5th Annual Highlands Fiesta de Mayo

The Annual Highlands Fiesta de Mayo Cantina Crawl takes place Saturday, May 2nd, 2026, from 12 p.m. to 5 pm. Tickets are $45 and include a Margarita Contest where local restaurants will be competing for the Best Margarita in Highlands! Participants will sample delicious 6oz. Margaritas and vote for their favorite! The fee includes free samplings and discounted food and drink specials at local eateries and pubs, as well as specials at many retail establishments. Live Mariachi music will be playing at the participating restaurants to add an authentic Mexican flair to the event! Check-in is at Huddy Park, 329 Bay Ave. Highlands, you may purchase tickets in the park the day of the event, 11 am – 12:30 pm. This is a rain-or-shine event.