This was to be the second day of my Great Allegheny Passage (GAP) October tour, but heavy rain ruined day 1. A trail closure near Kennywood, costly shuttle, less-than-thrilling scenery, and poor weather conspired against my original route. I planned to drive to Homestead, cycle to the Point in Pittsburgh and back, and then drive to West Newton to ride out to Boston and back.
When the downpour driven by a hurricane hit, I waited it out until about 1:00 p.m., decided it wasn’t worth the misery, and headed straight to West Newton to call it a day. I skipped the ride from West Newton to Boston entirely, enjoyed a relaxing evening, and woke up ready for a fresh start.
Looking at the bigger picture, I usually enjoy biking both the Great Allegheny Passage and the C&O Canal Towpath in mid-October. I generally start in Washington, D.C., and end up in Pittsburgh. It’s my tradition. I think I’ve racked up about eight of these 334-mile tours.
People sometimes ask why the president of the Ohio to Erie Trail rides the GAP every year. Part of it is nostalgia. This was my very first tour back in 2011. Mostly, it’s because the GAP is unmatched. Where else can you start in the nation’s capital, ride through a river wilderness on a historic towpath, climb into the Alleghenies, and descend into Pittsburgh’s industrial heartland on a continuous trail?
Do-it Your Way Philosophy
This year, I adopted a “do it your way” philosophy. On my previous tours, my goal was to go end-to-end and cycle every single mile. But as I get older and perhaps a bit wiser in the face of severe weather, I’ve learned to alter the plan. Skipping day one was the right thing to do.
One wonderful thing about bicycle touring is that there are no laws, no rules, and no one telling you you’re doing it wrong. Tours come in all shapes, sizes, and flavors. When you get on a bike to explore, you create something uniquely your own. That’s why I permitted myself to take a rain-check day. That is what touring is about for me: pleasure and enjoying the day on the bike.
Bicyclist or Tourist First?
I’ve shared this analogy before. It comes from a bicycle touring book I read years ago.
A seasoned bicycle tourist encountered a younger rider who insisted that cycling every single mile, no matter how difficult or miserable, was what makes a tour a success. The older tourist paused and said, “I see you’re a bicyclist who happens to be a tourist.
Puzzled, the younger rider asked what he meant. The veteran tourist broke it down: a bicyclist who tours focuses on speed, mileage, and physical challenges. A tourist who happens to cycle focuses on everything else—the sights, the local food, the small towns, and the people. The bike is just the vehicle for the adventure.
Simplistic. That analogy stuck with me, and without hesitation, I own being the tourist who happens to cycle. A tour for me is all about what happens between the start and the finish: the small towns, local diners, quiet time watching the world go by on the trail, and talks with locals and fellow travelers.
Worth Hitting the Brakes
Without a doubt, the highlight of my day was leaving Connellsville, climbing up through Ohiopyle State Park, and ultimately ending up in Confluence. Coming from the west, the climb seems to go on forever, but climbs like that give you time to soak in your surroundings.
What surroundings they were! Today was magical because the heavy rains left the hidden waterfalls and streams cascading noisily to the river below, blending with the rush of the river, surrounded by trees turning brilliant shades of fall color. I’ll return through this area in a few days. It will be fascinating to see the progress of the season’s change.
Today was all about immersion in nature: the crisp crunch of leaves under the tires, the sound of water, the occasional squirrel darting across the trail, and the rhythm of the climb. Your head is always pointed forward, taking in the rising scenery and the countless bends in the trail, each one bringing a fresh surprise and a brand-new view.
Memories Coming Home with Me
My morning started at the West Newton GAP Visitor Center, where a volunteer arrived early to welcome travelers. He spotted me. We’d talked the day before when I was arranging long-term parking for my car. Today, we had a wonderful discussion about the trail, trail visitors, and the complete unpredictability of the weather. I started the day with a smile and a good memory.
As the day progressed, I crossed paths with trail volunteers mowing grass, clearing storm debris, and keeping the corridor in top shape. Trails become popular for many reasons, but none of that happens without diligent maintenance that keeps them safe and welcoming. Every volunteer plays a small part, but together, those efforts create a lasting impact.
Later in the day, preparing to leave Ohiopyle, an elderly woman on an e-trike, accompanied by an elderly man on an e-bike, was catching up with eight or ten others of many ages. A conversation revealed they were a family cycling the trail for a day of exploration and adventure. They asked me to take their photo in front of the Ohiopyle depot.
This is why I work on trails. They create places where families and friends across generations come together, share an adventure, and experience life. That encounter stayed with me as I pedaled toward my Airbnb in Confluence, reinforcing everything I believe about the value of trails.
The wheel deal
Today offered a different experience from past tours, yet it felt familiar. I revisited places with fresh eyes, celebrated that trails make a difference in lives, and learned that a rainy day doesn’t ruin an adventure. It just gives you a fresh outlook on the journey
Miles: 54 miles from West Newton to Confluence
Views: Autumn color is unfolding, brightened by the rain
Unexpected Win of the Day: No breakfast and limited lunch options as small towns close on Mondays. However, I discovered mulitas at Sobremesa, a family-run Mexican restaurant, at lunch in Connellsville.









Happy Trails!
Tom on the Trails




Well done. No rules govern the length, timing, or direction in which the GAP should be ridden. There's no beginning or end, other than that the mileage follows the original Western Maryland Railway convention from Cumberland to Connellsville and was adopted for the former Pittsburgh & Lake Erie RR to Pittsburgh, although that is contrary.
Most riders are day trippers out for their ride from my backyard, or wandering beyond just to see what's on the other side of that mountain. Part of the reason I'm doing the GAP piece by piece is the trail's history of being put together section by section. It began a couple of miles from the Ramcat Trailhead near Confluence. Then, added more and pushed on to Ohiopyle. For years, that was "the bike trail".
Then they built a section from Rockwood to near the Pinkerton Horn. It stopped short because local volunteers knew how to build a trail, but the bridges were a step beyond their skill. To the north, the Ohiopyle-to-Connellsville segment opened, and people immediately envisioned a link to Pittsburgh. By 2001, the 100-mile milestone was reached, from Meyersdale to McKeesport, when the Casselman River Bridge opened with its new deck.
Finally, after a two-mile start in 1986, the GAP "made the Point" in 2014 and reached Pittsburgh. Maybe your next ride package could be doing the segments in order of being built.
I rode the D&L trail in eastern Pennsylvania last week. It was an organized boutique tour. It was nice. But I still prefer my freelance bicycle tourist mode. Enjoy the rest of your travels!