The Kentucky Derby

I live in Wisconsin, so by the time May hits I’m always feeling like it’s been a long Winter.  I get the math behind it, Winter is roughly 90 days every year, but every year those 90 days seem LONG!  In my mind May signals that we are in the home stretch and better days (& weather) are coming.  I couldn’t think of a better way to celebrate than a party!  For some reason the Kentucky Derby struck me as the perfect opportunity this year.  I can’t say that I have ever been a big fan of horse racing, but I am a fan of getting together with friends and an excuse to wear an obnoxious hat.  The Kentucky Derby is always the first Saturday in May, so this might just become an annual ‘welcome Spring’ event for us.  The 141st Kentucky Derby coincidentally fell on the same day as the Mayweather vs Pacquiao fight, which has been coined The Fight of the Century.  Needless to say it was easy to get my husband on board for a Derby party by saying the guests could stay and we would rent the fight.

Now that we had our theme it was time to determine a guest list and create our invites.  In today’s world there are a thousand ways to send out invites – evites, Facebook, MyPunchbowl and Pingg are all popular.  I decided to go a little more old school with traditional paper invites.  My husband and I had discussed it and we thought it would be fun for our friends to be surprised with an invite to a theme party.  It seems like all I get from the U.S. Postal service is junk mail and bills, so we wanted this to be a pleasant surprise.  I may have slipped and told a girlfriend or two, but judging from the reactions we got when our friends started to receive the invites, I definitely will keep my mouth shut next time.  Etsy had thousands of cute invites, but I decided to create my own.

The official time of Kentucky Derby race was posted as 5:24 CST.  Since the Kentucky Derby is also called the fastest 2 minutes in sports we wanted to add to some games to prolong the day and build to the hype of the race.  Of course all references to betting were referring to bets placed with Monopoly money!    

Horse Races

The basis of Horse Races was an old college drinking game where you bet a number of drinks on a specific horse (suit of cards) and your horse advances every time a card of the corresponding suit is flipped.  If your horse wins you get to disperse the number of drinks you bet, if you lose you drink the number you bet.

Since my college drinking days are long gone I modified the drinks to cold hard cash and instead of cards I used the roll of a dice to allow for a few extra horses.  Everyone selects a horse:  The One and Only, Deuces Wild, Three’s Company, All Four Love, Five Card Stud and Six Feet Under.  (You can name the horses whatever you want.  It could be cute if you used corresponding names to horses actually running in the derby.)  Then you select how many bets you want to place on the horse.  Each bet was $1.  To keep track of everyone’s bets we used 6 different color poker chips and each horse was represented by their corresponding chip.  We roll the dice and a horse advances every time their corresponding number is rolled.  The first horse to the finish line wins.  The pot is then evenly divided between the number of winning chips that were dispersed.  For example – The winning horse was Six Feet Under.  There is $30 in the pot.  Player A had 1 chip (or a $1 bet) on Six Feet Under and Player B had 2 Chips (or a $2 bet) on Six Feet Under.  Player A gets $10 and Player B gets $20.)  The horse track was created from a simple plastic table cloth from the Dollar Store.  I wrote Start on one end, Finish on the other and numbers 1 – 10 down the side.  I just used the corresponding poker chips for the horses.  You could use figurines of horses, chess pieces or even My Little Pony’s if you have some laying around.  That will be an add on for next year!

 I left the tablecloth or racetrack up the next day and the kids had a blast playing as well (we didn’t bet of course)!

50/50 Raffle

Everyone loves the chance to win money, so a 50/50 Raffle is always a big hit!  The rules are simple, the winning raffle ticket gets 1/2 the pot.  In this case the other 1/2 of the money generated from the 50/50 raffle went to the winners of the costume contest.  Just a side note – if you are ever planning a charity event or trying to raise money, a 50/50 raffle is an easy money generator!  I picked up some raffle tickets when I was at the Dollar Store getting the table cloth, but I’ve also seen them at party supply stores.  I got the double tickets and the guests kept one half and put the other in the bucket.

Costume Contest

As stated on the invite, we requested that everyone ‘wear their derby best.’  Most women interpreted this as big hats and men thought preppy bow ties.  My husband, who is always an original, decided to dress like a jockey – to each their own.  We did also discuss that it would be funny if we dressed as a horse, but with all of the running around associated with hosting (and the fact that I found a hat I really liked) we did not go this route.  Every guest got a vote for each the best dressed male and best dressed female.


As I mentioned before the other 1/2 of the money generated in the 50/50 raffle was split between the best dressed male and female.  Other ideas for prizes could include a bottle of bourbon for the male and champagne or a dozen roses for the winning female.  It could be anything really.  Just something to say ‘thanks for going all out.’  We had a TON of great costumes this year.  I loved everyone’s creativity.  We had everything from the traditional big hats to an equine veterinarian.

IMG_3824 IMG_3826

Betting on the Derby

We also bet on the Derby race itself.  I printed out all of the horse stats.  These usually come out a week or so before the race.  Betting was simple.  Win bets were $3, place $2 and show $1.  The pot was evenly divided between the number of winning tickets.  For example, if the Win pot was $40 and we had 2 winning tickets, each winning ticket was worth $20.  Odds were factored in by the number of people betting on each horse.  To help keep track I created these simple betting cards and put a jar out for each win, place and show.  Feel free to print and use at your Derby party!
Food & Drinks
I had a ton of fun planning the food and drinks!  Overall, I kept the menu pretty simple.  Since we knew we would be busy managing all the games, we wanted to go as low maintenance as possible on the food.  We simply had an assortment of sausages in slow cookers for the main dish.  Next year I would like to go a little more traditional and do ham sandwiches, which is also no fuss.  For side dishes we had a crock pot full of mac and cheese and a salad.  We also had some snack foods dispersed around the party.
Since guests were staying for the fight, we thought it would be good to have some late night snacks as well.  We luckily have a friend who makes absolutely delicious home made pizzas.  He set up a little pizza parlor in the kitchen and it was the hit of the party!  He even taught (well, tried to teach) me how to throw the dough.  Maybe I can get him to share his recipe and give us a tutorial in a future blog post.
It wouldn’t be a derby without Mint Juleps.
1 tablespoon mint simple syrup
Crushed ice
1 ounce bourbon 
1 fresh mint sprig
Muddle the mint, simple syrup and crushed ice in the bottom of the glass.  Pour Bourbon over ice.  Garnish with additional mint.  
I am not a Bourbon drinker, so this was a hard drink for me to swallow…literally!  If you have a Bourbon loving group a Bourbon bar would be fun!  Champagne and wine are also traditional derby drinks that we served.
Photo Booth
I created a simple photo booth to capture the fun of the day.  Etsy had a ton of fun photo props.  You can also find some props at your local craft store.  I simply bought some card-stock and did a Google search for ‘free photo booth props.’  TONS of great graphics came up, so I made my own.  I used the curtains in the kids playroom as a backdrop.  I set up the photo booth the night before and didn’t realize the backdrop got kind of washed out during daylight.  (You can see this in some of the photos above.)  The photo booth worked much better after the sun went down.  If you don’t have curtains you like for a backdrop, you could use a plain wall, hang a table cloth or use wrapping paper.
 Overall, a great time was had by all.  Thank you for stopping in and reading my 1st ever blog.  Please check back soon for additional party (or event) planning posts.  If you have any questions or have any feedback for future posts, I would love to hear it!

17 Comments Add yours

  1. Welcome to the blog world! I love all the details you put into your party planning – it sounded like a fun day for everyone. I have to say the costume contest and the photo booth are my favorite parts of your party! Those props are awesome.

    Liked by 1 person

  2. Very nice ideas ! In MD we get excited about Preakness ,so I can definitely feel the vibe.


    1. Thank you for stopping by! I absolutely love Maryland. I’m working on a post about a birthday party I threw my husband in Maryland 🙂


  3. Sounds like a great time! Love the photo-booth idea and making all the props yourself!


    1. Thank you so much for stopping by my blog! The whole photo booth took about 10 minutes to put together. I looked on Etsy and some people were charging $50+ for props, so it was definitely worth the couple of extra minutes 🙂


  4. What a great idea and loads of fun! I love the pictures! Welcome to the world of blogging! You are going to meet so many wonderful people through this, I know I have.


    1. Thank you so much for visiting my blog & for the support! Any advice for a new blogger?


  5. Lois Jones says:

    It looks like you had a blast! What a fun idea for a party and to enjoy your friends!


    1. Thanks for reading! It was a blast – I wish I could capture all of our laughs we had in the post 🙂


  6. Claire says:

    Looks like a great day – loved the theme – so nice to see some “non kids” themed parties 🙂

    Liked by 1 person

    1. Thanks for visiting!


  7. CraftyStaci says:

    That looks like a fun party, and I love that you sent actual paper invitations. I’m starting to miss those! Thanks for sharing at Talented Tuesday!

    Liked by 1 person

    1. Thanks so much for visiting!
      See you on Talented Tuesday!


  8. How fun and creative! It looks like everyone really enjoyed it! Thanks for sharing. #ConfessionsLinkUp


    1. Thank you so much for visiting!


  9. Barbara says:

    Enjoyed reading your blog.

    Liked by 1 person

    1. Thank you so much for reading!!


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