Bend's West Side Trailheads Are Finally Talking to Each Other

Bend's West Side Trailheads Are Finally Talking to Each Other

If you rode Wanoga last July and haven't been back since, you have an outdated picture of what's happening off Cascade Lakes Highway. The story most riders know is that Wanoga got Bend's first lapable downhill trails. That part is true, and it's also almost a year old. The part fewer people have clocked is what came after: a quieter, harder project to stop treating Swampy, Dutchman, and Wanoga as three separate trailheads and start treating them as one connected system. That work is happening right now, mid-build, with crews out on the mountain as recently as this summer.

For a decade, riders parked at whichever trailhead matched their plan for the day and rode out-and-back or looped back to the car. Getting from one zone to the next meant driving Cascade Lakes Highway or grinding out miles of old fire road that nobody particularly enjoyed. That's the piece the Central Oregon Trail Alliance has been chipping away at, and this is the summer several of those pieces are actually landing.

What Wanoga actually became

The Wanoga Downhill Trails project broke ground in mid-June 2025, and the first two trails opened to the public that July 9: an advanced flow trail with berms, drops, and rolling grade changes, plus a dedicated climbing route to get riders back to the top. A third trail, a blue-rated descent called Ponderosa, followed that October, funded through the same partnership. The full plan calls for five trails on the butte south of the Wanoga parking lot, separate from the sledding hill that still gets its own winter crowd. COTA had set a goal of finishing all five by the end of 2025, and public trail listings show three online by that October, which put Bend within reach of something it had never had: a purpose-built, session-able downhill zone, the kind where you can lap the same run a dozen times in an afternoon instead of treating every descent as a one-way trip.

The build itself reads like a who's who of freeride mountain biking. COTA hired Sensus R.A.D. Trails, the trail-building outfit owned by Cam Zink, with Cody Wilkins as lead builder. Bend-raised freerider Carson Storch worked alongside him, with Cam McCaul, Dusty Wygle, Arlie Connolly, and Jacob Guthrie rounding out the crew. Tom Lomax, the former director of operations at Mt. Bachelor, became what COTA's executive director Emmy Andrews called the connective tissue for the whole effort.

"This project has a lot of moving parts," Andrews said, crediting Lomax alongside the Bend Sustainability Fund, the Forest Service, and COTA's own staff and volunteers for keeping it on track.

Wilkins put it more simply once the dirt was down: get it while it's fresh, with a promise to come back in fall for a tune-up before winter.

Where the money actually comes from

Here's the detail that changes how you might think about your own lodging bill next time you have out-of-town guests staying in a Bend rental. None of this was funded by property taxes or a city bond. It came from the Bend Sustainability Fund, a Visit Bend program built on lodging tax revenue collected from hotels, vacation rentals, and RV parks. Since 2022, COTA has received more than $160,000 through that fund, with more than $110,000 of it earmarked specifically for Wanoga.

That's worth sitting with for a second. The five new trails you might rip through on a Tuesday evening exist largely because someone visiting Bend paid a lodging tax on their Airbnb last winter. It's a rare case where tourism dollars flow directly into infrastructure locals actually use, rather than sitting in a fund earmarked for visitor amenities that residents rarely touch.

The unglamorous middle mile

Wanoga was always going to be the visible part of a bigger plan. The harder, less photogenic work is the connective tissue: the West Bend Trails Project, a Deschutes National Forest plan approved in January 2025 after a lengthy federal environmental review. On paper it's dry stuff, roughly 8.8 miles of trail reroutes, 17.5 miles of new construction, and 17 miles of unauthorized routes getting decommissioned, along with changes to how 33 miles of forest roads get used. In practice it's the difference between three isolated trailheads and one system you can ride point to point.

Three of the westside's busiest launch points sit on the same stretch of Cascade Lakes Highway: Swampy, Dutchman, and Wanoga. Right now there's barely a way to ride between them without dropping onto old fire road. Dutchman, the farthest west and directly across from the Mt. Bachelor entrance, connects to Swampy mainly by way of Flagline, a trail that closes seasonally to protect elk calving through mid-August, or by 3.5 miles of doubletrack that doesn't do much for anyone's morale. The project COTA calls Bachelor to Bend is meant to fix that by threading real singletrack between the three, keeping riders off the fire roads and out of the sensitive habitat those roads currently cut through.

One piece of that puzzle is already done. Early in the 2025 building season, crews finished the C.O.D. Bypass, a green reroute that lets less experienced riders skip a technical black section of the C.O.D. trail without detouring onto a decommissioned road that ran straight through elk habitat. The bypass adds roughly 80 acres to the 400 acres of habitat already being protected in that zone, a small number until you consider it's habitat that used to get crossed by riders every week.

The Pine Drops Extension is the piece closest to done. Pine Drops itself already got rerouted off a steep fire-road climb and onto gentler singletrack switchbacks. The extension adds roughly three more miles, reaching all the way to the top of Upper Whoops so that trail can finally become a dedicated, descent-only run instead of a shared climb-and-drop. As of early July this year, COTA volunteers were out finishing that work by hand, meeting at Virginia Meissner Sno-Park to carpool up after machine crews had already cut the rough line. That's not a plan on a map. That's a trail that was still being packed by hand a few weeks before you read this.

What that means for a ride this week

If you're headed out to the west side trails this month, a few things are worth knowing before you clip in. Flagline, closed through mid-August for elk, should be open again by the time you read this, so Dutchman's one real singletrack option is back on the table. Pine Drops may still have fresh, loose sections near the top where the extension work just wrapped, which usually means slower riding and a little extra care until it settles in. And if you're used to treating C.O.D. as an all-or-nothing black trail, there's now a green option that lets you keep riding with someone who isn't ready for the technical section, without either of you bailing out onto the old road.

None of the pieces are quite finished. That's the honest version of this story. Bachelor to Bend is still very much a work in progress, and COTA has been candid that fire danger alone can shut down motorized trail work for weeks at a time, since equipment gets pulled the moment conditions get risky. What's true right now, in the middle of August, is that the westside trail network is closer to being one continuous system than it has been in Bend's history, and it's getting closer by the month rather than by the decade.

It's also worth knowing this riding is not limited to two wheels and two working legs. Oregon Adaptive Sports runs private lessons on the same trail network from early June through early September, using adaptive mountain bikes that often retail north of $15,000, with executive director Pat Addabbo describing the summer push as full of momentum for the program's riders.

The thing worth remembering

COTA stewards something like 600 miles of trail across the tri-county area with a volunteer base that runs past a thousand people. That's the kind of number that only means something once you've stood at Virginia Meissner Sno-Park at 9 in the morning, waiting to carpool up to a trail that isn't finished yet, next to people who are going to spend their Thursday packing dirt by hand for a run they may not even personally prefer to ride. Wanoga was the trail everyone noticed. The connector work is the trail nobody notices until the day they realize they rode from one trailhead to another without ever touching a fire road.

That's the kind of texture that doesn't show up on a map or a listing sheet, and it's exactly the sort of thing we like knowing about the neighborhoods we work in. If you're already living the Bend outdoor life and know someone who's thinking about making Central Oregon home, or if you're weighing your own next move here, Ninebark Real Estate is happy to talk through what a given neighborhood actually feels like day to day, trailheads included.

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