How to Enjoy an Adventure-Packed Weekend in Bend Oregon
Post Summary: Weekend in Bend Oregon
Yearning for high desert adventure? Then it’s time to plan an unforgettable weekend in Bend Oregon!
In this guide, I share everything you need to know before you go – from where to stay, activities to do, and can’t-miss sights. This way, you’ll experience the very best of Bend!
This post is sponsored by Visit Bend. All of the following recommendations, thoughts, and photos are my own!
Your Guide to Planning an Amazing Weekend in Bend Oregon
As the sunniest city in Oregon, Bend attracts adventurers all year long.
The small, beautifully designed city rests beside the eastern Cascade Mountains.
At 3623′ above sea level, the High Desert environment provides flourishing forests of pine and juniper trees, spring and summertime wildflowers, and a comfortable number of wet days (many of which involve snow!)
Why do adventurers love Bend? Because the city itself is adventurous. A glance at a map reveals the Deschutes River twisting through the heart of the city. In fact, much of its early history is connected to the mighty 252-mile river. Eventually, it drains into the Columbia River.
Without a doubt, Bend is the gem of Central Oregon!
No matter what type of outdoor recreation excites you, you can find it here. To name a few: it’s hiking, mountain biking, skiing, whitewater rafting, snowboarding, kayaking, ice skating, snowshoeing, fishing, or golfing.
However, the fun doesn’t stop there. Craft breweries, local coffee roasters, and boutique shops lie at every turn.
As Visit Bend says, “It’s where you go to play!”
Because this guide is jam packed with the best things to do in Bend, you can easily use it to plan a trip longer than a weekend. And don’t worry, if you stick with a true weekend getaway you’ll still see so much!
Quick Guide to Popular Neighborhoods in Bend
While visiting, there were 3 main neighborhoods that we kept coming back to for the food, brews, and views. Here’s a brief rundown to get you acquainted with the area before your weekend in Bend Oregon!
Downtown Bend (a.k.a. Old Bend)
Hands down, we spent the most time in Downtown Bend. Upon arrival, our first stop was (naturally) a coffee shop. So, our first impression of Bend formed here.
We noticed a blend of historic and new brick buildings, trees dotted with twinkling lights, and an unmistakeable welcoming feeling.
Bonus points for being pretty dog friendly!
Check out Downtown Bend for top-rated dining and tax-free shopping (especially Bend souvenirs) in a very walkable area. See below for my full list of the top things to do in Downtown Bend.
The Old Mill District
Next, South of Downtown Bend you’ll find The Old Mill District. Once the hub of logging operations, it has transformed into a charming, luxury shopping and living center — all while maintaining the character of its past.
Look at REI, for example. It occupies a former Powerhouse and is easily distinguished by 3 smokestacks. You can spot it from a mile away!
Pro Tip: If you plan on visiting 6 or more Oregon State Parks within a year, then pick up a $30 annual pass from REI. Near Bend, you can easily visit Tumalo State Park, LaPine State Park, & Smith Rock State Park. Also, $5 Sno-park passes are available.
Click here for the full list of shops.
What’s the best part of The Old Mill District? It’s riverside.
So, you can stroll or run on the scenic Deschutes River Trail. To my surprise, you can even whitewater raft and river surf at the Bend Whitewater Park! Or, you may enjoy tube floating or watching these activities from the shore — sipping your favorite drink.
Finally, this is the prime concert scene in Bend. View upcoming events at the outdoor amphitheater here.
Orchard District / Eastside
Like The Old Mill Districts’ iconic smokestacks, the Orchard District has a feature that you can see from miles away. But this one is much, much wilder.
I’m talking about Pilot Butte!
The lava dome / cinder cone is an extinct volcano right in town. Can you believe that?!
Standing tall almost 500 ft above the rest of the city, you cannot miss it. I’ll talk more about the Pilot Butte hike shortly.
Beyond the butte, the Orchard District is home to shopping malls with beloved stores and the best breakfast spot in Bend.
Where to Stay in Bend Oregon
- LOGE Camp – First, LOGE Camp is a hotel built for the outdoorsy. Rooms feature bike racks, Yeti coolers, and hammocks. YES, hammocks! Since it’s located on the edge of town, you can easily access trails that lead to the gorgeous Deschutes River. This is where we stayed, and can’t wait to return with our pup! Learn about the property’s sustainability initiatives here.
- The Oxford – On the other hand, you can stay in the middle of it all in this centrally located luxury hotel in downtown Bend. The Oxford offers a modern feel and rooms that include kitchens. Pets are welcome here too. Check out their sustainability practices.
- Pine Ridge Inn – Lastly, enjoy riverfront views from a sweet suite in the Pine Ridge Inn. Their cozy rooms feature include fireplaces, hot tubs, and king beds. Plus, you’ll be a short drive from The Mill District and Downtown Bend.
Can’t-Miss Things to Do in a Weekend in Bend Oregon
1. Catch Sunset at Pilot Butte
If you love chasing sunsets, then be sure to visit Pilot Butte. By far, it is definitely our favorite place to see sunset in Bend!
What to Know About the Pilot Butte Trails:
- At the top, you’ll look over the city of Bend and get a great vantage spot to see the Cascade Mountains. 360 degree views!
- From November 15-April 15, the road to drive to the top is closed. But, you can park at the Pilot Butte Trailhead Parking and hike 2 miles total. You can either hike on the road or on a trail.
- Dogs are welcome on leash. However, if you want to let your pup run it is convenient to take them to Big Sky Off-Leash Area (2.6 miles away).
- Bathrooms are available in the parking lot.
- In the winter, be sure to return to your car before the gates close for the night.
Pro Tip: Grab a coffee from Backporch Coffee Roasters before heading to Pilot Butte. This location is just down the street: 706 NE Greenwood Ave #140 Bend, Oregon 97701.
2. Explore Downtown Bend
Top Things to Do in Downtown Bend
- Sip delicious coffee at Thump Coffee or Lone Pine Coffee Roasters
- Swing by The Bend Store for local art and souvenirs like tees, hats, and stickers
- Shop Patagonia Bend for longlasting outdoor gear and exclusive location-specific styles
- Treat yourself at Bonta Natural Artisan Gelato
- Grab dinner at Bend Brewing Company or Deschutes Brewery Bend Public House
- Explore Drake Park (see below)
Browse a list of all the businesses downtown here.
3. Stroll Drake Park & Mirror Pond
To feel like you’re in a Hallmark movie, head over to Drake Park & Mirror Pond. Fortunately, the park was freshly dusted with snow when we went. No joke, I turned to Kyle and said “This looks like we stepped into a one of Hallmark’s holiday romance movies.”
Nevertheless, the park is equally stunning in the other seasons. In particular, I’d love to return to see fall foliage!
The best times to visit are when you’re already near Downtown Bend and at sunset.
In particular, there’s a spot near the Mirror Pond Parking Lot where you are high enough to see the mountains!
For free parking, opt for the street spots on NW Riverside Blvd.
Finally, as you walk through the pristine park keep an eye out for 3 heritage Ponderosa Pine trees that are a couple hundred years old. And, look around for beautiful Blue Spruce, Aspen, & Willow tress.
4. Score Deals on Outdoor Gear
Since so many people in Bend live active lifestyles, there’s plenty of secondhand / thrift shops to pick up discounted gear by brands like Patagonia, Columbia, and The North Face.
Our favorite was The Gear Fix, located in The Old Mill District. This one is a consignment shop, so you can also sell items you don’t love anymore.
All in all, it’s a win-win for you and the environment!
My favorite part? The dogs who greet you in store! If you follow me on Instagram, you may have seen them in my Story.
Top 4 Things to Do Near Bend for Adventurers
To make the most of your in a weekend in Bend Oregon, don’t forget to explore a little ways outside the city. Here are my recommendations for beautiful, thrilling, and memorable things to do near Bend.
5. Smith Rock State Park
For a slice of the Southwest, visit Smith Rock State Park. Although it’s only a 45-minute drive from Bend, it provides an entirely different landscape.
As you approach, the drive itself reveals impressive views. The jaw-dropping, warm-toned basalt and tuff rocks contrast deeply with the surrounding desert.
Up close, you may be surprised at the juxtaposition of the lush shores of The Crooked River and and the dry rock.
While you can get awesome views from the parking lot, I recommend going for a hike!
We opted for the Misery Ridge Trail, a steep & sweet 3.5 mile hike with ~1000 feet of elevation gain. Thankfully, it’s a loop trail. We completed it counterclockwise, and enjoyed getting up close and personal with the humbling rock formations before winding down beside the river.
Note: Be sure to pack ample water, as it gets very hot here in the summer.
6. Drive to Mt. Bachelor
You can’t talk about Bend without talking about Mt. Bachelor. At a brief 20-minute drive away from town, it’s a snowy paradise for skiers, snowboarders, and snowmobilers.
Uniquely, Mount Bachelor’s season stretches into late May!
With a Half Pipe, double Black Diamond jumplines, and adventurous lines through trees it’s well-loved by intermediate and advanced skiers and snowboarders.
Still, there’s plenty of space for beginners. Mt. Bachelor was kind enough to set us up for our first time skiing together! It just so happened to be on Kyle’s 25th Birthday too — we will never forget it!
If it’s your first time too, I highly recommend participating in a private or group lesson. This way, you can get the hang of it quicker.
As recommended, we stuck to the Little Pine lift. Then, we skied down Home Run. The views of the Three Sisters were likely the best we’ve ever seen!
Also, there are beginner routes in the Sunrise area.
Since this is a very popular area, we recommend arriving no later than 8:45 am (15 mins before opening) and staying until the early afternoon. It’s the best way to beat traffic in both directions!
7. Journey Through Lava Lands
Ever walked through a field of lava? We hadn’t before visiting the Lava Lands Visitor Center in Newberry National Volcanic Monument.
Its playful name is fitting because it’ll bring out your childlike sense of wonder.
Although the visitor center building is closed during winter, the roads and trails are still open.
To explore, we enjoyed walking on the Trail of the Molten Land. This trail follows the path the basalt lava flow created 7,000 years go! Plus, the interpretative signs make it easy to do a self-guided tour any time of the year.
Pro Tip: If you visit in the winter, you might be the only ones there! This was the case on the snowy day we went.
In the summer, you can ride a shuttle from the visitor center to the top of Lava Butte. Otherwise, you feel free to hike to the top for sweeping views.
If you have an Interagency Annual Pass (America the Beautiful) be sure to bring and display it! Or, see here for the complete list of accepted passes.
Lava Lands Visitor Center is a 12 mile drive South of Bend.
On the way, you’ll pass the High Desert Museum. Stop on the way back to discover native wildlife and local history. Both of these are very family-friendly activities for a weekend in Bend Oregon!
8. Hike to Steelhead Falls
Another family-friendly option is Steelhead Falls. At only 0.5 miles to the falls (each way) it’s quite the rewarding trail!
The trailhead is 32 miles from Bend. It’s a refreshing drive that’ll make you feel like you’re miles and miles away from the city. Plus, we saw quite a few deer in the area!
Besides the falls, we admired the distinct rock layers along the canyon. There’s so many glimpses into geologic time near Bend, and this was our most favorite.
In the summer, it seems to be a popular spot for cliff jumping and swimming. But, since it’s pretty rocky and the water flow is strong, I wouldn’t personally recommend this.
We went in winter (end of February) and had the trail to ourselves.
Because it’s maintained by the Bureau of Land Management, no fees or passes are required.
Wanna stay awhile? There’s a handful of dry camping sites adjacent to the parking lot.
10. Enjoy an amazing breakfast at McKay Cottage
Admittedly, I’m not a big breakfast person. So when I say that McKay Cottage Restaurant is at the top of my list of the best restaurants in Bend, that is truly saying something!!
We visited because of a recommendation received over on Instagram (Thanks again).
Not only was the historic bungalow charming, but the food was SO tasty!
Our favorite dish was the McKay Cottage Potatoes – a scramble of scrambled eggs, potatoes, cheese, green onions, tomatoes, bacon, & ham. The portion is so generous that we even shared it once as a light meal before hiking!
For my fellow coffee lovers, try the McKay Mocha. It’s made with locally crafted chocolate, espresso, steamed milk, and whipped cream. Naturally, I went with an iced version. Given the low temps, it’s safe to say to the waiter was surprised haha.
View the breakfast menu here and lunch menu here.
In a rush? You can order food to-go or pick up a fresh scone and coffee from the bakery.
11. Treat Yourself to Vegan Tacos at Toasty
When you’re in the mood for plant based goodness, Toasty the food truck is the place to go.
A few of the most popular dishes are avocado toast, tacos, and burritos. Our favorite was the Bend Bowl! Its spicy sauce really took it to the next level.
You’ll find Toasty amongst other trucks serving thai, beer, and other food in The Old Mill District’s Podski Food Cart Lot.
Conveniently, there’s outdoor seating or you can grab it to go (which is what we did).
We can’t wait to return to Bend and explore more of Toasty’s menu!
12. Visit Bend Brewing Company
Surely, no weekend in Bend Oregon is complete without visiting a brewing company at least once! Our top pick is Bend Brewing Company.
Located in Downtown Bend, the family friendly restaurant offers craft brews plus a generous food menu.
My drink of choice was the Apple Cinnamon Mimosa – a mixture of champagne, apple cider, and cinnamon whiskey. Lovely to cozy up with on a chilly night!
Besides the food, we greatly appreciated how friendly the team was. It felt like we were eating somewhere familiar, which is comforting while traveling.
Browse the menu here.
13. Grab dinner at Pastini
Last but not least, for a slightly more formal meal try Pastini. Well known for their Northwest wine and pasta, it’s the perfect place to celebrate a special occasion.
As a matter of fact, we celebrated Kyle’s birthday here with tasty tiramisu!
Pastini is located in The Old Mill District. So if you want a night of shopping and fine dining, look no further.
Also, you can find Pastini locations across Oregon.
Click here to see the menu.
Have questions about how to plan an amazing weekend in Bend Oregon? Leave a comment below!
In the meantime, you are welcome to access more travel resources on the Visit Bend website.
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