We've been toying with the idea of moving west for some time, and my recent retirement has made that possibility feel much more real. It's not a decision we're taking lightly, but after nearly four decades in the Mid-Atlantic - enduring Virginia's humid summers and cold winters - we're ready for a change.
My requirements are actually pretty simple. Since I can continue working from virtually anywhere, I want to be somewhere with outstanding road, gravel, and mountain biking right out the front door. Just as importantly, I need access to the same health insurance that has carried me through my ulcerative colitis journey and recovery.
With that in mind, we headed to the Sacramento area for two weeks to explore several communities and see whether one might become our next home.
Ashland, Oregon, was also high on our list, but unfortunately it couldn't check the health insurance box. That didn't stop us from making the five-hour drive north to the People's Republic of Ashland to experience it for ourselves.
I'm glad we did.
-
View from Mt. Ashland
View from the top of Mt. Ashland shortly before the start of my ride.
As much as I enjoyed downtown Ashland, it was impossible not to notice the mountains rising above town (above). Every time I looked toward the mountains, I found myself wondering what the trails up there were like. Saturday couldn't come soon enough.
I was immediately taken by the town's energy. Downtown was bustling without feeling crowded, and everyone we met was genuinely friendly and welcoming. We quickly found a few favorite spots, including The Noble Fox on Oak Street, where we watched Spain defeat Belgium before returning a couple of days later to catch Argentina punch its ticket to the semifinals. On our last morning we discovered another gem - Noble Coffee Roasting - which fueled us for the drive back to California.
-
Lithia Park
Ashland Creek stretches the entire length of Lithia Park feeding the park's duck ponds, Fairy Ponds, and swimming reservoir.
Beyond downtown, my personal highlights were a morning walk through Lithia Park (above) and what would become the highlight of the entire trip: a 15-mile descent from Mount Ashland back into town.
I had been looking forward to this ride for weeks. It would be my only opportunity to ride during our westbound adventure, and I wasn't about to waste it.
I reserved a bike from Ashland Mountain Adventures before we even left Virginia, so Saturday morning started early with a visit to the shop to install my pedals, make sure the bike fit me and was dialed in, and get everything ready for the shuttle.
Before arriving, I had spent plenty of time studying Trailforks and local ride reports, so I already had a good idea of the route I wanted to follow. Once we reached the shuttle drop-off, I ran my plan by a couple of locals.
The route (below) would take me down Bull Gap, Missing Link, Catwalk, Toothpick, Caterpillar, Lizard, and finish with the legendary Jabberwocky before a mixed surface descent into town along Glenview Drive.
Things worked out even better than I expected.
Not long after leaving the trailhead, I connected with Cody and Tyler (below), two riders visiting from Redding, California, and ended up riding with them all the way to town.
Having them lead the way was invaluable. More than once they gave me the confidence to tow in behind them through sections I probably would have skipped or walked on my own.
The ride was almost entirely downhill. Aside from one sustained climb near the end of Upper Bull Gap that briefly reminded me that my legs and lungs still worked, the remainder of the ride was pure descending.
-
Tyler: Lower Bull Gap
-
Cody: Jabberwocky
Fifteen glorious miles of smiles.
Upper Bull Gap absolutely blew me away.
After a fast doubletrack descent, the trail suddenly opened into an enormous jump park unlike anything I've ever seen on the East Coast. The jumps were massive - far beyond anything I've encountered in the Mid-Atlantic.
I stopped for several minutes hoping to catch someone sending one of the larger lines, but eventually rolled on toward the climb where I met Cody and Tyler.
From there the character of the ride changed completely with each new section. The trails narrowed into flowing ribbons of singletrack that alternated between mellow traverses and incredibly fast descents packed with sculpted berms, rollers, drops, and jumps that felt much more approachable.
Lizard carried that momentum all the way into Jabberwocky - now I understand why Jabberwocky has such a reputation.
The final descent was pure flow - big berms, playful jumps, perfectly shaped corners, and just enough technical features to keep things interesting without ever interrupting the rhythm. Before I knew it we were popping out onto the gravel road that carried us back toward town.
The ride ended with a short spin back to Ashland Mountain Adventures. I rolled into the parking lot just as the second shuttle of the day was getting ready to head back up the mountain.
On another day I probably would have loaded the bike back onto the trailer and gone again.
My lunch date, however, was calling.
I barely scratched the surface of what Ashland has to offer.
I'd love to return and repeat this ride, sample Time Warp, and spend a few days exploring the area's gravel and road riding. As we approached Jabberwocky, I noticed two riders grinding up the mountain on gravel bikes, no doubt earning a long descent of their own later in the ride.
Ashland clearly offers far more than just one outstanding shuttle ride.
-
Upper Bull Gap - the jump line
-
Finishing the last of the "climbing" along lower Bull Gap
-
Missing Links Trail, 5 miles into the descent
-
Tyler exiting one of the berms along Jabberwocky
I was especially grateful to have connected with Cody and Tyler during the ride. They generously shared local knowledge, provided great company, and even invited me to come ride their home trails around Redding someday.
-
Toothpick
Toothpick offered us an opportunity to “rest” our legs before the next descent down Caterpillar and Lizard.
Ashland may not check every box for our future, but it certainly checked every box for an unforgettable day on the bike.
This journal entry is a compiled summary of notes and impressions originally recorded in my Moleskine travel journal. Whenever I travel, I bring it along to jot things down so I don’t forget small details. I also carry a small Bluetooth photo printer to print select images (not the ones shown here) and paste them directly into the journal using adhesive-backed photo paper.
It’s a simple, tactile process that complements the slower pace of film photography and helps preserve memories beyond the screen.
Some of the links below are affiliate links. If you choose to use them, it helps support this site at no additional cost to you.