Skippy’s Burger Bar
KICKSTANDS UP: 10:00am
ROAD CAPTAIN: Jim G / Barlas B
DEPARTURE: Windy City HD parking lot
DESTINATION: Skippy’s Burger Bar – Thiensville, WI
LEVEL: 2
MILEAGE: 135 (about 4 hrs)
There’s nothing quite like rolling out for a 135‑mile ride that blends open‑road freedom with a couple of iconic stops along the way. The route winds through scenic stretches and easy‑cruising backroads, eventually climbing toward the Harley Oil Can Silo at Hilltop Haven. The silo stands like a beacon for riders—part landmark, part bragging rights, and fully worth the miles it takes to get there.
After soaking in the views and grabbing a few photos, the ride continues with that perfect mix of curves and straightaways until it’s time to refuel the riders, not the bikes. The final stop lands at Skippy’s Burger Bar, where lunch hits the spot after a morning in the wind. Burgers, stories, and the satisfaction of a solid ride make it the perfect wrap‑up before heading home.
