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The Great Appalachian Adventure 4

by | Sep 3, 2025 | Appalachian Trail

Damascus to Harpers Ferry (Mile 470 to Mile 1026)

Damascus was the first major ‘hiker vortex’ town we encountered. People would walk in, everyone planning to take a zero, enjoy a hot meal, see familiar faces, and hike on. However many hikers struggle to leave the comforts behind on departure day!

We managed to escape the vortex, mostly because of the clock ticking on the visa. There was however, a very jolly night with Slim, Bagel, Scoops n Blue, singing songs to the guitar. So, with a later start than usual, we took the Virginia Creeper Trail. This is one of the ‘Rail to Trail’ tracks that are becoming more common in the States. Old railroads – reliably flat, wide, and usually near water – have been converted into biking and hiking paths. On a dreary, drizzly morning, it made for a fast and pleasant walk out of town. 13 easy miles, and then back up into the mountains to rejoin the trail.

Virginia views

Shopping for trail meals – main source of nutrition for 5 months!

Our next major ‘highlight’ of the trail was yet another steep climb to high altitudes – the Grayson Highlands, home of the famous wild ponies. It would be 2-3 days of sustained high altitude during an unusually cold spring. The highlands were ecologically unique, with lots of balds. These are big, wide open spaces that have very few scraggly trees and lots of wide open meadows.

But, there were ponies. And snow. May 1 and there were tiny little flakes falling from the sky. In the morning, at the designated shelters (there is no free camping in the Highlands) hikers were waking up to frost, crunchy socks, and beautifully freezing scenery. Unfortunately it was also way too cold and wet to take photos

We hurried through, and began the final ascent to the famous ‘Friendship Shelter’. It is the first fancy shelter on the trail, with fancy meaning that it has four walls and a roof. Also, a hot shower (usually, but not always in service). There is a visitor center nearby that is friendly to hikers, heated, and has a land line which is most frequently used to order pizza from the nearby town. After leaving Damascus, this is THE highlight.

It is also the jumping off point for the shuttle to Marion – a handy town to re-supply, have a hot meal, go to an outfitters, and even do laundry if you stay at the hostel ‘Merry Hiker’. This hostel is conveniently located downtown above the outfitters.

From Marion, the next town stop was Pearisburg. Along the way we stopped at the appropriately-named Quarter Way hostel. 

Shelters are always a welcome sight

walkbridge over a river

The section approaching Roanoke passes through Dragon’s Tooth – dramatic rock formations that proved to be quite treacherous coming down in the wet. At the bottom, there’s a sign warning of a hazardous trail. Unfortunately they don’t give you the same warning coming from the other side

Descending the dragon’s tooth. Yes, that’s the trail

A misty day for the dragons tooth

Arriving in Roanoke was timed well to come off-trail for the annual Trail Days Damascus. It’s a yearly event to celebrate the Appalachian Trail community, and many previous, current and future hikers come together to celebrate the trail. We met a guy that was celebrating the 20th anniversary of his hike – a year where it rained over 75% of the days on trail! The weather for us had definitely been better (so far…)

Tent City at Trail Days in Damascus

Hiker parade at Trail Days

After Trail Days, we headed back to Roanoke to return the hire car and continue the trail. First up was McAfee Knob, which is the most famous spot for photos along the trail. There’s an outcrop of rock that with the right photo framing looks like you’re hanging out over a cliff. 

McAfee knob

Eagle deciding to jump. A few hikers prob felt the same way by now

Next stop was the Devils Backbone brewery. It’s a short distance from the trail, and they let thru-hikers stay for free in their campground. Unfortunately the beer was not also free. It’s a huge establishment and a comfortable place to stay

Devil’s Backbone brewery – before the crowds

Great weather led to campfires as an option

After the brewery, the next milestone is the Shenandoah National Park. For hikers, the highlight through here are the many cafes catering to day visitors to the park. Plenty of opportunities for sugar! However we took an even better option – a 2-day paddle down the Shenandoah river from Waynesboro to Luray. The daily elevation gain on the river was much better! The aquablaze, as it’s known, was a welcome reprieve from the hiking. There’s a series of minor rapids along the 40-mile paddle. Due to the low recent rainfall, the river was very low and led to some exciting rapids! We said goodbye to our reliable canoe and rejoined the trail at Luray, unfortunately just before the infamous rollercoaster
Paddling the Shenandoah river
Rapids – one where I was ok to have the phone out for
The “rollercoaster” is a 13 mile section of the AT at the end of Virginia that is infamous for 10 substantial ups and downs. It’s about 5000 feet of up and 5000 feet of down packed into 13 miles, with very little (nil) flat points in between. While I can understand why the hiking enthusiasts that run hiking clubs are proud of the challenge they’ve created, it really sucks when you’re 1000 miles into a hike that’s already challenging enough without having to endure this mess when a smarter route could easily wind through the terrain instead. I was not impressed. It’s a terrific example of marketing triumphing over elegant design. Maybe I was just hangry. Fortunately the Bears Den hostel is about 5 miles into the rollercoaster, and is really close to the Bears Den brewery. The brewery has a great garden and views through to the Washington monument in DC on a clear day (which we had!). A great spot to celebrate hitting the 1000 mile mark
Views of the Shenandoah
Bears Den Brewery – fantastic beer garden
After grumbling my way through the remaining 8 miles of the rollercoaster (turns out I wasn’t hangry – just grumpy), we finally made it to the end of Virginia! The AT runs through 500 miles of Virginia, which means it encompasses nearly a quarter of the whole trail. Following Virginia is the shortest state – West Virginia with only 4 miles. Maryland follows with 40 miles, and so some hikers will start at the Virginia border, and attempt to do the “4-state challenge” and cover Virginia, West Virginia, Maryland and into Pennsylvania in one day. However this means skipping through Harper’s Ferry, which is a gorgeous little town & full of history – it was quite pivotal in the US civil war period. It’s also the psychological half-way point of the AT, and a short train ride to take a side trip to see Washington DC. There were also a lot of hikers that start/end their section hike of the AT here – turns out not everyone can take 6 months off their life and do it all in one go… After a couple of rest days in Washington, it was back to the trail. Next up – Pennsylvania and it’s infamous rocks…
Finally! The end of Virginia!