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
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