Win Tickets ($36): Walking Tour of Portland’s Sinful Past: Shanghaiers, Saloons and Skullduggery | Portland 2018 St. Patrick’s Day Weekend, w/ Kick A** Oregon History Historian Doug Kenck-Crispin

We are giving away a pair of tickets to Walking Tour of Portland’s Sinful Past: Shanghaiers, Saloons and Skullduggery on March 17. To win, comment on this post why you’d like to attend. Winner will be drawn and emailed Monday, March 12.


From our sponsors:
Portland's Sinful Past Walking TourShanghaiers, Saloons and Skullduggery
March 17, 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 “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 podcast series Kick Ass Oregon History. Doug has been featured in the Portland Mercury, The Oregonian, Willamette Week, Portland Monthly and OPB’s Oregon Experience. He has a BA and an MA in History (Portland State University), with an emphasis on Public History and the History of the Pacific Northwest. A lifelong resident of the region, Doug enjoys a good yarn – the more bizarre and unbecoming the better – especially when they are true!

*This tour is best suited for those 21+

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66 Responses to Win Tickets ($36): Walking Tour of Portland’s Sinful Past: Shanghaiers, Saloons and Skullduggery | Portland 2018 St. Patrick’s Day Weekend, w/ Kick A** Oregon History Historian Doug Kenck-Crispin

  1. Morgen February 28, 2018 at 2:50 pm #

    Sometimes locals want to be tourists too…pick me, please!

  2. Jennifer February 28, 2018 at 3:07 pm #

    Yes, Morgen–so true!

    I’ve been listening to Doug Kenck-Crispin’s online podcast and would truly love to see and be a part of a “live show” (aka the tour).

  3. MJ February 28, 2018 at 4:29 pm #

    Please let the luck o’ the Irish be with me and help me win these tickets. I promise my Irish eyes will be smiling the whole tour. Learning more about the underbelly of PDX’s past would be a fascinating and unique way to spend St. Patty’s Day, that’s for darn sure.

  4. Rb. March 1, 2018 at 5:31 am #

    Yay! I love this kind of stuff.

  5. Marilyn March 1, 2018 at 5:35 am #

    I would like to attend because this sounds so interesting and my Irish beer loving husband would dig this!

  6. Jeannie Pruett March 1, 2018 at 2:34 pm #

    This would be an amazing adventure!

  7. Alicia Mishler March 1, 2018 at 2:55 pm #

    Sounds like a great way to learn about Portland!

  8. Teri Fisher March 1, 2018 at 4:09 pm #

    I have lived in Portland for 10 years now. I have always wanted to go on this tour! I have bought books about Portland’s Sinful Past, but have never made it to one of the walking tours. Also, I am trying to exercise more and I couldn’t think of a more fun way to get in some walking!

  9. April March 1, 2018 at 4:56 pm #

    I’d love to learn more about Portland’s history.

  10. Laura March 1, 2018 at 8:22 pm #

    This looks fantastic–I love that the OH is involved.

  11. Mollj March 2, 2018 at 4:33 pm #

    I’ve always wanted to go on one of these walking tours!

  12. Robin Wild March 2, 2018 at 7:00 pm #

    I would love to go on this tour! Portland history is amazing, both good and not so good.

  13. Kim March 3, 2018 at 9:04 am #

    I have done a similar tour in Seattle. So fun! Pick me. I’d love to compare the sinful pasta of both cities!

  14. Shadow Rose March 3, 2018 at 10:50 am #

    Always interesting and educational. I need to bring my boyfriend to this.

  15. Robert March 3, 2018 at 6:27 pm #

    This sounds very interesting. We would love to go!!!

  16. Elizabeth March 3, 2018 at 8:22 pm #

    This would be such an exciting experience.

  17. Matthew March 4, 2018 at 10:32 am #

    I would love to check this out!

  18. Diane McLaughlin March 4, 2018 at 6:55 pm #


  19. Lucy March 6, 2018 at 12:23 pm #

    I want to learn!

  20. TLH March 6, 2018 at 12:48 pm #

    We are new to Portland and this seems like a great way to get to know the city a little better!

  21. Sascha March 6, 2018 at 1:05 pm #

    I’m ready to learn!

  22. Leslie March 6, 2018 at 1:24 pm #

    Oh my goodness. What a fantastic way to spend St Patrick’s Day!

  23. Kristen M March 6, 2018 at 1:25 pm #

    Ooooh a tour of Portland’s dark side, this would be awesome

  24. Julie W March 6, 2018 at 2:21 pm #

    Oh my goodness!! I’ve always wanted to go on one of these tours!! That day will be a rare kid-free day for this momma! Would love to go please!

  25. Chris March 6, 2018 at 3:55 pm #

    I’ve heard about the tour and would like to be able to do it ! Please

  26. Leah Bonaduce March 6, 2018 at 3:55 pm #

    Oh man this would be super cool. In my younger years I used to frequent spots like Shanghai tunnels, berbatis, Paris theatre, old town pizza, etc. and I’ve heard they all are haunted and connected to the tunnels!

  27. Jennifer March 6, 2018 at 4:21 pm #

    This would be a wonderful way to spend a lovely March day. IRISH is all luck!

  28. Morgan March 6, 2018 at 8:24 pm #

    Always interested in this kind of thing, especially as a native Portlander!

  29. Deborah K. March 6, 2018 at 10:32 pm #

    I’ve always wanted to go on this walking tour! Shanghai me and tie me up; I’ll be there.

    I would be thrilled to get some tickets to this event. Thanks!

  30. Valerie W March 7, 2018 at 10:47 am #

    I’ve lived in PDX for three years now and have always wanted to do one of the tours available, this looks like a fun one too!! :)

  31. Lin March 7, 2018 at 1:38 pm #

    Yes. Me. Native Portlander would love to know some dirt.

    • Chuck H. March 7, 2018 at 4:48 pm #

      Not gonna lie…been trying to convince my wife to visit Mary’s strip club with me. What better way than some kick ass Oregon history to get her in the mood…

  32. Ashlee A March 7, 2018 at 2:44 pm #

    This will be my first St. Patty’s Day in Portland. What a fantastic way to kick it off!

  33. Meredith March 7, 2018 at 10:52 pm #

    Would love to check this out. Thanks so much!

  34. PJ March 8, 2018 at 12:41 am #

    This sounds friggin sweet. Slang me some tickets, pretty please. I would love to get drunk and walk around hearing about prostitutes and dirty, old, truly weird Portland.

  35. Lisa March 8, 2018 at 2:42 pm #

    A little bit of exercise + a little bit of history = a fun afternoon. Can’t think of a more entertaining way to learn about our city’s shaded past.

  36. Kristy March 8, 2018 at 3:29 pm #

    How fun this would be! Me and the Husband need a date!

  37. Shannon March 8, 2018 at 4:12 pm #

    This sounds like so much fun! Would love to celebrate Portland before getting my jig on later!

  38. Michael March 8, 2018 at 4:15 pm #

    I have committed plenty of sins in the downtown Portland area over the years . As a amatuer history buff I would love to see how our fore mothers and fathers got down back in the day!

  39. Lynn Elsdon March 8, 2018 at 7:49 pm #

    Well Oil Beef Hooked! Lol,…Now say that really fast! See,…now you speak the language too! ;)

  40. jamey billig March 9, 2018 at 3:26 pm #

    This sounds really interesting. I hope I win.

  41. Katie Fraser March 10, 2018 at 7:43 am #

    I have been wanting to take this tour since I saw it on some history channel show before I moved to Portland in 2011. Even if I don’t win tickets I want to experience this!! But Free makes everything more fun!

  42. molli taylor March 12, 2018 at 7:17 am #

    i have wantd t o do this since i moved to portland 14 years ago.

  43. Elizabeth March 12, 2018 at 11:28 am #

    I’ve wanted to do this since I moved here! It looks like so much fun!

  44. pattie March 13, 2018 at 12:16 pm #

    I love local history!

  45. Cathy March 13, 2018 at 1:51 pm #

    This sounds fun!

  46. Katy March 13, 2018 at 2:52 pm #

    Would love to win tickets to this! Happy St. Patricks day!

  47. Christine Van Halder March 13, 2018 at 6:26 pm #

    Please pick me. I have always wanted to go on one of these walking tours, but never seem to be able to afford the prices they charge.

  48. Kristi March 13, 2018 at 7:44 pm #

    Would love to win to give these tickets to my daughter and boyfriend for a fun weekend activity! (they are over 21) Looks like a lot of fun.

  49. Jade Webster March 13, 2018 at 8:35 pm #

    I’d love to do a Walking your this st. Patty’s day!

  50. Jade Webster March 13, 2018 at 8:36 pm #

    I’d love to do a Walking tour this st. Patty’s day!

  51. Maureen Davis March 14, 2018 at 1:36 am #

    I had both my knees replaced and now I am ready to party and really ready to do a walking tour.

  52. Keena March 14, 2018 at 10:44 am #

    Walking and drinking are two of the things that i love!!

  53. Cat March 14, 2018 at 6:28 pm #

    Wow, I grew up here and I don’t know about much of this rough and tumble Portland past! Would love to go.

  54. Mikey B March 15, 2018 at 3:23 pm #

    Kick @$$! I wanna go

  55. Hilary March 15, 2018 at 4:31 pm #

    Just found out my friend since preschool is going to be visiting this weekend!! Please hook us up!

  56. Cindy March 15, 2018 at 6:34 pm #

    I would love this! I went on one a while back and it was great. I would love to show my boyfriend how fun it is.

  57. Kaeli plaks March 15, 2018 at 7:07 pm #

    I’ve never done anything like this, seems like fun!!!

  58. Mark J Holan March 15, 2018 at 7:36 pm #

    My girlfriend and I were just making a list of things to do in Portland and this was number 2. What a great way to celebrate our relationship by touring Portland this way. We would be honored to win these tickets.

  59. Jenny March 15, 2018 at 8:31 pm #

    This looks scandalously fun.

  60. Nancy March 15, 2018 at 8:58 pm #

    I really want to do this

  61. Jeanne March 16, 2018 at 1:59 am #

    I never got to do this when I lived there, so why not know? I’d happily drive in this!! Sounds fun!

  62. Cailyn Green March 16, 2018 at 11:57 am #

    Hello! I am a huge Halloween fan and I love doing spooky true tours like this. I have done them in every city that I have lived in so far but I did not know Portland had one. I would love to spend a day walking around the city getting a history lesson while getting a good spook on. I teach at a local college so I often share my city adventures with my students and I would love to experience this and then let know how it went.

  63. Travis March 16, 2018 at 2:10 pm #

    “I’m a goona win!” -Mario

  64. Daphne March 16, 2018 at 6:27 pm #

    We love to go on tours, especially with obscure history involved! I’ve lived in the Portland area all my life and haven’t made it to this yet, but its been on my radar for a long time.

  65. Tara Keitz May 9, 2018 at 6:51 pm #

    Winner Winner Chicken Dinner

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