The District | May Events

Ben Harper + The Innocent Criminals 5/1

A musician, songwriter, guitarist, producer and activist, Ben Harper has released 14 studio albums and three live albums since 1994. In 2013, his collaboration with Charlie Musselwhite, Get Up!, debuted at #1 on the Billboard Blues chart and spent 24 weeks in the Top 10. It won a Best Blues Album Grammy for Harper and harmonica master Musselwhite. Harper’s albums, combined with an unceasing commitment to international touring, have helped him grow a fan base that spans several continents.


Orlando Story Club: Can you keep a secret. 5/3

Orlando Story Club: Can You Keep a Secret?

“If I let you in, you can’t tell a soul, especially not you know…” On The Orlando Story Club Stage, it’s all about the story of THE SECRET. Tell us a time where you couldn’t reveal something, about yourself, someone else. Maybe you where the one entrusted to keep a sensitive piece of information from igniting. Was it JUICY? Was it SCANDALOUS? What did you have to do so no one else found out? What went down?


Mother of all Baby Showers 5/5

THE One. The Only. The 3rd annual adults-only event for expectant and new parents presented by Orlando Health! $20K in giveaways, fantastic hands-on educational sessions, 50+ try it before you buy it businesses to check out, AMAZING swag bags for VIPs including a Baby K’tan diaper bag, tasty treats from local favorites including Maggiano’s, Smoothie King, Yogurtland and so much more!!!


Cinco de Mayo Block Party on Wall Street

Wall Street Plaza’s Cinco de Mayo block party is scheduled for May 5 and 6 and will feature live music by Audio Exchange, Who rescued Who, DJ Ricky, and live mariachi bands.


City of Orlando Bike to Work Day 

The City of Orlando’s 18th Annual Bike to Work Day, a community bike ride through Downtown Orlando with Mayor Dyer, will take place on Friday, May 5, starting at Orlando Festival Park.


Bike 5 Cities, National Bike Month 5/6

Discover safe bike routes and trails through Winter Park, Orlando, Casselberry, Maitland and Eatonville on a free, guided ride-along. Ride the entire 28-mile loop or join shorter rides at event sites that offer family activities, snacks and refreshments. Aid stations will be located along the route, and Ride Ambassadors will provide rider assistance while acting as escorts. Bike helmets are mandatory.


Wings for Life App Run 5/7

Wings For Life App Run Orlando is a run with people for all over the world for a great cause.


Orlando Ballet: A Cinderella Story 5/5 -5/7

Orlando Ballet presents: A Cinderella Story at Dr. Phillips Center for the Performing Arts |


The Running of the Chihuahua at Cocina 214 5/7

This will be the fifth year in a row that Winter Park restaurant, Cocina 214 (Facebook Website), will be hosting their Running of the Chihuahuas event.

In honor of Cinco de Mayo, the restaurant will be hosting a block party at 11 a.m. on Sunday, May 7. The day will feature a live DJ, Corona giveaways, Tito’s samplings, a photo booth, and a chihuhua race.

Guests are encouraged to enter their pet to compete in the race with a $15 donation to the Winter Park Lost Pets and A Cause 4 Paws Rescue. You can register your dog HERE.

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