High Rock

Where: Pen Mar High Rock Rd., Cascade, MD (For GPS purposes, try plugging in 14600 Pen Mar High Rock Rd. This is Pen Mar Park and High Rock is NOT in Pen Mar Park, but this gets you on the right road and you simply continue up past Pen Mar Park until you come to High Rock)
When: Well, it’s rocks so it’s there whenever.

I need to begin this post by telling you that High Rock is incredible but I demand to know who was in charge of naming it. Could you really do no better? It is a rock outcropping, and it’s quite high, but surely there was some other quality, some spirit of imagination that could have been looped in to the name instead of just… High Rock?

Look at this high rock.
Yeah, wow. What should we call it? Devil’s Peak? Widow’s Nest? God’s Pillow? Stairway to Heaven?
Let’s call it High Rock.

I have, strangely enough, the Vans Warped Tour to thank for introducing me to High Rock. In the strange way that Instagram algorithms work, a picture of some members of some band on the Vans Warped Tour doing community service on High Rock got propagated into my feed. What I noticed first was the great graffiti covering the rock they were standing on. Then I read the caption which said something like, “Vans Warped Tour doing community service cleaning graffiti off High Rock today” and I thought WHAT NO, YOU CAN’T CLEAN OFF THE GRAFFITI, THE GRAFFITI IS GREAT! It’s not often that graffiti enhances a natural landscape but from time to time, something just clicks and I have to say, in the case of High Rock, the graffiti somehow just makes the whole thing better. Don’t hate me, nature purists, I’m kind of a magpie and colorful things appeal to me.


High Rock lies on South Mountain in Northern Maryland (hee!) right along the Mason Dixon Line. It’s situated on the Appalachian Trail and is a popular lookout spot and hang gliding platform. People also somewhat frequently fall off and tumble to their death. Not trying to scare you or anything, just think you ought to be warned! This really is a rock you want to be respectful of. There’s no fencing or railing surrounding the rock, and the dropoff isn’t one of those fake-out ones where it looks like a sharp drop with dirt 2 feet below. It’s, you know, A DROP. So if you take kids, just keep a close eye on them. Especially with the wet weather we had, the combined effect of rain on spray paint is a quite slippery walking surface. Be safe, my dudes.

Despite the hard work of the Vans Warped Tour, High Rock, I’m pleased to say, is still covered in all manner of graffiti. We got up early on a Saturday morning and headed out since it was a good 60 mile drive from our house, and when we got there I was happy to see that the Vans Warped Tour had not eradicated all the graffiti I had been hoping to see. Rainshowers were moving in and out of the area quickly, and shortly after we arrived, a cloud moved over us and obstructed the view of everything beyond High Rock, lending it a surreal quality wherein you could not quite tell where the end of the rock was and the dropoff began or just how high up you were (1800 feet up, FYI). We were all alone up there and it felt like we really just perched up in the clouds.


The rain did begin driving a bit more steadily so we retreated to the car and waited a bit and eventually when the rain dissipated we made our way back up to the rock and were rewarded with a brief but stunning view of what lies beyond High Rock when it isn’t obscured by clouds:


As the sun broke weakly through the clouds, a few more cars pulled up and several of us stood and watched the valley below us open up for just long enough to get a view before the clouds started rolling back in.


Even this little friend enjoyed the rock (and is a good reminder to please leash any pets you bring along):


High Rock is accessible via hiking on the Appalachian Trail, but it’s also ridiculously easy to access by car. As in, you just drive up Pen Mar High Rock Rd until you see the small pull-out lot on your right with the rocks right next to it. Definitely wear workout gear and good shoes so that everyone who sees pictures thinks you hiked up a really tall mountain to get there, but your secret is safe with me. I found a hiking log of the trek up to High Rock and it mentions lots of switchbacks and a steep climb so just say that and nobody will ever know.

The best part of the trip to High Rock for me was when I posted pictures of it to Facebook and my dad posted a picture of himself there… in 1982. The rock was pure and free of graffiti and my dad was in stonewashed jeans, a crop top, and had bangs and a mullet. Time moves on, my dad definitely does not wear crop tops now, and the youth have covered the rock in paint, but through a fun wormhole in time known as the Internet, my dad at 19 and I at 31 were in the same place.


High Rock made me happy. My kids loved it, my husband loved it, the view were stunning, and even in the rain it was well worth the trip. I can only imagine it’s even better in the fall with all the foliage down below, so we’ll be making a return trek back then. Add this one to your hiking list for sure, definitely at least before the next Vans Warped Tour comes through and tries to de-graffiti it.

Bears Den Overlook

Where: 18393 Blueridge Mountain Rd., Bluemont, VA
When: Gates open daily 8 am – 9 pm

I had a moment yesterday. I was hiking with my girls, reassuring them we were about to see something REALLY REALLY COOL, and I thought to myself, “Wow. I am my father’s daughter.” My dad is your consummate outdoorsman. He ran a week-long 150 mile race through the Sahara Desert once for fun. Among his life goals is the desire to reach the highest point in each state in the US. Years ago, he took my sister and me on a “walk” that ended up being about 12 miles up and back the highest point in the state of Alabama. We nearly died (in our minds) and he was like, “What, you thought that was hard?”

Mostly, I’m not like that. I have moments of delusion where I fancy myself to be rather outdoorsy but by and large, I like air conditioning way too much to ever really claim the title. But, as is typical of delusional and fanciful people, I can easily be persuaded to forget my own nature and assume another when something compels me. Like pretty Instagram pictures of a rock outcropping along the Appalachian Trail that creates an overlook you can hike to. “Yeah,” I think to myself. “Yeah, I can DO THAT!”

So that’s how I came to abandon my plans to go to the pool and instead ended up on the Appalachian Trail. Viva delusion!

The spot I’m discussing here is Bears Den, located in Bluemont. Virginia houses 550 miles of the Appalachian Trail and Bears Den is located on the so-called “Roller Coaster” section of the trail, named for its hills. What was once the home of Dr. Huron Lawson has morphed over time into its current incarnation as a hostel for thru- hikers offering lodging, showers and bathrooms, and a campground. From Bears Den one can hike to an Overlook that perches above the Shenandoah Valley, offering incomparable views.

Luckily, Bears Den also has a day-lot for people who, rather than devoting massive amounts of time, energy and money to hiking the entire Appalachian Trail and sleeping wherever they can along the way, prefer instead to drive up, walk on it for a bit, and then get back in the car and go home. I read on the Bears Den website that the Overlook was a “short stroll” from the day parking lot and I thought, oh, that sounds great for us! We can totally do a short stroll!

Let me tell you something about the word “stroll.” It’s incredibly misleading. I spent three weeks in India in 2007 trekking the Himalaya because a trip there was presented in a way that specifically mentioned the phrase “strolling through alpine meadows.” (And also, again, delusion that I am the type of person who does things like trek the Himalaya.) I had incredible visions of Sound-of-Music style twirling and gallivanting through lush green meadows with glorious mountain views. What I did not take into account was that alpine simply means “relating to high mountains” and the phrase “strolling through alpine meadows” doesn’t promise that your “stroll” will be a simple, pleasurable walk. It means it’s gonna be a walk on a HIGH MOUNTAIN. And you’re going to be “strolling” for 12 hours at a time and be carrying a trekking pack that carries everything you’ll need for 2 weeks which your guides insist only includes two pairs of underwear.

India is another story for another time. But I just want to give you some background on how the word stroll continually misleads me. I again wrongly assumed we’d pull up in the parking lot, Maria von Trapp our way through some meadow, and end up at a rocky outcropping overlooking the Shenandoah Valley while also being able to claim we “hiked the Appalachian Trail.”

Well, that’s sorta what happened. To begin, we did park. Parking in the day lot at Bears Den costs $3 for the day. A small box is located at the top of the parking lot and inside are envelopes into which you will place your $3 parking fee, then detach an included flap to stick on your dash to let everyone know you paid.

This magnificent creation was also located in the parking lot:

Bears carved into a tree. Just the parking lot of Bears Den alone is one of my favorite new finds this summer.

There’s several available options for getting to the Overlook from here. I know them now that I’m looking at a brochure I picked up at the Lodge which includes a trail map, but at the time I didn’t know which way to go so I followed a group of hipster teenagers who could see I was trying to get my bearings and said “The rocks are this way.” Oh, helpful hipster teenagers. So kind and friendly!

So I went that way, to begin the “short stroll.”

The trail we took, I now see, was the Historic Trail, which is 1/2 mile long (each way) and labeled “moderate” in terms of difficulty. Hmm. Okay, I do believe it’s moderate for most adult hikers. My kids are not adults though and this was decidedly not-moderate for them, perhaps more on the side of “challenging” but I will say they handled it with great aplomb and were champs about the whole thing. Yes we all had to clamber up rocks. Yes they each fell and got a scrape on their knee. Yes I nearly took a thorned branch to the face while carrying my toddler. But we all made it through our “short stroll” just fine.

I did enjoy the hike but because I had been conditioned to think this would be a “short stroll” I started to get a little concerned when no outlook was appearing and the trail was getting more and more “moderate.” Why had we been walking so long? They said “the rocks” were this way. I started questioning my helpful hipster teenagers. Hipsters. Why did I think I could trust them? They weren’t even wearing clothing appropriate for hiking!! They tricked me and I hate them.

Oh wait, I hear voices. It’s the hipsters!! At the outlook! I can see it through the trees now. Nobody tricked me after all. Hello kind, sweet, friends, we meet again, here at this great spot nature has created for us all to enjoy together.

And this is what the Shenandoah Valley looks like from 1350 feet up. You can sit on these rocks and contemplate the land below and mentally congratulate yourself, “I hiked this.” Someone who is ACTUALLY hiking the trail will clomp past you, loaded down with their worldly possessions on their back and a cheerful dog walking alongside. Pay them no mind. You are a hiker too.

The map I later picked up suggests that the Blue Blaze Loop might be an easier path if you wish to attempt this trip with your kids (and I think you should! It was incredible!). The Blue Blaze Loop is only 1/3 mile and is labeled “easy” as opposed to the 1/2 mile “moderate” Historic Trail that I took. If your kids are bit older, the Historic Loop would probably be fine, but my toddler obviously had some difficulty and needed carrying through certain portions. If you’re toting a baby/small toddler in a backpack carrier, you could still do the Historic Trail, but would just need to be careful on the portions that require a bit of rock climbing. Next time we go I’ll try the Blue Blaze Loop and report back.

Regardless of which trail you choose to take to reach the outlook, I think your kids are going to love the hike. My oldest felt incredibly accomplished when she saw the destination she had worked hard to reach. “I AM A HIKER” she said. “I hiked the Apple Trail.”

“It’s actually the Appalachian Trail” I corrected her.


And you know, when you’re just about 6, that’s no small shakes. I never know how my kids will respond to the outings I plan for us; sometimes they don’t enjoy things I just swore they would love, and sometimes, like our trip to Bears Den, they surprise me and enjoy the hell out of something I thought they would merely tolerate. Both of them did so well I am convinced that they got more of my dad’s genes in them than I did. They just might be my father’s granddaughters.

My husband was incredibly jealous he was not able to do this with us (God bless the man, he works hard so I’m able to do things like hike a mountain in the middle of a weekday afternoon with my kids) so we are definitely planning a return trip soon. The overlook is westward facing so the sunset views have to be incredible. I would be tempted to bring a bottle of wine with me to enjoy the sunset with but then again, rocky paths + unsteady footing might just be asking for trouble. Not saying I wouldn’t still do it, just that I would temper expectations for how well the return hike would go. And bring Band-Aids.

Handy tips:

-Bring exact cash or coins to pay your parking fee. There’s no guard shack or attendant, so nobody’s going to swipe your card through a Square Reader or break your twenty.

-Wear appropriate shoes. I want to think this is self-explanatory, but if you wear sandals to hike the Appalachian Trail, you’re gonna have a bad time. 

-If you’re unsure which trail you’d like to take, walk up to the Lodge and grab a handy dandy map. It lays out every trail option along with length and difficulty of trail. Or, you can be like me and blindly trust a cadre of hipster teenagers. That’s your call.

-There’s no trash cans at Bears Den, so if you bring any drinks or snacks to enjoy up on the overlook, be a pal, pack the trash back out with you, and dispose of it later once you’ve left the park.

Most of all, I want to say that if you don’t think you’re an outdoorsy person who would enjoy this, try embracing a little delusion. You can do powerful things with delusion! I trekked the Himalaya on the fuel of delusion. Just tell yourself you’re a hiker. You’re tough. Tell yourself that girl from Novadventuring did it with two little kids, so if she can, you definitely can!

Because this is the view that awaits: