Win Tickets ($36): A Walking Tour of Portland’s Sinful Past: Shanghaiers, Saloons and Skullduggery | Downtown Portland

We are giving away a pair of tickets to A Walking Tour of Portland’s Sinful Past on September 16. To win, comment on this post why you’d like to attend. Winner will be drawn and emailed Friday, September 15.


From our sponsors:
Portland Walking ToursShanghaiers, Saloons and Skullduggery
September 16, 2017
4 p.m. | $18 | 21+

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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40 Responses to Win Tickets ($36): A Walking Tour of Portland’s Sinful Past: Shanghaiers, Saloons and Skullduggery | Downtown Portland

  1. Phil September 6, 2017 at 2:17 pm #

    This seems like it’d be a perfect date experience. Walking, learning and laughing about the history of the city.

  2. Jennifer September 6, 2017 at 2:54 pm #

    I’d love to get down with some good old fashioned shangaing and skullduggery!

  3. Bianca Salerno September 6, 2017 at 6:14 pm #

    I’ve been trying to win tickets for myself and a friend for a year now. We’re poor but we really want to go.

  4. Tonya Newton September 7, 2017 at 12:08 pm #

    I keep bugging my husband to do this. Maybe with free tix, he might!

  5. Rachel Foster September 7, 2017 at 2:31 pm #

    I love learning about history, this seems like such a fun tour!

  6. Katie Barlow September 7, 2017 at 2:55 pm #

    Love learning about the city and its history. This would be a blast!

  7. Doug September 7, 2017 at 3:17 pm #

    Sounds like a good time. Pick me.

  8. Rosy September 7, 2017 at 3:18 pm #

    As a Portland history buff this would be so great to attend! I love learning hidden secrets of this beautiful city.

  9. Robbie Lewis September 7, 2017 at 4:35 pm #

    It’s always fun going to explore the hidden gems that helped Portland become what it is today. I’d love to go with my girlfriend for a great afternoon adventure.

  10. Jenn September 7, 2017 at 4:35 pm #

    Yes please!

  11. Breann St. John September 7, 2017 at 4:55 pm #

    This tour would be a great way to spend my birthday. At seven months pregnant I can’t do any drinking, but I can still do some learning about Portland’s dark past.

  12. Elizabeth Stamp September 7, 2017 at 5:01 pm #

    I have Always Wanted to do this!!!!

  13. Mathew Trono September 7, 2017 at 5:17 pm #

    Always wanted to take a tour through PDX’s seedy past. Sounds like a lot of fun to me.

  14. Alan M September 7, 2017 at 7:40 pm #

    Sounds like a fun time for my birthday weekend.

  15. Jennifer September 8, 2017 at 7:53 am #

    Oh, please, please, please! This is one of the few Portland history tours I haven’t gone on and I desperately want to.

  16. Karen C September 8, 2017 at 10:43 am #

    Shanghai me!

  17. Jenn Lawrence September 10, 2017 at 9:30 am #

    Totally into it!

  18. JM September 10, 2017 at 9:44 pm #

    This ol’ gal is trying to get into a fitness routine and I cannot think of a more fun way to get my daily steps in than taking a walking PDX history tour.

  19. Megan Papis September 11, 2017 at 8:59 am #

    I love history, and I’d love to do this tour. It’s my boyfriend’s 30th bday this week, and this would be a great gift for him.

  20. molli taylor September 11, 2017 at 9:42 am #

    i have always wanted to do this. i’m not big on “touristy” things but love discovering the seedy underbelly!

  21. Julia September 11, 2017 at 12:50 pm #

    This is one of the only walking tours I haven’t done!!

  22. Michael Howard September 11, 2017 at 6:58 pm #

    Yas please

  23. Scott Lahn September 12, 2017 at 8:20 am #

    Totally up for sinful shenanigans!

  24. Mckenzie September 12, 2017 at 8:50 am #

    Would love to go and see the dark side of my city!

  25. Melody Frye September 12, 2017 at 1:17 pm #

    My friend and I were just talking last weekend about how we wanted to do this and how cool it would be.

  26. Kelsey Smith September 12, 2017 at 2:27 pm #

    Cool sounds fun

  27. PDX Buff September 12, 2017 at 4:58 pm #

    I’d love to get to take a live and in the flesh tour with the kick ass guy behind the Kick Ass Oregon History podcast.

  28. Katrina Matthews September 12, 2017 at 6:06 pm #

    I’m a Portland native and have never seen this. So fascinating!

  29. cherie September 13, 2017 at 9:07 am #

    My partner and I have been dying to go on this tour since we moved to Portland! We would absolutely love to check it out!

  30. Steve a September 13, 2017 at 8:18 pm #

    Would love to win to take the wife

  31. Danielle September 14, 2017 at 10:40 am #

    I really love walking tours.

  32. Lex Jimenez September 14, 2017 at 3:40 pm #

    I think this would be an awesome way for my wife and I to learn more about the roots of Portland! We’d love to check out what they have to say!!

  33. Natalie J Vandenberghe September 14, 2017 at 4:12 pm #

    Sounds interesting!

  34. Pamela Starks September 14, 2017 at 4:39 pm #

    I always wanted to do this ! ❤️❤️❤️ Hope I win!!!

  35. Deena September 14, 2017 at 7:09 pm #

    This would be so fun!

  36. Vicki doyle September 15, 2017 at 2:52 am #

    I would love to go with my husband. He loves loves Oregon history n our 12yr anniversary is that weekend and we love scary haunted stuff . We would love to go please pick me…

  37. Gretchen Downey September 15, 2017 at 9:12 am #

    We love Portland and love it’s history even more!

  38. Julia September 15, 2017 at 12:14 pm #

    My husband and I just moved to Portland and would love to learn more about this amazing city!

  39. Nate Fennern September 16, 2017 at 12:04 pm #

    I’m 25, born and raised in Portland and would love to learn about the city’s more infamous past…

  40. Melissa September 16, 2017 at 12:37 pm #


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