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Maryland Challenge Hike via Appalachian Trail

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Distance:
41.6 Miles / 66.9 km
Type:
One-Way
Difficulty:
Strenuous
Time to Hike:
20 hours, ~48 minutes
Features:
Appalachian Trail hike
Surface Type:
Dirt
Town:
Highfield-Cascade, Maryland
Directions:
39.719933, -77.507633
Added:
March 22, 2025
Updated:
April 06, 2025
Copy Trail Link Hiking this trail? Send a friend or family member a link to this trail guide for your own safety. Hike at your own risk (disclaimer)
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1,632'

Total Change
6,202'

Ascent
7,171'

Descent

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Maryland Challenge Hike via Appalachian Trail

We did this hike as a one day 41 mile benefit challenge hike for the Blue Sky Fund, but we recommend doing it as a 4 day backpack, as also described on this site, which we used for planning our hike. This is also a very busy portion of the AT. If you can only do a day hike, park at the I-70 Parking area and hike 2.3 miles north on the A.T. to see Annapolis Rocks and then 1 more mile to see Black Rocks.

The directions below should give you enough information to keep your orientation and know how far you have come. We will also highlight the places to camp if doing this is done as a backpack.

DAY ONE -10 Miles

  • Mile 0.0 โ€“ 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 โ€“ Side trail to High Rock, supposedly really good views.
  • Mile 5.3 โ€“ Raven Rocks Shelter
  • Mile 6.2 โ€“ MD 491 intersection. Couple of creek crossings near here
  • Mile 8.8 โ€“ MD 77 (Foxville Rd) intersection
  • Mile 10.0 โ€“ Ensign Cowall Shelter, camp here for day 1.

DAY TWO โ€“ 8.4 Miles

  • Mile 10.3 โ€“ 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 โ€“ 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 โ€“ Reach spur trail for Annapolis Rocks. 0.25 miles to the Rocks.
  • Mile 18.3 โ€“ Pine Knob Shelter, this is the Day 2 campsite.

DAY THREE โ€“ 12.8 Miles

  • Mile 18.9 โ€“ 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 โ€“ Boonsboro Mountain Rd, 1st crossing.
  • Mile 19.7 โ€“ Boonsboro Mountain Rd, 2nd crossing.
  • Mile 21.9 โ€“ Pass through Washington Monument Parking lot. Note: Coming south before reaching the parking lot is a spur trail to the Monument.
  • Mile 23.7 โ€“ 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 โ€“ Dahlgren Backpack Campground. Privy and hot shower.
  • Mile 24.8 โ€“ Reno Monument Rd.
  • Mile 25.7 โ€“ Rocky Run Shelter
  • Mile 26.2 โ€“ Lamb's Knoll Rd
  • Mile 27.9 โ€“ White Rock Cliffs
  • Mile 30.7 โ€“ Crampton Gap Shelter, this is the Day 3 campsite.

DAY FOUR โ€“ 10 Miles

  • Mile 31.1 โ€“ Crampton Gap/Gathland State Park Parking (Parking Lot Coordinates: 39.406,-77.6393). Continue on the AT by crossing Gapland Rd.
  • Mile 34.9 โ€“ Ed Garvey Shelter.
  • Mile 37.0 โ€“ Weaverton Cliffs Spur Trail.
  • Mile 38.1 โ€“ Route 340 Underpass.
  • Mile 38.4 โ€“ Railroad Crossing, turn right at C&O Canal Towpath
  • Mile 40.0 โ€“ Sandy Hook, Rt 340 Underpass
  • Mile 41.2 โ€“ Middle of Goodloe Byron footbridge into Harpers Ferry, WV.
  • Mile 41.6 โ€“ Train Station parking lot (small fee for 3 days).
    (Parking Lot Coordinates: 39.32442,-77.73)
Explore 22 trails near Highfield-Cascade, MD
  1. Parking

    39.719933, -77.507633
  2. Main Trailhead

    39.719665, -77.507
No community routes found. To add your own hike as a Community Route for this Trail guide, leave a Trip Report with an attached GPX file.

Hazards

Snakes
Poison Ivy/Oak

Seasons

All

Blaze Color

White

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Trail Guide By:
HikingUpward user profile picture
41.6 miles / 66.9 km

Weather Forecast

In Highfield-Cascade, MD

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