Love Bend/Sunriver. We usually stay in a VRBO or AirBnB for about a week in the summer in Sunriver since 2018. This year, we got a long-term rental 7/8-7/31, right across the street from the SHARC, so a prime location for us. My wife and I are big IPA fans (especially hazies and juicies).
Sunriver Brew Co. (I've only been to the Sunriver location) has good food, and good beers.
Crux has been our favorite brewery venue so far. El Sancho Taco Shack has a truck there, and they're phenomenal. Usually, 3-5 other food trucks as well. The beer is great.
GoodLife Brewery is cool with a large outdoor space (at least 2 cornhole sets).
Bend Brewing Co. is a great spot right on the river. Good food and beers.
Those Thursday night free concerts in Drake Park are great. In 2019, we saw one of the Marley kids and the Wailers.
We've taken our kids to the secret bar at McMenamin's Old St Francis. They were 14, 11, and 8 at the time. It was during the early afternoon, so it wasn't crowded at all. Our kids love Harry Potter, so the brooms and secrecy were a selling point for them. It was the bourbon drinks for my wife and I.
The original food cart pod at The Lot (intersection of NW Hartford Ave. & NW Columbia St.) is amazing. There's a permanent taproom there and lots of food carts to choose from.
Our kids love the candy store downtown (Cravin's on NW Wall St).
One of our favorite things to do in Bend is float down the Deschutes River. We use "Park & Float - Tumalo Creek Tube Rentals" near the skatepark that's super close to Bend Whitewater Park. You park, rent some tubes (or you can bring your own), they shuttle you a couple of mins away to Riverbend Park, you hop in the river and float for 2-3 hours, and get out at Drake Park where the shuttle is waiting and takes you back to your car. It's awesome. You float past the music venue (formerly Les Schwab Tires Amphitheater, now Hayden Homes Amphitheater). In 2018, we got to hear Amos Lee doing his sound check. This Friday, we're going to actually go in and see Dispatch and OAR, with special guest G. Love (sans Special Sauce).
Anyways, there's a ton to there, and beer is inexpensive (relative to the SF Bay Area). We're considering the area for our retirement (non-winter months though, as the wife can't stand being cold).