Mt. Hood is home of the $2 shuttle and everyone in Portland already knows about it!
Info below from MTB Project.
Need to Know
Lots of options for food and drink in Government Camp and Rhododendron. Slow down at trail intersections as there are hikers on Crosstown Trail #755. Parking at the Tollgate Trailhead, or Glacier View Sno-park must have a Northwest Forest Pass. The Mt. Hood Express runs a shuttle bus that can take you from Rhododendron to Timberline Lodge.
For those wanting a longer round trip ride, (an additional 20 miles of mostly gravel with some paved roads), they can start in Rhododendron on Still Creek Road (gravel Forest Road 2612) and head east connecting on some local roads towards Still Creek Campground. Catch Barlow Trail #601A and cross Hwy 26. Turn north up paved Westleg Road to Timberline Lodge. See the complete description in Still Creek to Timberline Lodge.
Ride or walk your bike through the parking lot of Timberline Lodge, past the swimming pool and amphitheater on your right, and the Magic Mile lift on your left. Start on the Mountaineer/Timberline to Town Trail on your left. Follow Mountaineer for about 1,500 feet past the pool until Timberline to Town breaks off on your left as you enter a ski run. From there, you'll pass through 4 consecutive ski runs and then head into the woods. There are some good photo ops with Mt. Hood in the background in the ski runs.
About 1.3 miles in, you cross back to the east side of the old Glade Ski Trail. As you go lower, there are some tighter corkscrew turns and vestiges of the old Blossom Ski Trail as well as the corridor that had a ski lift mounted city bus used as a gondola between Government Camp and Timberline from the 1950's to 1962. The trail should be distinguishable from these other routes. If you were worried about your brakes, there are occasional grade reversals to give them a break.
Just as you cross the old Glade Trail opening, you reach the intersection with Crosstown Trail #755. At this point, you need to slow down as there is hiker/biker congestion and less visibility of Crosstown riders coming from the east here. Take a right (head west) on Crosstown Trail #755. If you want to stop for refreshments in Government Camp, you can take a left (southeast) at Maggie's Trail #753to Thunderhead Lodge near the middle of town, or take a right (southwest) off of Maggie's Trail #753 onto Lucy's Trail that puts you down at the Mt. Hood Brew Pub. If you want to keep jammin', continue on Crosstown Trail #755 west to its terminus and pick up Pioneer Bridle Trail #795 at the Glacier View Sno-Park.
Crosstown Trail is rocky and sandy after the Timberline to Town Trail, but the trail tread and trail clearing corridor narrows after the Maggie's Trail #753 intersection as this section is not designed for a nordic ski trail groomer. Follow Crosstown Trail #755 west towards the Glacier View Sno-park and pick up the Pioneer Bridle Trail #795 which leads to the village of Rhododendron.
The Pioneer Bridle Trail #795 section of this ride is the more intermediate part of the ride as it descends Laurel Hill - the most difficult part of the Oregon Trail traveled by pioneers in wagons. Despite the overall drop in elevation, there are some short climbs in the first half of the trail. You are also traveling through sections of the old Mt. Hood Highway before Hwy. 26, especially where you pass through a tunnel. Once you cross Hwy 26, the trail difficulty becomes easier, with a fairly flat, wide trail the rest of the way towards Rhododendron. If you want to avoid this section, you can park along Highway 26 on the north side of the trail crossing.
The trail officially ends at the Tollgate Rest Area where a replica of the Tollgate for the pioneer wagons had to pay for access to the Barlow Road. Bikers can continue down Highway 26 1/2 mile to the town of Rhododendron and cool off at the Dairy Queen or another local dining establishment.
History & Background
Check out Timberline Lodge (The Shining was filmed there) built by Works Progress Administration during the Depression, for it's Cascadian architecture. Parts of the trail pass the corridor for the Mt. Hood Skiway, a city bus mounted on a ski lift as a large gondola between Government Camp and Timberline Lodge.
Check out the Mt. Hood Museum and Culture Center in Government Camp for historic displays on Mt. Hood and the Forest Service. The Pioneer Bridle part of the trail follows the path of the Barlow Road, a shortcut for pioneers heading to the Willamette Valley wishing to avoid putting their wagons on rafts down the Columbia River. However, this required they travel over Laurel Hill, noted in many of their diaries, as the most challenging part of the entire trip from Missouri. The pioneers had to lower their wagons with ropes around trees down steep parts of the trail. Check out more information on interpretive signs at the Tollgate Trailhead - the west end of the ride.