Didn't know where else to put this. Looking for some input from the local guys. Wife and I are looking to do a weekend away the first weekend of November. Trying to decide between Hood River and Bend. What say yous? And is there a downtown-type area to stay in where we could be walkable to all the eating and drinking establishments?
I thought there was a thread once about one or both places, but I can't find it, so...
Both are fantastic, but the drive to Bend and back can be rough, especially if there's any weather (though I'm beginning to think we'll never see rain again). Bend is much bigger as well, so plenty to do and you can walk around the downtown area with ease. That said, there's a bunch of cool stuff around the Bend area that you'll want to explore and having a car to get you around is ideal. It's a beer lover's paradise and many of the breweries have top notch grub either in house or with food carts on the property. Honestly though, summer is the ideal time to visit Bend. Unless you plan on skiing at Bachelor, but again, with our hot, dry summer not sure that's an option in Nov.
Hood River is much smaller, easier to walk around the downtown area and not a whole lot much to explore outside of the area unless you want to visit some wineries or hit some cool hikes. There might be some cool apple or pear orchards to visit in early Nov, but I think Sept/Oct is the ideal time for that. Hood River also has some excellent breweries with great food. pFriem is excellent. Double Mountain is very cool, great pizzas. The Naked Winery used to have a tasting room downtown that was a lot of fun. They changed their name to Evoke, same ownership. They've also expanded to other towns, but this was always a fun place to go.
Other odds and ends - Hood River is VERY windy, so it's no surprise the kite boarding, wind surfing, etc are VERY popular activities. Watching the colorful kites flying around the Columbia can be pretty cool. A wonderful spot to base out of if you want to explore the Gorge some more. Across the river is White Salmon, which is also a pretty neat little town with some good food and beer. Terrific views of Mt. Hood at Everybody's Brewing.
If just a weekend getaway, consider the fact that Bend is going to take roughly 8 hours (and likely more) of your time in travel there and back. Hood River will be more like 4 if traffic is snarled getting through Portland. Lastly, if you're a fan of fish, the Native Americans are able to catch salmon at will and they will sell their fresh catch near the Bridge of the Gods in Cascade Locks. You can get some terrific deals on fresh chinook, coho, sockeye and other fish that you aren't going to get in the stores (and certainly not as fresh).