FIRST FRIDAYS DOWNTOWN.

First Fridays Downtown

Join us the First Friday of every month for a free community event that is meant to showcase our beautiful Downtown businesses! Your downtown Middletown neighborhood businesses, boutiques, eateries, & galleries keep their doors open late, just for you! Explore all the new faces and places downtown, visit with your neighbors, and have a great time! The fun is from 5-8 p.m.

May First Friday

Cinco De Derby Margarita Contest!

It is Cinco de Mayo AND downtown Middletown’s kick off to Derby Day Celebrations, 5/2/25! Come see us at the DMI booth at Governors Square! From 5-8pm!

We will have music playing at Governors Square, our annual margarita contest, and a derby hat contest!

-Derby Hat Contest:
Don your best Derby hats and visit us at the DMI booth to enter into a raffle contest!

-DORA Margarita Contest: 21+
Our DORA restaurants and bar establishments are battling for the title of BEST MARGARITA in Downtown Middletown. Come join, grab your scorecard from the DMI Booth then taste and vote for your favorite! $2 samples. Start at any of the Margarita Crawl locations!

See you downtown!

Visit the Facebook Event Page for live updates!

Learn more

Meet the Competitors in the Margarita Competition!

The Swire Inn

Bloody Coconut Margarita
Middies Pub & Grub

Island Rita
West Central Wine

Mint Julep Margarita
The Slice

Pickle Rita
Olde Central Tavern

Sunshine Rita
White Dog Distilling and Bourbon Bar

Bourbonrita

Other specials!

Iron Rose Mercantile

During first Friday we will have an open hat bar! Trucker or Cowboy hats will be available to create!
Grab a margarita from the local bars, bring a friend and create a hat for the derby!!!
Pendleton Art Center

Studios open for First Friday! 5-9pm
Live music in the lobby!
Monarch Designs

10% off your purchase if you're wearing a Derby Hat Kids' crafts starting at $5
Three Moons Boutique

Star Wars earrings buy 1 get 1, 50% off. DnD dice holders 20% off.
Queenpin Thrones

Mocktails available!
Enter a raffle for a discount rental of Throne chair's or Photo Booth
Whiste Stop Shop

Sample Margarita Bar/Cookie with recipe, while they last!