| |

Bend, Oregon — How to Drink Lots Of Delicious Craft Beer…And Lose Weight

If you’ve never had the chance to travel to Bend, Oregon, you need to pop it up to the top of your to-do list ASAP!

Bend, Oregon is an outdoor adventurer’s playground! Surrounded by national parks and with a river literally running right through the center of the town, it’s a sight to behold. Here’s just a taste of what I got into, all while getting my work done in between. Tons of hiking, mountain biking, waterfalls, award-winning beers, vegan and vegetarian deliciousness, and friends made from across the US.

Want a discount code for a free hard copy of the book? Help me celebrate 1 year of being published!


This site participates in the Amazon Services LLC Associates Program and other affiliate programs and may earn from qualifying purchases. You’re never charged more, but it helps out little by little! Check out “Privacy” in the top menu if you need to know more!


I actually spent more on delicious beers than on food, and still lost 5lbs over two weeks because of all of the exercise and outdoor adventures Bend, Oregon offers!

Hope you get some inspiration to head to Bend! If you do, hit me up…I may just decide to join you! Here’s the lowdown!

redmond caves bend oregon
Redmond Caves — I literally saw a roadside sign for caves and was like “aaaiiight!”

Bend, Oregon Day 1-2

Flew from CLT (Charlotte) to MSY (New Orleans) to SEA (Seattle) to RDM (Redmond)

12:00am PST Wednesday : Arrived in RDM
Head to my first Airbnb via taxi less than 2 miles from the airport. (Nope, no Uber or Lyft in Redmond!)

1:30am PST: Attempt to sleep for a couple hours; keep in mind my brain was on east coast time, so it was about 4:30 in my head!

8:00am: Start hiking 2 miles back to airport and get rental car. Who needs a cab when your backdrop is so beautiful!?

9:30am: Grocery shopping!

Super budget saver tip here; make sure you use the kitchens at the Airbnb for most of your meals! I bought food for breakfasts and lunches and would typically hit a happy hour for some eats and a beer in the afternoons. Plan ahead and save loot!

READ NEXT: 12+ Tips For Learning How To Slow Travel & Live Like a Digital Nomad
Yellowstone Norris Geyser Basin: Hot, Bubbly, Heaven & Hell On Earth

10:30am: Discovered real caves roadside, in Redmond, just waiting to be explored! Nobody around; just me!

11:30am: Set out to explore the amazing high desert beauty of Smith Rock State Park, logging about 7-8 miles and 1200€² in elevation gain.

Smith Rock State Park Oregon
Smith Rock State Park, outside of Bend, Oregon. Check out that trip!
They like their craft beers.
sprinter van

Also met a couple amazing folks traveling the summer in their radded-out sprinter van conversion!

7:00pm: Appropriately dropped into Smith Rock Brewing to grab a pint and do some writing. Check their hours; they close early!

8:00pm: Ended an amazing day by stopping at Wild Ride Brewing to get a flight and check out their beer scene. If you like dark, malty deliciousness, make sure to try their Bitch Stout!

Bend, Oregon Day 3-4

11:00am: Checked out of first Airbnb and headed to pick up a fat boy mountain bike from a buddy for the week. Sweetness.

3:00pm: Checked in to new AirBnB less than a half mile from the center of Bend!

5:00pm: Set out on a 10mi ride around Bend to check out the scene. Bend, Oregon has an amazing amount of bike lanes! Even on their faster 45mph roads, which are essentially mini highways, there are bike lanes. Coming from Charlotte, NC, where you take your life into your own hands cycling the city’s “bike lanes”, this was amazing.

Dillon Falls Bend Oregon
Dillon Falls, just minutes from any doorstep in Bend.

The next day was a work day! Yeah. Didn’t leave the Airbnb all day and did a marathon session catching up on some client work. 

The thing about living the life nomadic is that you actually have to pay the bills!

Oddly, I often find it easier to work when I’m on the road since I don’t have any house chores or other things to pull me away, regardless of the amount of awesome things to explore around me!

Over two weeks in Bend, including the 4th of July, and I never once feared for my safety while I was on two wheels!

Connect & Share This Article

Bend, Oregon Day 5-6

9:00am: Set out for Tumelo Mountain, where I was joining up with the Bend Meetup group I joined for the trip. If you’re going to be somewhere for a week or so, make sure you hit the Meetup boards. Most groups are more than happy to invite an out-of-towner in for a week or so.

10:00am: Hiked Tumelo Mountain, elevation just under 7,800€².

The Baller view from Tumelo Mountain
The amazing view from Tumelo Mountain

3:00pm: Hopped on the bike again and waved at the crowds while riding by the Pride Festival going on in Drake Park. Ending at Goodlife Brewing Company to hang with some old friends and watch the Subaru Games Bouldering Championships.

Holy Epicness Batman!

8:30pm: Headed to Crux Fermentation Project to check out Cruxapalooza. Unfortunately, they were winding down and stopped selling beer tickets when we arrives, which is no Bueno.

11:30: Cycled, totally sober, back to the Airbnb, with little but a headlamp and the Oregon sky to guide me.

The next day…

Morning: Work morning while exhibiting my awesomeness at being hungover.

1:00pm: Headed to some of the nearly 300 miles of mountain bike trails in the area for a demo day. Rode a Yeti ASR 29” totally free down the Funner Trail.

That. Bike. Is. Bitchin.

4:00pm: Decided to go hike near Devil’s Lake for a few miles. So here’s the deal; I hike a lot, and am often well-prepared for anything. But occasionally I get a little cocky, just like everyone else at certain points, and underestimate.

It’s typically at those points where Mother Nature puts me in my place.

A 4-5 mile hike (with two guidebooks and a map) turned into a nearly 10mi hike with covered trails with massive areas of up to 10-foot deep snow at elevations above 7000 feet…in June. I ran out of water just before sundown, didn’t have my Lifestraw, nor any warm clothing for an overnight.

The beauty and the beast of Three Sisters Wilderness
The beauty and the beast of Three Sisters Wilderness

Truth be told, I was fine and had my headlamp to head back to the road (eventually) via Strava and other GPS, but it just goes to show that we shan’t forget that…

Mother Nature brought you into this world, and she can take you out.

9:00pm: Dinner and a Black Butte Porter at Deschutes Brewery.

10:00pm: Passed the funk out. That was a good day.

Day 7

Work Day.

4:00pm: hiked about 4-5 miles of the Deschutes River Trail, literally steps outside the north border of Bend, in the National Forest.

There you go! That was a full first week in Bend… and week two was more of the same. Do yourself a favor and get Bend, Oregon on your short list for the summer months!

What I’ve been drinking, slowly, while writing: Allagash James Bean with Coffee (And it is friggin’ good!)

Cheers!
— Jason

Travel Planning Tips

Figure out where you are going & how are you getting there…
I suggest using at least 2 to 3 different travel search sites. Start with Skyscanner or Orbitz or Booking …or whatever aggregator site you prefer. Then when you see what airlines to use, check their respective sites for better deals or rewards flights.

Figure out where you’re going to stay…
If you’re interested in hostels, search Hostelworld or Hostelling International. For longer-term or more private digs, look at Airbnb, VRBO, or you can look for hotel rooms in the links from the search engines listed above. 

Get comprehensive travel insurance, or in the least, travel medical insurance if internationally…
Especially with Covid not going anywhere, get covered. Start with an insurance aggregator like Insure My Trip, or with SafetyWing, World Nomads, or another. Then decide what is important to you; trip cancellation, baggage coverage, medical, or all of the above. And get a yearly evacuation plan, since you’ll have to get home after your emergency! 

Need more resources? Click here!

Related Posts