hwtm icons row

Kentucky Derby Party – Poster Printables

Quick Jump To » Comments

Kentucky Derby Party Games

Hello to everyone from {a very sunny} NYC! I just finished up my first appearance on the Today Show (something that’s honestly been a dream for years – hooray!!)… and wanted to share a couple free downloads from the segment.

The theme was Kentucky Derby Party ideas, and since the show was running a little late we only about 3-1/2 minutes to work with so we skipped over a few things, but I was so happy that Kathie Lee & Hoda made a point to get to the game because this is an easy way to add a fun element to your party… and best of all it’s PERSONALIZED!

Kentucky Derby Party Games

These are “Derby-ized” versions of the classic Pin the Tail on the Donkey game. I designed some new posters for “Pin the Hat on the Southern Belle” and “Pin the Jockey on the Horse“. You can add your own favorite faces to the Southern Belle Poster and to the individual Jockeys. I like the idea of not telling guests about this ahead of time and just enjoying the laughter when they see the game (and some familiar faces) revealed. This game can be especially entertaining after a couple cocktails!

Links to download everything are below. I’m running out the door to meet with some colleagues for lunch then do walkthroughs of venues for an event we’re hosting here in July! Hope everyone enjoys watching the Kentucky Derby tomorrow and celebrates with a Mint Julep (or Mint Julep Cupcake!)



Pin the Hat on the Southern Belle Poster
(Make sure to personalize this poster with your own photos!)

Southern Belle Hats

Pin the Jockey on the Horse Poster

(Make sure to personalize the Jockeys your own favorite faces!)


  1. Marisol May 6, 2011 at 9:22 am

    Congrats! Great accomplishment!!

  2. HiLLjO May 6, 2011 at 9:47 am

    Those are too, too funny! LOVE the ideas.

  3. Jessica Wilcox-Modern Moments Designs May 6, 2011 at 9:59 am

    I have the TV on (I never have the TV on during the day) waiting to see your pretty face!! I’m so proud of you Jenn!!! You go GIRL!!!!! Happy {early} Mother’s Day gift to you!!! You deserve it!

  4. Keisha - Cupcake Wishes & Birthday Dreams May 6, 2011 at 11:27 am

    Congrats on making it onto the Today Show!!! Yeah!

  5. Monique of Enchanted Expectations May 6, 2011 at 12:52 pm

    Congrats to you. Long time coming & much deserved!

  6. Janyce May 6, 2011 at 1:09 pm

    How can I find the Mint Julep cupcake recipe?

  7. laura~eye candy event details May 6, 2011 at 1:32 pm

    I watched & you did FANTASTIC! Great job – you looked like a natural! =)

  8. samantha May 6, 2011 at 2:39 pm

    Caught you on the today show great ideas. So I check out your blog can’t wait to tell my friends the love it congratz.

  9. susan@pocacosa May 6, 2011 at 4:21 pm

    congrats-so happy for you!

  10. Melissa May 6, 2011 at 6:12 pm

    Awesome job Jenn you were awesome so cool and collected.Enjoy NYC.

  11. rosa May 7, 2011 at 1:22 am

    wow!!! fantastico grazie per condividere con noi tutto questo saluti dall’italia rosa

  12. Al May 7, 2011 at 2:55 am

    What a fun post! The pin the hat on the Southern belle is hysterical! http://www.skylarkmanor.com

  13. CreativeBusyHand May 7, 2011 at 8:46 am

    Thank you so much for this post. I want to let you know that I posted a link to your blog in CBH Digital Scrapbooking Freebies, under the Page 10 post on May. 07, 2011. Thanks again.

  14. Maureen Anders May 7, 2011 at 5:56 pm

    I watched live and you did a GREAT JOB! You SO fit in w/ the show – you owned the segment and didn’t make it seem to rushed but still covered a lot! ;-) GREAT WORK!

  15. Amy May 9, 2011 at 12:25 pm

    How adorable, such a great segment! Do you have the pom. champagne cocktail recipe to share? Thank you!

  16. Mae May 25, 2011 at 2:08 pm

    lol I love this idea.

  17. JEANMARIE September 27, 2012 at 7:57 pm

    I found just what I’ve been searching DAYS for!

  18. Stacye Clark April 26, 2013 at 8:01 am

    How did you place the personized picture on the jockey? Do you make a jockey for each person, or just have photos ready for pinning.

    • alyssa April 26, 2013 at 9:39 am

      Hi Stayce! You can print the posters and photos of friends separately (and glue them on), or if you’re familiar with a photo editing program you can paste them on through the computer. It could be really fun though to have it either way you propose- whatever you think will be more fun at your party :)

  19. Candace December 5, 2014 at 11:42 pm

    I would love to do this for a party I am throwing…could you tell me what size poster your printed both the background and jockeys in? I want to go to staples with these images but have no idea how to size it right…

    • jenn s. December 6, 2014 at 8:44 am

      Hi Candace –

      So glad you like this idea! The poster is 18×24 and the jockeys are set up on tabloid (11×17″) paper.

      The printable files are already formatted at those sizes, so you should need to resize anything. :) You can also print online at places like Print My, Vista Print, or Print Runner if that’s easier. Good luck! :)

  20. Jessica W July 13, 2015 at 8:07 pm

    Where would you recommend these get printed out and what size?

    • jenn s. July 15, 2015 at 5:58 am

      Hi Jessica –
      The most affordable route would be an online printing company like or Vista Print. The poster is sized at 18×24″, so that’s what I’d recommend, but you can blow it up to 1.5 times that size without losing quality if you’d like it larger. :)

Comments are closed.

Browse Party Ideas: