: Katie Falkenberg

Behind the Scenes with Oregon’s Sidekicks

Get to know the pals behind “Travel Oregon with Travel Oregon.”
July 27, 2023

Tucked into a pocket of Oregon’s magnificent wilderness, the Travel Oregon remote office is an enchanting site to see. 

Amidst the old-growth Douglas firs and mossy undergrowth, a friendly beaver, who introduces himself as SustainaBill, chats with Kayakyak about their plans for a retreat to the Oregon Coast. Rosa and Telephone Paul swap notes about the latest trends and events in Oregon, while a pair of pals, Left Boot and Right Boot, lace up in search of a new hiking trail.  

The outdoor office is buzzing with excitement — they have worked over the past year with Oregon guides and tour operators to invite visitors (and resident Oregonians) to try something new with some help from experts. Whether it be snowboarding for the first time or taking a wine tour along a Scenic Bikeway, these native Oregonians are eager to welcome all to experience their favorite activities through the eyes of a resident expert. Let’s hear from each of them about their love for Oregon.  

An Eager Beaver and a Chatty Kayak

Between recycling a few documents and researching their next paddling trip, SustainaBill and Kayakyak answer a few questions. 

So, SustainaBill, why do you want to share Oregon with the rest of the world?

Well, I was born here and call this place home. A lot of people who’ve visited Oregon have only scratched the surface of what this great state has to offer. The beauty of this place isn’t just about the mountains, trails and 363 miles of public coastline … it’s the people – the experts and enthusiasts who want to share their side of Oregon with visitors.

When people come to Oregon they can’t stay in dams, so where do you recommend they stay?

While I would love to show everyone around my nesting chambers, I think you’re right. If you’re looking for a place to rest after a day of adventuring, I would turn to all of Oregon’s green getaways. There’s a whole bunch of eco-friendly hotels for your sustainable vacation.

Kayakyak, what do you love about Oregon’s waterways?

That’s easy to say! I love the blue waters, seabirds, sea stacks, aquatic life, sandy shores, rocky shores, the salty air on my face, friendly fisherman, [they talk so animatedly, she must pause for a breath] breathtaking views, hidden coves, whale watching, ease of accessibility and of course paddling with new friends I meet in Oregon. Plus, eating great seafood on Oregon Food Trails along the Coast when hunger strikes.

I can see why they call you Kayakyak.

It’s obvious, isn’t it? I can’t help but yakking away! Get me a guide’s ear and I’m chatting a nautical mile a minute.

A characterized telephone pole in front of Baghdad Theater in Portland.
Telephone Paul's favorite hangout spot on Hawthorne in Portland.

In the Know with Telephone Paul and Rosa

An easygoing guy, Telephone Paul is happy to talk about the events he’s excited for and the city he loves: Portland. Rosa perks up at the mention of wine and food — two of her favorite topics. 

A tall guy like Telephone Paul has got to have quite the appetite. Where’s your go-to spot when you get hungry in Portland?

I can’t choose just one! It all depends on the mood and where my appetite takes me. Sometimes you’ll find me at a food-cart pod trying dishes from all over the world. Other times I get a craving for something a little fancy, so I roll on over to an award-winning restaurant. You just got to go where your tummy takes you, y’know? Like last week I wanted disco waffles with a side of drag and boom, there I was at a Diva Drag Brunch. It was a true gift to the senses.

We hear you’ve got the scoop on anything and everything going on in the Portland area. What are you excited about this season?

I’m personally looking to take a step outside the city this season to broaden my horizons. Just the other day someone stapled a poster for music festivals to rock out at. I’m also thinking of taking my cowboy hat for a spin at a rodeo in Pendleton. In the Rose City, you can also do all sorts of stuff for the sweet price of free.99. If you’ve got yourself some leg-powered wheels, bike your way through Portland’s greenways. In the summer, you’ve got to cool off, so take a dip to chill out, or take a hike in Forest Park. That place is huge, man.


So, Rosa. There’s a lot to know about wine tasting and wine making. How did you learn so much about it all?

As an influencer, I’m always looking to expand my palette. I’m on the road seeking the crème de la crème of wine and food, which is easy to find in Oregon’s food paradise. Definitely consider booking a guide to tour the stunning vineyards and wineries that produce Oregon’s famous pinot and bubblies. For a little help, check out this beginner’s guide to Oregon wine.

You can find great wine and food all over Oregon, so it’s hard to pick where to go. What would you say to visitors who are looking for recommendations?

My first tip is to always know your seasons. If you’re envisioning a trip full of wine bike tours through lush greenery and budding vines, get something on the calendar in the spring and summer. It’s equally as beautiful in the fall and winter, and especially great for getting a perfect Instagram shot —there’s less people around to photobomb you. Plus, harvest season in Oregon is perfect for the pumpkin spice latte vibes.

Puppet boots and two hikers on a forest trail.
Dan with his sidekick Boots hike at Catherine Creek near La Grande. Photo by Katie Falkenberg

One Boots, Two Pals, and the Dark Sky

A dynamic duo, Left Boot and Right Boot are the ultimate buddies you’ll find on the trail. After the offices close, Dark Sky comes to take over the night shift. 

So Boots, how do you two pick a great hiking trail?

We’re big on research — getting inspired to go out is easy. You ever read what’s on TravelOregon.com? They’ve got tips for outdoor activities for days. Plus, our guide pals know how to take the stress out of planning and just get going on a trail. We also stay in the know about conditions before we head out — don’t want to get stuck in the rain without our Ten Essentials or get somewhere and find the trail is closed.

Do two ever clash on what trail to take?

Left Boot: Yes.

Right Boot: Never.

Left Boot: Well, I guess there was that one time you wanted waterfalls and I wanted mountain peak views. Or that other time where I wanted a steep climb to a sweet vista and you wanted an easy stroll through the wildflowers. Or that time –

Right Boot: Yeah. I guess we do clash. But at the end of the day everyone wins if you’re hiking in Oregon.

Dark Sky, I know it’s in your name but I have to ask, are you afraid of the dark?

I am the dark.

I think it’s fair to say you’ve been around for…a while, but it wasn’t until recently that people have started taking notice. How do you feel about it?

It’s about time I’m appreciated. I guess all it took was for visitors to learn about Oregon’s first state park to earn certification as an International Dark Sky Park to pique their interest. If you’re heading to Prineville to come and see me, ask the gravity-bound expert guides who have their feet on the ground. Sign up for guided stargazing experiences to learn everything you need to know about me.

About The

Amy Garay
Amy Garay grew up in Salem and now calls Portland her home. When she's not editing stories and social for Travel Oregon as their content editor, she's snapping shots of her travels, visiting small bookstores and lounging on picnic blankets in parks.

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