“Hey, I hate to ask but I need a huge favor,” said Brad “the boss” Waldron. “I need to deliver a car to Oregon, but I thought we could do a little mountain biking while we are up there.”

Hmmmmm.

Let’s see.

Oregon.

Credit for a favor for the boss.

Mountain biking in both Bend and Ashland.

More breweries than you can shake a C02 cartridge at. 

Being forced to put on pants, take a shower and leave my home office.

All these things had me thinking about what kind of friend/employee I would be if I didn’t help the boss out with his difficult errand. 

And considering neither of us had ever ridden Bend or Ashland it seemed highly likely this roadtrip could quite possibly be the adventure we both so desperately need before we go into full blown winter and quite possibly another extended Covid lockdown.

The drive North out of California is pretty nondescript until you get close to Mt. Shasta, where the terrain turns twisty-turny and you can feel the transition from the flat miles of Northern California ticking over onto the hills of Southern Oregon. And I start to dream of the sweet, sweet hero singletrack dirt in them there glorious turning leaves filled hills. 

We roll into Bend pretty late in the afternoon and after checking into our hotel through the protective plexiglass shield we can feel the hunger pangs, having not eaten anything but one sad little burger at the McDees hours early. It becomes apparent pretty clear almost immediately eats are secondary to what must be the largest collection of brew pubs per capita anyplace we’ve ever been. We make the mistake of falling for the oldest trick in the book and we go to the most “famous” brewery in town, Deschutes Brewery. Now don’t get me wrong, the food was passable and the beer was fine, but it was a little like going to Boudin’s Bakery on Fisherman’s Wharf for an authentic San Francisco experience. In other words, it wasn’t.

The next morning we swung into one of several local bike shops, bike/ski shops are almost as prevalent as breweries, to get the inside line on the local trails and to pick up a trail map as a sort of safety blanket. 

Since we weren’t looking for something “epic” the wrench suggested we give a trail called Funner a go as an introductory taster. It was approximately 12 miles roundtirp with most of the first half a gradual up and then a fun(ner) rip back to the car.

“I don’t ever remember being passed by so many fast people,” said Brad Waldron, as another young woman ripped by us on a cross country race bike and sporting full lycra team kit. 

It’s true. Bend seemed to be loaded with a larger contingent of athletes, and a smaller number of baggie shorts/t-shirt wearing dirts. 

This didn’t stop us from enjoying our rip down Funner. It is such a great stretch of flowy trail we decided to get up early and sneak in a second run before hitting the road, but this time we rolled up Funner and looped back down Tiddlywinks. Tiddlywinks is full of surprises and opportunities to get after it. 

A little late check out shower and we were packed up and back on the road headed for Ashland. 

Where Bend has a more polished and curated feel, Ashland is more of a wild, mountain town. And, although we really enjoyed Bend, Ashland stole our hearts. It just felt like we had escaped the city and found ourselves swept away to the mountains. The hotel was a dump, the pizza place was a ghost town and the Safeway was close by. We made ourselves at home and in the morning rolled over to meet up with our friend Sue and her husband Bill “Wild” Rousel at Ashland Mountain Adventures. They hooked us up with a shuttle to the top of Mount Ashland and the next hour plus is a just blur of stunning deep and steep mountain bike fantasy riding. The locals all said they were sorry the trail was so chewed up and we should come back in the Spring when they have had time and condition to “fix” all the crappy trails. We just smiled and snickered to ourselves, because if this was their version of ruined we can’t wait to find out how they ride when they are at their prettiest.

And with our final run off the mountain behind us the shuttle service shut down for the year and we were showered, loaded up and headed for home.

And as the Oregonians say, “you don’t want to come here, the weather sucks and there is no good riding. Stay in California.” 

Now I just need to come up some “errands” for the boss to run in Oregon come Spring.