5 Best Spots to Celebrate Cinco De Mayo in Winter Park

Cinco de Mayo has become a cultural holiday for Americans, much like St Patricks Day and Oktoberfest. There is no shortage of Cinco de Mayo events Winter Park – there are endless events and parties at local restaurants & bars. No matter your reasoning for celebrating Cinco de Mayo in Winter Park, you will find plenty of things to do. Around this time of year, people are out and about now that the weather is nicer. Not only is this day is a national holiday in Mexico but for most here in Orlando FL, Cinco de Mayo 2019 is a day to party and celebrate with friends!

Annual Running of the Chihuahuas & Cinco De Mayo Block Party

Sun, May 5, 2019, 9:00 AM – 9:00 PM EDT

Chihuahuas are invited to participate in the 7th Annual Running of the Chihuahuas, where the participant’s race for the title of “Top Dog”. For a $15 donation, locals can enter their pup into the race for a cause, as all proceeds will benefit Winter Park Lost Pets and Poodle & Pooch Rescue. Stick around for our Cinco De Mayo & 8 Year Anniversary Block Party for giveaways, samples, & drink specials!

Cocina 214 – 151 East Welbourne Avenue Winter Park, FL 32789

Winter Park Cinco De Mayo Block Party

Sun May 5, 12:00 AM – Sun May 5, 12:00 AM

Join Pepe’s Cantina for their third annual Winter Park Cinco De Mayo Block Party! Featuring: Live DJ $3 Tecate & Tecate light $4 Volcan Silver Tequila shots $5 House Margaritas

Pepe’s Cantina | Winter Park – 433 W New England Ave, Winter Park, FL 32789

Cinco De Mayo at The Alfond Inn

Sun May 5, at 12 PM – 8 PM

Come celebrate Cinco de Mayo at The Alfond Inn Bar & Lounge!

Live Entertainment
Specialty cocktails and appetizers
Don Julio tequila sampling & giveaways between 4pm and 6pm
Partners include: Patron, Don Julio, and Altos Tequila

Hamilton’s Kitchen will be open for normal dinner service and will feature Cinco de Mayo inspired specials.

Hamilton’s Kitchen – 300 E New England Ave, Winter Park, Florida 32789


It’s a FLATS Fiesta in Winter Park ALL CINCO Weekend

May 3 at 11 AM – May 5 at 9 PM

Enjoy food and entertainment all Cinco weekend long.

Friday May 3rd
Saturday May 4th
Sunday May 5th

Festivities include balloon artists, pinatas, games + giveaways!
2 for $5 tacos and beers for Cinco De Mayo!

Tijuana Flats (Aloma) – 1955 Aloma Ave., Winter Park, Florida 32792

Cinco de Chuy’s

Sunday Funday, May 5

Only one day of Cinco de Mayo just isn’t enough – so we’re celebrating Cinco de Chuy’s ALL WEEKEND LONG! Join us May 3rd, 4th and 5th to enjoy your favorite Tex-Mex and specials on drinks & appetizers! Visit www.chuys.com to learn more.

Sunday Funday, May 5
$1 Floaters
$1 OFF Perfect Margaritas
$5 Regular House Ritas
$8 Grande House Ritas
$1 OFF Dos Equis
$5 Queso or Guacamole

170 South Orlando Avenue – Winter Park, Florida 32789


Share this post:

About Us

Find the updates on everything in Winter Park and the Orlando area, right here. With constant updates from us; you, family, and friends can truly live the life that the wonderful city of Winter Park has to offer.