06 May

Kentucky Derby Party – Poster Printables

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!)

Leave a Comment


Marisol SAYS:

Congrats! Great accomplishment!!

May 6, 2011 at 9:22 am


Those are too, too funny! LOVE the ideas.

May 6, 2011 at 9:47 am

Jessica Wilcox-Modern Moments Designs SAYS:

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!

May 6, 2011 at 9:59 am

Keisha - Cupcake Wishes & Birthday Dreams SAYS:

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

May 6, 2011 at 11:27 am

Monique of Enchanted Expectations SAYS:

Congrats to you. Long time coming & much deserved!

May 6, 2011 at 12:52 pm

Janyce SAYS:

How can I find the Mint Julep cupcake recipe?

May 6, 2011 at 1:09 pm

jenn s. SAYS:

HI Janyce – Here’s a link to the recipe :)

May 6, 2011 at 5:30 pm

laura~eye candy event details SAYS:

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

May 6, 2011 at 1:32 pm

samantha SAYS:

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.

May 6, 2011 at 2:39 pm

Melissa SAYS:

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

May 6, 2011 at 6:12 pm

rosa SAYS:

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

May 7, 2011 at 1:22 am


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

May 7, 2011 at 2:55 am

CreativeBusyHand SAYS:

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.

May 7, 2011 at 8:46 am

Maureen Anders SAYS:

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!

May 7, 2011 at 5:56 pm


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

May 9, 2011 at 12:25 pm


lol I love this idea.

May 25, 2011 at 2:08 pm


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

September 27, 2012 at 7:57 pm

Stacye Clark SAYS:

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.

April 26, 2013 at 8:01 am

alyssa SAYS:

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 :)

April 26, 2013 at 9:39 am

Candace SAYS:

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…

December 5, 2014 at 11:42 pm

jenn s. SAYS:

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! :)

December 6, 2014 at 8:44 am

Jessica W SAYS:

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

July 13, 2015 at 8:07 pm

jenn s. SAYS:

Hi Jessica –
The most affordable route would be an online printing company like http://www.printmypictureonline.com/ 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. :)

July 15, 2015 at 5:58 am
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