Bend, Oregon Itinerary: 4 Day Itinerary for Ultimate Adventure

We love all the outdoor adventures in Bend, Oregon. From hiking and biking to rafting and climbing, you’re sure to find an adventure that speaks to you. Besides outdoor adventure, Bend is known for its great food and numerous breweries. Do the Bend Ale Trail or hop on an e-cruiser and pedal your way through a brewery tour. The farmers market is awesome and the restaurants in Bend pride themselves on using local ingredients whenever possible. Whatever your style, Bend has dozens of activities to enjoy on a 4 day itinerary. In fact 4 days in Bend is only going to give you a small taste of everything the city has to offer.

Do you like arts and music? It seems like there is always a festival or event going on. Make sure to check out Visit Bend events page for the latest in concerts, races, and special events.

In the summer, some of the breweries offer free yoga and there are free concerts at Les Schwabb amphitheater.

The High Desert Museum has amazing experiences for the whole family. The museum weaves together history, culture, art, and nature to help visitors get a deeper understanding for the area around Bend. The kids will love the animal exhibits and you will love learning so much about nature and history.

Last, there’s plenty of shopping in downtown Bend and at the Old Mill District.

With so much to see and do, I hope you enjoy Bend as much as we do! here is our recomended itinerary to get the most out of your trip to Bend:

Bend Itinerary Day 1: Explore Cascade Lakes Highway

Breakfast in Bend

First stop of the day, head to Great Harvest and order your bread to pick up later and while you are there grab a scone to snack on for you hike today.

Great Harvest Bend Oregon 4 Day Itinerary Road Trip — Great Harvest Bread Co might legitimately have the best breads we’ve ever tasted
Photo credit and copyright The Bend Bulletin

If you need more food for your day of hiking and exporing, run into Market of Choice for some picnic foods.

Cascade Lakes Highway

Now you are ready to explore! It’s a straight shot on NW Colorado Ave out of town and up towards Mt Bachelor. You may want to stop at the Cascade Lakes Welcome Station (Ranger Station) on the way to get your Northwest Forest Day Pass to use when parking at the trailheads (only $5). You can also buy it online here and print it out.

I recommend driving at least out to Elk Lake to take in the views and if it’s warm, bring a swim suit or rent a SUP to play in the lake. If you only have time for one hike, you should hike to the top of Tumalo Mountain. If you are up for a more strenuous day hike, take on the South Sister.

Time to Eat

It’s now time to get a feel for this rad town. Grab drinks and food at The Lot (NW Colombia St and NW Hartford) or Deshutes Brewerey and then walk past Drake Park to go explore downtown Bend.

Bend Oregon 4 Day Itinerary The Lot — The Lot food truck court is a rad hangout for lunch or dinner
Photo credit and copyright Visit Central Oregon

Check out The Bend store on NW Wall. Head down NW Minnesota and check out some of our favorites– Dudley’s Bookshop Cafe, Navidi’s Olive Oil & Vinegars, Bonta Gelato, or Thump Coffee.

If you need more suggestions on things to do, Visit Bend is just around the corner. If you like beer, pick up your Bend Ale Trail passport at the Bend Visitor Center see how many breweries you can check off on the Bend Ale Trail. Get 10 stamps and the Bend Visitor Center will give you a free souvenir. Or you can get the app here to stamp your passport at each brewery you visit.

Bend Itinerary Day 2: Smith Rock and Steelhead Falls

Climb or Hike

Stop by Trader Joes and stock up on more food and snacks for the day then head north to Smith Rock.

Bend Oregon 4 Day Itinerary Smith Rock — Smith Rock is an unique and iconic sight that you must see if you visit Bend

Smith is great for hiking or if you feel adventurous, hire a climbing guide and try your hand at some world class rock climbing. Or if you are an intermediate climber and looking for a fun multi-pitch, check out Wherever I May Roam. A classic 4 pitch 5.9 that will give you epic arial views of Smith.

Note: It can get really hot here in the summer so dress in layers and bring lots of water.

Cliff Jumping Anyone?

The good thing if it’s hot, there is a perfect adventure to finish off your day. Drive 20 minutes east to Steelhead Falls trailhead and hike half a mile to the waterfall. If you feel brave, find a good spot to do some cliff jumping. Remeber to always use caution and check the depth of the water first.

Brewery

There are so many great breweries to choose from in Bend it may be hard to pick one. Today might be a good day to sign up for a brewery tour (check Groupon for some rad deals).

If you want something different or are starving, stop by the food trucks in Tumalo. This small town is just between Redmond and Bend and has a rad cowboy feel to it.

Bend Itinerary Day 3: Mackenzie River area

Explore the Mackenzie River Highway

It’s time to head west to the Mackenzie River Highway today. There are so many great hiking, biking, and adventuring to do along the Mackenzie River and Highway that the hardest part will be deciding which to do and what you’ll have to save for the next trip.

Bend Oregon 4 Day Itinerary Mackenzie River Trail — Exploring Clear Lake along the Mackenzie River Trail near Bend

It’s a relatively short hike to get to the famous Blue Pool and gorgeous waterfall. The only negative is that it can be quite crowded so try to go early or in the shoulder season. We went in on a weekday at the end of May and had the pool all to ourselves.

Bend Oregon 4 Day Itinerary Blue Pools — Blue Pools is a must see stop on a trip to Bend

Dinner

Stop in Sisters for dinner if you don’t mind spending a little extra or want to soak in it’s artsy vibe. But if you haven’t had your fill of breweries, then I’d head back to Bend and maybe give Immersion Brewery or Crux Fermentation a try.

Tip: Sister’s has a great campground in town that you can use as a jumping off point for your Bend itinerary.

Related Blog: 5 Adventures on the Mackenzie River Trail

Day 4: Mountain Biking Phil’s and Floating the River

Phil’s Trail network has some of the best mountain biking in the country. You don’t have to be an expert moutnain biker to enjoy the trails here. Just read our Ultimate Guide to Mountain Biking Bend to find the perfect trail for you.

Mountain biking Bend, Phil's Trail — The iconic ride of Bend, Phil’s Trail
Photo credit and copyright MTBR.com

Now that you’ve worked a sweat. Go rent inner tubes and float down the river. Get all the details of how to float here.

Related Blog: Ultimate Guide to Mountain Biking Bend

Got more time?

There is never enough time in Bend. I could easily spend 4 days doing just one of the activities on this Bend itinerary. If you have more time you can stay longer at each place or head south and check out the High Desert Museum, the Lava Cave, or hike/mountain bike Peter Skene Ogden trail.