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Fifty 50

5 Star Route / Bend, Oregon / Published: Oct 2018 / Directions
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Skyliners Road with cyclists
Leading out! / October 2022
Dropping into the single-track on gravel bike.
Dropping into the single-track, mile ~ 2.5.
Woman riding single-track trail.
Trees marked orange.
Orange = Saved tree
Taking a corner on Ben's Trail.
Bumpy, red cinder road.
The bumpy red cinder road, ~ mile 4.
Good dirt road for gravel bike.
Back on good dirt! ~ mile 5.
Riding bike in the forest.
Group bike ride on dirt road near Bend, Oregon.
Descending dirt road on gravel bike.
Riding up single-track to the welcome center.
The single-track into the Welcome Center.
Paved bike path near welcome center.
The paved bike path, ~ miles 12 to 16.
Descending the paved bike path.
Riding through the tunnel under the highway.
Climbing up into Tetherow.
Climbing into Tethrow.
Single-track near the Lair.
The last single-track, ~ mile 17.
Old dirt road with gravel cyclists.
The White gravel road in the Phil's system.
The Highlands Trail.
The wide double-track of the Highlands Trail.
The paved bike path in Northwest Crossing.
Ride metrics for Captain O on Fifty 50 route.
Captain O's ride metrics.
Grove Market Hall
The Grove. Coffee time!
*
Route:
Loop | 21 mi
*
Gain:
1,200 ft
*
Surface:
~ 65% gravel, 10% single track, 15% bike path, 10% paved
*
Technical Difficulty:
Moderate
*
Navigation:
Challenging
*
Locale:
Urban Backcountry
*
Tire Suggestion:
45 mm+
*
Options:
---

A route that is close in to central Bend, short in distance, and has a good variety of terrain to work on technical skills. This is a go-to route when time is limited, or the weather is colder and you’re looking for something a bit “flatter” where you can keep moving and warm. It’s just a fun riding route!

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Map
Brown = gravel / dirt road
Blue = single track
Red = paved road
Purple = paved bike path
GPX Download   Version 2.0

Highlights & Remarkable Spots

Brooks Scanlon Haul Road / ~ Mile 2.5

Haul Roads and Rail Spurs Bend

Bend was once a world exporter of timber. Mile 2.5 marks the location of one of the old haul roads used to bring timber into the Bend mills along the Deschutes River.This map highlights many of the old haul roads. Click on it for a larger view. Yellow = Brooks-Scanlon Lumber Company. Brown = Shevlin-Hixon Lumber Company.

West Bend Forest Project / Miles 2.5 to 12.5

Westside Bend Project Trees

Along this section of trail you are riding through the West Bend Project, a 15-year forest management effort that includes tree thinning, brush mowing, and controlled burns. The project received Congressional funding through the federal Collaborative Forest Landscape Restoration Act. There are only 20 such demonstration sites nationwide. The goals of the Project are: to restore forest ecosystems, reduce the potential of high-severity wildfires, and provide economic and social benefits to local communities. For more information, see the resource page in the right sidebar (desktop) or towards the bottom of page (mobile).

Tetherow Resort / Mile 16

Tetherow Resort Sign

At one point, this high-end resort and golf community was a struggling endeavor that was on the brink of failure. As reported in 2009, “Only 59 of 302 plots have sold and just ‘a handful’ of homes have been built on them. The master developer, Arrowood Tetherow, had to unload most of its residential lots, plus the property where it planned to build a hotel and the golf course itself. Now it’s getting pressure from another one of the developers, Virtual Realty Enterprises of St. Louis, which has filed a notice of default for failure to pay $12 million on an $18 million line of credit.” [Bend Bulletin]

Phil's Trailhead / ~ Mile 19

Phil's Trailhead parking lot

“We started riding out in this area on dirt roads,” Phil Meglasson said at the trailhead last week. “We spotted a deer trail up here, which eventually became Phil’s Trail. We just followed it through. You didn’t use any tools in those days; you just rode, and rode the trail in that way.”

As Meglasson and his friends started using tools and building and developing trails, their efforts led to the formation of the Central Oregon Trail Alliance in 1992. Since then, COTA volunteers have worked closely with the U.S. Forest Service in building and maintaining area trails. The Phil’s Trail System is now nationally known because of its wide assortment of singletrack trails. [Bend Bulletin]

Ride Details

When We Like to Ride This

Our favorite time to ride this route is early spring and late fall. Not too much climbing, not too much descent. During the summer months, it can get busy and dusty.

Terrain & Riding

A great sampler of terrain typical to the Bend, Oregon area including some bumpy red gravel, twisting singletrack, and return-to-start fast doubletrack. It is classic eastside Cascades Forest with ponderosa pine, manzanita and basalt rock outcroppings.

There are ~ 2.5 miles on single-track that is rated mountain bike easy+. Those with good technical bike handling skills will ride it “clean”; others may need to put a foot down once or twice.

The Start

Lat / Long: 44.058913, -121.356767

Northwest Crossing roundabout. At the Grove Market.

Notes & Options

Route Notes

  1. On the paved bike path, be sure to check your speed as this is a very popular trail with users of all abilities.

Comments

Have you ridden this route? Got a question? Join the discussion!

Love Where You Ride! Learn More

Central Oregon Trail Alliance (COTA)This route includes a significant amount of single-track trail. The Central Oregon Trails Organization (COTA) manages and maintains these trails for riding. Like Dirty Freehub, they are a non-profit. We encourage you to give back with time, money or talent to COTA or your local trails organization. It is easy to forget that trails and routes require your ongoing support.

Podcasts

Ben’s Trail (It was a downhill trail? What?)

Here more about the original design of Ben’s trail from author, Ben Husaby. This podcast is about trails that are located in Bend, Oregon.

Single-Track Trail Etiquette (Who has the right of way?)

Ever wonder who has right of way on those single-track trails? Downhill rider? Uphill rider? The runner? Who? In this episode of The Connection, we speak with Emmy Andrews the Executive Director of the Central Oregon Trails [...]

Be Informed!

West Bend Project - Mowing

West Bend Project

“What is going on? All these trees have been cut!” This is the initial reaction many of us have to the tree thinning occurring just west of Bend. But … take a minute to get informed.

Read More »

Keep it Local! Learn More

Grove Market Hall

The Grove Market Hall

This is a great place to stop after the ride to grab a cup of coffee or a bit to eat! There’s an assortment of options from a burger, to Italian, to Thai street food.

Ridden and Reviewed by:

LindaE (aka Gravel Girl)

LindaE (aka Gravel Girl) / Team Dirty Freehub

She loves a good day of gravel, like most people like a good book. She’s always amused by the outdoors and the wild adventures. Gravel Girl is a Co-Founder of Dirty Freehub.

KevinE

KevinE / Team Dirty Freehub

He should have “Never Stop Exploring” tattooed on his chest! He loves adventures on bikes and is a Co-Founder of Dirty Freehub.

Explore Similar Routes:

Bend Shorts Deschutes National Forest Unannounced

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