Mountain Biking Bend, Oregon: Funner & Tiddlywinks

If you’re following my Instagram, you might have seen that Greyson and I were in Oregon last week. We drove up from Truckee and my parents drove down from eastern Washington, and we met in the middle! Our first destination was Bend, Oregon, one of my favorite towns. It’s got climbing, hiking, river floating, amazing beer, and awesome restaurants. It’s also known as a popular mountain biking location, and Greyson and I have ridden there a couple times before, checking out a section of the Deschutes River Trail and riding a bit in the Phil’s Trail network. While I had fun riding on those trails, they didn’t seem “mountain bike destination” quality, and I wanted to check out the best of what Bend has to offer.

Mountain Biking Bend Oregon // tahoefabulous.com

From our research (internet based and talking to the super friendly staff at Crow’s Feet Commons), riding up Funner and down Tiddlywinks was the most highly recommended. The trailhead was pretty easy to find – we followed directions from MTB Project to the parking area at the green gate, located here, about 9 miles from downtown Bend.

Mountain Biking Bend // tahoefabulous.com
Via Strava

From the parking lot, we headed up on Storm King, which we only rode a small section of. After about 0.7 miles, the trail forked and we took a sharp right on to Funner. Funner has sections that are two way, and parts that are split into uphill and downhill only. Those are clearly marked, and it’s important to stay on the correct side, as people come bombing down the downhill sections, not expecting to see someone climbing up. The climb from the gate to the top of Funner (including the Storm King Section) is about 5 miles and 1,000 feet of climbing. It’s never super steep on the climb, but it can be sandy and leg sapping and there are very few breaks from the uphill grind. The trail is rated as intermediate, but it followed a trend I noticed in lots of the trails I’ve ridden in Bend – long, long stretches of easy riding, punctuated by very occasional volcanic rock gardens that are difficult-to-impossible for me to ride.

At mile 5, we hit the top of Funner and a parking lot. From here, the start of Upper Tiddlywinks isn’t super obvious but isn’t too hard to find. The first part of Tiddlywinks is a fun mix of bermed downhill stretches, short punchy climbs, and flat-ish rock gardens. That goes for about 1.1 miles, and then we started to climb again. We climbed about 200 feet in 0.8 miles, but at that point the climb felt pretty rough after so much time in the saddle climbing. Even though none of the climbing was very steep, 8 miles of riding that was mostly climbing or flat really wore me out!

With that, we were finally at the top and ready to descend Lower Tiddlywinks. The trail immediately launches into big, bermed corners, table top jumps and other man made features, with a few natural rock drops built in. I had a blast on the trail – it reminded me a lot of Freund Canyon in Leavenworth with the style of trail building. As for difficulty, all of the tabletops and rock features are rollable, though it’s a great trail for practicing getting some air. There are a few doubles and more complicated features, but everything has a very obvious ride around. We descended ~1,100 feet in just over four miles, and I had a smile on my face the whole time. At mile 12.3, we hit the intersection with Storm King and headed back to the car. Total, we rode just over 13 miles with almost 1,400 feet of climbing and a moving time of 2:12.

Mountain Biking Bend // tahoefabulous.com
Via Strava

I had a great time on Tiddlywinks and it was absolutely worth the climb up – this is the kind of riding I was hoping for in Bend. Additionally, the trails are very well maintained and very well marked. The only thing that was a little confusing to me at first were “Y” marker signs when the trail split. We figured out that this meant the fork was going to come back together soon, and often the “Y” sign delineated an easier and harder route for that short section. If you’re an intermediate or higher rider, I’d highly recommend this route. I think it would be doable for a more advanced beginner, but you’d have to walk quite a few sections and the downhill part might not be worth the climb to the top. If you’re more on the beginner side, I’d recommend Ben’s Trail in the Phil’s Network or the Deschutes River Trail for scenery.

Trail Stats
Location: Wanoga Trails, Bend, Oregon
Mileage: 13 miles
Elevation Gain: 1,390 feet
Difficulty: Intermediate
See my Strava route here.

Mountain Biking the Deschutes River Trail

Mountain Biking the Deschutes River Trail, Bend, Oregon // tahoefabulous.com

Greyson and I brought A LOT of gear on this road trip to Bend, because we weren’t sure how the weather was going to be. We brought skis/snowboards, camping gear, hiking gear, snowshoes, mountain bikes, climbing gear and swimsuits! We ended up not using all of it, but we made the most of what we could do.

deschutes 2

One thing I was really looking forward to was mountain biking in Bend. It’s one of the (many) outdoor activities Bend is known for, and I was excited to give it a try. As I’m feeling fairly out-of-shape bike wise, I wanted to try a trail that wasn’t going to be too difficult technically or exertion wise.

We stopped in an awesome bike store/beer & wine bar/coffee shop, Crow’s Feet Commons, and picked up a Bend bike trail map to add to Greyson’s “map library” (aka the overflowing side pockets in the Toaster). We decided on the Deschutes River Trail, as it was easily accessible and close to town and rated as beginning/intermediate in both terrain and exertion.

Map via Google Maps
Map via Google Maps

We jumped on the trail a few miles out of town (directions here) from a dirt parking lot right next to the river. After a few minutes of fire road riding we found ourselves on a gorgeous dirt trail that paralleled the Deschutes. Unfortunately, despite the supposed “beginner/intermediate” nature of this trail, we fairly quickly arrived on some technical rocky sections. I consider myself a strong intermediate rider, but I had to get off and walk a couple of these sections, especially as I was not expecting them! However, the rocky sections were over in less than a quarter mile, and the rest of the trail (that we rode) was smooth sailing – definitely beginner.

Trail Map and Elevation Profile via Strava
Trail Map and Elevation Profile via Strava

For me, the best feature of the Deschutes River Trail was the awesome packed dirt. I’m used to the decomposed granite that turns to sand that the Tahoe area trails are “famous” for, so this forest soil was a welcome change! I felt like I couldn’t slide out if I tried (note: I am sure that is not true). The trail meanders along with the Deschutes, giving gorgeous views of the river and the strange lava beds the area is famous for. The Deschutes is also a popular whitewater kayaking destination, so I’m sure that in certain times of year, you can watch people shooting the rapids.

deschutes 5

The trail heads south from Bend and travels about thirteen miles south to Sun River, so you could definitely make a day of it for a longer, 26 mile ride. We ended up just riding about a 9 mile out-and-back section of the trail, but I imagine most of the trail is similar. It was muddy in spots, so be sure to check conditions and practice good trail etiquette if you’re riding in the winter or spring. Additionally, the trail is mixed use, and used considerably by hikers and bikers, so be sure to keep your speed under control to avoid user conflicts.

deschutes 6

Overall, I enjoyed this trail. Though I didn’t experience the whole thing, I’d rank the section we rode as “beginner” with a short “intermediate to advanced” but easily walkable section on the technical side of things, and definitely “easy” for exertion. I can’t wait to get back to Bend and ride the whole Deschutes River Trail, as well as trying out some of the harder trails.