Ye Olde Frederick 300 is a club favorite, designed by Crista Borras and ridden almost annually since the late 1990s. Starting from Frederick, the route heads north, skirting South Mountain as far as Thurmont and then turns west to climb MD77 through Catoctin Mountain State Park. Just short of the summit, it heads roughly north-north-east into Pennsylvania and through the rolling apple and peach orchards of Adams County. Along the way it climbs Jacks Mountain Rd, with its multiple false summits and swooping descent to a covered bridge.

From Arendtsville, the route turns northwest and begins a long, stair-step climb with many steep sections, just to get you properly fatigued before the climb up Big Flat. After turning left on Shippensburg at mile 59, you’re finally ascending the false summit before Big Flat (altitude 1650 feet) before a rapid descent to a stop sign at Pine Grove Rd, followed by the real climb to the summit of Big Flat (altitude 2040 feet). Nine miles–including the sweetest descent on any of our routes–brings riders to a much needed rest stop and control in Shippensburg.

By this time, you’ve done about half the climbing of the ride, so keep your spirits up, it does get a little easier, with the lovely sequence of Mud Level Rd, Oakville Rd and Red Shed Rd. If you want to get back to Frederick, there’s just one more big climb over South Mtn on Whiskey Springs Rd, and then the terrain is rolling all the way home, with a stop in East Berlin for pizza, to get you ready for that long haul down to Thurmont for a final chance of resupply before the last miles in to Frederick.

Google drive with cue sheets and brevet card.