Hike the Appalachian Trail: From Mason-Dixon to the Potomac

Speak with local history experts, visit Harpers Ferry and learn about the region’s traditions and culture as you spend four days hiking the Appalachian Trail’s “Maryland Challenge.”
Program No. 21357RJ
6 days
Starts at

At a Glance

Complete the entire Maryland stretch of the Appalachian Trail! Inspired by participants who took our popular program “Hike the Appalachian Trail in Four States!” (#18537), this hiking adventure takes on a different section of the trail — “The Maryland Challenge” — stretching 41 miles from the Mason-Dixon Line to the Potomac River. While some super-endurance hikers tackle all 41 miles in a single day, we will cover the distance at a more leisurely pace, spanning the state of Maryland over four days. Meet some knowledgeable locals and hear from regional experts on topics such as the geology of the Appalachian Trail, Civil War history and traditional healing plants and medicinal herbs.
Activity Level
Varies by date
Hiking up to 12 miles daily over varied terrain.
Small Group
Small Group
Love to learn and explore in a small-group setting? These adventures offer small, personal experiences with groups of 10 to 24 participants.

Best of all, you'll ...

  • Brave the steepest descent in Maryland down to a small tributary of Grove Creek and cross Little Antietam Creek on your way to summit Quirauk Mountain.
  • Meet a Civil War expert who transports you back to the fierce fighting that took place at South Mountain.
  • Follow a portion of the C&O Canal Towpath along the Potomac River to historic Harper's Ferry.

General Notes

The Retreat Difference: This unique, often basic and no-frills experience at a Road Scholar Retreat includes opportunities for early morning exercise, interaction with the local community for insight into local life, an authentic farm-to-table or locally sourced meal, a live performance or event, and a value-priced single room. This program is based at Shepherd’s Spring, 15 miles from the closest AT crossing. Sag wagons transport cyclists to and from starting and ending locations each day. Due to the nature of this program, listening devices are not available.
Suggested Reading List
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