Cruisin' the Catskills — Regional H.O.G. Rally 2026

About Cruisin' the Catskills

The Catskill Mountains of New York State are one of the North-East's great motorcycle destinations — a sprawling range of forested peaks, river valleys and small historic towns within a two-hour ride of New York City. Route 28 through the heart of the Catskills is the signature road, threading along the Esopus Creek past Woodstock, Phoenicia and Fleischmanns before climbing toward the Delaware County highlands. County roads branching north and south from this spine offer endless variation — quiet valley floors, steep climbs to ridge-top views, and stretches of smooth blacktop through dense deciduous forest.

Cruisin' the Catskills is a celebration of this riding terrain and the community that loves it. Events held in the Catskills region typically draw riders from New York, New Jersey, Connecticut, Pennsylvania and further afield — the variety of routes and the concentration of classic American small towns makes the area a natural gathering point for the North-East Harley-Davidson community. Key destinations in the region include the village of Woodstock (steeped in music history), the Catskill Center for Conservation, the historic town of Kingston on the Hudson, and the scenic Rip Van Winkle Bridge crossing.

The Catskills are at their best in late spring and early autumn — the foliage colour in October is exceptional, while June brings clear roads and long evenings. Summer weekends draw touring riders from the whole region, with the mountain towns offering accommodation, good food, and the unhurried pace that makes multi-day motorcycle touring in this part of New York so appealing.

For Harley-Davidson riders, the Catskills deliver the full experience — sweeping mountain roads for cruisers, historic character in every town, and a riding community that welcomes visitors warmly. Global Rider members attending Cruisin' the Catskills can RSVP through the platform, coordinate travel with other riders, and share route suggestions for the surrounding area.