Big Backpacking Trip Ideas

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I've been working on my upcoming summer plans, which also has me thinking about bigger backpacking trips/adventures that I would love to complete someday. Most of these trips require some creative routing, since there obviously isn't established trails to do most of what I would like to do. Does anyone else have crazy trips planned like this? Any input?

-South Washington Cascades Loop:
Start at Mt Rainier, connect with the dark divide area, hike over to Mt. Adams, north through the Goat Rocks and back to Mt. Rainer. Probably 80% of this has existing trail, the rest will require some road walking or route creation. The biggest gap is between Mt. Rainier and Dark Divide.

-Hells Canyon - Wallowas
Start at the northern end of Hells Canyon, hike south, up the Imnaha River, connect with the Minam River and hike out. 95% of this is currently trail, will use small backroads to complete the trip. The only real gap is a small segment between Hells Canyon and the Imnaha River.

-Portland to Hood River
I do a lot of hiking in the Gorge, but haven't done a longer, continuous trip. This isn't really feasible, but I would love to be able to take the MAX (our light rail system) as far as possible to the east, start walking, connect the trails in the gorge, emerge in Hood River, hop on the Amtrak, and take the train back into Portland. Most of the Gorge can be linked by trail, but connecting these trails to Portland and Hood River is a ways off. Still fun to think about though.

-Sound to Coast
Begin in the the Duckabush or Dosewallips Valleys in Olympic National Park, hike through the park, down the Bogachiel River, connect to the coast, and hike up he coast to Lake Ozette. Much of this is trail, but will need to road walk between the the end of the the Bogachiel trail and the coast.

Yeah, you're right, fall is probably the best time to do it, maybe even get some good fall colors and fresh snow on the higher peaks. It seems like there would be a few areas to stockpile food, the Hell's Canyon section would likely be the longest stretch without resupply. With my route, the trail heads to Wallowa Lake for resupply (and the very important showers and beds, restaurant?) before continuing on through the Eagle Cap Wilderness. I would love to get back into Glacier National Park--I would imagine that it is the most spectacular stretch of the CDT. My main trip this summer is in the Sierras. Have a few places that we hiked through on the PCT that I would like to revisit.
260! Wow! Even if you averaged 20 miles a day it would take two weeks. To truley appriciate it, you would need about three weeks. I would think late September into early October would be the best time. Before the trip, you could hang food and supplies where the trail meets the roads and Wallowa lake. I have a couple spring trips planned for Hells Canyon. I love that area. I am also contemplating hiking the entire CDT trail through GNP later in the summer.
I think it's at least 200 miles...I had the mileage at one time, seems like it was 260 or something. I was trying to figure out the best time of year to do it, since I would imagine the summer to be pretty brutal in Hell's Canyon, but doing it too early would be harder in the higher elevations of the Wallowas. Would be pretty epic...
Forrest, I misunderstood, I thought you meant hiking from the mouth of the Imnaha, following the river into Eagle Cap. I was wondering why you wouldn't take a route along the snake river trail or the high trail. Last year, while planning my spring Hells canyon trip, I realized the potential to connect hells canyon and eagle cap. I forgot about it since then. This sounds like an amazing trip! The elevation changes and contrasting environments would be like no other. Now you have me thinking about doing this. Have you figured out the mileage? It's gotta be pushing 200.
I didn't know that there was a group working on new trails...that would be great. I have the same complaint about I-84 and the other roads/trains, but I guess at the same time, it gets me to my trails pretty fast! It is certainly hard to get away from the civilization on many of the trails, but there are quite a few that stay in the quieter (maybe not totally wild) areas of the gorge.

If interested, I posted a quick map of my proposed Hells Canyon/Wallowa trip:

T: We must be on the same wavelength...two of my week-long treks this year are the same as yours - Matterhorn via Ice Lake and circumnavigating Three Sisters. Forrest: Did you know that there is a group trying to connect a circuit of trails in the Gorge so one could possibly hike a loop from Corbett area to the Dalles? Not sure how far along they are, but the last I heard they were in the planning stages. My only complaint about the Gorge is the noise from auto traffic and trains. It doesn't always feel like the wilderness when you look down and see I-84 or WA-35 :0) Some shorter trips I would like to do this year: The Olympics and The Enchantments...possibly Goats Rock. It's tough to find places in Washington that are dog-friendly backpacking areas.
I don't have anything off trail planned except a couple of summits hopefully He Devil Peak and the Matterhorn. I believe this mountain is at Ice Lake in the Wallawas where I plan to go in July and I'll take my 3rd trip in a row into the Seven Devils over Labor Day never summitted though. Maybe head to the 3 sisters area sometime but just kind of talk right now. The trips you both talk about sound awesome though!
T. Simons_81
I have done portions of many of the trips you are contemplating. The Imnaha river is mostly followed by a road out of hells canyon, which in a way is a shame. The imnaha river valley is breathtaking and would be even more so wild, but it allows access to dug bar and many ranchers live along it. However; there are some trails that meander throughout the area. I have many big trips on the back-burner. Every year I end up traveling miles off trail trying to complete a loop and see the less seen. One major trip I have always wanted to do also involves Hells Canyon. The trip would start out traveling through the guts of the Seven Devils and then drop down into Hells Canyon to the Snake River. From here you could either A: have a hired guide float you out or ... B: bring a lightweight pack raft ant float across the river and hike out the Oregon side. You could do something similar in the Frank Church Wildernes/Salmon river.