Planning a mini-vacation up to Bend within the next month or two. It is my first time to Bend so was hoping some of you might have some suggestions re: accommodations / activities? Definitely hoping to get a ride or two in but also want to experience as much of the town as possible!
Went up to Bend over New Years and stayed in the Old Mill District. Nice area close to downtown, but easy enough to get around to difference parts of town or surrounding area. I would say if you have the time to go down south of Bend and check out Crater Lake. I’m planning another trip to Bend this summer, and I’m planning to head back there again. Plenty of trails to run along the river (a bonus of the Old Mill District is that it is on one of the trails), or you can drive to any number of the other trails, either along the rivers, or out east to more dessert. I didn’t have my bike, so I can’t comment on the riding, but just from driving around, there are plenty of areas to get rides in. Hopefully my next trip includes my bike.
Plenty of microbrews with really good beer out there.
Tip: drink plenty of water to stay hydrated. High dessert climate out there and easy to get dehydrated.
Check out Bend Vacation Rentals. We rented the Awbrey House with three other couples and it was great. Right across the river from downtown. If that is too big for the size of your party they have many other options.
http://www.bendvacationrentals.com/
Enjoy. Bend is a great town.
rent or bring a mountain bike and hit up Phil’s trail. Go to Deschutes Brewery and get a stout on Nitro. You can buy their stout in the bottle but can only get it on Nitro at the Brewery. 1000x’s better at the Brewery. Head to Smith Rock and go rock climbing (not in Bend but close enough) or even just hike around it. Then go back to Deschutes Brewery and get another stout. Good food as well by the way. Probably too cold still to float the river, although maybe not.
Hey there! We just moved to Bend a few months ago. It’s amazing.
You can find plenty of rentals on VRBO if you’re interested in a home or condo. I would recommend Bend proper, not Sunriver or the outlying areas if you want to be able to walk from your place to eat/drink. If you’d prefer a hotel, The Oxford is right downtown and has a boutique vibe. The Old St. Francis School is part of the McMenniman’s group and is cool and funky. There’s also a nice Marriott at the Old Mill (Old Mill is essentially a mall, but located on the river with a great running path.)
There are lots of great places to eat and drink fantastic beer. Crux Fermentation Project is our current favorite. Amazing beer, cool fire pit, good food. The Sparrow Bakery is to die for. Zydeco downtown for upscale, delicious food. That’s just a start.
I believe that Pine Mountain Sports will rent/demo bikes, both road and mt. I’ve been in there a few time for snow shoes and they’re very friendly. We’ve got dirt right outside our house so I haven’t explored Phil’s Trail System yet, but have only heard good things.
Smith Rock is about 40 minutes N of Bend and it’s definitely worth driving to for a hike. It’s gorgeous. Or bike out there from Bend just to look. It’s truly amazing.
PM me if you have any specific questions 
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Check out the lava tube cave just south of town, pretty cool (actually bring a jacket because its pretty cold in there).
We call Hop Venom, liquid heroin. That stuff is SO good. We also love their RPM. The tasting room at Boneyard is an old garage, standing room only, grungy, but cool. Very nice people working there.
I love BEND! I still can’t believe we’re living here. Woowoooooo!
Rented this place last year for Leadman. Great location, short walk to the river and to downtown area. Nice that it has the option of adding on the extra suite should you need to sleep more than four. http://www.vrbo.com/479844
+1 on Smith Rock. The loop along the river up past Monkey Face on the Verde trail and over Misery Ridge is a fantastic trail run (or could do in opposite direction, but rougher crank starting right out up Misery Ridge). Crater Lake is awesome, but a way longer drive ~ especially before they open the north gate in summer; it varies depending on snowpack each year, but probably still closed when you’re talking about so you’d need to add another hour or so driving each way to come back around from the south.
Also +1 on the brewery suggestions. Deschutes is fine, except the locals look down on it as the Disney of micros nowadays as it has by far the largest commercial footprint beyond OR; Boneyard is probably the most hip at the moment, but I dig 10 Barrel and Good Life as well.
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[quote OneGoodLeg
Also +1 on the brewery suggestions. Deschutes is fine, except the locals look down on it as the Disney of micros nowadays as it has by far the largest commercial footprint beyond OR; Boneyard is probably the most hip at the moment, but I dig 10 Barrel and Good Life as well.
More stout for me. There is a brew pub between Smith Rock and Bend that is pretty good as well. They have a Monkey Face porter I enjoy, but darn it the name of the place is escaping me. Spent many a night post climb having a drink there
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I dunno if it’s the actual brewpub you’re thinking of or another taphouse also serving it, but MF porter is from Cascade Lakes brewing in Redmond.