Looking for a challenge? This route from Woodbine might be just what you are looking for. Starting innocently enough, the route heads southwest from Woodbine across rolling terrain, through Damascus, to the first control at the Dickerson Market. Then the fun begins as it climbs Mountville Rd over Mar-Lu ridge (yes, the hard direction), plunges back down to the town of Jefferson, goes over a series of rollers to Burkittsville (made famous in the movie, "The Blair Witch Project"), and then heads over South Mountain at Gathland State Park, passing the only monument to war correspondents. The descent from South Mountain is followed by an even nicer descent down Burnside Bridge Rd. (with a view of the famous bridge itself at one point) to historic Sharpsburg, and then an easy five miles to Shepherdstown, WV, where riders can reward themselves from the delicious goodies at the Shepherdstown Sweet Shop. Don't eat too many sweets though, because the climb back across South Mountain on Reno Monument Rd is somewhat steep. The road is named for a monument at the top to General Reno, who died at the spot during the civil war. No cyclists have died on the climb - at least so far. After climbing back over Catoctin Mountain on Shookstown Rd., the route follows rolling piedmont east to the final control in New Windsor, before turning south back toward Woodbine. Save some energy for those final 15 miles, because  they include two very pretty, but steep, climbs on Buffalo Rd. and a few short steepies on Watersville Rd. Riders will finally be rewarded by a pleasant half-mile of downhill to the finish. Estimated climbing is 9100 feet.

Lights and reflective gear are required for riders starting before sunrise at 07:09 AM and finishing after sunset at 04:44 PM.

Not sure what reflective gear means? "Between sunset and sunrise and during other low-light conditions, all riders must wear a reflective vest or some other device that clearly places significant reflective material on the front and back of the rider. During these times all riders will also wear a reflective ankle band around each ankle."

Ride Materials.