One Weekend In Bend, Oregon: An Outdoorsy 3-day Itinerary
Mountain landscape, clear blue lake water, biking, hiking, skiing, and more. No matter what season you decide to explore Central Oregon in, it will surely be a trip to remember! Here’s exactly how to spend one weekend in Bend, Oregon. It’s the perfect 3-day itinerary for fellow 9-5ers (plus, it’s written by a local, so you’ll be sure you’re exploring the best gems!)
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Quick Side Note! This post was written by Morgan, a former local of central Oregon! This way, you can be sure you are reading the best and most accurate Bend weekend guide. Read more about Morgan at the end of this post!
Table of Contents
3 Days in Bend (Quick Itinerary)
I know everyone has different styles of travel, so before you dive into all the details, here’s a quick overview of how to spend 3 days in Bend. If it looks like your kind of weekend, be sure to keep reading to make your trip planning super simple!
- Day 1: Breakfast at Looney Bean, rent a kayak or SUP, float the Deschutes River, Hike Pilot Butte
- Day 2: Breakfast at Big O Bagels, Road Trip to Painted Hills OR hike at Smith Rock State Park, Live show at Tower Theatre, and Dinner at McMenamins
- Day 3: Breakfast at McKay Cottage, Hike Peterson Ridge East, Lunch at EuroSports, Shop Downtown Bend
How do I get to Bend, Oregon?
The closest airport is located in Redmond, Oregon (RDM), which is about a 20-30 minute drive from Bend. It is a small airport (in 2025, it is undergoing some expansion construction) with the most common connecting flights being out of Seattle-Tacoma (SEA/TAC) or Portland (PDX). Although Uber and Lyft are available in the area, I suggest renting a car so you have the flexibility to enjoy the food carts, get to the trailhead, and take the scenic routes while you’re in town.
You can also utilize the Cascade East Transit (CET) bus routes in the area if you are traveling on a budget. But check their schedule ahead of time because they don’t always operate on the weekends.
What is the best time to visit Bend?
Each traveler is going to have different goals when visiting the area. Wanting to check out the local ski resorts or go snowshoeing? Winter season typically begins about mid-December, that’s when the local ski resorts (Mt. Bachelor and Hoodoo) open for the season. Of course, that all depends on the snowfall of the season.
Bend, Oregon, is classified as a high desert, which means it is hot and dry. Summers in the area reflect this the most from June-September. Wildfire season is more common each year in the area. If you plan to travel in the summer, just come prepared and possibly even purchase travel insurance in case your plans change instantly.
If your heart is set on visiting in the summer, I suggest traveling before mid/late-June. This way, you get to enjoy the warmer weather before it gets 100+ and before the wildfire smoke takes away your opportunity to view the gorgeous scenery. Visiting in the summer also allows for a chance to check out a concert at Hayden Homes Theater throughout the summer months, right in the heart of Bend and along the Deschutes River.
Note: Hiking in the summer requires a pass that is a lottery system to obtain, depending on the trail you are trying to access. Plan ahead and have a backup in case you are unable to get a pass.
Annual Events in Bend
- July 4th – Bend hosts a Pet Parade that gets busy fast. Streets are blocked off downtown for the parade route but it’s a lot of fun to experience!
- Second weekend in July – Sisters Outdoor Quilt Show and Sisters Rodeo
- October 31st – Typically, kayakers and stand-up paddle boarders dress up for Halloween and float down the Deschutes River in their costumes. It’s best to find parking at the Old Mill District to be able to walk to the river bridge for the best view. This way too you can also check out the shopping opportunities in the area.
Where should I stay in Bend?
After a full day of exploring Bend’s breweries, trails, and mountain views, having the right place to rest makes all the difference. Whether you’re looking for a cozy cabin tucked in the pines, a modern downtown boutique hotel, or a budget-friendly spot with easy access to the outdoors, Bend has a wide range of options to fit every traveler’s style and budget. Here are some of the best places to stay in Bend!
- Budget-friendly Option: Days Inn by Wyndham Bend, typically around $100 and less a night for a stay. There are lots of motels and budget-friendly hotel options in the area to choose from.
- Mid-range Option: Riverhouse is located just north of Bend, where it’s a 10-15 minute drive to downtown. It’s super cozy, and (as the name suggests), it sits right on the river!
- Luxury Option: Tetherow Resort is located on the outskirts of town but offers golfing, a pool, a fitness center, and a shuttle service to get to and from Mt. Bachelor, Redmond airport, and various spots around Bend. Check current pricing and availability here!
- Dog-friendly Stay: Campfire Hotel offers options for your furry companion to join you on your trip!
- Unique Option: McMenamins offers a unique experience by staying in a former school. There is a soaking pool onsite, restaurant, and secret bar/lounge area to enjoy.
3-day Bend Itinerary
It’s time to dive into exactly how to spend 3 days in Bend! During this long weekend, you’ll see some amazing views, try some tasty food trucks, and explore some local gems!
Day 1:
Morning:
Grab some coffee and food at Looney Bean where you can sit outside and enjoy the peaceful space and watch the Deschutes River. The coffee shop has easy access to a walking trail alongside the river if you choose to walk and enjoy the morning.
After you’ve enjoyed your morning wake-up, it’s time to head to Bend Kayak School to rent a stand up paddleboard or kayak for the afternoon.
Afternoon:
Now that you have your paddleboard or kayak, it’s time to hit the water! This is a great way to spend a few hours in the afternoon getting to see Bend from a different perspective. Plus, the water on the Deschutes River is calm enough that you can always turn back and head back to where you parked your car.
Note! The Deschutes River does have one section that is popular for surfers to practice on, so if you happen to make it that far, it’s easy to exit the river and re-enter where it’s calmer.
By now, you have worked up an appetite, and it’s time to find some lunch. Travel to Podski where you can enjoy local beers and ciders on tap and choose from multiple food carts (Thai, tacos, sushi, burgers, and more).
Evening:
Now that you’ve gotten to see a bit of Bend from the river, let’s hike Pilot Butte to see more of the landscape from a gorgeous viewpoint! This hike doesn’t require a hiking pass, but the parking lot will be blocked off and closed after sunset (so just be sure you start an hour or so before sunset and then hustle down before it closes). This hike is just under 2 miles, but is also all uphill, so be ready!
Day 2:
Morning:
Today will be an early morning hiking adventure or drive (choose your own adventure) so grab breakfast at your hotel, stop by Big O Bagels for something to-go.
Option 1: Set out for about a 2-hour drive to Painted Hills (pictured above) in John Day, where one of the 7 Wonders of Oregon is located. This area allows for some easy hiking/walking throughout the area to explore the hills.
Option 2: If a 2-hour drive isn’t something you’re interested in, you could check out a closer 7 Wonders of Oregon, at Smith Rock State Park (pictured below).
The park is located in Terrebonne, about a 30-45 minute drive from Bend. The park does require a pass to be purchased, but there is a kiosk in the parking lot where you can buy one for a couple of dollars for a day visit. There are picnic tables around the area where you can sit and enjoy the area, or you can adventure down the many different hiking paths offered around.
Afternoon:
Depending on which option above you chose, you may have stopped along the way to grab some lunch. If not, there are some more food carts (can you tell by now it’s a popular option in Central Oregon) located in Redmond. Check out Blacksmith Public House, Wild Ride, or General Duffy’s Waterhole before driving back to Bend.
Evening:
Your evening calls for a live performance at Tower Theatre or catching a movie at Regal Cinema, before dinner at McMenamin’s restaurant.
Day 3:
Morning:
Start your final day in Bend with breakfast at McKay Cottage. Note: it gets busy fast here, so be sure to call ahead and see if they take reservations.
If they don’t, going earlier is better to ensure you don’t have a long wait time. If you’re getting out the door a little later and McKay Cottage is incredibly busy, stop by Bruchie’s food cart in Sisters (about a 30-minute drive from Bend) for some delicious breakfast food options (check their social media page for up-to-date information on their hours).
Afternoon:
After you have your hiking pack ready, it’s time to drive out to Peterson Ridge East in Sisters, Oregon. This 5.3-mile hike will offer a scenic view of Central Oregon.
Before heading back to Bend, take a stop for lunch at EuroSports or The Barn for drinks and food cart options. There is outdoor seating available that’s located in Sisters, so you have the opportunity to browse the local stores and enjoy what the town has to offer while you are there!
Evening:
Your evening will be a relaxing one to wind down from your trip and prepare for your travel back home. Take advantage of shopping downtown and check out some of the local stores, as well as stores like Patagonia and Fjall Raven.
Other things to do in Bend
There are lots of other activities to try and take advantage of while in the area! If you have longer than a weeknd in Bend, be sure to check out some of the following!
- Cascades Lakes Kayak Tour – $140/person
- Chocolate Tour with chocolate samples – $89/person
- Bike Rentals – $25/person
- LOTS of hiking options and availability. Check out AllTrails and make sure to check if you need a parking pass before getting to the trailhead
- Vector Volcano for classic arcade games
Where (else) to Eat in the Bend:
- Food carts:
- Toomie’s
- Note: the restaurant closes for a few weeks in October to allow staff a vacation each year.
- Wild Rose
About the Author!
I lived in Central Oregon for five years, Bend for two years, and Sisters (neighboring town) for three. In that time, I had the opportunity to explore and experience a lot of what Central Oregon has to offer.
I also help book travel as a Travel Agent so if you have any questions when visiting or planning your trip to Bend, or anywhere else in the world, reach out to me on my Instagram or send me an email! Make sure to sign up for my email subscriptions to stay up to date on new blog posts! I promise, I won’t bombard you with emails, maybe 1 every 3 months or so. Wishing you the best on your next adventure!
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