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What's Happening: Top Things to do in Orlando in May

Updated: May 3, 2022

This month, The Date Night Orlando has got you covered.

Whether you're looking for a low-key night out or an epic party, we've got the perfect spot for you. From the hottest restaurants to the newest exhibits at local art galleries, here are our top picks for things to do in Orlando this month.

boyfriend and girlfriend at a festival enjoying drinks with the girlfriend wearing a flower crown sitting on the grass

Red Velvet Burlesque Show

Through May

Savoy Orlando


Red Velvet Entertainment is the number one Orlando burlesque show in the Orlando area. With burlesque shows every week, we provide some of the most intricate and exotic burlesque and cabaret performances in the country. We offer new and exciting performances that have never been seen before. With a combination of unparalleled choreography mixed with classical burlesque dance routines, we strive to outperform any other burlesque show in the industry. If you have never been to a burlesque show, do not hesitate and contact us today to learn more about how to reserve your tickets.

Red Carpet Couture at OM°A

May 2nd 5 PM - 9 PM

Orlando Museum of Art

GA $150

Arrive in style and strut the red carpet into Orlando’s newest fashion event, coinciding with The Met Gala. The evening includes fashion presentations, top-shelf spirits, luxury catering, OM°A’s world-class art exhibitions, and much more! *This is a 21+ only event.

- Vogue’s Met Gala Red Carpet Arrivals Live Stream, kindly provided by our partner Ascend Studios - Red Carpet Paparazzi photo op Fashion Presentations by Tammara Kohler of Fused Fashion - Open Bar, serving top-shelf spirits courtesy of ABC Fine Wine & Spirits - Luxury Catering and Hors d'oeuvres (while supplies last) - Music by premier DJ Demi Korrin - 360° Photobooth - Full Museum Gallery Access - And more!


Downtown Comedy

May 4th 8 PM

Bynx Orlando

Free Admission

The 1st Wed of every month, Downtown Comedy brings you the best up and coming comedians in Orlando and across the country!!! Expect a great time and drop-ins from touring professionals. Show is FREE but reservations recommended as space is limited.

Seating is first come first serve, arrive early for best seats.

May The 4th Party

May 4th 7 PM - 11:30 PM

Dezerland Auto Museum

SABER the moment with an EPIC May 4th party! 7p - 11:30p. Event will be held in American Classics. DJ - Food - Drink Specials. This night is all about Star Wars and Cosplay. Star Wars inspired costumes are HIGHLY ENCOURAGED!

- FREE (age-appropriate) Drink Ticket with Entry - Dance Party - Car Show -Photo ops with Movie Cars

Cinco de Mayo

May 5th from 5 PM - 9 PM

Marketplace at Avalon Park

Free Admission

East Orlando's premier food hall, featuring: Rosso Specialty Coffee, Sip 'N Roll, Cheese to Share, Pico de Gallo, KBBQ Kitchen, NOLA Avalon Park, Brazas Chicken, LemonShark Poke, BBQ 50, Bowigens Beer, Avalon General Store.

OM°A 1st Thursdays May - The Influence of Fashion

May 5th 6 PM - 9PM

Orlando Museum of Art

$20 (non-members)

The first Monday in May marks the biggest night in fashion. Let’s keep the celebration going on the 1st Thursday in May for The Influence of Fashion.

Fashion mavens, arbiters of style, influencers, and artists are invited to celebrate the power that fashion has on art, culture, and entertainment.

Ghost Tour of St. Petersburg ~ May 2022

May 6th - 29th 7:30 PM - 9 PM

Ghost Tour of St. Petersburg and Tampa Bay, FL

GA $20

Ghosts and haunted houses, restless spirits and lost souls, ageless curses and hidden treasures…stories that have been passed down from generation to generation, containing secrets only whispered about in history books. Join us for an illuminating Ghost Tour of downtown St. Petersburg and peer into the shadows and mysteries of the "Sunshine City"! Tours depart every Friday, Saturday, and Sunday in May. Reservations required.

2022 Spring Garden Festival

May 7th from 9 AM - 1 PM

849 West Ave, Clermont, FL 34711-2139, United States

Free Admission

Join vendors of specialty plants, nurseries, garden art and garden related crafts at the Clermont Garden Club and City Lake Park in Clermont.

Kentucky Derby on Park

May 7th 4:30 PM - 8:30 PM

Winter Park Events Center

Tickets · $100 - $5,000

Join Orlando’s Best Derby Party - Winter Park Style!

As a guest at Derby on Park, you enjoy 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)

Wanda Sykes

May 12th 8 PM

Dr. Phillips Center for the Performing Arts


Recognized by her peers and the world as "one of the funniest stand up comics of our time", comedy legend Wanda Sykes brings her larger-than-life personality to the stage once again to share her hilarious tales of parenthood, aging, race, and politics.

407 Food Fair May 14th 2 PM - 7 PM

Ivanhoe Park Brewing Company

MAM Events in partnership with Stuff to do in Orlando presents the 407 Food Fair! This monthly food & craft festival will be held the second Saturday of the month at Ivanhoe Park Brewing Co! It is the perfect way to enjoy all things local in one spot!

Each month will feature a different food theme and you will be able to sample the food offerings from 8-12 food vendors and shop from local vendors all while enjoying the views and brews of Ivanhoe Park Brewing!

Megacon 2022

May 19th - 22nd

Orange County Convention Center

GA From $27

Experience one of North America's largest Comic, Sci-Fi, Horror, Anime, and Gaming events. Four BIG days of citywide events, family-friendly attractions and world-renowned celebrities await.

Join hundreds of thousands of fans who are just like you.

Show Hours: Thursday 4 PM – 9 PM Friday 10 AM – 7 PM Saturday 10 AM – 7 PM Sunday 10 AM – 5 PM

Taste of Baldwin Park

May 26th 5:30 PM - 9:30 PM

Baldwin Park Lake Fountain

GA from $55

Join us for Taste of Baldwin Park presented by Park Life Group at Keller Williams Winter Park. Our lively event by the fountain in beautiful Baldwin Park features all-inclusive wines, craft beer, food stations, a live band. It will be as fun night-out to start the memorial day weekend on Thursday 5/26/22. Tag/invite friends. Charity Partner: Benefits Caring By Sharing United a 501 (c)3 non-profit.

All Tickets are All-Inclusive Include “Unlimited Tastings" from 25 + vendors, craft beers, wine, specialty cocktails, soda/water, live music | VIP upgrade gets Early Entry with Open bar + more Get Early Bird Prices Ends 5/13


May 27th - 29th 12 PM - 11 PM

Downtown Orlando


The Orlando Carnival Downtown festival has been infusing the joys of Caribbean culture and music into Orlando for more than three decades, and this year will be no exception, possibly the most exciting after 2 years of Covid imposed house arrest for all.

The annual festival brings pageantry, parties, art vendors and foods from Trinidad & Tobago, Jamaica, Guyana, Barbados and other Caribbean nations.

Through the years there have been numerous top ranked recording artists performing at the event, including Dancehall reggae artists Tony Matterhorn, Serani and Menace, alongside Soca stars Raymond Ramnarine, Machel Montano, Bunji Garlin, Fay-Ann Lyons, Skinny Fabulous and many more for the grand finale of nonstop rhythmic rapture.

Carnival on the Runway

May 27th 6 PM - 10 PM

Dezerland Park Orlando

GA from $15

Carnival on the Runway is a special designer showcase. High Fashion meets Carnival...on the Runway.

This annual event showcases Carnival Costumes from amateurs and designers. Sign up to showcase your design in Carnival on the Runway 2022.

Brew & View: Jurassic Park

May 27th 7 PM - 9 PM

Ivanhoe Park Brewing Company

Not all of our firsts were a success! The first movie a dinosaur chewed on our audio cords and left us with some technical difficulties!

But, we want to do this classic movie justice and give it another shot!

Orlando Balloon Festival 2022

May 27 - 29 11 AM - 11 PM

Blue Jacket Park

Hot air balloons (weather permitting), food trucks, retail vendors and activities for the family!

15th Annual Hurricane Party Music Festival in Historic Downtown Sanford

May 28th 12 PM - 12 AM

Historic Downtown Sanford

Presale $40 / $45 Day of show

Sanford's oldest and largest music festival since 2006, West End's Annual Hurricane Party keeps growing every year. With 7 stages and 40+ bands in the venues and streets of Historic Downtown Sanford, live art, vendors and food trucks, the Hurricane Party is our way of paying homage to Mother Nature for a tranquil hurricane season.

Orlando Carnival Downtown Official Jouvert

May 28th 7 AM - 2PM

Dezerland Orlando


Orlando Carnival Downtown presents their annual Jouvert! May 28th from 7am - 2pm . Paint, powder, water - Food and Drinks on Sale.

Continuous Happenings: Orlando

Weekends at the Winery


Lakeridge Winery

Free Admission

Enjoy our expansive vineyard green, including delicious food, live entertainment, and of course your favorite Lakeridge wines at our outdoor bar.

Art and Jazz Night

Every 3rd Thursday

Historic Downtown Sanford

Free Admission

Art and Jazz Night is the product of Historic Downtown Sanford’s thriving (and growing!) arts community.

Stroll the streets and visit the participating locations, all within a comfortable walking distance from one another… Stay tuned to this event page to learn what each stop has to offer!

Giants, Dragons & Unicorns

Now - May 8th

Orange County Regional History Center


The World of Mythic Creatures features unique cultural objects to highlight the surprising similarities and differences in the ways people around the world envision and depict mythic creatures. The exhibition includes models and cast fossils of prehistoric animals to investigate how they could have – through misidentification, speculation, fear, or imagination – inspired the development of several legendary creatures.

Epcot International Flower & Garden Festival

Now - July 4th

Epcot Orlando

The official start of winter is still a few days away, but spring is already in the air because our horticulture team at Walt Disney World Resort is busy producing topiaries, hanging baskets, flower towers and more in preparation for the 2022 EPCOT International Flower & Garden Festival.

The Downtown Clermont Farmer's Market

Every Sunday from 9am - 2pm

Historic Downtown Clermont

Free Admission

We have over 40 local vendors selling local produce, meat, honey, eggs, seafood, handmade gifts, and home goods.

Heroes & Monsters: Jean Michele-Basquiat

Now - June 30th

Orlando Museum off Art


Heroes and Monsters presents a rare group of paintings from a private collection that is being shown for the first time at the Orlando Museum of Art.

Seven Seas Food Festival

Now - May 8th

Sea World Orlando

Regular Park Admission

On Thursdays, Fridays, Saturdays, and Sundays sip and sample your way around the world with exciting flavors and local craft beers, plus live performances. And from Feb. 25 – March 6, 2022, you can let the good times roll with limited-time food, cocktails, entertainment, and live music thanks to the Seven Seas Food Festival’s special Mardi Gras edition!

Comedy, Karaoke and Cocktails


The Dreams Lounge

Free Admission

PRO & NEW comedians 🎙 ( Featuring comedians seen on HBO, Netflix, Hulu, Instagram, YouTube, Comedy Central, BET ComicView, Def Comedy Jam, All Def Digital & MORE! )

Sunday Jazz Jam

Sundays 5pm-8pm

Pilars Martini

Free Admission

Play, Listen or Enjoy - Pilars Jazz Jam LIVE in Pilars Loft. A community-driven jazz interplay; inspired by the 1940’s and ‘50’s ‘old-school’ hang hosted by the “Pros” Sunday’s at Pilars from 5p-8p. Pilars Jazz Trio has comprised of many of the finest Central Florida Musicians, and each Sunday is unique because you never know what special guests including the best jazz talent in Florida-will drop in for the ‘hang’ since Jazz Jam began in September 2015.

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