THE TRAIL: Tucked on a plateau overlooking the Willamette River and bedecked with new upgrades like maps, trail markers, and an ADA-accessible path, Oregon City’s 332-acre Canemah Bluff Nature Park is all but gift-wrapped for high-and-dry winter walks.

The cliff bench rises just a half-mile upriver from Willamette Falls—the Northwest’s largest waterfall by volume—and once served as canoe portage for Native tribes who gathered near the falls to fish and trade. (Canemah means “canoe place” in Chinook.) Oregon Trail pioneers blazed rudimentary roads in the mid-19th century; a cemetery dating to 1864 lies beneath large oak trees.

For a mile-and-change loop, start at the 0.2-mile crushed gravel Camas Springs Trail, prairie habitat that will bloom in spring with camas and trillium. Stop at the new stone-lined overlook, where you can survey the Willamette winding below forested hillsides as the falls rumble just out of sight. Continue on through a dense sliver of fir, alder, and maple, then trace an old roadbed lined with massive wedges of basalt. Within a half-mile of the trailhead, the road ends at the gates of the Canemah Historic Pioneer Cemetery.

Continue along the Spur Trail to the Old Slide Trail, which climbs 0.4 miles through corridors of ash trees, linking to the Licorice Fern Trail amid a dusky forest of ferns, alders, and vine maple. Follow this path to a new trailhead that exits into the Canemah neighborhood. Keep left on Fifth Avenue to rejoin the cemetery road, and leisurely make your way back to the main trailhead.

Post-Hike Watering Hole: At the two-year-old Oregon City Brewing Company, vinyl records spin and elk horns catch the glow of screens listing 40 beers on tap. Five house brews note the OC’s past territorial supremacy, like the crisp Provisional Pilsner and Doc McLoughlin Scottish ale. Bonus: the pub abuts Olympia Provisions’ new OP Wurst eatery.