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Flag Mountain Loop Hike

From Oregon Hikers Field Guide

Tom, Dick, and Harry Mountain from Flag Mountain (bobcat)
Toll gate, Pioneer Bridle Trailhead (bobcat)
Picnic shelter, Tollgate Campground (bobcat)
Shady woods, Pioneer Bridle Trail (bobcat)
Toy soldiers (Cladonia bellidiflora), Pioneer Bridle Trail (bobcat)
The loop described with road walk sections traced in orange (not a GPS track) (bobcat) Courtesy: Caltopo
  • Start point: Pioneer Bridle TrailheadRoad.JPG
  • End point: Flag Mountain
  • Hike Type: Loop
  • Distance: 6.8 miles
  • Elevation gain: 1060 feet
  • High Point: 2,530 feet
  • Difficulty: Moderate
  • Seasons: All year
  • Family Friendly: No
  • Backpackable: No
  • Crowded: No



Flag Mountain is a 2,500-foot ridge that separates Camp Creek and Still Creek, both tributaries of the Zigzag River. The trail itself is only three miles long, but it offers a couple of viewpoints towards Mount Hood and its foothills. This description involves a longer loop that includes sections of the Still Creek Trail and Pioneer Bridle Trail: there are a two back road sections, and on the Bridle Trail you are hiking very close to Highway 26, but the loop offers a variety of habitat and is a good low elevation outing at almost any time of the year. If you don't have a Northwest Forest Pass, you can begin this hike at the Flag Mountain West Trailhead or the Still Creek Trailhead.

At the trailhead, you can visit the replica Oregon Trail tollgate, refurbished in 1993. The maples on either side of the gate are Oregon Heritage Trees and were planted by one of the gatekeepers: they are at least 130 years old. An interpretive sign offers information on the Barlow Toll Road, which ended at this point. You can also get a view of the alder-lined Zigzag River from the bluff here.

Follow a trail from the west side of the parking area. This leads down under tall trees to a historic covered picnic area at the Tollgate Campground. (The campground is open from the second week in May to October.) Continue to some restrooms: you can drop down to the bank of the river and take a short riverside trail before heading up again to the campground road. Pass a “throne” carved in an old stump and reach the westernmost part of the campground, where you’ll find a trail leading through the salal into mossy woods. Drop and cross a little footbridge over a creek, and then bend right above an abandoned camp. Reach another unofficial campsite, and go left on the trail to reach Road 20 close to its junction with busy Highway 26.

Turn left here: you’ll now be walking about a mile on Road 20 past numerous private cabins. Keep left at the junction with Holden Drive, and cross the Zigzag River on an old bridge. The road bends to the left and passes junctions with Roads 20-C and 20-D. There are fresh scars in these woods from the November 2015 windstorm that brought down many conifers. Reach Road 20-E and go left about 50 yards. You’ll see the signed Flag Mountain Trail #766 on the right.

Pass between two old cabins. Then, the trail heads steeply up a Douglas-fir/hemlock slope to make three switchbacks. Hike under a mossy outcropping, and then curve up to the ridge crest. A user trail leads right along the outcropping to a memorial bench and views across the Still Creek valley to Hunchback Mountain. (The bench honors Kathi Beck, one of nine Prineville Hot Shots among the 14 firefighters killed on Storm King Mountain, Colorado, in July 1994.) From the mossy knoll, the Flag Mountain Trail keeps rising steeply in an understory of salal, sword fern, and rhododendron to a ridge crest viewpoint at a clump of hairy manzanita bushes. The view north takes in Enola Hill, West Zigzag Mountain, and the top of Mount Hood. From here, dip slightly and rise steeply before the trail levels on the crest again. Gently ascend to another manzanita-decorated viewpoint. The views here stretch farther east up the Zigzag River valley to Laurel Hill and Tom Dick and Harry Mountain. Drop slightly again, and then reach Flag Mountain’s viewless high point. The trail now undulates along the ridge crest in secondary forest before making a serious descent to the old east trailhead on the bermed FR 2632-160 spur road. Walk out along this gravel track, now sprouting baby alders, to the current Flag Mountain East Trailhead at a bend in Road 32.

Keep left and walk around a bend on this narrow paved road. After about a quarter mile, you’ll see where the Still Creek Trail crosses it. To extend the hike, you can add an in-and-out to Still Creek from here (see the Still Creek Hike). Otherwise, go left on the trail and wind down through a sword fern carpet under larger trees and old snags. Pass a spring and, at a junction, keep left to descend to Camp Creek. The trail then proceeds along the south bank of Camp Creek – you’ll see the Camp Creek Campground across the way. Reach a junction at a footbridge over the creek, and cross the bridge. Here you’ll find the small parking area at the Still Creek Trailhead.

Behind the parking area, find a trail that heads up the bluff above a campsite. Soon join the Pioneer Bridle Trail, constructed by the Civilian Conservation Corps in 1937, and go left. Pass under powerlines, and continue on a wider track while attempting to ignore the traffic noise from Highway 26. Cross Road 30, and continue the gradual descent on a gravel trail surface under young Douglas-firs and hemlocks. The trail crosses Road 28 and comes very close to the highway. Take the sturdy bridge over the Zigzag River. After this, the trail, now narrowed to the width of a footpath, winds a little as it remains close to the highway. Then separate a little from the din of traffic, and cross Road 26. This section negotiates pyroclastic flows from Mount Hood’s Old Maid eruptions; here grow more spindly conifers on a mossy carpet sprouting clumps of reindeer lichen and pinemat manzanita. Cross a boardwalk over a swampy area before reaching Road 24. Now you’re in a lush, wet forest dominated by cedars with a running stream burbling next to the trail in the wet season. Reach an old road bed that passes close to the Zigzag River. The tread narrows after you pass a locked gate. Up on the bluff above the river, pass a sign commemorating the Barlow Road’s accession to the National Register of Historic Places in 1992. Soon pass through the replica toll gate, and reach the Pioneer Bridle Trailhead.

Fees, Regulations, etc.


  • Maps: Hike Finder
  • Flag Mountain Trail #766 (USFS)
  • Green Trails Maps: Government Camp, OR #461
  • Adventure Maps: Mt. Hood Area
  • U.S. Department of Agriculture, Forest Service: Zigzag Ranger District
  • Discover Your Northwest: Mt. Hood National Forest North: Trail Map & Hiking Guide
  • U.S. Department of Agriculture, Forest Service: Mt. Hood National Forest
  • National Geographic Trails Illustrated Map: Mount Hood
  • National Geographic Trails Illustrated Map: Mount Hood Wilderness

Trip Reports

Related Discussions / Q&A

Guidebooks that cover this hike

  • Day Hiking Mount Hood: A Year-Round Guide by Eli Boschetto
  • Afoot & Afield: Portland/Vancouver by Douglas Lorain
  • 70 Hiking Trails: Northern Oregon Cascades by Don & Roberta Lowe
  • 62 Hiking Trails: Northern Oregon Cascades by Don & Roberta Lowe

More Links

Page Contributors

Oregon Hikers Field Guide is built as a collaborative effort by its user community. While we make every effort to fact-check, information found here should be considered anecdotal. You should cross-check against other references before planning a hike. Trail routing and conditions are subject to change. Please contact us if you notice errors on this page.

Hiking is a potentially risky activity, and the entire risk for users of this field guide is assumed by the user, and in no event shall Trailkeepers of Oregon be liable for any injury or damages suffered as a result of relying on content in this field guide. All content posted on the field guide becomes the property of Trailkeepers of Oregon, and may not be used without permission.