Wisconsin Dragon 26 Ride

Event date: 
Sun, 07/05/2026 - 8:30am

Wisconsin Dragon Ride – July 5, 2026
H.O.G. 15 for '26 Challenge Ride

Ride Captain: Chris Roddick

Meet: 7:00 AM
Safety Briefing: 7:15 AM
KSU: 7:30 AM

Departure Location:
Woodstock Harley-Davidson

Distance: Approximately 450–500 miles

Pace: Brisk

Ride Style: Challenge Ride / Endurance Ride / Technical Backroads

Destination: Wisconsin's Dragon & Gays Mills Overlook

Why Go?
Wisconsin's Dragon is one of the Midwest's best-kept riding secrets. Named after the famous Tail of the Dragon in Tennessee, this figure-eight route through southwest Wisconsin features endless curves, elevation changes, ridge-top views, and lightly traveled backroads. The route winds through the Driftless Region, one of the most scenic riding areas in the Midwest.

H.O.G. 15 for '26 Challenge Stop
This ride is an official Harley Owners Group 15 for '26 Challenge destination. Riders can check in at the Gays Mills Apple Orchards overlook to earn credit toward their challenge coin.

Ride Highlights

Official H.O.G. 15 for '26 Challenge stop
Wisconsin's Dragon figure-eight route
Hundreds of curves and elevation changes
Scenic Driftless Region roads
Gays Mills Apple Orchard overlook
One of Wisconsin's premier motorcycle roads
All-day riding experience

Challenge Stop Information

Check-In Location:
Historical Marker for Gays Mills Apple Orchards Scenic Overlook

Located on WI-171 approximately one-half mile east of the intersection with WI-131.

This overlook offers panoramic views of the surrounding valleys and orchards and serves as the official challenge ride check-in location.

Ride Expectations

This is a long-distance, all-day ride.

Expect:

Approximately 500 miles
10–12+ hours in the saddle
Limited stops
Efficient fuel and rest breaks
Brisk pace between stops
Technical roads requiring rider focus
Return after dark is possible

This ride is intended for experienced riders who enjoy longer days and challenging roads.

Event location:
WI-171
Gays Mills WI 54631
See map: Google Maps
Event route: 
GPX File(s):

Closed Event: Chapter activities are conducted primarily for the benefit of H.O.G. Chapter members. Closed Events are those events open to Chapter members and one guest per member.  All guests must sign an event release. Be aware, all rides and events are subject to change or cancellation due to weather or other circumstances beyond our control.

Impairment Policy: The consumption and use of alcohol is a serious personal responsibility involving the safety of family, riding friends and the individual HOG member. Alcohol consumption before or during a motorcycling activity is not safe, responsible behavior. Woodstock Chapter #5668 does not allow the use of alcohol or drugs before or during a riding event* and does not furnish alcohol at Chapter rides. Riders whose skills are observed or suspected to be impaired by alcohol or drugs before riding cannot join the ride. Riders using alcohol or drugs while riding will be asked to leave the ride. It is the responsibility of each Template Chapter member to support the consistent enforcement of this policy

Photography Policy: Photographing, filming, recording and videotaping of activities and events will be occurring Woodstock Chapter events. By entering the H.O.G.® event area, you irrevocably grant permission to the Harley-Davidson Motor Company® and its agents to photograph, film, record and/or videotape you and use (and authorize the use of) your name, image, likeness, voice, and/or biographical or other information in any and all media now known or hereinafter developed in perpetuity for any and all purposes.

Event Coordinator: 
Chris Roddick
Head Road Captain

headroadcaptain@woodstockhog.org