Portland Walking Tours

In the Spotlight: Meet Portland Walking Tour Guide Damon Kupper Live on the Streets of Portland and on Stage in Great Expectations

February 3rd, 2016


Damon Kupper is a triple threat: great guy, talented tour guide, and accomplished actor. We are proud to have him as our longest running tour guide at Portland Walking Tours, and thought it would be fun to learn a little bit more about him and pick his brain about his latest show, Great Expectations at Portland Center Stage. Read on to find out what brought Damon initially to Portland, what he’s learned about life from being in Great Expectations, and if he sees any commonalities between acting and giving tours.

Married with two young sons, Damon enjoys engaging in both the larger community narrative and the fantastical realm of bedtime stories. He bike-commutes whenever he can and enjoys fixing up his family’s old home in SE Portland. A proud company member of Third Rail Repertory Theater, Damon is also a Drammy winner and has graced many prominent Portland stages as well as regional theaters across the country. His travels have taken him across the globe where he has worked as an instructor for various educational theater programs and entertained as a street performer. As if that isn’t enough, Damon has a masters degree in acting from UC Irvine and completed the two year actor training program from Pacific Conservatory for the Performing Arts.

Mad skills for a tour guide, right? It is definitely safe to say that when it comes to Damon, we always have Great Expectations!

1) How long have you lived in Portland and what brought you here? What do you like about living here?

I was lucky enough to come to Portland as an actor with Artist Repertory Theatre eleven years ago. We were presenting a bilingual (English/Vietnamese) production of A Midsummer Night’s Dream. Portland immediately attracted me. I am from a small town in California but have lived in and enjoyed the vitality of larger cities. In Portland I found a wonderful balance of an accessible vibrant city that is also easy to escape from. Great people, beautiful parks and architecture, and dynamic port city history.

2) How did you get involved with PWT and how long have you been giving tours? Which tours do you give?

I joined up with Portland Walking Tour as one of its first guides 10 years ago. I love to dive into history and get down and nerdy, so giving tours was a great fit for me. I have always enjoyed traveling and seeing the spark in the eyes of those on the road of adventure. I have given a wide variety of tours including the Epicurean Excursion, Flavor Street, Underground and Best of Portland tours for both public and private groups. I know I have had an impact on making Portland a desirous destination.

3) What do you enjoy most about giving tours for PWT?

I love the being out on the streets of Portland, rain or shine, and seeing locals and visitors make the link to how city planning, risk, respect, and a scoop of weirdness make Portland such a fantastic destination. I also gain so much from the stories and observations of those I meet as a tour guide.

4) Do you have a few favorite tour stories you can share with us?

I have had people stop me on the street and tell me,“You are the reason we moved here.” I’ve enjoyed older residents giving me their first-hand experiences from some of Portland’s most harrowing moments (the expelling of Japanese citizens, the Vanport Flood, labor strikes). Portland’s grittier past is often a thin scratch under the modern Green.

5) Why should someone take a tour with PWT?

Portland is a very open city but being guided on the journey gives people an excuse and support to go beyond normal ‘yelp’ help and share community in a small group of adventure seekers. I love when people have a particular interest in an aspect of the city that they want to explore (art, food, political scandals, etc.) but many people simply want to take advantage of useful tips that a guide can offer.

6) Tell us about the production of Great Expectations at PCS. What can we expect when we go? Is it ok if we haven’t read the novel and aren’t familiar with the story?

GE is a rich, humorous, and poignant story. The play condenses the novel and it does in a creative and often narrative style. Our job is to make it clear. But to know who Miss Havisham or Mr. Jaggers is beforehand can only add to the fun.

7) What role(s) do you play?

I wear a few hats and two wigs. You’ll see me in the roles of Mr. Pumblechook and Mr. Wemmick as well as a few other cameos. See if you can find them!

8) What have you enjoyed most about being part of this production and working at PCS in general?

PCS holds a unique place in the Portland theatre community. They do some of the largest musicals and classics as well as some of the most cutting edge pieces you’ll find…and they do it in an historic platinum level LEED building.

9) What have you learned (about life, theater, anything) from being a part of this play?

It is a coming of age play about building character and facing the fears and frustrations of our expectations. It resonates strongly in me from my own navigations in life, especially now as a father of two boys myself. Like all great dramas, one can find new observations with every twist of the kaleidoscope.

10) Why should someone go see Great Expectations?

It is one of the best casts of actors you’ll find in the city, if not the best, and you’ll have the chance to be moved and guided and embrace some incredible language and characters. The Gerding Armory Theatre is its own destination as well.

11) What similarities are there between acting and giving tours?

All the world is a stage, but the streets of Portland and the tour groups themselves make for a unique ensemble and quite an impressive set to share stories in.

To experience the magic of a Portland Walking Tour with any of our talented guides, join one of our seven different tours and book advanced tickets at portlandwalkingtours.com. To catch Damon in Great Expectations at PCS before it closes on February 14, visit pcs.org/expectations.

Great Expectations was featured on the Big Red Arrow Hot Sheet! Check it out to find more fun things to do in Portland!

Article by Natasha Kelly


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