40+ Best Things to do in Orlando in May: Events and More

Hello, May! Spring is giving way to summer, and things are heating up. Cinco de Mayo, Mother’s Day, and Memorial Day Weekend all mean there are lots of May events in Orlando.

Let’s start things off with Cinco de Mayo, and keep the party going all month long.

Cinco de Mayo Events in Orlando

LIME Mexican Grill Cinco de Mayo
Thursday, May 5, all day
LIME Mexican Grill, Lake Nona
Live music from DJ Chino, drink specials, giveaways and more

Winter Park Cinco de Mayo Party
Thursday, May 5, 11am – 7pm
Pepe’s Cantina
$5 beer, margarita, and tequila specials and more

Cinco De Mayo Block Party at Rocco’s
Thursday, May 5, 2pm
Rocco’s Tacos and Tequilla
Live entertainment, street food, and drinks all day and all night.

Cinco on the Street
Thursday, May 5, 3pm
Thornton Park District
Celebrate Cinco de Mayo with The 808, Burton’s Thornton Park, Cavo’s Bar & Kitchen and Graffiti Junktion on East Washington Street. Beer pong, flip cup and cornhole, as well as exclusive drink specials, local food, a mariachi band and DJs performing throughout the night. Tickets include two free margaritas.
Tickets $10 in advance, $20 at the door

Cinco de Mayo at Avalon Park
Thursday, May 5, 5pm – 9pm
Town Park at Avalon Park

St. John’s Salsa Summit & Cinco de Mayo Pub Crawl
Thursday May 5, 6pm
Historic Downtown Sanford
Take part in the ‘Nacho Average Salsa Competition’ as you sample salsa at various locations and cast your votes at the Ladies 327 booth. Plus,a live Mariachi Band, drinks specials and more.

Cinco de Mayo at Hourglass
Thursday, May 5, 6pm – 11pm
Mariachi band, piñata room, multiple beer drops, a randall, and a new merch drop. The party kicks off at 6 PM with a few free kids-friendly Piñatas. The Mariachi band starts at 7 PM followed by our Adult Piñata Room at 8 PM.
A similar Cinco de Mayo event will also take place at Hourglass Brewing’s Hourglass District location.

Bar Louie’s Cinco de Mayo Specials
Thursday, May 5, all day
Multiple Bar Louie locations
Guests can score $3 off of Bar Louie’s limited-time Tostada Burger. And, for the perfect pairing, wash down the zesty burger with a Cinco Rita for just $5 all day. Plus, $4 Pacifico and a $3 Sidecar of Sauza Tequila.

Jumbo Margaritas at Hard Rock Cafe Orlando
Thursday May 5 and Friday May 6
Hard Rock Cafe Orlando
Enjoy one of three new JUMBO 36 oz. margaritas for a limited time! Choose from Baja California Blackberry Rita, Mexico City Mango Rita and Cancun Orange Cadillac Rita.

Don’t forget the tacos! Here are our picks for impressive taco spots in Orlando.

Make plans for Mother’s Day in Orlando: Brunch, Events, and More 

May 1 – 8, 2022 Things to Do / Events in Orlando

Reyes Mezcaleria Turns Five
Sunday, May 1, 2022
Brunch from 11am-3:30pm, mariachi 1-2pm, raffles PLUS the first 20 guests to purchase the birthday cocktail will receive a complimentary Reyes Mezcaleria shirt! Reservations are not required but strongly recommended.

Wine, Cheese, and Chocolate Perfectly Paired
Wednesday, May 4, 6pm – 9pm
Quantum Leap Winery
Class starts at 7pm, doors will open at 6pm!
This class includes favorite wine, and cheese and chocolate pairings for the class of 5 wines, 4 cheeses, and 4 Peterbrooke Chocolatier of Winter Park chocolate confections.

Night on the Red Carpet II: Back to Broadway
Thursday – Friday, May 5 & 6, 2022, 7:30pm
Northland Church
This spring, the CFCArts Community Choir will present Night on the Red Carpet II: Back to Broadway, featuring favorites like My Fair Lady, Oklahoma, or Hello, Dolly!, the magic of Disney’s Beauty and the Beast and The Lion King, and new blockbusters such as Hairspray, Rent, or Moulin Rouge.
Tickets starting at $10

Up, Up & Away Balloon Festival
Friday – Sunday, May 6 – May 8
Lakeland Linder International Airport
This annual event is an educational and community exposition for residents and visitors that includes hot air balloon launches, twilight glows and tethered rides, live music, vendors, food, and a myriad of activities for attendees of all ages.

Movie Night – When Harry Met Sally
Friday, May 6, 8:30 p.m.
Leu Gardens
Tickets are purchased online in advance until sold out. Tickets on sale May 2. Leu Members receive free admission to all movies, first come first serve.

Uptown Vibes – Altamonte
Friday, May 6, 7:00pm – 9:00pm
Uptown Altamonte – Cranes Roost Park
Bring on the good times and the good vibes! This concert series features more than just live music, bringing you interactive games and amazing food and drinks for all to kick back and relax. This May, enjoy a celebration of Latin culture with music from Lati-2.
Admission is free. Food and drinks available for purchase.

A live Salsa explosion with the “Son Con Sabor” Band
Friday, May 6, 8:00pm
Tuffy’s Music Box & Lounge
Grab your dancing shoes and come out and enjoy a free evening of live salsa, merengue, and bachata.

Baby Owl Shower
Saturday, May 7, 10:00am
Audubon Center for Birds of Prey
A special morning of activities including special meet and greets from Center bird ambassadors, conservation themed activities, crafts and more. Admission is free in lieu of a gift from the Center’s Wish list.
FREE with donation

Date Night in the Plaza
Saturday, May 7, 8:00pm – 10:00pm
Uptown Altamonte – Cranes Roost Park
Treat yourselves to an evening of live music, fun games and more. Enjoy Saturday night jazz in the park featuring After 5 Duo. Food and drinks are available for purchase. Patrons must be at least 21 years of age.
Admission is free. Table seating is limited.

Date Night in the Plaza at Cranes Roost Park | Image credit: City of Altamonte

A Night in my Shoes Black Tie Gala
Saturday, May 7, 6:00pm
JW Marriott Orlando Bonnet Creek Resort & Spa
Guests will start the evening mingling over drinks and live music before making their way to the Griffin Ballroom where a five star meal will be served. Celebrations and dancing will continue into the night with live performances all night long featuring live music and immersive entertainment.

Taste of Africa – Food and Music Festival
Saturday, May 7, 12pm – 9pm
Eagle Nest Park Metrowest
The festival is a wonderfully lively family day out with African-influenced crafts, games, goodies, and music.

Kentucky Derby on Park
Saturday, May 7, 4:30pm – 8:30pm
Winter Park Events Center
4-hours of fun at the ultimate Kentucky Derby viewing experience with two massive drop down screens TVs(Link to Venue!), unlimited food, premium open bars, music inside & outside, dancing, Best Hat contest with amazing prizes, Valet Parking all included with ticket (Derby attire encouraged – inside & outside event)
$85 and up

May 9 – 15, 2022 Things to Do / Events in Orlando

Sip and Shop
Tuesday, May 10, 5:30pm – 7:30pm
Oviedo Mall
Wine and food stroll, special offers and discounts, giveaways, live entertainment and much more!
FREE, advanced registration for wristband recommended

Plant Street Market’s 7th Birthday
Wednesday, May 11, 11am – 11pm
Plant Street Market / Crooked Can Brewing
Vendors throughout the market will be offering $7.00 specials all day long. Crooked Can will also feature an “open house”. This is a great opportunity to get a look at the behind the scenes action, speak to the owners, brewers and receive complimentary tours of Florida’s highest volume taproom brewery.

Art Distilled – NEW Event
Wednesday, May 11, 5:30pm
Orlando Museum of Art
Enjoy an art appreciation presentation, facilitated discussions, gallery connections, and a themed cocktail. Beer and wine also available.

Popcorn Flicks in the Park – Legally Blonde
Thursday, May 12, 8:00pm
This film is a part of Enzian’s Popcorn Flicks series, which is currently taking place at the Winter Park Events Center once a month and it’s FREE and open to the public! These films are presented with open captions.

Mather’s 5 Year Anniversary
Thursday, May 12, 7:00pm
Mather’s Social Gathering
Doors open at 4:00 pm, entertainment begins at 7:00 pm. Fancy dress is required. All seating will be reservation only, standing room will be limited to first come, first served.

Florida Highwaymen Meet & Greet
Saturday, May 14, 10am
Orange County Regional History Center
A group of 26 African Americans found success as artists in the segregated South of the 1950s. Meet some of these remarkable artists and hear their stories. You’ll have an opportunity to purchase their uniquely Florida artwork.

407 Food Fair
Ivanhoe Park Brewing
Saturday, May 14, 2pm – 7pm
Monthly food & craft festival will be held the second Saturday of the month at Ivanhoe Park Brewing Co
FREE – food and product pricing varies

Second Annual Charity Cornhole Tournament – Shelly’s Warriors
Sunday, May 15, 11am
Ace Cafe Orlando
Single elimination bracket style cornhole tournament at Ace Cafe in Orlando, FL featuring a $200 cash prize for the first place team and a prize to be determined for the second place. All proceeds will be used exclusively to support families in need.
The entry fee is a minimum donation of $50 per team

Orlando Mimosa Fest
Sunday, May 15, 11am
Tin Roof at ICON Park
Live music, a variety of mimosa flavors, yummy food, and a photobooth.
General Admission $14.99, VIP $34.99

1st Annual Karts & Kegs
Sunday, May 15, 2:00 pm
Henry’s Depot Food Hall Sanford
From the creator of Sofas & Suds comes the next form of a device racing and drink chasing event. Karts & Kegs will be an all-day celebration of Sanfords Golf Cart culture

Authentic Selves: Poetry Reading and Open Mic
Sunday, May 15, 7:30pm
Timucua Arts Foundation Orlando
Announcing Timucua’s new monthly poetry and open mic series, Authentic Selves! Held the 3rd Sunday of every month at Timucua.

May 16 – 22, 2022 Things to Do / Events in Orlando

Orlando International Fringe Theatre Festival
May 17 – 30, 2022
Loch Haven Park
The Orlando International Fringe Theatre Festival is a 14-day immersive cultural experience held annually in mid-May, featuring 850 ticketed theatrical performances and a free outdoor music festival.
Prices vary

John Michael from Meatball Seance_Photo by Ashleigh GardnerJohn Michael from Meatball Seance at a past Fringe Festival | Photo by Ashleigh Gardner

MEGACON Orlando 2022
May 19 – 22, 2022
Orange County Convention Center
Experience one of North America’s largest Comic, Sci-Fi, Horror, Anime, and Gaming events. Four BIG days of citywide events, attractions and world-renowned celebrities await.
Price vary

Oviedo Brewing Company Night Market
Friday, May 20, 5:00pm – 10:00pm
Oviedo Mall
Featuring fresh local variety of produce as well as craft items, ready-to-eat food, and more. A fun evening outdoors as we enjoy craft brew & local flavors under the evening stars!

Gallery Opening Party and Mixer- Fringe Festival
Friday, May 20, 7:00pm – 8:00pm
Visual Fringe HQ – The Lowndes Shakespeare Center
Donations appreciation

Shen Yun 2022
May 20 – 22, 2022
Dr. Phillips Center for the Performing Arts
Shen Yun invites you to travel back to the magical world of ancient China. Experience a lost culture through the incredible art of classical Chinese dance, and see legends come to life.
$80 and up

Sanford Riverwalk Rhythm & Brews BBQ Fest
Saturday, May 21, 12pm – 10pm
Fort Mellon Park
Mouthwatering BBQ from 20 competing cooks and refreshing craft, import and domestic brews
$10 and up

Feeding Ukraine
Saturday, May 21, 6:00pm – 10:00pm
Rosen Shingle Creek Resort
The Adam Michael Rosen Foundation proudly presents Feeding Ukraine. This food and beverage tasting event supports Chef José Andrés and World Central Kitchen (WCK) in their mission to deliver hot meals to Ukrainian refugees.
$200 and up

The Ultimate Garden Party “Escape to Elegance”
Saturday, May 21, 1:00pm – 5:00pm
Loews Sapphire Falls Resort at Universal Orlando
1st Annual Ultimate Garden Party featuring entertainment, silent and live auctions, games, delicious hors d’oeuvres and libations. The best part? 100% of proceeds support Second Harvest Food Bank of Central Florida’s efforts to fight hunger in our community.
$150 and up

May 23 – 31, 2022 Things to Do / Events in Orlando

Taste of Baldwin Park
Thursday, May 26, 5:30pm – 9:30pm
Taste of Baldwin Park is a annual foodie night out featuring all-inclusive wines, craft beer, food stations, a live band. It’s a fun night out with friends or a date night.
Starting at $50

The Seasons
May 27 & 28, 2022
The Plaza Live
A multi-sensory orchestral performance with Orlando Philharmonic Orchestra.
Tickets $35 – $50

Top Annual Orlando Events for 2022 - The Seasons Creative City ProjectImage credit: Creative City Project

15th Annual Hurricane Party Music Festival
Saturday, May 28, 12:00 pm
Historic Downtown Sanford
Tickets $40

Paul McCartney
Saturday, May 28, 2022
Camping World Stadium
Catch Paul McCartney live at Camping World Stadium on Sat. May 28

Diversitastic! Dining Experience: Cuba
Sunday, May 29, 5pm – 8pm
Black Bean Deli
This monthly dining series from FusionFest offers you the chance to immerse yourself into exploring the tastes, sights, sounds, and mindsets of another part of the world. Tickets include a unique full-course menu + drink, along with live entertainment, storytelling and chef talk.

Sounds of Wekiva Live Music
May 6 – May 28, Fridays and Saturdays
Wekiva Island
Fridays and Saturdays starting at 7 p.m. Don’t forget to bring your chair so you can relax in style.

Cocktail and Paint Class – Orlando Fringe
Sunday, May 29, 7:00 pm
The Play What You Can Stage – The Lowndes Shakespeare Center
Becca Koopferstock (@koopcreates) will lead participants through a paint class of a colorful guitar! All supplies will be provided and a cocktail ticket will be given on arrival to the class (any age can paint, must be 21+ to drink alcohol). You’ll leave with a finished painting to take home. Only 12 seats!