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(Last Updated On: August 15, 2019)

I’ve been to Deadwood, SD more times than I can count. I grew up in Wyoming just over an hour from there. Some of you have probably never even heard of Deadwood, so before I get into my trip recap, let me give a little background on Deadwood! It has quite the storied past, so if you’re feeling so inclined, you can read up even more on your own here.

Located in the western part of South Dakota in the Black Hills, this quaint little town actually got its start illegally! The settlement illegally began in the 1870s on land that had been granted to American Indians (probably not too shocking, given the history of the US). Shortly thereafter, the black hills gold rush brought a slew (like 5,000 back then) of people to the area. Deadwood quickly became known for its lawlessness – gambling, prostitution, murders…Wild Bill Hickock was actually murdered there. Both Hickock and Calamity Jane are buried in the town’s cemetery. The town managed to survive gold rush and busts, multiple fires, smallpox, war, and in 1961, the entire town was designated a national historic landmark.

Fast forward to now, and Deadwood is still a small, but bustling gambling town. This past weekend, my friends and I were visiting to participate in Deadwood’s annual Oktoberfest. I’ve been to many an Oktoberfest weekends throughout the years, but Deadwood’s Oktoberfest is one of my favorites! We arrived in Deadwood around 11:00, and checked in to our hotel, the Mineral Palace. I will be honest here: MP is not my favorite hotel in Deadwood. It’s a bit on the older side, and still has smoking rooms, which is unfortunately what we got placed in. But Oktoberfest is a super busy time for the town, so options are pretty limited, and book up quickly. Luckily one of our rooms was available when we arrived, so we were able to drop our bags, freshen up, and hit the town to begin the festivities.

They hold a variety of events over the whole weekend, but all my favorites are held on Saturday. What might that include? Well, for starters, I should make a confession: I’m obsessed with dogs. Like really obsessed. And the first two events of the day are wiener dog races, and a wiener dog costume contest! I was lucky enough to meet the eventual winner of the costume contest…an older wiener dog, named Haley, who normally walks with the assistance of a doggy wheelchair. Haley’s costume for the contest was an old school covered wagon, and look how adorable she is:

After the dogs got to have their fun, it was time for my friends and I to have ours. Also on the docket of activities during Deadwood’s Oktoberfest are what they call the Beer Barrel Games, and my crew and I were entering into the events under the team name “We’d Tap That.” This year’s games included:

  • One team member rolls a keg down the street weaving in between the cones, nails five nails into a stump, and a 2nd team member rolls the keg back up again
  • One team member walks down the street weaving through the cones while carrying a tray with five pints on it, transfers the tray to a 2nd team member, who then walks back up again
  • One team member holds two full beer steins straight out for as long as possible
  • Two team members have 30 seconds to stack mini cups as high as possible

There were 24 teams who entered the games in total. I have no idea where my team placed, but we definitely didn’t win. We sure had fun though! And drank all the included keg beer we possibly could.

After the games had concluded, we had the rest of the evening to enjoy our time in Deadwood. Since we had drank our lunch, we first grabbed delicious burgers at Mustang Sally’s for some sustenance. Next, some of us tried our luck doing a little gambling. I was one of them, and I lost all I was willing to lose in like 30 minutes. Accepting my defeat, we then head off to the highlight of the evening: karaoke at the Oyster Bar. We try to hit up karaoke pretty much every time we are in Deadwood, but this time was definitely the most fun I’ve had there! I think it was the crowd; everyone was happy-go-lucky, singing along, and cheering for those singing. It was great! I participated in a number of duets with my bff Amanda, including “I’ll Make Love to You” by Boys II Men, and “Wannabe” by the Spice Girls. Then K-Swizzle made an appearance (no joke, I made the DJ announce me as such) for her rendition of “Baby Got Back” by Sir Mix-a-Lot.

After we had had our fill of karaoke, it was time for some dancing. One of the things I love about Deadwood vs. other small gambling towns I’ve visited, is that there are actually things to do BESIDES gambling. You aren’t only limited to the casinos, as there are bars with live music and dancing. Bodega is one of my favorites, and that’s where we spent the remainder of our evening.

What I definitely did not enjoy about the weekend was the 6-hour drive home (I live in Denver, CO) the morning after. The drive is quite beautiful, and the trees are in peak colors right now in the Black Hills, so I had hoped to get some scenery pictures for you all, but mother nature decided to rain on my day (literally) instead.

Do you have a favorite Oktoberfest celebration?? Let me know! Comment below, or hit me up on Facebook, Instagram, or Twitter.

That’s all for now. Happy traveling 🙂

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  1. Jessica October 5, 2017 at 11:53 am

    Love the history in the black hills! Been there once. I need to go back again. Thank you for sharing!

    1. Kara October 5, 2017 at 1:09 pm

      Definitely worth a second visit 🙂

  2. Stacey Billingsley October 5, 2017 at 12:40 pm

    I love Deadwood! We’ve only been for a day, but I really enjoyed the atmosphere, and I also enjoy the series, so I think that added to my enjoyment. We stopped here one day during our South Dakota trip, and we didn’t have time to stay very long. We headed to Devil’s Tower right after this. I’d love to go back, especially during this festival. It looks like it would be so fun!

    1. Kara October 5, 2017 at 1:08 pm

      Ahhhhh, Devil’s Tower! My grandma had a massive ranch not too far from there when I was a kid. I have visited many a times. It’s a great national monument that often gets overlooked for things like Mount Rushmore and the like. Glad you enjoyed!

  3. Kim October 5, 2017 at 5:11 pm

    I’ve never heard of Deadwood but man that looks like fun!! Even down to the dog costumes! Lol

    1. Kara October 10, 2017 at 11:12 am

      Deadwood is definitely a fun town 🙂

  4. Gina October 5, 2017 at 6:03 pm

    This looks like a lot of fun – thanks for sharing!

    1. Kara October 10, 2017 at 11:08 am

      Thanks for reading!

  5. kiersten October 5, 2017 at 6:57 pm

    What an amazing town! I love places that are off the beaten path like that. And it would be a great weekend trip from Denver!

    1. Kara October 10, 2017 at 11:08 am

      Definitely close enough to Denver for a weekend trip! I’m also based in Denver, so I would suggest a 3-day weekend if you can swing it.

  6. Julie October 5, 2017 at 7:33 pm

    South Dakota is definitely within road trip distance for me! I’m going to put this on my list, for sure. Thanks for sharing!

    1. Kara October 10, 2017 at 11:07 am

      Thanks for reading!

  7. Christina October 5, 2017 at 9:03 pm

    I need to go there it looks like so much fun. That little dog was the cutest! Going to add that to my list of places to go

    1. Kara October 10, 2017 at 11:07 am

      Yes, she was! I was so happy when she won the costume contest 🙂

  8. Jacqueline Ridgeway October 6, 2017 at 9:31 am

    I love Deadwood! I remember going as a kid, and we have plans to take our kids in the next few years when they are a bit older. Love all your pics. You had me scrolling back and laughing with those chairs with legs! LOL! Thanks for all the pics and tips!

    1. Kara October 10, 2017 at 11:05 am

      That’s great you’ve been before! Definitely better for kids once they’re a little older. Lots of kid-friendly things to do near Rapid City (Mount Rushmore, Bear Country, Kosmos, Reptile Gardens, etc.)

  9. Christy October 6, 2017 at 9:33 am

    Sounds like a fun town and love all their Octoberfest activities!! I have never been an Octoberfest. I will have to go one day!!

    1. Kara October 10, 2017 at 11:04 am

      Oktoberfest is one of my favorite annual festivals (wherever I wind up going for it)!

  10. Tiffany October 6, 2017 at 9:50 am

    I so need to go visit SD. It looks beautiful and has such wonderful history.

    1. Kara October 10, 2017 at 11:04 am

      Definitely! Scenery and history abound.

  11. Melissa October 6, 2017 at 1:21 pm

    This looks like it was a lot of fun!

    1. Kara October 10, 2017 at 11:04 am

      It definitely was!

  12. Cerin October 6, 2017 at 2:06 pm

    What a neat town! Those chairs made me lol!

    1. Kara October 10, 2017 at 11:03 am

      We got a kick out of them as well lol

  13. Alisha October 6, 2017 at 5:30 pm

    This actually reminded me of a road trip my parents and I did when I was a kid. I’m almost positive Deadwood was one of our stops!

    1. Kara October 10, 2017 at 11:03 am

      That’s great! Family roadtrips are the best 🙂

  14. Amanda October 8, 2017 at 6:45 pm

    What a cool place! I love your pictures! Looks like a lot of fun!

    1. Kara October 10, 2017 at 11:03 am