Killington–Rutland Loop
~53 miles • Big loop
North on Rt. 100, left on Rt. 4 into Rutland, left on Rt. 7, left on Rt. 103 toward Ludlow, then left on Rt. 100 back to start.
Killington–Proctorsville Out & Back
~18 miles round trip
Scenic villages, the Proctorsville Green, and stops at Singleton's Store and Crow's Corner Bakery along the way.
Route 100 North to Plymouth
~11 miles • Flat to rolling
A relaxed cruise north through a scenic valley with gentle terrain — perfect for warm-up days.
Gravel Ride to Plymouth via Lynds Hill
Gravel • Climbing
Exit Killington on Rt. 4 West, right on 100A, left on Lynds Hill Rd for a 1.5-mile climb, then descend into Plymouth. Finish at Long Trail Brewing on the Ottauquechee River.