Bend, Smith Rock & the Trail of Ten Falls

A cinder cone volcano rising above central Bend with a paved road and trail to the summit — the 360° view from the top takes in all five major Cascade peaks simultaneously: Hood, Jefferson, the Sisters, Broken Top, and Bachelor. The best single orientation point to Oregon's volcanic landscape before two days of active exploration.

A paved riverside trail threading through Bend's revitalized Old Mill District along the Deschutes River — stretch your legs after the Cascade crossing, watch the whitewater kayakers, and follow the trail past the converted mill buildings to get oriented to the city.

The original Bend brewpub that launched Oregon's craft beer industry — the Black Butte Porter and Mirror Pond Pale Ale were brewed here before the brand went national. The downtown taproom still pours small-batch pilot beers and seasonal releases unavailable at the main brewery.

Oregon's premier rock climbing destination and one of the state's most dramatic state parks — the Misery Ridge Trail climbs 700 feet in under a mile to a ridgeline view of the Crooked River gorge, the Monkey Face spire, and the snow-capped Cascades to the west. The complete loop is 3.2 miles of steep basalt terrain through a landscape that looks more like the American Southwest than the Pacific Northwest.

The river-level return leg of the Smith Rock loop follows the Crooked River beneath the basalt columns and climbing walls — shaded, flat, and cool compared to the ridge above. Watch climbers on Monkey Face from directly below; the canyon perspective is completely different from the summit view.

A converted 1911 railroad depot in the small farming town of Terrebonne, a mile from the Smith Rock entrance — burgers, sandwiches, and local beers on the patio after a full morning on the canyon walls.

Bend's largest craft brewery on its lively downtown strip — the patio deck overlooking the Deschutes River is one of the best places in the city to watch the late-afternoon light hit the hills east of town. The IPA program and the seasonal releases keep the crowd local despite the brewery's national profile.

The courtyard brewpub inside this converted 1936 Catholic school — house-brewed ales on tap alongside burgers, fish and chips, and pub classics. Fire pits, string lights, and the old-school campus setting make it feel like destination dining. You're already sleeping here; dinner is a short walk from the soaking pool.

The anchor of Oregon's largest state park — South Falls drops 177 feet over a basalt ledge and the trail passes behind the curtain of water through a cave carved by centuries of flow. The Trail of Ten Falls connects ten named waterfalls in a single 7.2-mile loop through old-growth Douglas fir; the four falls accessible from the South Falls trailhead are the most dramatic.

The deeper section of the Trail of Ten Falls follows Silverton Creek through a narrow canyon past Lower South Falls (93 ft, walk-behind), Lower North Falls, and North Falls (136 ft) — the light in the canyon reaches its best angle in the late morning. The complete out-and-back to all four waterfall caves from the South Falls trailhead is 4 miles.