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Mountain Biking Bend, Oregon: 5 Epic Rides You Must Do

Mountain Biking Bend_ 5 Epic Rides You Must Do

When it comes to bikes and trails, the Rockies are rad and Moab is sick, but there is a reason Oregon is known for its pristine mountain biking. Oregon’s old-growth forest not only makes for spectacular scenery, but it also creates sleek, smooth trails that you can swoop and fly down. The entire state has great biking, but Bend is the mountain biking capital of the whole PNW.

Bend’s most popular trail system is Phil’s. If you’re looking for gnarly, steep drops and features, Phil’s might not be for you. If you’re into long, smooth downhill rides with big berms, Phil’s is the best mountain biking destination you’ll find and it’s especially true with its top two rides in the area: Phil’s and Whoops.

Phil’s is the iconic ride that’s great for beginners to intermediates. If you’re a bit more experienced, Whoops is more fitting for you. There isn’t a much better name for this ride. It’s a completely rock-free trail with wide berms and, you guessed it, “whoops” galore. Whoops can be accessed from almost anywhere in Phil’s trail system.

On top of Phil’s, there are tons of trails that extend beyond into more National Forest areas. Other popular areas include the Tiddlywinks trailhead on the Cascade Lakes Highway and the Tumalo Falls Loop at the very end of Skyliners Road, stemming west from Bend.

There are endless ride combos to choose from but if you’re looking for some of the very best trails to take, here are my recommendations:

Mountain Biking Bend Loop 1: Ben’s – Phil’s/Kent’s

Mountain biking Bend, Phil's Trail
The iconic ride of Bend, Phil’s Trail
Photo copyright MTBR

Starting Point: Phil’s Trailhead

Length: 12 miles, 2-3 hours

The Draw: An easy and moderately long ride that lets you ride the entirety of the iconic Phil’s Trail. Great for beginners and intermediates.

The Route: Start this ride on Ben’s trail which will be on your right-hand side when you reach the trail map for Phil’s. Ben’s is a great trail and it’s a bit unfortunate that it’s uphill only because it would be an amazing downhill (hint: if you go close to sunset, you might get away with downhilling it).

Ride Ben’s for 5.5 miles until it dead ends at FR 300, a parking area, and the junction for Whoops Loop. Here you can choose to combine with Whoops or head left down the fire road until you see a trail sign on your left for Phil’s.

Cruise your way down the fun Phil’s trail to the trailhead where you started.

Combine with: Upper Whoops, 20 miles, 4-5 hours

Mountain Biking Bend Loop 2: Upper + Lower Whoops Loop

Mountain biking Bend, Lower Whoops
Lower Whoops delivering stoke-worthy rides as always
Photo copyright Mike Albright via

Starting Point: NF-300 Junction

Length: 8 miles (for Upper + Lower) or 4 miles (for just Lower), 1-2 hours

The Draw: Probably one of the best intermediate MTB rides ever. Steep and fast (but not too fast) and filled with big berms, jumps, and tabletops. Beginners could pull it off, but it is amazing for intermediate to advanced.

The Route: This is a very simple route to navigate. From the junction of NF-300, simply follow the Pine Drops/Whoops Uphill trail for 2 miles. After 2 miles, you’ll reach a junction along a dirt road. Here you can continue uphill (left) along Upper Whoops Access Road to get to Upper Whoops, or you can just turn around and head down Lower Whoops. Whether you extend to Upper Whoops or just head straight down Lower Whoops, you’ll be enjoying some epic fun riding.

Lower Whoops is a bit more fun as far as flowy jumps and turns and is worth extending to when combing it with other rides in Phil’s trail system.

If you’re making a ride out of Whoops itself, ride to Upper Whoops for a longer trip.

Combine with: Ben’s and Phils (Loop 1) by starting at Phil’s Trailhead, 20 miles, 4-5 hours

Mountain Biking Bend Loop 3: Ben’s – Phil’s – Kent’s – KGB – Ben’s

Mountain biking Bend, Kent's to KGB
One of the few flat sections of the steep KGB trail
Photo via

Starting Point: NF-4610 Junction

Length: 5.5 miles, 1 hour

The Draw: A short but diverse ride giving you a taste of all the Phil’s trail system has to offer. A good workout with the ascent up KGB.

The Route: This starting point lies right along the midpoint of Ben’s Trail. Start by heading uphill (west) on Ben’s Trail. As mentioned before, this is a nice, smooth, and gradual uphill-only trail. You’ll ride this for 3 miles and you’ll hit the junction for Whoops.

You have the option to combine routes here or head left on the dirt road, up a few hills, to Phil’s trail which will be on your left.

Start down Phil’s fun ride but at the very first junction you reach, take a slight left onto Kent’s trail. Kent’s is almost identical to Phil’s but is slightly more steep.

Enjoy the flowy turns but don’t get too comfortable. After 2 miles on Kent’s, you’ll head left onto KGB which involves a steep ascent followed by more gradual ascents once you hit Ben’s and go left.

Ben’s will bring you back up to NF-4610 where you started.

Combine with: Lower Whoops Loop, 9.5 miles

Mountain Biking Bend Ride 4: Tumalo Falls Loop

Mountain biking Bend, Tumalo Falls Loop
Starting the ride from the pretty overlook of Tumalo Falls
Photo copyright Greg Heil via

Starting Point: Tumalo Falls/Trailhead

Length: 9.5 miles, 2 hours

The Draw: Ride along the pretty North Fork of Tumalo Falls and downhill one of the most popular trails in Bend, Mrazek. This is a great ride for intermediate riders looking for a scenic ride with slightly more technical downhilling than most of Bend.

The Route: Start this route from Tumalo Falls overlook. From the falls you’ll continue along the Tumalo Falls/North Fork trail for 3 miles. This stretch is reminiscent of the Mackenzie River and is filled with many pretty small waterfalls and old lava rock.

When you reach a junction, you’ll cross the river and begin down Mrazek. Follow Mrazek until you reach the sign for Farewell Trail which you’ll take back to Tumalo Falls.

More details on the route here.

Mountain Biking Bend Loop 5: Tiddlywinks or Tyler’s Traverse (Point-to-Point)

Mountain biking Bend, Tiddlywinks
The smooth trail of Lower Tiddlywinks
Photo copyright

Starting/ Ending Point: Tiddlywinks trailhead/Wanoga Sno-park, Cascade Lakes Welcome Station

Length: 12 miles (for Tiddlywinks) or 15 miles (for Tyler’s Traverse), 2-3 hours

The Draw: Pure downhill from the Cascades back down to Bend. Different trails offer more technical riding with rocky drops, while others offer easier terrain and flowy berms. Does require a shuttle or two cars/drivers so you can get back to your car at the top.

The Route: From the parking lot trailhead, ride south along Upper Tiddlywinks trail for 3 miles. After 3 miles you can split left to Tiddlywinks, the easier ride of the two, or you can continue straight on the Kiwi Butte Trail for a 1 mile or so more where you’ll hit the junction for Tyler’s Traverse on the left.

If you ride Tiddlywinks, enjoy good old fun downhilling for 4 miles. Tiddlywinks is much like Phil’s and Whoops and is great for all abilities. You’ll eventually finish Tiddlywinks and hit the junction for Storm King trail where you’ll head right. Continue downhilling Storm King for a little more than 3 miles of more easy and fun terrain. Finally, you’ll intersect Catch and Release where you’ll head left (to the right is the route you would come down if you take Tyler’s Traverse). Finish at the Ranger Station.

If you ride Tyler’s Traverse, have fun on this downhill-only trail filled with jumps, obstacles (with bypasses), and berms. Tyler’s Traverse is very similar to Whoops with a few more technical sections and is great for intermediate or advanced riders. Tyler’s will eventually end at a junction where you’ll continue down Catch and Release, a great easy, and fun downhilling to the Ranger Station.

Camping Nearby

Bend does have one campground at Tumalo State Park, which isn’t close to the epic mountain biking and also fills up quickly. Not to worry, though. Bend is filled with SO MUCH epic free camping it would be a crime not to capitalize on it. All of Bend’s mountain biking trails lie in the National Forest and within the National Forest, dispersed camping is completely legal (but PLEASE remember to follow Leave No Trace principles.) Dispersed campsites are found along roads marked NF on maps/Google Maps.

Any one of these roads will surely have some sort of land you can make camp at but here are some top spots due to their proximity to mountain biking trails.

  • NF-4610 coordinates: 44.038352, -121.419245 – Trailhead for Ben’s. Best for camping in bigger rigs or tents.
  • NF-300 coordinates 44.032063, -121.461899 – Trailhead for Whoops (prime location if you want to lap this trail). Best for vans or small rigs.
  • NF-406 coordinates 44.052061, -121.401747 – Best for any size rig or tent. Right across the street from Ben’s.

Pro Tip:

Need a shower after MTBing? Freshen up with some fun cliff jumping at Steelhead Falls.

Get directions here.

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Mountain Biking Bend_ 5 Epic Rides You Must Do

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Thursday 10th of June 2021

You are awesome!

Manny Monterrubio

Tuesday 17th of September 2019

Hi Gabi, just came across your page and hoping you’ll be able to advise. I travel to Bend from Boise many times a year but never during October. Finally, if weather permits, which is my concern, I’ll be traveling to the area in three weeks, first week in October for mountain biking. Question, how are the trails in the Deshutes, west of Bend OR? Thanks and great page!


Friday 27th of September 2019

That's awesome! We haven't been there at that time to know for sure but I'm guessing it's probably a really great time to MTB there! Spring is a great time to bike there so fall is probably similar. It's good if it a rains a little to get rid of the dry, sandy summer conditions but it does take a whole day for trails to dry out if it rains a lot. Does that answer your question? If you need any other info let me know!

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