Two trailheads on Anchorage’s southeastern outskirts give access to a network of crisscrossing and connecting trails in the section of the range that hems in Anchorage Bowl. They’re all off Hillside Drive, which skirts a suburb of sparkling glass houses and gorgeous views of the skyline, inlet, and Mt. Susitna to the west. City buses do not reach Chugach State Park in this area, so you’ll really need a vehicle to get to the Hillside trailheads. Day-use parking costs $5 per vehicle.
For the Glen Alps Trailhead drive south on New Seward Highway and turn east toward the mountains on O’Malley Road. Follow it to Hillside Drive, where you turn right, then left on Upper Huffman Road. In 0.5 miles, go right again onto aptly named Toilsome Hill Drive. Toil steeply uphill for 2.5 miles to reach the Glen Alps parking lot ($5 day-use fee).
On warm summer weekends every space in the lot fills with cars, so get here early or take the Flattop Mountain Shuttle (907/279-3334, www.hike-anchorage-alaska.com, $22 round-trip) from downtown. Take a look from the nearby overlook, and then head up the Flattop Mountain Trail for even better views. This extremely popular 1.5-mile trail gains 1,500 feet and is very steep near the top as you scramble through the boulders.
Also from the Glen Alps Trailhead are several moderate and very scenic hikes: Little O’Malley Peak, 7.5 miles round-trip; the Ramp and Wedge, 11 miles round-trip; and Williwaw Lakes, 13 miles round-trip. A great mountain bike route is the 11-mile (one-way) Powerline Trail that also takes off from the Glen Alps Trailhead and goes over 3,550-foot Powerline Pass all the way to the Indian Creek Trailhead on Turnagain Arm.
Continue north on Hillside Drive past Upper Huffman Road and take a right on Upper O’Malley Road. The second left leads to Prospect Heights Trailhead, where the Wolverine Peak Trail leads to the top of this 4,455-foot mountain (11 miles round-trip). You’ll discover great views of the Alaska Range and Anchorage, but go in late summer when the snow has melted.
© Don Pitcher from Moon Alaska, 10th Edition