Weekend: Bend, Oregon

Bend, Oregon provides an easy weekend getaway from all over the Pacific Northwest (and still good, but maybe not as easy from other spots). A lot of folks might not think high desert when they think of Oregon, but that’s what Bend is considered. But as you get to know Bend, you’ll appreciate its stunning mountain views, outdoor adventures, year-round sunshine, and laid-back vibe—but it’s also a welcoming and inclusive destination for LGBTQ travelers.

A long weekend here is a perfect opportunity to explore scenic hiking trails, float the Deschutes River in the summer or ski the slopes of Mt. Batchelor in the winter, and sip craft beer year round at one of the city’s many breweries.

Keep reading for some of my favorites in town as well as tips for making the most of Bend’s nature, culture, and charm for your weekend in this outdoor-loving town.

Getting There

Bend is a relatively easy 3-4 hour drive from Portland most times of the year. There’s beautiful scenery along the way, whether you choose to drive via Mt. Hood or take the southern route near Detroit Lake and through Sisters. In winter, road conditions can definitely add to travel time time and in summer increasingly frequent and severe wildfires can sometimes impact roads, so it’s advisable to check road conditions and be prepared for changing conditions.

There are other options to get here, such as bus service from Portland or bus connections from Amtrak’s nearest station in Chumult, about 65 miles away. But arriving and departing by car or air are definitely the more efficient ways to get here.

Know Before You Go

Bend is car-friendly and easy to navigate, but bikes are also a great option—especially in summer. As well, Downtown Bend is quite walkable. Note, however, if you’re not planning to drive, a close-in hotel might be important as ride shares are sparse outside of central areas. Of course, if you’re planning to explore outside of Bend a car will be key, including going to places like Mt. Batchelor, Smith Rock, Lava Butte, or the Cascade Lakes.

Once you’re in Bend, the city advertises over 300 days of sunshine per year, but most times of the year, you’ll want to bring an extra layer or two: it can still get cold, especially at night or if you’re headed to higher elevations. And while somewhat atypical, it rained on our July 4, 2025 trip, proving it’s good to be prepared for a little of everything.

Do make note: Bend isn’t much of a late-night town. If you’ve read other posts, you’ll notice the absence of a “nightlife” section below. There are some late-night events for Bend’s Winter Pride, so check their site for a list of happenings if you’re in town for that. The rest of the year, nearly all of the breweries close at 10 or earlier, and their kitchens (as well as most restaurants) may close earlier than that, so plan accordingly. As well, while ride shares are generally available around town during the day, it’s a different story at night. Even in downtown, there were few available at 8:30pm and none at 10pm on our most recent trip.

All of this backs up the idea that Bend has retained a laid-back, small-town feel, despite having grown a lot (and gotten a lot more expensive) in recent years.

LGBTQ Safety

Bend is known for its inclusive and progressive vibe, especially being a smaller city. Bend’s Winter Pride Fest—including events on and off the slopes at the end of winter—and queer-owned businesses help foster a welcoming atmosphere. While more relaxed than Portland or Seattle, you’ll likely find visibility and a warm welcome in local spaces.

Statistically, the city of Bend scores 83 out of 100 in HRC’s Municipal Equality Index, with strong legal protections, but varying municipal programs for LGBTQ support and representation. And statewide, Oregon is considered one of the safer states in terms of transgender protections and a relative lack of anti-trans legislation. Conversely, Safehome.org’s rating for LGBTQ safety only gives Oregon a C grade, which in this case is a call to be mindful outside of more populated areas. For what it’s worth, the Safehome rating is a mix of legal protections and reported hate crime statistics so the quality and quantity of data, plus the statewide rating means it’s imperfect, but few other resources include hate crime statistics in their formulas.

Sightseeing Highlights

I could easily spend a weekend in Bend and not make it beyond downtown. It’s walkable, full of great breweries, restaurants, shops, galleries, and outdoor patios (and the riverfront lawn at Bend Brewing checks most all of these boxes all at once). And the Deschutes River flows beautifully right through town. The Old Mill District is also great for shopping, dining, and riverside strolls. Plus, Bend’s year-round events and summertime farmers markets are great ways to feel like a part of the community.

A few other fun spots to explore in Bend include:

• The Deschutes River Trail is great for in-town strolls or lazy cycling and the parks on both sides of the river are perfect for R&R
• The Deschutes River isn’t just scenery, either. Rent or bring with you an inner tube and float down river and through the Bend Whitewater Park. You can walk back through the parks or catch the Ride the River shuttle by buying a $5 all-day pass. Or get out your paddle board to glide across the water of Mirror Pond (technically an impoundment of the river, but I had to look that up).
• Pilot Butte is the highest-elevation point within the city. While you can drive to the summit, there’s also trailhead parking at the base. either way, you’re rewarded with panoramic views at the top.
• Shevlin Park (just on the outskirts of the city) is another great place for hiking, trail running, cross country skiing, or whatever you’re into. The park’s 650+ acres are full of trails through the trees and along Tumalo Creek, plus picnic areas to refuel before or after your exercise.
• And then there’s the last remaining Blockbuster, in case you have a hankering to rent a DVD or just snap a photo for your IG.

Of course, being a haven for nature lovers, the fun isn’t just in town. Nestled at the edge of the Cascade Mountains, Bend has year-round adventure: hiking, biking, skiing and snowboarding, and all sorts of water sports.

• Mt. Batchelor might be my favorite place to ski in Oregon. The runs are long, the lines aren’t necessarily, and it’s such an easy drive from downtown Bend. In the summer, there’s a bike park, and zip lines. If you’re only coming for the day during ski season, Deschutes Brewery typically runs a bus from and back to their Portland brew pub—with a apres-ski stop at their Bend brewery before the ride back.
• Newberry Volcanic National Monument has some of the most interesting lava formations I’ve seen outside of the Big Island of Hawaii. From the Lava Lands Visitor Center, there are trails throughout the park for year round adventures, including cross-country skiing and snowshoeing when there’s snow on the ground.
• Smith Rock State Park is a favorite for rock climbers, but there’s much more here than just climbing. Explore the trails, enjoy the views, or come here for tent camping March to November (RVs are not permitted, though).
• Cascade Lakes Scenic Byway (also called the Cascade Lakes Highway) covers a little over 60 miles near Bend and is dotted with a variety of lakes filled with fresh cold water from the surrounding mountains’ melted snow. The lakes and mountains make for beautiful vistas whether you’re driving the highway or have gotten out to stretch your legs and hike, paddleboard, or kayak in the area.

Eating and Drinking

Bend is often called Beer Town USA—it’s home to 30 craft breweries. I haven’t checked out all of them, but I’m well on my way. In fact, whether you’re serious about it or just having fun, the Bend Ale Trail is a fun, self-guided beer tour—with rewards.

Check out the Ale Trail link for a full listing of local breweries. Some of them I’m most likely to frequent include:

• Deschutes Brewery (with a pub in Portland too) is one of the originals here. Their Bend Public House has a taproom, restaurant, and a small amount of outside seating. You’ll recognize their connection to the area through their beer names: Mirror Pond Pale Ale, Black Butte Porter, and so on. Hilariously, the Bend pub also pours the Kirkland Signature Lager they make for Costco. Oh, and the food is good here too.
• 10 Barrel is another Bend original (also with a pub in Portland). Their two locations in Bend include their original West Side pub, just across the river from downtown, and a much larger and relatively new East Side brewhouse and pub. Both have good beers, good food, and nice outdoor patios.
• Crux Fermentation Project, in a former Aamco Transmission Shop, is also of my favorites. Besides a delicious assortment of brews and decent food, they host a handful of local food trucks and have a sprawling lawn full of picnic tables and games—and a fire pit for cooler times. Conveniently, it’s also a 15-minute walk from the campground where I’ve most frequently stayed in Bend (see info on that below).
• Sunriver Brewing is right next door to 10 Barrel’s West Side pub (in addition to their original location in nearby Sunriver). It’s a solid destination on its own, but is also a good back-up plan if you’ve headed to 10 Barrel and they have an endless wait.
• Good Life Brewing is a few blocks from Sunriver and 10 Barrel’s West Side pub. In the summer, they have a huge lawn behind the brewery that’s full of picnic tables, food trucks, a fire pit and a playground for the kiddos.
• Bend Brewing Company hasn’t always had my favorite beers, but their food is good and the riverfront location can’t be beat.
• Silver Moon Brewing, an easy walk from Deschutes, has regular live music to complement its brews and on-site food carts.

Bend also has a delicious local food scene. In true Oregon style, there are plenty of food trucks, farm-to-table fare, and quirky brunch spots. A short sampling of places I’ve most enjoyed (besides brew pub food) include:

• Jackson’s Corner is a wildly popular spot for breakfast and brunch, and does dinner too. Go early or be prepared for a wait (in line to order, and again for your food). The Turkish eggs, Bloody Mary, and country potatoes were all really good, but be careful on the sidewalk across Delaware Street: I twisted my ankle something bad on the uneven concrete by the fire hydrant 😫
• Dogwood at the Pine Shed is a an walk The Camp RV park or very easy from the Campfire Hotel. It’s a great place to grab a cocktail in their lounge-y bar or large outdoor patio and listen to what the DJ du jour is spinning. And with a rotating collection of food carts, there’s good food too. When we were there last in July 2025, the roast beef sandwich from ‘Wich Doctor and the chicken banh mi from Dinky Dau were excellent.
• Crosscut – Warming Hut #5 is more of a beer (and cocktail) place, but you can order tasty Detroit-style pizza next door at Abe Capanna’s to soak up the booze.
• Cafe des Chutes serves up tasty breakfast eats and pastries. Be prepared for a wait if you’re not there early (or maybe even if you are), but if you can tolerate the wait, it’s delicious.

Lodging

Bend has a nice variety of hotels, including the major chains to earn or cash in your points, and lots of more quaint and local options. As noted above, if you want a walkable weekend, choosing something in or near downtown will be important. But also pay attention to parking details: a few blocks might make the difference between spending a lot of extra coin to store your car or having free parking.

The list below is by no means all-inclusive, but should provide helpful details to help choose whatever works for you:

• The Camp is a small 1950’s era RV park that’s been renovated in recent years to appeal to urban adventurers and as a base camp for wilderness seekers. It’s not the cheapest campground you’ll find, but has easy access to town (and Crux, as noted above) with cute, if not private, sites. I’d skip sites 14-20 if you can—they’re the smallest and have the least screening from adjacent campers. Also note: bring your own table and chairs; there’s a communal picnic tables and BBQs (and fresh coffee in the AM), but the there aren’t picnic tables or seating at the individual sites.
• The Newberry Hotel, a Hilton property, used to be a Doubletree. I haven’t stayed here since the switch-over, but even before the update, the property was pretty decent and has free parking, plus it’s quite central.
• One block over from the Newberry is the Oxford Hotel. It’s quite nice and also very conveniently located. Take note though: the one block walk you’ll save compared to the Newberry means valet-only parking, which is $32 per night and street parking is metered.
• The Campfire Hotel is one I haven’t stayed at, but they’ve often hosted Winter Pride events and I’d say would be a good choice for a LGBTQ-friendly place to stay, as well as being walkable to downtown.
• The Waypoint Hotel was the host hotel for 2025’s Winter Pride, so I’d also expect it’s a good option for LGBTQ-friendly lodging, though I haven’t stayed here either.