Oregon: Bend Multisport Adventure With BYO Magazine

July 17 - 21, 2022

“Back in the day, Bend was a logging town. Today, we’re a lager town. And porter. And IPA.

Brad Ring Hiking

Brad Ring, Publisher of Brew Your Own Magazine, personally invites you to join him on this exclusive and epic beer adventure.

Bend is an amazing little city in Central Oregon, which is considered one of the best outdoor sports hubs and one of the best beer towns in the country. It is perfect for our active beer tour. Let’s start with the beer.

Bend, Oregon Breweries and Beer

Despite Bend having a population of just over 100,000 and the whole county registering a bit over 200,000 residents, the Bend Ale Trail is composed of over two dozen breweries. Plus quite a few distilleries, cideries, wineries, and kombucha brewers. So while Portland, Oregon is known as a great beer city, Bend has more breweries per capita. Two of the most well-known are Deschutes and 10 Barrel but there are so many breweries and beer to try.

Here are just a few of the many beers you can look forward to trying, these ones voted as favorites by Bend locals in the Source, a local magazine:

  • Black Butte Porter from Deschutes Brewery
  • S1nistor Black Ale from 10 Barrel Brewing
  • Nut Crusher Peanut Butter Porter from Wild Ride Brew
  • Black Ace Cascadia Dark Ale from Bevel Brewing
  • Sweet As Pacific Ale from GoodLife Brewing Company
  • King Krispy Pilsner from Deschutes Brewery
  • RPM IPA from Boneyard Brewing (nine-time IPA winner)
  • Vicious Mosquito IPA from Sunriver Brewing
  • Strata IPA from Worthy Brewing
  • Tropic Pines IPA from Bend Brewing Company

Outdoor Activities in Bend

Locals are passionate about their free time and, in addition to supporting the many area breweries, love spending their leisure time 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.

Bend With BYO Magazine

Bend is much more than the combination of its beer and outdoor activities. The small city has a walkable riverfront, top quality restaurants, and friendly people. The city accumulates accolades galore, including (of most relevance to us) the Best Multi-Sport Town in America as determined by Outside Magazine and one of the 8 Best Beer Cities in the US by CNN.

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.

This trip is a private tour for the BYO Magazine community.

Private Tour Info

This is a private tour with BYO Magazine. It can also be set up as a private tour for your own group with a minimum of 10 people.

Start planning your private tour


  • Dates: July 17 - 21, 2022
  • Cost Per Person: $3,000
  • Optional Single Supplement: $600
  • Private Tour Minimum: 10
  • Activities: Biking, Hiking, River Rafting, Kayaking/Canoeing/Stand Up Paddleboarding, and Beer Tasting!
  • Difficulty: All Abilities
  • Guides: To Be Determined

Book this Tour

Trip Highlights

  • Visit mutiple breweries each day with your host Brad Ring from BYO Magazine
  • 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
  • Bicycle in the foothills above Bend with a view of the Three Sisters mountains serving as a carrot in front of you

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 (if you have not yet) and take a little time to visit the six-barrel Old St. Francis Brewery, which sells its beers only on the hotel grounds, for takeaway, or via direct shipping. We'll enjoy dinner in the Old St. Francis Pub.


This morning we head to famous Mt Bachelor, considered the number one ski resort in Oregon and one of the best in the country, but 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.  On our way back into Bend, we'll stop at the Deschutes Brewery Tasting Room, which is located at the famous brewery itself, before heading for dinner at the biergarten at GoodLife Brewing.


We have a leisurely morning before picking up and getting on our road bikes to head out on 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. In the late afternoon, we will do a two-mile walking tour from our hotel of area delights including a brewery (Bend Brewing), distillery (Crater Lake Spirits), kombucha maker (Humm Kombucha), and a well-known local eatery, Laughing Planet, for dinner.


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. In the afternoon, we start our trifecta brewery tour in Bend's west side neighborhood: to 10-Barrel Brewing for an insider's tour and tasting; Sunriver Brewing for dinner; and the Boss Rambler Beer Club for a final evening drink. All three within a block of each other!


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.

Book this Tour

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.

Book this Tour
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.
  • All organized beer tastings. Beers at dinner or lunch are on your own.
  • 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.

Book this Tour

Save my Spot

Not ready to book yet? Save your spot by sending us an email request to "pencil you in" on our registered list. Save your spot today.

I'm Interested

I'm interested in this tour, but want to know more. Get in touch with us.

Plan a Private Tour

Looking to book this itinerary as a private tour? Complete our private tour inquiry form to get started.

Get Travel Inspiration Delivered Directly to Your Inbox

Sign up for our newsletter to receive regular updates on our upcoming adventures.