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I'm planning a trip out to the northwest this summer. I'll be limited on time, but would like to squeeze a lot in. For an itinerary I'm thinking:

Day 1: Fly into Bend. Bike ~4 hours.

Day 1 night: Drive down to Crater Lake National Park.

Day 2: Hike Crater Lake. Drive back to Bend and check out the town.

Day 3: Get to Seattle. Meet up with friends in Seattle.

Days 4-5: Hike either Mt. Rainer or someplace in the Olympic Peninsula.

Day 6: Drive up to Whistler checking out Vancouver on the way. Get a quick hike in, in Whistler

Day 7: Bike Whistler

Day 8: Drive back to Seattle and fly back

Some questions I have about Bend are:

1. What's the top bike shop(s)?
2. Any trail recommendations, is there a classic must ride trail?
3. Hardtail or full-suspension 29er? I enjoy both depending on the trail
4. Any recommendations for things to see and do? What are some good bars in town?
5. Is there a bus or train from Bend to Seattle? (Update: I just looked up flights and it's seems like they're only ~$100 so I'll probably do that)

General Questions are:
I'll probably camp most of the trip -- any specific campgrounds I should stay at?
Any other recommendations for the trip?
 

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You renting your bike here? When during the summer are you coming. If possible, try to come after August 15, as some of the best rides become more accessible as an elk calving area closes down a key trail until then. I ride 26 Full-Suspension, but it seems more and more so that 29er hard tail is about the best option - trails are generally flowy and smooth. Tumalo State Park is the best park close in to town and has reasonable access to the trail network, but you will likely want to just ride to the trail head or shuttle service. Otherwise, Cascade Lakes Highway has lots of beautiful campgrounds. If late August, a great ride is Dutchman-MWT-Happy Valley-Mrazek, gives you a heck of an introduction to Bend. If earlier, hit the Phil's trail complex or Wanoga.

Cogwild shuttles are super cheap, so if you are only riding one day, you would be well served to do a shuttle to get the most riding in, covering the most ground.

Beertopia is Bend, so picking a single bar is pretty impossible. Just go downtown, to Galveston Avenue, or elsewhere following the suds.

Mt. Bachelor will be in its first full season for biking, if that is your thing, too.

Resources:

http://forums.mtbr.com/oregon/mt-bachelor-dh-bike-park-opening-september-2013-a-869813.html
Cog Wild Mountain Biking Tours in Bend, Oregon 97701Cog Wild Bicycle Tours & Shuttles | Bicycle Tours & Shuttles
The Bend Ale Trail Beer Tour
 

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Trails: Flagline-Swampy, then South Fork-Tumalo, then back up Skyliner, down Whoops, then Phil's. Or mix it up a bit. More technical stuff on the south side (Storm King, COD). You could spend 3 days just riding different routes down from the Dutchman Flat parking lot and shuttling back up.

Bike shops: Crow's Feet Commons has bikes, beer, and coffee. It's also right by Mirror Pond. Pine Mountain is right under Cog Wild.

Beer: Deschutes Brewery is fun to visit and I like their downtown pub. I also like the Cascade Lakes setup across the river, riding distance from Cog Wild.

Things to do: Stand-up paddle or kayak on the river. Hike Middle Sister. Visit the High Desert Museum.
 

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^ I have a hard time saying a trip to Crater Lake for someone from outside the area would not be "worth it". Obviously, it is entirely subjective and relative to the person's interests. If you don't get to visit an area with such an incredible natural treasure that is of interest to you, taking advantage of that option is totally worth it. I love Bend, but Crater Lake is truly special, and if this is his best chance to visit, then he should enjoy it.
 
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