It's been quite some time since I was there, but I'll be there at the end of this month and I'm absolutely, positively hitting the Boneyard Brewery. I've never been, but their flagship IPA is my favorite beer in the world. So I'm hoping their brewpub lives up to the hype. There are several great breweries in Bend now, but I haven't tried many of them as a lot of them have popped up recently. But if you're not a beer guy, I probably don't need to belabor the brewpub point.
A little further north is a town called Redmond that's a city on the come. I'd like to check out
Wild Ride Brew when I'm there. They've got some interesting beers with a few different food carts on site that you can order from and sit down at the common area to eat/drink.
Downtown Bend is neat. Again, haven't been in several years, but it's got a lot going on. It's a small, walkable area with plenty of options for eating and drinking. It can get a little crowded, though. Parking can be a bear. There's a McMenamins there - the Old St. Francis School. If you've never been to a McMenamins, it's worth checking out as the architecture and art work are really neat. The food however is lackluster, over-priced and the service can be very surly. Maybe have a drink and some tots so you can check it off your list, but you can do a lot better for food, especially for what they charge.
If you've never been, you're going to really enjoy it. The people there get outside and squeeze every drop out of the summer days. River floats, mountain biking, hiking, you name it, Bend is a playground for outdoor fun. I'll ruminate on it some more and circle back. Too bad my Bend trip isn't this weekend, it would have been nice to meet you.