
This Saturday marks the return of the longest running sporting event in United States history – the Kentucky Derby. The race, dubbed “the most exciting two minutes in sports,” dates back to 1875 and hasn’t missed a year since, surviving the Great Depression, both World Wars, and more recently, the pandemic in 2020.
Considering the Kentucky Derby is known as a celebration of southern culture in the United States, Maine isn’t the biggest celebrator of the horse race, but we like any excuse to drink mint juleps and wear a big goofy hat, so we sought out the best places to be this Saturday.
What’s your favorite way to celebrate the Kentucky Derby? Head to our Facebook and Instagram pages and let us know! Did we miss an event? Email info@portlandoldport.com and let us know.

Dock Fore: Get pints of Bud, Bud Light, Rolling Rock and Miller High Life for only $1.95 from 3-7PM, compete in contests and win a prize for Best Hat. Mint Juleps will also be available. The party goes from noon until midnight!

Fleet Fleet Maine Running: Let the horses have a breather, and do the running yourself with the Dash for the Derby 5K, starting at Fleet Fleet Maine Running shoe store. Registration is $35, and closes at 11:59PM on May 5th, or you can register at the race for $39. Proceeds benefit A Running Passion & the Animal Refuge League of Greater Portland.
The Portland Club: Join the Portland Club for their annual Kentucky Derby Party starting at 5:00PM. They’ll have food, drinks, and new this year – a best hat contest! The races will be playing on their 100” projector, as well as all the other TVs in the club. Tickets are $20 those 12 and over. Under 12 get in for $5, and Portland Club members get in at no charge. Get your tickets here.

Coals: It’s time to put on your fanciest hat and get ready for the Kentucky Derby at Coals! Join in on the fun with their Derby Day contest where you can show off your best bonnet for a chance to win some amazing prizes. And even if you don’t win, there will be plenty of delicious food and drink specials to keep you satisfied all night long. So grab a mint julep, settle in with some tasty vittles, and cheer on your favorite horse as you soak up the excitement of the Kentucky Derby at Coals.