I was researching off-road biking opportunities in Pennsylvania and decided to head north to Pittsburgh to ride the Great Allegheny Passage and the C&O Canal trail to Shepherdstown WV, a distance of 242 miles. I considered using a Pittsburgh-based bike tour operator to manage the trip, but realized I could save money and make the reservations myself. I bought an excellent Specialized bike bag to handle my clothing and toiletries and made reservations in towns along the way, figuring that I could easily handle 60-70 miles per day.

I arranged for my sister to fly to Pittsburgh so that she could take my car and meet me at the endpoint in Shepherdstown. She also was looking forward to spending some time with her best friend from Penn State, so the plan worked out for everyone.

The drive from Nashville wasn’t bad since I broke it up with a night in Covington, KY across the Ohio River from Cincinnati. I secured my S-Works Crux gravel bike to my sturdy Küat rack and never even detected a rattle.

Even thought I’d spent the first 22 years of my life in SE Pennsylvania, including 4 years at college in Lancaster, I’d never spent any time in Western PA, and was looking forward to seeing it by bike. Anyone arriving via the I-376 tunnel will agree that the downtown skyline girdled by three rivers is impressive. Pittsburgh is known for its overcast skies and this day was no exception. The area just beyond the downtown area looked a bit forlorn and I was disappointed that I didn’t get a chance to visit the Oakland and Shadyside neighborhoods near the University of Pittsburgh, although I grabbed a shot of the Cathedral of Learning from the freeway.

The drive to the airport was a breeze and after picking up my sister we headed to her friend Anita’s house in North Versailles. Anita recommended an Italian restaurant nearby which was good. I then headed to my hotel in Monroeville after dropping them off. The Monroeville Mall was the site of the classic horror movie Dawn of the Dead. The infrastructure in that area of the Pittsburgh metro area is pretty poor. As I made my way up and down over winding, hilly roads in the rain, it was hard to see the lanes since most of the reflective white and yellow lines had worn off.

The next morning was cold and overcast as I headed over to Anita’s to pick up my sister so that we could head over to the Boston GAP trailhead. The day started inauspiciously when Anita’s dog bit my right hand. Fortunately the dog had been recently vaccinated. Then I slipped on her wet front step with my cleats on. On our way to the trail access point on the Youghiogheny River we stopped at a CVS in McKeesport where the pharmacist graciously cleaned the surface wound and wrapped it. It really wasn’t that bad and I never gave it another thought. At the trail, I loaded up the bike and said goodbye and headed off.

For the first 20 miles I was totally alone. The trail was in superb condition as it made its way through the Laurel Highlands with the fast-moving Yough on my left. The only town I passed through was Connelsville, which has seen better days. I also saw several wild turkeys before arriving at my first overnight spot, Ohiopyle, a distance of 56.4 miles.

Ohiopyle is famous for its Class IV whitewater rafting. The rafting and the GAP riders sustain the small Appalachian village’s economy. I spoke with a few other riders at the one motel off the trail and ended up joining them for drinks and dinner next to one of the outfitters. It was pretty quiet since it wasn’t quite tourist season. After dinner, I had a conversation with the young receptionist who told me about the endemic drug and alcohol troubles in the area. She seemed very grateful for the riders and kayakers. I asked her about the nearby Fallingwater, Frank Lloyd Wright’s famous residential project. One would’ve needed a car to get there, unfortunately.

The next morning was sunny and mild, finally! After a good breakfast I walked around Ohiopyle before checking out and heading out for Cumberland MD, the eastern end of the GAP. The ride was magnificent, with broad valleys and the mountains in the distance. Soon I was riding over a long bridge spanning a valley that must have been 50 meters high. Again, I encountered only a handful of riders. In the distance I could see Mount Davis, the highest point in the state at 3,200’ elevation. In Pennsylvania the Appalachians are pretty worn down as they cross the state from the southwest to the northeast.

After about 40 miles, I stopped in Meyersdale, PA for lunch. A few miles beyond Meyersdale I came to the Eastern Continental Divide, something I’d never heard of. To the west, all rivers empty into the Gulf of Mexico eventually; to the east, the Chesapeake Bay.

After passing through the divide the next landmark was the 3,291’ Big Savage tunnel, built in 1912 by the Western Maryland RR through Big Savage Mountain. A few miles later I arrived at the famous Mason-Dixon Line, named after the surveyors who established the colonial border between Pennsylvania and the colonies of Virginia and Maryland before the Revolution. It was later the demarcation line between the free and slave-owning states.

Now in Maryland, the next town was Frostburg, and then a wonderful 17 mile descent down the Alleghenies to Cumberland, MD, where I checked in at the wonderful Fairfield Inn right on the trail next to the Potomac River. They really cater to their cyclist guests and they had an outdoor space where I was able to hose down my bike before storing it. After a 73.8 mile day, I was ready for a shower and a nice dinner.

I ate at an outside table at The Manhattan Social, a nice local restaurant downtown. After dinner, I walked around the town, which was once a thriving railroad center and the embarkation point for settlers headed to Ohio and beyond. Sadly, the town once known as the Queen City has experienced a 50% population decline since 1940 and its per capita income is now ranked 305th out of 318 US metros. Despite its decline, the city has great bones and could enjoy a revival as those looking for a beautiful natural area discover a new place to settle.

Fortunately, May 16 was also sunny and mild, so after a leisurely breakfast I set off on my third day of riding, this time on the flat and occasionally muddy C&O canal trail, with the swollen Potomac on my right. The area had been hit with heavy rain earlier in the month so I knew that I’d be pretty muddy at the end of the day. The trail was bordered with purple and white phlox, among other flowers, and the well preserved locks were worth a brief stop. As in the past two days, I rarely saw any other riders, even though the weather was mild.

The highlight of the day was going through the famous Paw Paw Tunnel, one of the great engineering feats of the 19th century. The 3,118’ tunnel was completed in 1850 and saved the canal builders from the impossible task of following six miles of Potomac horseshoe bends. The canal runs through the tunnel and cyclists are forced to stay on the unlighted path that rises 3 meters above the water surface. I opted to walk my bike across with my bike light on. A woman traveling in the other direction didn’t have a bike light so I directed my beam towards her so she could safely proceed.

I stopped at the Devil’s Alley campsite a while later and had a conversation with a young couple from Ohio headed west. We agreed that the ride was magnificent despite the occasional mud.

As I neared my destination, Hancock MD, I was pleased to be able to jump off the towpath and ride the paved Western Maryland Rail Trail from Little Orleans directly to Hancock, which I reached in mid-afternoon. I’d booked a room at the 1820 Trail Inn, where I was the only guest. The octogenarian owner and his wife opened the house for me after I hosed down the bike and my legs in their parking area. The house was large and conveniently located uphill from the village center and the trail. Like Ohiopyle, the little town would be in trouble without the bikers and hikers on the C&O trail.

Given my taste for the macabre, I gently asked my hosts, who lived down the street, whether the house was haunted. They tactfully replied that some guests had shared their experiences. I was hoping to hear or see something that night. But first I walked down to the river for dinner since I’d only eaten a Clif Bar for lunch.

I ate at the Potomac River Grill and devoured an order of fresh Maryland crab cakes, hand cut fries and cole slaw. After settling my tab I explored the atmospheric town, which looked entrancing on the mild spring evening as the sun began to set. My first stop was St Thomas Episcopal Church, built in 1836, and its historic cemetery, where a Confederate Army physician was buried. A few hundred yards away was Saint Peter Catholic Church, built in 1834 to serve the needs of the Irish and German immigrants who built the C&O Canal. At the Catholic cemetery, I was joined by the parish Golden Retriever and a few minutes met its owner, the parish priest, who gave me a brief tour of the church.

Sadly, the night was peaceful with no ghostly manifestations. My hosts arrived around 8:00 to make me a big breakfast and then joined me at the dining room table. We had a delightful conversation about the town and their families before I headed out to the garage to retrieve my bike and head out for the final leg to Shepherdstown.

Before jumping on the trail, I stopped by a bike shop and had them check the sealant in my tires and was good to go. I followed the paved trail for a while before getting back on the towpath. At one point the trail was covered with a few inches of water, right next to a granite bluff. I navigated it successfully, but was glad when I was out of the Potomac’s flood stage. Since I wasn’t in a hurry, I stopped at a few locks on the way.

I found the Thomas Shepherd Inn easily and the owners graciously provided a hose to wash off my bike and shoes and let me store it overnight. My sister arrived a few minutes later from some meetings in Baltimore. We walked through the historic town and had dinner at a local farm-to-table restaurants and drinks at the now-closed Bistro 112.

The next morning I arose early and took a long walk around this beautifully preserved colonial town just across the Potomac from the Antietam National Battlefield, which I’d visited numerous times in the past.

I highly recommend a trip down the GAP and the C&O Canal, a ride that takes the rider through spectacularly wild and beautiful SW Pennsylvania and Western Maryland mountains and countryside and prominent historical sites often difficult to reach by car. I’d love to do it again with a small group, perhaps going all the way to Washington DC.