Sitting in the shadow of Mt. Hood is a 2,500-foot ridge called Flag Mountain. It stands between two branches of the Zigzag River - Camp Creek and Still Creek – and includes a variety of habitats, from sub-alpine meadows to marshy foothill woodlands. The best way to explore this mountain is via a three-mile loop trail which can be expanded to an almost seven-mile trek with a few extra detours.
The most frequently used trailhead for the Flag Mountain Loop Hike is the Pioneer Brindle Trailhead* which kicks off with a nice slice of history in the form of a rebuilt Oregon Trail tollgate. It’s based off an original structure, and was refurbished in 1993. Two maple trees planted by a gatekeeper stand on either side of the tollbooth – they’re estimated to be at least 130 years old.
The trail leads from a parking area to the Tollgate Campground, then off through a mossy woodland with a dense understory of salal. There’s a stream and a footbridge crossing just ahead, then a section of an abandoned campground. Just past this you’ll take a left on the trail to hit Road 20 and the junction with Highway 26.
Your left turn here will take you about a mile along Road 20, past private cabins and up to a junction with Holden Drive. You’ll want to stick to the left here as well, which leads you over an old wooden bridge and past Roads 20-C and 20-D. Keep an eye out for 20-E, and take a left about 50 yards down. This will lead you to the signed Flag Mountain Trail #766.
This trail bends straight back into a woodland of hemlocks and Douglas firs, leading up a slope along a set of three switchbacks. There are some terrific mossy outcroppings to admire on the curving rise up the crest to a short summit point. You have the option here of taking a user trail along the ridge to a memorial bench, which is a great place to pause and drink in views of Hunchback Mountain and the Still Creek Valley.
From back on the main trail, walk along the mossy ridgetop and head back upslope through the woods. The understory here is deliciously rich, which strong showings from sword fern, rhododendron, and salal. The path will eventually lead out to another ridge crest viewpoint, this one looking out to West Zigzag Mountain, Enola Hill, and Mt. Hood. The trail will next dip, then rise again steeply to another crest. It’s another viewpoint, with a sweep of the horizon including Tom Dick and Harry Mountain, Laurel Hill, and the Zigzag Valley. There’s one more of these dip-the-rises ahead, with this section leading up to Flag Mountain’s summit.
There’s no view up here due to the trees, but it’s a nice ramble along the ridge crest under the shade of Douglas firs and hemlocks. The path then winds downhill for a long section, before hitting the old east trailhead on the Forest Road 2632-160 spur. Take this gravel track through baby alder trees up to the new Flag Mountain East Trailhead at a bend in Road 32. Take a left here, and hike on the paved road for about a quarter mile, keeping an eye out for the Still Creek Trail junction.
You can tack on some extra trail miles here by hiking the Still Creek in-and-out, otherwise swing to the left and head downhill through a section of the forest wild with sword fern growth. There are some really lovely old trees here, including some terrifically gnarled snags, as well as a spring. Up ahead is a junction with Camp Creek. Take a left, and head along the south bank of Camp Creek, past a campground, and look for a parking pull-off junction right in front of a footbridge.
From here look for a trail behind the parking area that heads up to the bluffs – this will hook you up to the Pioneer Bridle Trail, if you take a left. You’ll cross a wide track under hanging power lines next, and you’ll be able to head the rush of traffic from Highway 26. Look for an intersection with Road 30, and descend down to a gravel track back into dense woodlands. You’ll wind even closer to the highway as you cross Road 28, then after a footbridge over the Zigzag River you’ll pull away into the woods.
The trail will fade out into a dirt path, winding across Road 26 and through spare groves of conifers and pinemat manzanita. There’s a boardwalk ahead to keep your feet away from a swampy section of the trail which dries up as you cross Road 24. The lowlands here are full of wet, mossy growths, tall, lichen-covered cedars, and networks of seasonal streams. Keep on to an old road bed that veers close to the Zigzag River and up past a locked gate. You’ll rise up along a bluff next, then see ahead the Pioneer Bridle Trailhead where you started.
*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 instead, but we encourage you to buy a pass and support the trails.
Directions: Click here or the link below the map to get turn by turn directions.