Win Tickets ($36): Valentine’s Day Weekend Walking Tour of Portland’s Sinful Past: Shanghaiers, Saloons and Skullduggery | Learn About Downtown’s Seedy Past

We are giving away a pair of tickets to Valentine’s Day Weekend Walking Tour of Portland’s Sinful Past: Shanghaiers, Saloons and Skullduggery on February 16. To win, comment on this post why you’d like to attend. Winner will be drawn and emailed Friday, February 15.


From our sponsors:
Portland Walking ToursA Valentine’s/Oregon’s Birthday Walking Tour of Portland’s Sinful Past: Shanghaiers, Saloons and Skullduggery
February 16, 2019
4-6 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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68 Responses to Win Tickets ($36): Valentine’s Day Weekend Walking Tour of Portland’s Sinful Past: Shanghaiers, Saloons and Skullduggery | Learn About Downtown’s Seedy Past

  1. Rosy January 28, 2019 at 1:56 pm #

    This sounds like a fun night full of history! Love learning about Portland’s darker side of history

    • Kath January 29, 2019 at 6:49 pm #

      Very cool

    • Joe February 5, 2019 at 12:36 pm #

      I would love to celebrate Valentine’s Day with this history tour, I cross my fingers !

  2. Amber January 29, 2019 at 11:34 am #

    This would be a fantastic experience on our 23rd wedding anniversary – I have always wanted to attend a walking tour after living here just about my whole life and the seedier the better :)

  3. Leslie January 29, 2019 at 11:35 am #

    I would love to celebrate V Day with a history tour! So much fun!!

  4. Bree January 29, 2019 at 12:13 pm #

    OOoooh! So fun!

  5. Linda January 29, 2019 at 12:14 pm #

    My husband would love this kind of thing for Vday! I love historical tours. *crossing my fingers*

  6. Katherine January 29, 2019 at 12:51 pm #

    It looks like an interesting tour and I still have no idea what to do for Valentines day so this be neat!

  7. Heather January 29, 2019 at 12:51 pm #

    My partner is a Portland native and he’s never been to one of these tours. It would be fun to experience it with him!

  8. Karen January 29, 2019 at 1:40 pm #

    Sins and skullduggery!

  9. Jeremy January 29, 2019 at 1:43 pm #


  10. cassi January 29, 2019 at 1:50 pm #

    We are both new to POrtland and saw something about this on a history show we once watched (intrigued us to move here!) I did not even know you could do this as an event this would be amazing!!! Plus my birthday is a few days before-what a great present!

  11. Kelsie minter January 29, 2019 at 3:28 pm #

    I love dirty history!!!

  12. Jake January 29, 2019 at 3:55 pm #

    I’ve always wanted to do this and my girlfriend just moved in with me! This would be an awesome date to teach her about her new city!

  13. Carl Boyd January 29, 2019 at 4:36 pm #

    Because Doug Kenck-Crispin is my damn spirit animal, and I haven’t met him yet!

  14. Jamie January 29, 2019 at 8:37 pm #

    Sounds exciting!

  15. S.W. Conser January 29, 2019 at 10:57 pm #

    Just moved my folks to Portland from Chicago last week. They think they’ve escaped a den of vice and iniquity; and need to be set straight, pronto.

  16. Cara January 30, 2019 at 12:48 pm #

    Oh hell yes. This looks rad

  17. Cathy January 30, 2019 at 1:56 pm #

    This would be a great Valentines Day experience for my husband and I.

  18. April January 30, 2019 at 4:42 pm #

    This tour sounds interesting.

  19. Tasha January 30, 2019 at 5:58 pm #

    What a great valentines idea!

  20. Adriana Peraza January 31, 2019 at 11:16 am #

    Just moved here think it would be fun to hear some history behind this beautiful city.

  21. AJ January 31, 2019 at 3:14 pm #

    I’ve always wanted to do one of these tours – pick me!!

  22. Cristine Day January 31, 2019 at 11:28 pm #

    Sounds like a great way to spend an evening!

  23. Ron T. February 1, 2019 at 1:53 am #

    Valentines day, Sinful Past. Sounds like love to me. Wait; I wanna go.

  24. Benito Juarez February 1, 2019 at 9:51 am #

    I’d love a chance to fall in love with this city all over again. Happy early V day.

  25. molli taylor February 1, 2019 at 12:36 pm #

    oh hey, portland has a seedy past just like me! i knew i loved this city. count me in!

  26. mara z February 1, 2019 at 10:56 pm #

    My partner hates Valentine’s Day but maybe this will peak his interest.

  27. Jeanne Turner February 5, 2019 at 8:15 am #

    Would love to go on this walking tour! My husband would totally dig it :)

  28. Danny Goode February 5, 2019 at 9:46 am #

    this is an awesome giveaway…would love to learn more about Portland.

  29. Josie February 5, 2019 at 12:25 pm #

    I would love tickets to this event to be able to surprise my boyfriend for Valentine’s Day! We love history and getting outdoors!

  30. Steven Estes February 5, 2019 at 12:27 pm #

    This sounds awesome- yes, please!

  31. Michele Peters February 5, 2019 at 12:42 pm #

    What fun!!!!! I need to know about all of this!!!!! Fabulous opportunity.

  32. Coleman A February 5, 2019 at 2:52 pm #

    PLease please PLEASE pick me! This sound super cool!

  33. Sarah Durant February 5, 2019 at 3:01 pm #

    What fun!! Love the history.

  34. Beth February 5, 2019 at 4:16 pm #

    My sweetie and I have always had a fascination with the seedy, dark under belly of things. Would love to see Portland’s closet!!!! Please pick me!

  35. Roz February 5, 2019 at 4:16 pm #

    I have a fascination with the dark side of cities! Please pick me! I would love to go.

  36. Rachel A. February 5, 2019 at 8:56 pm #

    Yes please!! I’d love to learn more about PDX and take my girlfriend who could use a night out! (Also it’s our anniversary )

  37. Melissa fowler February 6, 2019 at 6:02 pm #

    This would be cool

  38. Jeff linsday February 6, 2019 at 6:03 pm #

    This would be fun

  39. Jay February 7, 2019 at 1:18 pm #

    I’m always down for skullduggery.

  40. Lance February 7, 2019 at 2:49 pm #

    Seedy and Sinful “Past” We’ll see.

  41. Ellen February 7, 2019 at 6:50 pm #

    I’d love to go! Thanks!

  42. Pickle girl February 7, 2019 at 7:28 pm #

    Born and raised, deserve this v-day holidaze!! KPW

  43. Dawn February 8, 2019 at 12:04 pm #

    This sounds like a fun outing!

  44. pam February 11, 2019 at 10:38 am #

    Hi!! Friend is going a rough patch and is flying in to Portland to escape and get some fresh air. would be awesome to take him to this and cheer him up.

  45. Wayne February 11, 2019 at 2:13 pm #

    Never. Been on one of these tours. Sounds like fun!

  46. Cindy Smith February 12, 2019 at 12:03 pm #

    Fun!!! What a great way to learn about PDX’s dark side.

  47. KC February 12, 2019 at 12:14 pm #

    This sounds like so much fun!!!

  48. Rebecca Sanchez February 12, 2019 at 12:23 pm #

    I’d LOVE to attend this as I’m a history buff! I hope I win so I can shout out to all about this!

  49. Dannette Cara February 12, 2019 at 12:34 pm #

    I would really LOVE to win these tickets! It’s my birthday week (Feb 13th!)

  50. Michelle Blake February 12, 2019 at 1:09 pm #

    I have never been on one of these tours. Sounds like fun.

  51. Jenny February 12, 2019 at 2:20 pm #

    That would be a great surprise! Thanks for the chance.

  52. Brandi L February 12, 2019 at 2:48 pm #

    Sounds interesting.

  53. Brig Otis February 12, 2019 at 3:33 pm #

    Avast !!

  54. Shelly Wilkerson February 12, 2019 at 7:14 pm #

    What an original idea for Valentine’s Day! Would love it!

  55. Matt February 12, 2019 at 10:03 pm #

    That sounds awesome!

  56. Lee Widener February 13, 2019 at 7:40 am #

    Perfect date for me and my sweetie!

  57. Susank February 13, 2019 at 9:41 am #

    A perfect urban hike.

  58. Leigh February 13, 2019 at 12:27 pm #

    My partner and I love walking tours with dark and seedy stories!

  59. Cole February 14, 2019 at 2:39 pm #

    This sounds so up our alley!

  60. Jenna February 14, 2019 at 2:51 pm #

    I want to win because it will be my birthday and I love learning about fun facts of Portland and Oregon! Also my history buff brother will be in town and I want to show him this lovely city in a walking tour! Its what we like to do in different cities!

  61. Beth February 14, 2019 at 3:32 pm #

    I love shady and seedy! Would love to go!

  62. Roz February 14, 2019 at 3:33 pm #

    A seedy past seems appropriate for Valentine’s Day!

  63. Roz February 14, 2019 at 3:34 pm #

    Who doesn’t love a seedy past? Seems appropriate for Valentine’s Day!

  64. Jill Travis February 14, 2019 at 3:36 pm #

    My sister and I would love this!

  65. Erin B February 14, 2019 at 5:29 pm #

    Mysterious and fabulous*

  66. Melany Hughes February 16, 2019 at 12:24 am #

    Hello, It be absolutely Awesome to go tour the tunnels and learn about the history & how it unfolded that unfolded

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