The Best of May: 50+ Upcoming Events in Orlando this Month

Events in orlando - Orlando International Fringe Theatre Festival

While the arrival of spring means some rainy days are ahead, it also means the events calendar is full of activities to keep you entertained. From dinner pairings to concerts and outdoor movies, here are our top picks for events in Orlando this May.

Cinco de Cinco Anniversary Week
Through May 4
Reyes Mezcaleria
$5 food and drink specials every day of the week to celebrate Reyes Mezcaleria’s 1st anniversary! Tuesday 5/1 – $5 Carnitas Tostadas & $5 Loaded Coronas (w/ Bacardi Limon), Wednesday 5/2 – $5 Tamale & $5 Frozen Margaritas, Thursday 5/3 – $5 Queso Fundido & $5 Rosè by the glass, Friday 5/4 – $5 Chorizo Grilled Oysters & $5 Palomas
Menu prices vary

Pizza in the Field
Tuesday, May 1, 6pm
Sugar Top Farms
Join Bruno Zacchini and team for an intimate three course dinner outdoors at Sugar Top Farms.
$40; $25 wine pairing available

Chef’s Dinner / Tequila and Taco Pairing
Tuesday, May 1, 7pm
The Waterfront Orlando
Monthly chef’s dinner with a changing theme; May’s pairing is a Tequila and Taco themed dinner.

Comedy Night
Tuesday, May 1, 9pm
Hourglass Brewing
Monthly comedy night hosted by Real Laughs of Real Radio 104.1. Papa Bees and Wako Taco (located next door) stay open late to serve food during the event. Arrive early for good seats.
FREE admission

Culture Pop! Enchanted Florida
Wednesday, May 2, 6-9pm
Maitland Art Center
Interactive art experience featuring a preview of the Enchanted Florida exhibition, live music by The Moss Park Trio, light bites and cash bar with wine & craft beer.

Greek Dinner
Wednesday, May 2, 6:30-8pm
K Restaurant
Enjoy five-courses of Greek food paired with Greek wine.

1st Thursdays: Healing Arts
Thursday, May 3, 6-9pm
Orlando Museum of Art
Discover local artists, listen to live music and mingle with an eclectic mix of people. There will be cash bars serving wine, beer, soft drinks and water, and café offerings from area restaurants. This month’s theme has paintings and poetry, sculpture and dance, all designed to heal.

Latin/Asian Beer Pairing Dinner
Thursday, May 3, 6-10pm
El Buda Latin Asian Restaurant
Guests will be treated to a flight of sakes (Japanese rice wine) accompanied by a four-course tasting menu of Asian & Latin cuisine-inspired dishes featuring local seafood and produce, and prepared using sake as an ingredient.

Five-Course Discovery Dinner at Big Fin Seafood Kitchen
Thursday, May 3, 6:30-9:30pm
Big Fin Seafood Kitchen
There will be five courses served with guest’s choice of wine or cocktails throughout the evening. As with every Discovery Dinner, the menu remains a mystery until the food arrives at the table. *Orlando Date Night Guide event

ECHL Kelly Cup Playoffs: Orlando Solar Bears vs. Florida Everblades
Thursday, May 3, 7pm and Friday, May 4, 7pm
Amway Center
Join the Orlando Solar Bears for the Kelly Cup South Division Finals vs. the Florida Everblades.
$14 and up

Jake’s Beer Festival
Friday, May 4, 6-9pm
Loews Royal Pacific Resort at Universal Orlando
Jake’s Beer Festival happens only twice each year and features more than 50 local and regional specialty craft beers, delicious and tasty foods, live entertainment and more. The event takes place under the hotel’s outdoor Wantilan Pavilion.

Jim Norton
Friday, May 4, 8-11pm
Hard Rock Orlando

Movie Night at Leu Gardens: Breathe
Friday, May 4, 8:30pm
Leu Gardens
This month’s outdoor movie is Breathe. The gardens open at 6 and the movie begins at 8:30. Outside food and alcohol are permitted – enjoy responsibly!
$6; free for members

Leu Gardens movie night
Leu Gardens Movie Night. Image credit: Leu Gardens

Orlando Ballet presents Contemporary Wonders
May 4-6, Show times vary
Dr. Phillips Center for the Performing Arts
Following the success of Beauty & the Beast, Arcadian Broad will once again compose and choreograph a hypnotic telling of the Alice in Wonderland story, as seen through the eyes of the Mad Hatter. The evening will conclude with an Orlando Ballet premiere of New York-based choreographer Jessica Lang’s From Foreign Lands and People.
$19 and up

Cinco De Derby
Saturday, May 5, 11am
Orange County Brewers
An event showing what happens when the Kentucky Derby and Cinco de Mayo collide featuring $4 Vienna lagers, $5 Mint Juleps – our Bleached Blonde Ale treated with mint and bourbon and oven-fired taco pizzas!
FREE Admission

Cinco de Mayo Block Party!
Saturday, May 5, 11am-2am
Pepe’s Cantina Church Street
Block party at Pepe’s Downtown Orlando location featuring a mechanical bull, cash bars, DJ, and more!
Menu prices vary

Cinco De Mayo at Cocina 214
Saturday, May 5, noon-10pm
Cocina 214 (Winter Park)
All day specials to celebrate Cinco De Mayo and commemorate Cocina’s 7 year anniversary in Winter Park. There will be giveaways and drink specials throughout the day.
Menu prices vary

Image credit: Cocina 214

Cinco de Mayo at Mango’s
Saturday, May 5, 3pm-2am
Mango’s Tropical Cafe Orlando
Live Mariachi bands, drink specials, and the Cafe Bar will feature an all inclusive package including all you can eat chicken or ropa vieja tacos and all you can drink margaritas or shots for $35.
Menu prices vary

Derby de Mayo on Park
Saturday, May 5, 3:30-7:30pm
University Club of Winter Park
Orlando’s First ever Kentucky Derby/Cinco de Mayo party experience – Winter Park Style! 4-hours of unlimited food, drink, live music + cheer for your favorite horse. Derby Day attire encouraged.
$69 and up

“Los Liam’s” 3rd Annual Cinco De Mayo Block Party
Saturday, May 5, 4pm
Liam Fitzpatrick’s Restaurant and Irish Pub Lake Mary
Cinco de Mayo Block Party will feature 3 DJs, a live band, salsa dancers, live main stage music and special entertainment, tasty bites and drink specials all event long, plus a special VIP experience. A portion of admission will benefit Just Our Soldiers’ Helpers Inc. (J.O.S.H.)
$5-$10; VIP packages available

The Kentucky Derby at Soco
Saturday, May 5, 4-7:30pm
Soco Thornton Park
Come to Soco and celebrate the South’s most prestigious sporting event. Traditional Julep, complimentary for those wearing derby attire.
FREE Admission<

Cocina 214’s Annual Running of the Chihuahuas
Sunday, May 6, 10am-2pm
Cocina 214 Winter Park
This family-friendly event invites locals, visitors and pet-lovers alike to continue the Cinco De Mayo celebration with the beloved Chihuahua run, fresh margaritas, authentic Tex-Mex cuisine and festive delights. Proceeds from the Chihuahua run will benefit Winter Park Lost Pets and the Poodles and Pooch Rescue of Florida.

Sunday, May 6, 1pm
Enzian Theater
Monthly indie film showcase and competition open to Florida filmmakers and students.

Enzian Theater Maitland
Image credit: Enzian Theater

Florida Supper Chef Collab Dinner
Sunday, May 6, 6:30pm
The Ravenous Pig
The Ravenous Pig’s Guest Chef Series continues with a Florida Dinner prepared by Chefs James Petrakis & Nick Sierputowski of The Ravenous Pig and Clay Conley of Buccan, Palm Beach.

25th ANNIVERSARY CONCERT: Yo-Yo Ma & Colin Jacobsen
Tuesday, May 8, 8pm
Dr. Phillips Center for the Performing Arts
$100 and up

James Taylor & His All-Star Band with special guest Bonnie Raitt
Wednesday, May 9, 7:30pm
Amway Center
$66 and up

Thornton 2nd Thursday Wine & Art Walk
Thursday, May 10, 6:30-9:30pm
Thornton Park District
Pick up a glass and map, then stroll the district visiting over 25 businesses offering tastings.
$15 (cash only)

Popcorn Flicks in the Park: Planet of the Apes
Thursday, May 10, 8pm
Central Park, Winter Park
Pack a picnic for a free outdoor movie screening in the park hosted by Enzian Theater.
FREE Admission

Fall Outdoor Movies in Orlando 2017

Always & Forever An Evening of Luther Vandross Starring Ruben Studdard
Thursday, May 10, 8pm
Hard Rock Live
$33 and up

10th Annual Florida Music Festival
May 10-12
400 S Orange Ave, Orlando
Over 150 bands in pubs, clubs and outdoor stages over 6 blocks of Downtown Orlando.
FREE Admission to all participating venues (21+ & Capacity restrictions apply)

Little Shop of Horrors
May 10-13
Central Florida Community Arts at Central Christian Church
Tickets starting at $12

Art & Music in the Park and Food Truck Bazaar
Friday, May 11, 6-9pm
Lake Concord Park
Get something to eat on one of the dozen food trucks from the Food Truck Bazaar and shop at the local businesses and artisan booths selling unique jewelry, photography, ceramics, paintings, and many other great products.
FREE admission

Patti Labelle
Friday, May 11, 8pm
Dr. Phillips Center for the Performing Arts
$39.50 and up

2nd Taste of Soul – Soul Food Festival
Saturday, May 12, 11am-7pm
Festival Park
A family feast of sight, sounds, and tastes of the African American culture and other diverse cultures of soul food cooking.

Rotary Craft Beer Festival
Saturday, May 12, 3-7pm
Town Park, Avalon Park
Sample craft beer from local Orlando breweries.

Cheese 101
Saturday, May 12, 6:30pm
East End Market
Class led by La Femme du Fromage which takes an in depth look at the cheese making process as well as tasting 6 different styles of cheeses. Includes a glass of sparkling wine or non-alcoholic beverage; cash bar also available.

Bill Nye The Science Guy
Saturday, May 12, 8pm
Dr. Phillips Center for the Performing Arts
$49.50 and up

3rd Annual Accidental Music Festival Marathon!
Saturday, May 12, 1-10pm
SODO Shopping Center
The daylong Marathon will feature 18 ensembles and soloists performing music almost exclusively by living composers.
FREE Admission

DeLand Indie Market Summer Edition
Sunday, May 13, 11am-5pm
Artisan Alley, DeLand
Curated event that is held 4 times a year showcasing artists, boutiques, vintage and handcrafted vendors, food and live music.
FREE Admission

Justin Timberlake | Man of the Woods Tour
Monday, May 14, 7:30pm
Amway Center
$105 and up

August Greene featuring Common, Robert Glasper & Karriem Riggins
Tuesday, May 15, 8pm
Dr. Phillips Center for the Performing Arts
$49.50 and up

Orlando International Fringe Theatre Festival
May 15 – 28
Orlando Loch Haven Park
This 14-day arts festival is the longest running Fringe Festival in the United States, celebrating 27 years as “Orlando’s most unique cultural experience”.
Prices vary

Doughnut & Beer Pairing
Wednesday, May 16, 7-9pm
Orlando Brewing
Dig into organic mini doughnuts paired perfectly with four Orlando Brewing organic brews (5oz sampler glasses) at this guided pairing.

Sunset at the Zoo
Thursday, May 17, 5:30-7:30pm
Central Florida Zoo
Stroll the zoo after hours at this adults-only event which includes live music plus craft beer and wine for purchase.

Orlando Sentinel Foodie Awards Celebration 2018
Thursday, May 17, 6-9pm
Celine Orlando
An evening featuring the 2018 Foodie Award winners and finalists inviting guests to sample dishes and drinks from more than 20 restaurants and live entertainment.

Wine, Cheese, and Chocolate Perfectly Paired!
Thursday, May 17, 7-9pm
Quantum Leap Winery
Pairings of 5 Quantum Leap wines, 4 La Femme du Fromage cheeses, and 4 Peterbrooke Chocolatier of Winter Park chocolate confections.

Wine Cheese and Chocolate perfectly paired at Quantum Leap Winery

Thursday, May 17, 7pm
CFE Arena

Orlando Ballet presents Fast Forward
Friday, May 18, 7:30pm
Bob Carr Theater

Taco Takeover
Saturday, May 19, 2-9pm
Wall Street Cantina
Taco Takeover is a bar crawl for taco lovers & margarita enthusiasts. (This is a 21+ event)
Tickets start at $19.99

Royal Wedding Brunch
Saturday, May 19, 7-11am
The Pub Orlando
Celebrating the wedding of Prince Harry & Meghan Markle with televised events, $3.25 Old Speckled Hen, themed cocktails, festivities, raffles & giveaways.
Menu prices vary

Central Florida Top Brewer Beer Fest
Saturday, May 19, 1-5pm
Lake Concord Park North
“Top Chef” style competition featuring local breweries such as Deadly Sins Brewing and Hourglass Brewing. Along with their competition beer, breweries will be bringing along some of their favorite and special beers

Beer ‘Merica Craft Beer Festival
Saturday, May 19, 3-7pm
Gaston Edwards Park
What better way to celebrate American Craft Beer Week? Enjoy live music, food, and complimentary craft brew samplings. Proceeds benefit The Camaraderie Foundation.

Sanford Art Walk – “Animals”
Saturday, May 19, 6-9pm
Sanford Welcome Center
A juried art show and a walking tour of the art venues located in historic downtown Sanford.
FREE Admission

Milk District Market: The Return
Sunday, May 20, 11am-5pm
2428 E Robinson St, Orlando, Florida 32803
All ages, all day event featuring a plethora of Vintage/Handmade/Unique/Reto/Upcycled/Antique vendors, as well as food trucks, pop-up shops, live music, and drinks.
FREE Admission

Yoga at the Zoo
Monday, May 21, 6-7pm
Central Florida Zoo
Channel your inner animal during an hour-long evening yoga session at the Central Florida Zoo.

Chef Night with Pizza Bruno
Tuesday, May 22, 6-8:30pm
Emeril Lagasse Foundation Kitchen House & Culinary Garden
Learn the history and methods of the wood-fired oven, and get creating your own pizza, the Bruno way.
Tickets start at $25

Orlando Date Night Guide: Girl’s Night Out!
Wednesday, May 23, 7:30pm
Orlando City Stadium
Enjoy our Girl’s Night Out Ticket Package courtesy of Orlando Date Night Guide & Orlando Pride. Come watch the Pride take on the North Carolina Courage and see international soccer stars Alex Morgan, Marta, Sydney Leroux, Ashlyn Harris and more!
Tickets start at $40

MegaCon Orlando 2018
May 24-27
Orange County Convention Center
Convention spanning 4 days covering Comic Book, Anime, Sci-Fi/Fantasy, & Pop Culture.
Tickets start at $25

Vias Imports Italian Wine Dinner
Thursday, May 24, 6:30-9:30pm
Urbain 40
On Thursday, May 24, imagine you are wandering through the streets of Italy and join us for our five-course Vias Italian Wine Dinner.

Say Cheese!
Friday, May 25, 5:45-7pm
First Drop at at The Ritz-Carlton Orlando, Grande Lakes
Celebrate National Wine Day with charcuterie, exclusive wine pairings, and more.

Movieola: Zootopia
Friday, May 25, 6pm (movie begins at 8:15)
Downtown Orlando’s free outdoor movie series is back! Pack a picnic and head to Lake Eola Park for monthly outdoor screenings of family-friendly flicks all summer long. Pre-movie activities begin at 6pm, and movies start at 8:15pm. The Central Florida Zoo will be on site for animal meet and greets before the movie.

Central Florida’s BBQ Blowout
Saturday, May 26, 11am-9pm
Center Lake Park
Featuring live musicians and entertainers as well as 10 professional BBQ teams vending a variety of BBQ.
FREE Admission

Rock N’ Blues Concert and Car Show
Saturday, May 26, 5-9pm
Lake Concord Park
Morry Sochat & The Special 20’s will headline the concert, where there will also be more than 150 classic cars, muscle cars, and hot rods for car enthusiasts to enjoy, as well as a contest for best car.
FREE Admission

Orlando Carnival Downtown 2018
Sunday, May 27, 12-10pm
Camping World Stadium
Festival filled with pageantry and a weekend of parties that celebrate the culture of the Caribbean.
Tickets start at $15

Gay Days
May 29 – June 3
Area theme parks/hotels
Occurring over 7 days during the first week of June, GayDayS® is comprised of multiple events staged at world famous attractions, gay & lesbian nightclubs, and unique venues secured for the purpose of creating an inclusive LGBTQ atmosphere.

Luis Miguel: ¡México Por Siempre! Tour
Wednesday, May 30, 8:30pm
Amway Center
Tickets start at $76.95

Chef’s Night: Disney Boardwalk Resort Chefs
Thursday, May 31, 6-9pm
Second Harvest Food Bank
Chef’s Night is an evening at the food bank featuring some of Central Florida’s best chefs and cuisine, all to benefit our Darden Foundation Community Kitchen’s Culinary Training Program.

Love this post? Plan your date nights for the year with our list of the Top Orlando Events for 2018.


Download the Date Night Guide App on your Android or iPhone, where you’ll find hundreds of local events curated for couples. Simply access the Google Play or Apple App Store today to get started.

Feature image credit: Orlando Fringe


Comments are closed.