The Ultimate Bend Oregon Itinerary (How To Spend 4 Days In Bend)

Post Summary: The Best 4 Day Bend Oregon Itinerary

Are you already sick of the rain this winter? One of the most common complaints we hear about living in the PNW is the dark and dreary winter months. But that’s actually not the case everywhere!

If you’re looking to escape the rain and gray skies this season, may we introduce you to Bend, Oregon. This adventurous city is located in the PNW’s high desert region, with an average of around 12 inches per year. Bend also has the highest average number of sunny days in the state (sitting at 158!) which makes it a year-round hub for outdoor activities like skiing, hiking, biking, cave exploring, and more!

In this post, we’re telling you exactly how to plan your weekend in Bend, Oregon and pack each day with outdoor adventure, yummy food, and lots of amazing views. Let’s get started!

The Ultimate Bend Oregon Itinerary (4 Days of Adventure!)

This post is sponsored by Visit Bend. All images, writing, and opinions are our own!

How To Get To Bend, Oregon

Bend is located in Central Oregon, near the foot of the Cascades mountains on the east side. If you are an Oregon local, chances are that you are coming from big cities like Portland or Eugene to spend a weekend in Bend!

The easiest way to travel to Bend, Oregon is by car, but there is also an airport in Bend if you REALLY need to fly in. The airport is actually in the neighboring town of Redmond, (code RDM) but it’s only 30 miles from downtown Bend.

Here are some travel times if you are coming by car (to account for in your Bend Oregon itinerary):

Distance From Portland to Bend: 176 miles – 3 hours and 15 minutes.
Distance From Eugene to Bend: 128 miles – 2 hours and 30 minutes
Distance From Seattle to Bend: 330 miles – 6 hours 30 minutes

Note: These drives require driving over mountain passes! If you are planning a trip to Bend in winter, make sure to save Oregon’s TripCheck webpage, and put together your own DIY winter car emergency kit.

Where To Stay In Bend Oregon

There are lots of incredible places to stay in Bend in winter. However, if you are seeking lots of outdoor adventure, we suggest staying at the LOGE Camp in Bend! LOGE’s motto is “Live Outside, Go Explore” and they help you do exactly that.

Bend’s LOGE Camp provides free bike rentals, has Deschutes National Forest trails literally right outside your door, and Mount Bachelor ski resort is less than a 30-minute drive away.

They are also very remote work-friendly too. We found that the lobby cafe had everything we needed for sending off quick emails or getting a little work done before our adventures. There were tons of collaborative tables to sit at, and if the weather was warmer, we could even sit outside on a clear day.

We noticed that LOGE Camp does a great job of fostering community. There are tons of places to gather with your friends all over the grounds to debrief about your full day of exploring outside. From fire pits, covered awnings, and a patio with a hot tub, there’s so much to choose from!

To book a room at LOGE Camp in Bend, click here!

Bend Oregon Itinerary Day 1

On the first day of your Bend weekend itinerary, it’s a good idea to orient yourself. After you check into your accommodations, we suggest spending a bit of time walking around the heart of the city. There are so many things to do in downtown Bend, but we figured it’s best to start out with a walking tour!

Take a Walk of the Deschutes River Trail

Starting off your Bend Oregon itinerary, you need to check out the Deschutes River Trail in the Old Mill Area. This section runs through the heart of downtown on either side of the river, spanning a 2.7-mile loop. It’s paved and perfect for strollers, scooters, and great for children on bikes.

Take the whole family out for a chilly outing, because there are parks, shops, and restaurants along the way to take a break and warm up. It’s one of the best things to do in downtown Bend that’s outside and in the fresh air! Grab a coffee and treats at some nearby Bend, Oregon bakeries (like Jackson’s Corner or Strictly Organic) and take a stroll!

Looking for the bike trail? The biking-specific section of the Deschutes River Trail is an 11-mile trail beginning at the LOGE Camp and ending at Benham Falls Overlook.

Take a Similar Trip: Walk the Greenbelt Trail in Boise, Idaho

Bend Oregon Beer Trail - Bevel Creek Brewing

Dinner at Bevel Craft Brewing

Bevel Craft Brewing is owned by Nate and Valerie Doss, who are among the best disc golfers in the world! They spent countless hours visiting breweries all over the world on their disc golf tours and collected a wealth of knowledge about the kind of business they wanted to run.

Their hop-centric microbrewery is certainly noteworthy, but we were especially enamored by the space they created. This outdoor oasis consisted of picnic tables, high tables, fire pits, and yes, a mini-disc golf area!

The resident food trucks surrounded the outdoor area and created a vibe that is absolutely perfect for meeting your friends for dinner and beer.

If we lived in the city, we know this would be our go-to Bend brewery!

Bend Oregon Itinerary Day 2

Hike to Tumalo Falls

Tumalo Falls is one of the most popular hikes in Bend to do any time of year, but it’s especially beautiful in the winter season! Once the first snow falls, the park closes the access road to reach the main parking lot. Therefore, grab your snowshoes or microspikes and get ready for a winter wonderland trail!

The Tumalo Falls via Tumalo Creek Trail is a 6.5-mile round trip from the Skyliner Sno-Park, Make sure to take a Northwest Forest Pass with you, to put on your car’s dashboard. If you are lucky enough to make it all the way to the parking lot, expect to pay a $5 entrance fee at the kiosk.

The trail is widely used in the Oregon winter season, so you can expect snow to be packed down on the trail. It can get slippery, so make sure to wear shoes with good traction, or put on a pair of microspikes to prevent slipping.

Once at the falls, the views are incredible! Stick the lower falls for a view of the cliffs and surrounding forest, or hike up the short trail to see the falls from the top. It’s one of the most iconic things you can add to your Bend Oregon itinerary!

Coffee and Breakfast at Spoken Moto

One of our favorite Bend Oregon coffee shops is hand-down, Spoken Moto!

The ambiance and interior are the perfect blends of industrial and laid-back, perfect for meeting like-minded creatives and makers! Situated in a warehouse building, communal tables and merch are intermixed with vintage motorcycles and bikes. On a nice summer day, you can expect their garage doors to be open, and someone working on or discussing their dope rides!

Another great feature of Spoken Moto is their food truck court right outside! Come during any time of day for some good grub to go along with your coffee. It’s our one-stop-shop to fuel up before another adventurous day exploring Bend.

Are you camping in Bend Oregon? Here are 6 ways to make coffee while camping.

Things To Do In Bend, Oregon - The High Desert Museum

Visit The High Desert Museum

If you’re visiting during the colder months, winter activities in Bend Oregon don’t necessarily have to involve snow! Stay inside, stay warm, and have fun at the High Desert Museum! Built-in 1982, this 135-acre complex south of Bend has an abundance of ways to learn about the high desert environment in Eastern Oregon and beyond.

From watching playful sea otters to discovering the exploration and settlements of the West, this museum has something for everyone. We personally like to spend time in museums during the first days of our trips. This way, we can learn about the geography of the area, the history of the communities, and educate ourselves on the unique conservation efforts surrounding outdoor activities.

Places To Visit in Bend - The High Desert Museum

The High Desert Museum has summer hours (9 am-5 pm) and winter hours (10 am-4 pm). General admission is between $14-$17 depending on the time of year you visit.

This is one of the coolest things to do in Bend with kids because they have shows with live animals, a live-action historic village, and lots of interesting exhibits!

Best Restaurants in Bend - Wild Rose Thai

Dinner At Wild Rose Thai

According to our readers and followers, one of the most highly recommended restaurants in Bend was dinner at Wild Rose Thai! You won’t find any Pad Thai here – they specialize in Northern Thai cuisine and encourage you to discover new and unique dishes!

Some of our favorites are the Sweet Sausage Fried Rice, Kabocha Curry, and Sukiyaki. It was a perfect blend of flavors from creamy coconut milk to spicy chili, and lots of yummy noodles. This place is quite popular, especially on the weekend. We highly recommend that you make a reservation to secure your table in advance!

Bend Oregon Itinerary Day 3

Berty Mandagie at Smith Rock State Park in Winter

Hike Around Smith Rock State Park

What’s a Bend Oregon itinerary without a stop at Smith Rock State Park?

If you like a good mix of hiking, climbing, photography, and simply some good ‘ole exploring, you’ve gotta visit!

Take the short but VERY steep Misery Ridge trail to the top for some epic view. For a more meandering stroll, check out the 2.8-mile Wolf Tree Trail, which leads you through a quieter section of the gorge.

Keep your eyes peeled for river otters or herons in this deep canyon!

Bend Oregon Outdoor Activities - Smith Rock State Park

Is Smith Rock too crowded for your liking? Take the alternative route to Gray Butte Trail. It’s to the far west of Smith Rock, and on USFS/BLM land. It provides great views of the park’s iconic peaks, without the traditional masses of hikers.

Hiking around Smith Rock State Park is one of the most popular things to do in Bend, Oregon! To explore with fewer crowds, we recommend coming in the morning, or if you can, visit on weekdays.

Breakfast At The Sparrow Bakery

No trip to Central Oregon is complete without trying The Sparrow Bakery’s famous Ocean Rolls! Stop by this iconic Bend Oregon bakery for some made-from-scratch pastries, delicious meals, and good company. This is a great place to meet friends for brunch before your next big adventure.

Take an Adventure With Wanderlust Tours

Wanderlust Tours is a company in Bend that takes explorers on half-day journeys in Bend, Sunriver, Sisters, and surrounding areas. From snowshoeing near Mt Bachelor in the winter to canoe paddling along the Cascades Lakes Scenic Byway in the summer, there’s an adventure waiting for practically everyone!

Their naturalist-led tours are incredibly informative, and you return from your trip having deep knowledge and respect of the area. We were lucky to join them for a cave tour during our 4 days in Bend, Oregon! (More on that below.)

Wanderlust Tours does a great job of offering a variety of adventures and we already have a shortlist of ones we want to book when we create another Bend Oregon itinerary. On our list next is the Prohibition Tour (where they tour cave locations that were used to illegally distill alcohol in the caves!) and a Cascade Lakes canoe tour in the summertime.

Explore Boyd Cave

During our Bend weekend itinerary, we explored Boyd Cave with Wanderlust Tours. Boyd Cave is one of the few public Bend, Oregon caves that anyone can explore free of charge and without a permit!

We highly recommend either booking a trip with Wanderlust or planning your own adventure. Either way, make sure to bring a helmet, 2-3 sources of light, and wear clothes you don’t mind getting dusty! The cave eventually gets too small for humans to pass through, but you can spend a good two hours exploring the cave and reaching the end.

Emily Mandagie exploring caves in Bend, Oregon

Be prepared for a bit of climbing around big rocks, and banging your head on narrow rocks jutting out from the ceiling. (Hence, the helmet suggestion) It’s a great time, and an excellent spot to take photos as well!

Note: Because this is a public cave, there is a much higher chance of spotting trash, cans, and graffiti. If you want to volunteer your time, Wanderlust Tours runs cave cleanups, where you help keep them free of trash and get to explore the cave at the same time! Inquire with the Wanderlust team about how you can get involved with these efforts to keep Bend caves clean and accessible. 🙂

Other Bend Oregon caves to explore: (check to see if your desired cave requires special entry permission!)

Redmond Caves
Lava Tubes
Hidden Forest Cave
Skeleton Cave

Plan Some Stops Along The Bend Ale Trail

If you love beer, you’re going to LOVE Bend! One of the most fun things to do in Bend is planning some stops along the Bend Ale Trail.

The Bend Ale Trail is an at-your-own pace beer tour, showcasing the best brewers and craft beers in the city. You can download the app to track your progress or pick up a physical passport book at the Bend Visitors Center.

Make sure to download a Bend Oregon breweries map too before you go. (And have a designated driver of course!)

Some suggestions to enjoy the libations in the city:

Go to BrewFest in May (The Bend Oregon beer festival)
Take a brewery tour – like the Deschutes Brewery Bend Tasting Room
Try the tasting room at Crux Fermentation Project

Bend Oregon Itinerary Day 4

Grab Coffee at Lone Pine Roaster

One of the best Bend Oregon coffee roasters (in our humble opinion) is Lone Pine Coffee Roasters. We met someone during our weekend trip and they recommended the downtown Bend location, and we couldn’t get enough of it!

Lone Pine Roaster’s Downtown location is incredibly beautiful, with plants atop practically every counter, shelf, and floor space! It felt like a little green oasis in the middle of town. This is a great spot to visit with friends, with lots of conversation corners and cozy seating.

Emily Mandagie hiking in Oregon at Steelhead Falls

Visit Steelhead Falls

Looking for an Oregon waterfall hike with a little bit fewer crowds than Tumalo Falls? Might we suggest the short and sweet hike to Steelhead Falls! It’s located along the Deschutes River, on land owned by the Bureau of Land Management. The trail to Steelhead Falls is only a half-mile from the parking lot, making it a great trail for kids or a quick stop to stretch your legs after a long drive.

This is also a great outdoor activity for a number of reasons. If you’re looking for free Bend, Oregon campsites, this is an excellent spot for an overnight stay! Campsites are first-come-first-serve, open all year round, AND pets are allowed! Great views, free stay, and you can bring Rover? We know we’re camping in Bend next time we visit!

Berty Mandagie visiting Tumalo Falls in winter

More Outdoor Activities In Bend Oregon

Looking for more things to do in Bend, Oregon? If you have a few more days to spare (say, you’re planning 1 week in Bend, Oregon!) here are some unique things to do in the area: (including day trips from Bend!)

Explore Newberry National Volcanic Monument
Drive the Cascades Lakes Scenic Byway
Oregon Badlands
Hike Pilot Butte in the city
Visit Paulina Lake and Paulina Hot Springs
Looking for things to do in Bend in winter? Head up to Mount Bachelor. From backcountry skiing in Bend Oregon to the Snowblast Tubing hill there’s a snow activity for everyone!