day 1: Roxbury <> Bloomville
Choose your adventure. Depending on where you stay, you can start this loop from Bloomville, Hobart, Stanford, Grand Gorge, Roxbury, or really just about anywhere in between. I vote Roxbury, because it gets the big on-road climb out of the way early. You can also avoid the on-road climb all together by making this a there and back ride staying entirely on the trail between Roxbury and Bloomville.
Ignore Google Maps. The section of trail that runs from Grand Gorge to Roxbury is not marked on Google Maps. It’s a lie, the trail exists here, albeit in somewhat rougher shape than the other sections. Traillink has the full map, as does the trail’s own website.
Bibliophiles beware. Hobart may very well be your happiest place on earth. There are no less than five (!!!) bookstores on the main drag of this tiny village: Lion Eye Books, Blenheim Hill Books, Liberty Rock Books, Creative Corner Books, and Adams' Antiquarian Books.
Easy eats in Hobart or Stamford. Coffee Pot, Stamford Coffee, and T P’s Cafe are all good options for quick and easy eats. While you’re in Stamford, use the Stamford Railway Station as the backdrop for a good bike selfie.
Get an awesome dinner. The Bull & Garland in Hobart and the Brushland Eating House a little further afield in Bovina Center are two excellent and renowned restaurants. Be sure to reserve ahead.
Stay… anywhere! There are a lot of options in the area. If you’re going round trip from Roxbury, The Roxbury Motel and The Roxbury at Stratton Falls (same owners) are convenient and one hell of an experience. They literally call it “the Roxbury experience”. Rent a cottage if you want to go full send. For less fantasy and more Brooklyn Upstate vibes, The Bull & Garland above also has rooms. Plenty of the usual B&B fare in the area too.
Day 2: Boiceville <> West Hurley
Get breakfast at the Phoenicia Diner. Do. Not. Skip. This restaurant is phenomenal and oh so conveniently located directly en route to the Ashokan Rail Trail trailhead. I recommend any of the skillets to start your day.
Choose your adventure, again. Do the loop of the Ashokan reservoir, half of which is on road and hilly, or make an easier day of it by going there and back on the trail.
Keep ignoring Google Maps. Again, the trail is not marked. Google Maps will send you down Route 28. Definitely DO NOT bike down Route 28. The trail is there, you’ll find it. Same as above, Traillink has the full map, as does the trail’s own website
Snack at Bread Alone. It’s a top-notch local bakery that is near the trailhead on Route 28. Get a post-ride snack or grab a loaf to take home.
Eat at Cucina. Great place to gorge on pasta after two days in the saddle. While you’re there, check out Woodstock and take a stroll down Tinker Street.
