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Mt Hood Wilderness
The Mt. Hood National Forest and the Columbia River Gorge National Scenic Area together form a huge wilderness for playground residents of Portland.  There are three ski resorts, countless waterfalls and a vast network of trails including the 40 mile Timberline trail which encircles the eponymous volcano.  
Right: The south face of Mt. Hood where the Timberline Ski Resort is located
The southwest face of Mt. Hood sports the best meadows on the mountain.  In particular on the way to Paradise Park  which is an easy day hike from the Timberline Ski Resort
11.8 miles return, 2200ft
Left: The Meadows preceding Paradise Park

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North of Paradise Park and west of the mountain, the feature attraction is Ramona Falls below 

Paradise Park itself is a vast treeless meadow with sprawling views but somewhat sparse flowers, however there were little streams that packed quite the photogenic punch.  From our 2008 hike:
From our day hike to Paradise Park :

"...the meadows here are much drier than at Mt. Hood's North Cascade cousins and shade is harder to find on a hot summer day.   The trail dips in & out of a series of gullies until climaxing with 800ft deep Zigzag Canyon.  Once past this chasm however the effort starts to pay off as the next series of gullies are filled with bright beautiful flowers."

 "The chasm carved out by the Sandy River is just amazing.  The river itself was practically a trickle, but the wide channel, steeply cut banks and the trail washouts are testament to the awesome power of this river."
  7 miles return, 1100ft  
Right: Flowers along a creeklet in Paradise Park  
Ramona Falls is the kind of cascade that photographers dream about. 
The trail keeps going past the falls to Yokum Ridge, a worthy destination it itself. 

14 miles return, 3600ft
Right: Ramona Falls

In contrast the north face of the mountain features a lot more snow and ice.  The most scenic approach is from the west via the Top Spur Trail over Bald Mountain.  The trail forks at half a mile with the PCT going right and offering a great view of Mt. Hood before descending into the Muddy Fork Valley.  The left fork is the direct route to Cairn Basin and the North side of Mt. Hood.   Although it isn't shown on maps, it is possible to take the PCT as far as this viewpoint and loop back onto the other trail.  After three miles there is a junction with the left trail leading to Cathedral Ridge approach and the right fork ascending to McNeil Point and meadows that surround the McNeil Point Shelter.

Direct out & back hike to McNeil Point is 10 miles return, 2000ft
Right: The Shelter at McNeil Point
There are several approach trails on the north side of Mt. Hood and they average around three miles, Vista Ridge at 2.7 miles is the most direct route and thus the most popular.  It reaches the Timberline Trail at Wyeast Basin, a distance of 5.7 miles from the Top Spur trailhead. 

Elk Cove is a worthy destination for a day hike but the real prize on the north side of Mt. Hood is the route from Dollar Lake to the Barrett Spur.
Left: Elk Cove Above: The Ladd and Coe Glaciers from Barrett Spur

Elk Cove via Vista Ridge 8.8 miles return, 2000ft.  

The summit of Barrett Spur is an additional 3.6 miles return, 2000ft from Elk Cove
The biggest challenge in completing the Timberline Trail is the crossing of Eliot Creek which has suffered wash outs in recent years.  Once past that obstacle the trail climbs up to Cooper Spur, the site of the Historic Cloud Cap Inn.  The trailhead is at 5850ft and nearly at the tree line.  The shelter at Cooper Spur is only a mile from the parking lot.
The remaining section of the  Timberline Trail south of here is less appealing as it crosses the recent devastation of the Gnarl Ridge fire and the two ski resorts, Mt. Hood Meadows and Timberline.
Right: The shelter at Cooper Spur