Damascus, Virginia: The Friendliest Town on the Appalachian Trail (and the TransAmerica)

 I took a day off in Damascus, Virginia (a.k.a. Trail Town, USA) to sample the Virginia Creeper Trail and the Appalachian Trail

Damascus is a confluence of seven different trails and routes. It’s no wonder why. Deep in the heart of the Appalachians, the town of just 1,025 people is surrounded by fabulous scenery and cultural significance.

Damascus lives up to its reputation as “the friendliest town on the Appalachian Trail.” Everyone I met here genuinely cares about the hikers and bikers that pass through and wants to help us on our journey. Stop and meet them!

Virginia Creeper Trail

Ride the Virigina Creeper Trail

I had heard great things about the Rails to Trails Conservancy, which repurposes decommissioned railways into a nationwide trail network. So I jumped at the chance to ride one of their biggest success stories — the Virginia Creeper Trail.

The U.S. Forestry Service estimates that over 200,000 people visit this trail each year. That provides enough business for eight bike rental and shuttle services in Damascus. They’re all so friendly that they recommend each other. I went with Bicycle Junction and rented a bike because Blucifer is just a road bike with skinny size 28 tires, so I didn’t want to stress him out on the gravel. The shuttle carted us up to Whitetop Mountain for the group to enjoy the 17 miles of downhill, dropping 2,000 feet in elevation.

For TransAm cyclists whose bikes can handle the gravel, the DIY way is to pedal yourself up to the top of Whitetop Mountain on the road, which is on the route anyway. For Westbounders, you could even take the trail down into Damascus instead of the road!

I was happy to do it the touristy way. Blucifer got treated to a chain cleaning at Sundog Outfitter while I was out riding not-Blucifer. The mechanic didn’t charge anthing. I repeat. Friendliest. Town. On. The. Trail.

Appalachian Trail in Damascus VA

Walk a mile on the Appalachian Trail

I believe that through-hikers and traveling cyclists are two species of the same genus. We’re both on these months-long, muscle-powered, transformative journeys. We’re both outside all day swatting at bugs and dodging rainstorms. We’re both roughing it with the occasional splurge.

We cyclists can meet our on-foot counterparts in Damascus. This is where our route intersects with the Appalachian Trail, which stretches 2,190 miles from Georgia to Maine. Each May, Damascus hosts a big Trail Days Festival that attracts thousands of hikers, past and present.

If you want a glimpse into the life of a through-hiker (minus the heavy pack), you can walk a few miles on the Appalachian Trail from Damascus. I went up the stairway marked ‘Appalachian Trail’ and started following the white blazes on the trees. A segment of this trail is trail is now on my autumn hiking wish list.

Damascus Old Mill Inn

Feel the LOVE at the Old Mill Inn

As the saying goes, Virginia is for lovers. You can find the photo-op to prove it at the Damascus Old Mill Inn. My stay at this historic landmark hotel stands out a lodging highlight of the entire cross-country trip. It’s the perfect retreat for trail-weary hikers and bikers. They even have a special room rate just for us.

If you can’t stay the night, I recommend stopping by for a local craft beer, a good meal, and a photo with the LOVE sign that reflects on the water. Did I mention they serve local gourmet cheesecake? Main ingredients: love and friendliness.


7 Trails Grill Damascus

Eat at the 7 Trails Grill

This is another good spot in town to mingle with locals and trail travelers alike. The bike mechanics at Sundog mentioned there’d be live music, so I mozied on over for some entertainment. Good times! I learned that “country outlaw” is a music genre.

Damascus is also on The Crooked Road, Virginia’s music heritage trail. The town attracts talent from all over the Appalachian region. Between 7 Trails Grill and the Old Mill Inn, you’re likely to find a good live music performance, and a local craft beer to go with it.

Damscus Old Mill Inn

My spin on it: if you’re needing a day off from the road (or a “zero day”, as the through-hikers put it), Damascus, VA is the trail-friendliest place to do it.

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  • Reply
    Ken Moore
    August 24, 2019 at 2:10 am

    What a remarkable journey this has been for you and all of us following your blogs and pictures. Kudos Cynthia for finding the beauty in our country that is so refreshing for us to see and find solace in. The mention of all the friendly people along the way and their support for all you bikers and hikers. This restores our uplifting faith in humanity and you are doing it in such a unique fashion. We will all hate to see this come to an end — what a GREAT accomplishment.
    Aunt Mary

  • Reply
    August 24, 2019 at 7:30 pm

    A very nice little write up about Damascus, thanks so much! It was great meeting you as well. I’ve enjoyed reading entries on your blog site too, some cool stuff indeed. Best wishes from that “Sundog ” mechanic guy 🙂

  • Reply
    Douglas Brownfield
    August 27, 2019 at 1:43 am

    Hey there Cynthia! I’ve enjoyed all your posts, especially the one about Berea KY, but Damascus tops them all! Makes me want to visit there. Officially on my “Bucket List” now.

  • Reply
    Eddie Howington
    November 11, 2020 at 3:18 pm

    I have rode the Creeper Trail for years. And yes the nice friendliest people you’ll ever meet. I ride with Blu Blaze bike rental as you enter Damascus. Rick and his team more excellent and have great bike.

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