Gunsight Butte is a 8.2 mile lightly trafficked out and back trail located near Mount Hood, OR that features a great forest setting and is rated as difficult. The trail is primarily used for hiking and is accessible year-round.
A nice 2700ft of overall gain over 4 miles (2350ft base-to-summit). Then 4miles back down. Some blowdown, snow in the winter, but overall a well-kept trail that turns into a nice ridge-hike. Look at the attached images for a complete map. Also, when you reach the first intersection (where the Gumjuac trail that you'll start in on intersects with the trail to Gunsight Butte), take the hardest right possible (just to the right of the trail sign) and NOT the 4x4 road. The trail looks overgrown and covered with blowdowns, but it clears-up within 40 feet.
Work them legs! Getting up to Gunsight Butte is just a nice, steep, and steady 2700 ft of overall gain. There are a couple decent views of Hood and Lookout Mountain towards the top, but it's more of a steady uphill slog that turns into a ridge hike in the last couple miles towards Gunsight Butte.
Once you've hit the multi-way intersection about 2.6mi in, take the sharpest right you can (to the right of the old road, not on it). And then, well... hike on.
Mee-Maw, Pop-Pops, and Aunt Margaret won't like this one. There are a few blow-downs that require a little scrambling, and Big Margie (she hates that name, but it's apt) will want to stop every 1/4 mile because the gain never stops. There simply aren't any flat patches: you're ascending until you get to Gunsight, and descending on your way back down. Still, little Timmy might make it if you haven't given him too many Mountain Dews and Pop-Tarts. H∑ll, he might even have a good time.
And the best part? No pesky tourists. They're too busy a few miles away taking pictures of Timberline Lodge and sucking-down overpriced (but delicious) hot chocolate, so this trail is nice and quiet.
There will be snow in the winter, but thanks to good 'ol global warming, you have a better chance of skiing at Ski Bowl than you do having it be problem. Still, the butte is at just under 6000ft, so wear some boots and bring gaiters in the winter.
And oh yeah: enjoy!