PenMar Feud Hike!
Details
🌄 PenMar Feud Hike: Raven Rock → High Rock → Pen Mar Park 🔥🍁
Saturday November15th, we’re hitting one of the most scenic Appalachian Trail sections around HFB style!!! — and we’re doing it point-to-point so we get maximum views without the out-and-back.
We’ll start at the Raven Rock Road Trailhead, close to Smithsburg MD, pass the Raven Rock Shelter, climb to High Rock Overlook, and finish at Pen Mar Park.
(You can google Raven Rock Road Trailhead for the address to start. Its a long, wide pull-off on the regular road, not a parking lot)
The end parking lot address is Pen Mar Park, 14600 Pen Mar High Rock Rd, Highfield-Cascade, MD 21719
➕ Fun history twist:
We’ll be walking the actual ridgeline where surveyors Mason & Dixon argued over the PA/MD boundary, giving this route its nickname:
The PenMar Feud Hike.
Old-school state-line drama. Modern-day adventure energy.
✅ ~5–5.7 miles
✅ Moderate — the first mile has a steep, rocky climb, then it flattens into beautiful ridge walking
✅ 10/10 views — overlooks, ridge lines, big skies
Plan:
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Meet at Pen Mar Park to drop a couple cars.
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Drive together to Raven Rock Trailhead.
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Hike → Raven Rock Shelter → High Rock → finish at Pen Mar Park.
After the hike: Celebrate the ridge we conquered!
We’ll make a stop at Springfield Manor (winery/brewery/distillery) for a celebratory toast — all ages welcome (beautiful property + snacks + views).
✨ great people, chill vibes.
Come for the views. Stay for the laughs. Enjoy the brew.
And now, come for the colonial-era boundary beef, too.
If you’re in, text and let me know to expect you, drop a comment if you can help shuttle!