Hi all, looking for some guidance on how many days should someone plan to spend when visiting Bend. I'll be traveling solo, driving from Portland. Would two days be enough time to take in the sites, activities, and good times Bend has to offer? Thanks for your guidance!

We spent three nights when we visited in 2016 - I really liked Bend and probably could have easily filled another full day.

Here's my report from that trip - Bend starts at #65:

Today it rained…on the road in the PNW

What are your interests? I agree that there's plenty to do nearby to fill 3-4 nights. We went to Smith Rock, Newberry Crater, McKenzie-Santiam loop and also spent time wandering around Bend, eating, touring Deschutes Brewery.

Be sure to include a several hour visit to the High Desert Museum on your visit to Bend. They also have a daily raptor show that you have to sign up for in advance. Also south of town is the Lavalands Visitor Center which covers the volcanic history of the area including the Newberry Caldera which has two lakes in it with the original cone in between them. For a real blast from the past, you can visit the last Blockbuster Video store on earth on Third Street.

Hi Patty , my interests are mostly outdoors-focused - hiking, biking, walking. I'm not the best when it comes to water-related activities, but had considered kayaking. And to unwind, food and some great beers is always on the list.

So much to do around Bend. Hiking, biking, rafting, and lots of brew pubs. You could stay for a week.
A hike I like is to Benham Falls- easy trail along the Deschutes River. Trailhead is probably a 20 min drive from town. There is another segment of the Deschutes you can access from town. Nice hike- no waterfalls though. Another hike is at Smith Rock, popular for rock climbing but there are hiking trails too.
SunCountry Tours offers some nice rafting trips. The Big Eddy is a favorite and not too wild and crazy.
In Bend there is a self guided Ale Trail or there is a Bend Brew Bus which is a tour.
The Old St Francis School is a fun place to stay- walking distance to downtown.
There's a few ideas.

Like for any new destination, I'd say do your research, make a "wish list" and see how long it would take. Guessing for some a day or two would be plenty. But I'm also sure there are residents been living in the region for decades without seeing everything.