I did the NOBO prehike to MAHHA 2011 - this year I want to go SOBO maybe from Pen Mar. Here's a preliminary itinerary for anyone who's interested in a southbound hike (so far I count SoundMan and BlackWolf as interested). I'm not locked into number of days or miles, so this is just a conversation starter. This is a 3-day hike covering 31.2 miles - depart Pen Mar Wednesday, 17 October, arrive Gathland Friday, 19 October.
And by the way, I don't know anything about this section, since I've never hiked it, so I'm open to suggestions on a better itinerary. This is just an itinerary I pulled off the web somewhere.
DAY ONE -10 Miles
Mile 0.0 – Parking is at the Pen Mar County Park . If leaving a car overnight you should park in the gravel lot across from the park as the main parking lot is locked each night. The trail begins just to the right of the Overlook Pavilion and A.T. Sign, go 0.3 miles North on the AT, cross the RR Track and then reach the PA Line (Mason Dixon Line). Stop, take a photo. turn around and then head South on the AT, passing Pen Mar Park. Note: If backpacking you could leave your gear at Pen Mar Park and pick it up as you return south.
Mile 3.1 – Side trail to High Rock, supposedly really good views.
Mile 5.3 – Raven Rocks Shelter
Mile 6.2 – MD 491 intersection. Couple of creek crossings near here
Mile 8.8 – MD 77 (Foxville Rd) intersection
Mile 10.0 – Ensign Cowall Shelter, camp here for day 1.
DAY TWO – 8.4 Miles
Mile 10.3 – MD 17 (Wolfsville Rd). There is a short 0.1 mile spur trail to an AT parking lot, 10-12 cars (Parking Lot Coordinates: 39.6283,-77.5593). Cross Wolfsville Rd to continue south on the AT.
Mile 15.6 – Reach a couple of unmarked trails to Black Rock Cliffs in about 5.3 miles. Trail is pretty short to the cliffs.
Mile 16.6 – Reach spur trail for Annapolis Rocks. 0.25 miles to the Rocks.
Mile 18.3 – Pine Knob Shelter, this is the Day 2 campsite.
DAY THREE – 12.8 Miles
Mile 18.9 – I-70 AT Footbridge and spur trail to I-70/Rt 40 Parking Lot, 40 cars (Parking Lot Coordinates: 39.5355,-77.6040)
Mile 19.0 – Boonsboro Mountain Rd, 1st crossing.
Mile 19.7 – Boonsboro Mountain Rd, 2nd crossing.
Mile 21.9 – Pass through Washington Monument Parking lot. Note: Coming south before reaching the parking lot is a spur trail to the Monument.
Mile 23.7 – Turners Gap (Alt US 40, Old National Pike). Parking is directly across the road on the east side of the Inn closest to the AT (Parking Lot Coordinates:39.4841,-77.6198).If leaving car there, ask permission of the South Mountain Inn Lodge staff.
Mile 24.0 – Dahlgren Backpack Campground. Privy and hot shower.
Mile 24.8 – Reno Monument Rd.
Mile 25.7 – Rocky Run Shelter
Mile 26.2 – Lamb's Knoll Rd
Mile 27.9 – White Rock Cliffs
Mile 30.7 – Crampton Gap Shelter, this is the Day 3 campsite.
The Fall MAHHA 2012 hang site is just a few hundred yards up a hill from Crampton Gap, to my recollection.