Guided routes
The roadbook
This is the chapter’s roadbook: the guided motorcycle routes the Woodstock H.O.G. rides through the season, each mapped in the Harley-Davidson Ride Planner so you can open it and follow it from your own bars. They run across the Catskills and the Hudson Valley, from a 46-mile morning around Windham to the 168-mile Grand Tour of the Catskills.
Last updated July 2026
Catskills rides
Loops in the range, from a morning around Windham to the all-day Grand Tour.
46miles~2 hr
Windham Mountain Loop
The Windham Mountain Loop is a 46-mile run through the northern Catskills around Windham, the ski town on Route 23. It stays high the whole way, all ridge roads and mountain air, and it is the shortest guided ride on the calendar.Ride Planner55miles~2 hrDevil’s Tombstone Loop
The Devil’s Tombstone Loop is a 55-mile ride linking both Catskill cloves, up Kaaterskill on Route 23A and down Stony Clove Notch on 214 past the Devil’s Tombstone campground. It is the classic Catskills day ride, and the one the chapter runs most.Ride Planner55miles~2 hrNorthern Catskills Loop
The Northern Catskills Loop is a 55-mile tour of the high country above the Mountain Top towns, all sweepers and long views over the escarpment. It holds the ridge the whole way and keeps the traffic behind you.Ride Planner66miles~2.5 hrColgate Lake Loop
The Colgate Lake Loop is a 66-mile ride out to the quiet water above East Jewett, through the backroads of the northern Catskills. Low traffic, good pavement, and a still-lake stop in the middle.Ride Planner80miles~3 hrWoodstock Loop
The Woodstock Loop is an 80-mile ride out of Woodstock and back, the home circuit through the towns the chapter knows best. A good first ride if you have never turned a wheel in the range.Ride Planner92miles~3.5 hrCatskill Foodie Ride
The Catskill Foodie Ride is a 92-mile ramble built around where you stop to eat, strung between the mountain-town kitchens and roadside counters the chapter rides for. Come hungry and ride it slow.Ride Planner95miles~3.5 hrMoto Coffee Run
The Moto Coffee Run is a 95-mile ride chained between coffee stops, built for a slow start and a caffeine-first pace. More about the pull-offs than the miles.Ride Planner120miles~4 hrAshokan Reservoir Loop
The Ashokan Reservoir Loop is a 120-mile ride anchored on the big water west of Woodstock, with Route 28A tracing the reservoir’s south shore in open sweepers. Long water-and-mountain views and forgiving pavement most of the way.Ride Planner147miles~5 hrPepacton Reservoir Loop
The Pepacton Reservoir Loop is a 147-mile ride into the western Catskills, where Route 30 runs the length of the reservoir in long, empty curves. It is one of the best riding roads in the region, and worth the distance to reach it.Ride Planner168miles~6 hrGrand Tour of the Catskills
The Grand Tour of the Catskills is a 168-mile all-day ride that strings the range’s best roads into one loop, cloves and reservoirs and ridge country in a single sitting. Full tank, full day, lunch stop built in.Ride PlannerBeyond the mountains
Rides that drop to the Hudson Valley and the Shawangunk ridge.
82miles~3 hr
Olana Historic Ride
The Olana Historic Ride is an 82-mile run east to Olana, the Persian-style estate the painter Frederic Church built on a hill above the Hudson. The climb to the house opens some of the best river views in the valley.Ride Planner117miles~4 hrMohonk Mountain Loop
The Mohonk Mountain Loop is a 117-mile ride south to the Shawangunk ridge and the grounds of Mohonk Mountain House, the Victorian resort above New Paltz. Ridge roads, hairpins, and the white cliffs of the Gunks on the back half.Ride Planner143miles~5 hrMinnewaska Scenic Loop
The Minnewaska Scenic Loop is a 143-mile ride down to the Shawangunk cliffs, taking the switchbacks of Route 44/55 as they climb the ridge past Minnewaska. It runs one of the most photographed motorcycle roads in the state.Ride Planner145miles~5 hrHyde Park Presidential Ride
The Hyde Park Presidential Ride is a 145-mile ride across the river to Hyde Park, home of the Roosevelt estate and the country’s first presidential library, run along the Hudson’s east bank. History at the turnaround and river roads much of the way.Ride Planner155miles~5.5 hrSchoharie Valley & Iroquois Museum Ride
The Schoharie Valley Ride is a 155-mile run northwest into the Schoharie Valley farm country, out to the Iroquois Museum near Howes Cave. Open valley roads and long straights, a different feel from the mountain loops.Ride PlannerRide smart
Mountain weather turns fast, and the clove roads stay wet and shaded long after the valley dries out. Watch for sand in the switchbacks through spring, keep a gap in the group on the steep grades, and check that Platte Clove is open before you point at it.
Ride them with us
These roads are better with a crew. The Woodstock chapter rides them through the season. See what’s on the calendar, get to know the chapter, or put in your application.