Oregon: Bend Multisport Adventure

“Certainly travel is more than the seeing of sights; it is a change that goes on, deep and permanent, in the ideas of living.

Mary Ritter Beard

Bend is an amazing little city in Central Oregon, which is considered one of the best outdoor sports hubs in the country.

Locals are passionate about their free time and using it outside. Road biking, mountain biking, rock climbing, trail running, and hiking are all world class in the region. In the winter, locals flock to Mt. Bachelor for skiing or to the vast nearby national forests for cross country skiing and snowshoeing. We’ll do as the locals do on this multisport tour by engaging in road biking, hiking, river rafting, and kayaking (or canoeing or Stand Up Paddleboarding) on our five-day tour.

Much of our activity takes place on or near the Deschutes River, which winds through town, or with background views of the Three Sisters, the white-capped mountains of the Cascades Range (the third, fourth, and fifth highest peaks in the state). The weather in Bend is part of the appeal, as it is east of the Cascade Mountains and thus gets much less rain than the western part of Oregon.

But it is not just nature that draws us to Bend. The small city of around 100,000 residents has a walkable riverfront, top quality restaurants, friendly people, and an amazing brewery scene. Bend accumulates accolades galore, including (of most relevance to us) the Best Multi-Sport Town in America as determined by Outside Magazine.

Yes, it can be a little difficult to get to Bend. You will fly first to Portland, Oregon or Seattle, Washington, and then on to the local airport. Trust us, it’s worth it. The city is amazing, the outdoor activities are top class, the weather is excellent, and you will rejoice you made that extra effort once you arrive.

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  • Cost Per Person: $2,600
  • Single Supplement: $600
  • Private Tour Minimum: 10
  • Activities: Biking, Hiking, River Rafting, Kayaking/Canoeing/Stand Up Paddleboarding
  • Difficulty: All Abilities
  • Guides: Allan Wright, Beth Peluse

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Trip Highlights

  • Bicycle in the foothills above Bend with a view of the Three Sisters mountains serving as a carrot in front of you
  • Kayak, canoe, or Stand Up Paddle Board on the Deschutes River (tandems available if you prefer a partner)
  • Hike on Mt Bachelor, one of the best ski resorts in North America, and earn your views from the top
  • Enjoy a short but exciting river rafting trip on the Upper Deschutes
  • Enjoy all that Bend, Oregon has to offer, including great breweries, fun restaurants, and an outdoors vibe

We meet in Bend just after lunch, giving you time to arrive that day. If you prefer a more leisurely travel schedule, you can arrive ahead of time and enjoy a free morning before we meet. We start out with a splash (literally) as we head to the Deschutes River that rolls right through the center of Bend. You have the option to kayak (single or tandem), canoe, or Stand Up Paddleboard on the placid waters while admiring the city from the river. You can even try more than one activity if you can get someone to switch with you!  After our activity, we'll check into our downtown hotel and enjoy an outdoor dinner at one of Bend's many great restaurants.


This morning we head to famous Mt Bachelor, considered the number one ski resort in Oregon and one of the best in the country, which is also a huge draw for active locals in the summer. You have two options to hike on the mountain this morning: choose the long route by hiking up to the top of the mountain from the base or get a little help by taking the gondola up over half way. Lunch is on your own high on the mountain at the ski resort restaurant. In the afternoon, we will return home with a stop at Seventh Mountain Resort for a little whitewater river rafting on the upper Deschutes River. The rafting is short but fun and gives us a different view of the river than we had yesterday.  Tonight, we'll have a variety of takeout options from local restaurants and relax at a local park.


We have a leisurely morning before getting on our road bikes and participating in the 37-mile Twin Bridges loop ride. Starting and ending in Bend, we’ll travel on small side roads, have views of the Cascade Mountains, and enjoy a stop in the village of Tumalo (population 500) for lunch. Extra mileage is available for those wanting a longer workout. After our ride, we will do an optional two-mile walking tour from our hotel of area breweries (Bend Brewing and Deschutes Brewing), distilleries (Crater Lake Spirits), and kombucha makers (Humm Kombucha).


Today, we experience a different type of hiking, one that is much less taxing than the hike up Mt. Bachelor. We spend our day on the famous Deschutes River Trail north of the city. We’ll walk four miles from Riley Ranch Nature Reserve downriver to Tumalo State Park, where we’ll enjoy a nice picnic lunch prepared by your guides. The hiking is moderate and you'll be alongside the river the entire way. After lunch, you'll have the option to double your mileage by walking back or catch a shuttle with our support van and perhaps wander around Bend for a little sightseeing or shopping. This evening after dinner you have the option to watch a movie at the Old St. Francis Theater in our hotel.


After breakfast, we will take a relaxing morning walk in downtown Bend to explore the city as the locals do. We’ll start from our hotel and visit the Bend Whitewater Park, where kayakers and other adventurers test the man-made rapids designed just for fun.  We’ll then continue along the river to the Old Mill District, Bend’s downtown shopping hub. We can return directly to the hotel for a two-mile loop or extend by walking along the Deschutes River before checking out of our hotel.

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Trip Accommodations


McMenamin's is an iconic brand in Oregon. The company purchases old buildings with character such as schools, churches, historic hotels, and even Elks lodges and turns them into hip, fun hotels, restaurants, and breweries. The Old Saint Francis School is the perfect example. Previously a private school, with multiple buildings on expansive grounds, McMenamin's turned it into a hotel with a pub, brewery, soaking tubs, and even a movie theater on site. There are secret rooms hidden throughout the property and enterprising guests are often surprised to find fully functioning bars behind the hidden doors. This is a great property and ideal for a Zephyr Adventure.

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Arrival & Departure

We will meet you just after lunch in Bend, Oregon on the first day of the tour, with a pickup either at the local airport or our downtown hotel. The tour ends in the late morning at our hotel in Bend, from which you are welcome to shuttle with us to the airport or continue on your journey. Note that if flights are too expensive flying into Redmond - Bend Airport, you might consider making the three-and-a-quarter (beautiful) drive from Portland in a rental car.

What's Included?
  • At least two Zephyr guides accompany each trip and a third is added as necessary.
  • Double occupancy lodging is included. If you are traveling solo, we will match you with another traveler of the same gender. However, you may pay a single supplement to have your own room.
  • All of your dinners and breakfasts are included. Gratuity for these meals is also included. In general, we leave lunches open so that you have time to explore and enjoy the local flavors en route.
  • All your transportation is included once you meet your guides on the first day.
  • All equipment rental*, activities, trail fees and permits are included. *E-bikes are available for an extra charge for our day of biking. Please contact us for details.
  • NOT INCLUDED Beverages, desserts, lunches, gratuities to your guides, personal expenses and travel to and from the destination.

September is an ideal month to be outdoors in Central Oregon. The average high temperature during the day in Bend this month is 74 degrees, while nights get down on average to a crisp 38 degrees. There are only an average of five days of rain in the months and leaves will be turning colors in the hills.

Extending Your Stay

We believe Oregon likely packs more outdoor adventures into its borders than perhaps any other state. Portland, Oregon is an interesting mid-sized city well worth exploring. One nice option is to fly into Portland, rent a car, and make the three-hour drive to Bend, perhaps stopping at Mount Hood on the way. Crater Lake, Oregon is only two hours south of Bend and is one of the premier national parks in the state. Eugene, home to the University of Oregon and 2.5 hours west of Bend, is an amazing small city with a great downtown area, a nearby wine region, and lots of trails. If you have the extra time, the Pacific Ocean makes for a fantastic vacation!

Changes to Your Itinerary

While everything under “What is Included” will remain the same, the actual restaurants, hotels, and activities listed in our itineraries are subject to modifications. Changes that are out of our control are common – a restaurant closes or loses its awesome chef, a winery changes its visiting hours, a hotel gets remodeled, a road or trail undergoes construction. You are entrusting us to create an outstanding vacation for you and so it is possible we may take the liberty of making necessary changes (even at the last minute, during the guides’ scout trip) to the itinerary that will improve your overall trip experience. If there is any one experience that is going to make or break your trip, please discuss this with us in advance! We will attempt to keep our website itinerary as current as possible and communicate any major changes with you in the weeks prior to the tour.

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