Win Tickets ($36): A Valentine’s/Oregon’s Birthday Walking Tour of Portland’s Sinful Past: Shanghaiers, Saloons and Skullduggery

We are giving away a pair of tickets to Walking Tour of Portland’s Sinful Past on February 11. To win, comment on this post why you’d like to attend. Winner will be drawn and emailed Friday, February 9.

From our partners:
Portland's Sinful Past Walking TourA Valentine’s/Oregon’s Birthday Walking Tour of Portland’s Sinful Past: Shanghaiers, Saloons and Skullduggery
February 11, 2018
4 p.m. | $18 | 21+

Meet @ Floyd’s Coffee
118 NW Couch St., Portland, OR 97209

As a nexus for labor and shipping in the Pacific Northwest, Portland often had the repute of a rugged, rough and tumble town, more than willing to allow the miners, loggers, and fishermen an opportunity to part with their hard earned cash in whatever debaucherous manner they chose.

In addition to the shanghaiers and con men, always on the prowl, saloons, gambling halls and bordellos also thrived in “Whitechapel,” “The North End,” or Old Town, as we know it today. Some of these storied establishments have come and gone, but others have survived, and many say that Portland, or “Strip City,” still has that vulgar and rugged reputation to this day.

Join Historian Doug Kenck-Crispin as we visit locations of famous saloons, bars and bordellos, card rooms and gambling dens, some of which are still in operation today!The tour will meet at Floyd’s Coffee at 118 SW Couch St. Feel free to arrive early and have a coffee! The tour will “end” outside of Mary’s Club, one of Portland’s most hallowed strip clubs*. At the conclusion of the tour, you can join Doug inside for an adult beverage!

Doug Kenck-Crispin is the Ribald Resident Historian from He is the co-producer of the bi-weekly podcast series Kick Ass Oregon History. Doug has been featured in the Portland Mercury, The Oregonian, Portland Monthly and OPB’s Oregon Experience. He has a BA in History, and is nearing completion of his MA in Public History, with an emphasis on the History of the Pacific Northwest (Portland State University). A lifelong resident of the region, Doug enjoys a good yarn, the more bizarre and unbecoming the better, especially when they are true!

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82 Responses to Win Tickets ($36): A Valentine’s/Oregon’s Birthday Walking Tour of Portland’s Sinful Past: Shanghaiers, Saloons and Skullduggery

  1. Cara January 17, 2018 at 2:57 pm #

    This sounds like so much fun!

    • Laurie Gallinat January 18, 2018 at 3:22 pm #

      I love wine and Chocolate and I’d love to what this experience would be like.

    • Bryan toland January 26, 2018 at 2:43 am #

      I’m new to Portland so I could use a history lesson, along with a date night with my woman.

    • Cheryl Ouyang February 6, 2018 at 12:28 pm #

      My husband in Chinese; what a fun and cultural way to spend the day!

  2. Jennifer January 17, 2018 at 4:20 pm #

    Valentine’s Day is about celebrating love, but February 11 is made for celebrating our love of Portland. I’d love to partake in that PDX adoration!

  3. Katie January 17, 2018 at 7:59 pm #

    I love Valentine’s day, but I love Oregon more. I’ve lived here all my life and it would be incredible to see Portland in a way that I could learn something in the process. What better way to see our amazing city than a walking tour?

  4. Elizabeth January 18, 2018 at 2:04 am #

    I have been wanting to do one of the walking tours for awhile now! This would be great!

  5. Jenn January 18, 2018 at 12:16 pm #

    This is the one major Portland tour I have never done. Rain or shine, I’d LOVE to show my love of Portland and its storied past by going on this tour.

  6. Scott January 18, 2018 at 3:12 pm #

    Sounds fun.

  7. Aurelia January 18, 2018 at 3:24 pm #

    Let’s do this!

  8. brin January 18, 2018 at 3:54 pm #

    So fun!!! I would love to take someone to do this!!!!

  9. Leslie January 18, 2018 at 3:56 pm #

    My husband and I both love history. As a matter of fact, he bought us tickets to see the The Treasures of Tutankhamun as one of our first dates while we were still in high school in the 70’s! Taking him on this humorous history tour of our favorite city would be a fun and unique way to say “I love you still, after all these years!”

  10. Meghan January 18, 2018 at 4:18 pm #

    Always wanted to do this!

  11. Julia January 18, 2018 at 4:55 pm #

    I would love to take my partner to this!!!

  12. Laura January 18, 2018 at 5:01 pm #

    This would be such a cool tour to take!

  13. Alicia January 18, 2018 at 7:28 pm #

    I was a tour guide for Boston and would love to learn more about the history here in PDX

  14. Karen January 18, 2018 at 7:48 pm #

    A lifetime in Portland and I’ve never toured Portland’s seedy past. Would love to win these tickets!

  15. Nicole Mangan January 18, 2018 at 10:49 pm #

    Sounds like a hell of a time! I have always wanted to one of these!

  16. Jack January 18, 2018 at 11:06 pm #

    This sounds awesome, I would love to do this!

  17. molli taylor January 19, 2018 at 5:17 am #

    as odd as this seems , this is pretty much my perfect valentines date. i’ve always wanted to do one of these.

  18. Pam Louie January 19, 2018 at 6:15 am #

    I have been wanting to do this tour for a long time and would love to take my boyfriend who is from the East Coast. He thinks Portland is just cloudy and rainy all the time so I want to take him “underground” to see another side of Portland!

  19. Robert January 19, 2018 at 11:27 am #

    sounds like a swell time!

  20. Christine Skorjanc January 19, 2018 at 2:26 pm #

    This would be fun & love learning about the area

  21. Sedona January 20, 2018 at 1:30 pm #

    Sounds like a really great date with the husband. He’s from the east coast and doesn’t know a lot about the pacific northwest’s history. I bet he’d love to go :)

  22. Frank Byers January 21, 2018 at 2:45 pm #

    Because my friend needs to get out of the house and have fun.

  23. Mollj January 22, 2018 at 8:20 am #

    This is something my husband would flip for, so I’d love to be able to take him!

  24. Adriane Ceglie January 22, 2018 at 10:59 am #

    This is a walking tour I am unfamiliar with. I would love to hear more about Portland’s seedy side, past and present.

  25. Marie January 22, 2018 at 4:19 pm #

    I don’t have a Valentine in Portland and this sounds like an anti-establishment way to spend the holiday.

  26. Valerie January 23, 2018 at 12:58 pm #

    What a cool tour! Would love to join this.

  27. Rachael January 23, 2018 at 1:56 pm #

    This would be so fun! And such an alternative idea to most people’s Valentine’s plans!

  28. diana January 23, 2018 at 4:29 pm #

    would be cool to learn a bit more about Portland

  29. halle January 23, 2018 at 5:54 pm #

    sounds like too much fun to pass up!

  30. panda January 23, 2018 at 10:12 pm #

    grrr! sounds devilish!

  31. AMCMURRY January 24, 2018 at 7:20 am #

    Lived here since 1976 and never done this…intriguing idea

  32. Tracy Ritz January 24, 2018 at 9:00 am #

    Always see this and never have dine it would love to go!! Great valentines day gift!!❤

  33. Dan Koss January 24, 2018 at 11:00 am #

    My GF and I NEED a spooky and macabre V-Day!

  34. April January 25, 2018 at 2:32 pm #

    This would be a fun Valentine’s date!

  35. Courtney January 25, 2018 at 3:30 pm #

    Oh my gosh this would be fun!

  36. Brian Jim January 25, 2018 at 7:25 pm #

    always wanted to do this tour… just need to win the tickets to go!!!!!!!!!!!!!!

  37. Jennifer Apple January 26, 2018 at 9:30 am #

    Would love this!

  38. david January 26, 2018 at 9:58 am #

    i am always in love with learning more about this fair city, esp with those who seek to preserve those stories that made, and make, portland a special place with the truthful, oft sordid history. pearl districts be damned; long live old town;-!

  39. Jill Travis January 26, 2018 at 11:39 am #

    This would be a sweet treat to enjoy with my sister.

  40. Sydney January 26, 2018 at 1:28 pm #

    this is very intriguing…

  41. Jen January 26, 2018 at 5:29 pm #

    Sounds like an interesting time!

  42. Diane McLaughlin January 27, 2018 at 9:53 am #


  43. Leah January 30, 2018 at 12:35 pm #

    I’ve never done a walking tour and I’ve lived here for 10 years. I do adore Mary’s!

  44. Lance January 30, 2018 at 12:47 pm #

    I would love to walk in the footsteps of my ancestors.

  45. Katy January 30, 2018 at 2:51 pm #

    I would love to do this!!

  46. Crystal Zingsheim January 30, 2018 at 3:09 pm #

    I’m writing a film that includes this storyline in Portland’s history and would love the opportunity to learn more for my research and makeout while I do. Appreciated!

  47. Ken January 30, 2018 at 3:13 pm #

    This would be so rad and a perfect date!

  48. Jackie January 30, 2018 at 4:41 pm #

    My husband is from CO and I’m always doing my best to fill him in on what history I know about the area but sounds like this guy is the expert!

  49. Barb finn January 30, 2018 at 9:02 pm #

    My dad was born in pdx in 1913. His grandfather was a policeman in albino in the 1800s. I’ve heard stories…but never done this tour. Would love to win these tickets!

  50. arianne belt January 31, 2018 at 6:16 am #

    What a gift?! This is the perfect date for my partner & I-having been gone for 20yrs….I just moved back to my hometown of Portland (and boy has it evolved into an entirely new city, than what it was, when I left for College in 1997). This tour sounds like the perfect intro for both of us, as I am feeling somewhat new to the city, as well….having been gone so long, id love to rediscover it with her & this tour. Sounds like a blast!!

  51. xonia hendrix January 31, 2018 at 1:31 pm #

    what a fun time! would love this!

  52. Frances L February 1, 2018 at 3:36 pm #

    I love history and learning about my home! Sounds like a blast

  53. michelle Mathews February 1, 2018 at 5:12 pm #

    This would be perfect right before our rez at Little Bird for dinner! Yes please. lets get creeped out by the wicked shit that went down before we were around this town!

  54. Dana February 2, 2018 at 9:13 am #

    I keep hearing about this tour…we would love to hear about Portland and take this fun tour. Thank you for the opportunity

  55. tracy February 2, 2018 at 11:06 am #

    Portland has the best history, learning about where we live is always fantastic!

  56. Jenn February 5, 2018 at 7:49 am #

    I love the podcast Doug puts on and am incredibly keen to experience his “live show” (aka the tour).

  57. Kristy February 5, 2018 at 9:57 am #

    Been curious about this! Sounds fun!

  58. Kobi Hensley February 5, 2018 at 10:21 am #

    We’d love to go! I’ve always wanted to do this!

  59. Krystina February 6, 2018 at 8:37 am #

    Would love to go with my boyfriend. Brings a new meaning to Valentine’s date to learn about the more naughty side of the city.

  60. Yung Ouyang February 6, 2018 at 12:29 pm #

    I am Chinese and enjoy learning about local culture.

  61. Cheryl Ouyang February 6, 2018 at 12:30 pm #

    My husband is Chinese; what a fun way to spend the day!

  62. Jennifer February 6, 2018 at 12:44 pm #

    I NEED a date night with my manpanion. We are too boring.

  63. Shelby February 6, 2018 at 12:54 pm #

    I’d love to take my partner for valentine’s day!

  64. Brandy February 6, 2018 at 12:58 pm #

    Ive been trying to make one of these tours for a long while now, but have always either been working or had other plans. What a perfect way to spend a pre-holiday afternoon!

    (It beats making up my own walk on the topic, which believe me I have considered…all the former bordellos in this town have to have good stories…LOVE stories…)

  65. Jenny February 6, 2018 at 1:17 pm #

    I would love to take my mom on an adventure! This would be so interesting!

  66. AJ February 6, 2018 at 1:23 pm #

    This would be so much fun!

  67. Elizabeth February 6, 2018 at 1:39 pm #

    Oh I would absolutely love this tour!!

  68. Becky February 6, 2018 at 1:57 pm #

    Always been interested in Portlands history.My grandmother told me about underground establishments with gambling fights and prostitution.she was friends with the head madam back in the 40s

  69. Brittany February 6, 2018 at 2:34 pm #

    I love all things scary/disturbing and am relatively new to Oregon! Would love for the opportunity to explore the city and learn about its past!!!

  70. Chelsi February 6, 2018 at 3:16 pm #

    Oooooo I would love this!!!!! Pick me pick me!!

  71. Joanna Williams February 6, 2018 at 8:08 pm #

    It would be so much fun to get to show this side of Portland to my husband!! He loves anything history, and this would be such a much darker side of history for him to see!!

  72. JSSUBO February 6, 2018 at 10:55 pm #

    I got my spanky pants on and my Monkey Shoes waitin’ by the door. Need I say more? Cheers!

  73. Stephanie February 7, 2018 at 5:58 am #

    This would be a cool experience!

  74. Jennifer February 8, 2018 at 10:23 am #

    It’d be such a spectacular way to celebrate Oregon’s birthday (a few days early) by walking along her streets learning about who stomped along those paths long before us.

  75. Melody Axe February 8, 2018 at 11:44 am #


  76. Jeannie Pruett February 8, 2018 at 12:44 pm #


  77. Kimberly B. February 8, 2018 at 4:02 pm #

    This definitely sounds like a unique experience.

  78. Matthew February 9, 2018 at 10:38 am #

    Sounds very interesting, educational, and fun

  79. Ladu February 9, 2018 at 12:35 pm #

    I’ve been wanting to attend one of these tours for ages. What a perfect time to experience.

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