Work is already underway to reshape one of Bend’s key climbing routes. The Pine Drops trail, a two-mile stretch climbing nearly 500 feet, has long been the gateway to Lower Whoops, a favorite jump trail that challenges riders with adrenaline and flow. Originally, Pine Drops was classified as a beginner-friendly green trail. Yet, a tough 100-yard haul up a steep fire road section disrupted the ride’s rhythm and accessibility.

Addressing this, the Central Oregon Trail Alliance (COTA) took bold steps early on, routing Pine Drops off the fire road and onto a dedicated singletrack path. With the addition of smooth switchbacks, the climb softens without sacrificing engagement, turning Pine Drops into a seamless green climbing route.

But Pine Drops’ transformation is only just beginning. COTA is now focused on the Pine Drops Extension, a significant upgrade adding nearly three more miles of trail. This extension connects to the summit of Upper Whoops, a steep descent currently reached by a strenuous 3-mile fire road climb or pedaling up the descending trail itself. With the extension, riders will gain a manageable singletrack climb to Upper Whoops’ peak, allowing that section to become a pure descent experience.

Set for the 2026 building season, this expansion is more than distance; it's about harmonizing trail use with rider skill levels. It invites newcomers to ascend comfortably while enabling advanced riders to focus on thrilling descents.

Meanwhile, COTA worked early this season on the C.O.D. Bypass. This green bypass detours riders away from a technical black trail section via an old decommissioned road that cuts through sensitive wildlife habitat. Protecting 80 acres of forest, the bypass preserves the ecosystem while connecting riders through a continuous beginner-friendly route—an elegant balance of recreation and conservation.

Lastly, the much-anticipated “Bachelor to Bend” project will stitch together several trailheads—Swampy, Dutchman, and Wanoga—currently isolated by doubletrack or road segments. New singletrack connections are planned to pull riders off fire roads and protect elk habitat in the region. These additions will greatly improve access and trail variety while supporting sustainable trail practices.

Bend’s trail network is evolving with deliberate care—offering fresh, accessible adventures while respecting the fiercely independent landscape. For riders seeking new routes that match their pace and skill, Pine Drops and the surrounding projects signal a turning point. Prepare for climbs that invite steady effort, descents that challenge with flow, and nature that dares you to move thoughtfully through it. Pack your hydration, check your tires, and anticipate the ride—the trail community is crafting the next chapter here, where adventure and stewardship pedal side by side.