Lucky you. You just found ORLtoday’s Plan Ahead, a list of some of the biggest events to plan for that are taking place throughout Orlando each month.
Take out your calendar, grab your day planner, or text all your friends — these are the top events we recommend heading to this month. Psst: Don’t forget to bookmark this page and come back; we update our guide monthly.
(Don’t see anything you like? Check out our full events calendar.)
Festivals
Winter Garden Wine Walk | Thursday, June 5 | 6:30-9 p.m. | Farmer’s Market Pavilion, Winter Garden | $17.85+ | Sip and stroll your way through downtown Winter Garden to more than a dozen food + wine tasting locations.
Orlando Seafood Festival | Saturday, June 7-Sunday, June 8 | 11 a.m.-9 p.m. | Festival Park | $7.45+ | Eat your way through this festival featuring fresh seafood, arts + crafts, live entertainment, and a marine exhibit.
Orlando Saigon Night Market | Saturday, June 7-Sunday, June 8 | 1-9 p.m. | Festival Park | $10+ | More than 100 global vendors will have their goods available, from fashion and gifts to food and drink.
5th Annual Facets of Freedom Juneteenth Festival | Thursday, June 19 | 10 a.m.-10 p.m. | Orlando Family Stage | Free+ | Join this festival for family lunch + learn opportunities, music, dance, and spoken word performances.
Catch a big show at the Kia Center or go for a DJ set at the Vanguard.
Photo via @elasesinoentertainment
Concerts
Tchaikovsky’s Fifth | Sunday, June 1 | 2:30 p.m. | Steinmetz Hall | $20+ | The orchestra’s power will be on full display in the final performance of the Classics Series.
Shakira | Wednesday, June 4 | 7:30 p.m. | Camping World Stadium | $85+ | Grammy winner Shakira brings her “Las Mujeres Ya No Lloran” World Tour to Orlando.
Who’s Bad: The Ultimate Michael Jackson Experience | Friday, June 6 | 7 p.m. | House of Blues | $24+ | Relive the King of Pop’s greatest hits + dance moves at this tribute show that’s toured for 20 years.
Classic Albums Live: The Eagles - “Hotel California” | Saturday, June 7 | 8 p.m. | Dr. Phillips Center for the Performing Arts | $29.50+ | Hear this classic rock album performed note for note, cut for cut, just as it was recorded.
Post Malone | Tuesday, June 10 | 6:30 p.m. | Camping World Stadium | $125+ | Singer + rapper Post Malone is joined by artists Jelly Roll and Sierra Ferrell for “The BIG ASS Stadium Tour.”
Melendi | Thursday, June 12 | 8 p.m. | Kia Center | $72+ | Hear the renowned Spanish singer perform hits from over the years of his career.
“The Lord of the Rings: Return of the King” Live in Concert | Friday, June 13-Saturday, June 14 | Times vary | Walt Disney Theater | $70+ | Watch the finale of this fantasy trilogy on screen as a symphony orchestra performs the score live.
Luke Bryan | Friday, June 13 | 7 p.m. | Kia Center | $53+ | Shake it at the “Country Song Came On” Tour featuring special guests George Birge, Ashland Craft, Adrien Nunez, and DJ Rock.
DJ Pauly D | Friday, June 13-Saturday, June 14 | 10 p.m. | The Vanguard | $20+ | Dance along to a live house + top 40 set by this star from “Jersey Shore.”
Stray Kids World Tour | Saturday, June 14 | 7:30 p.m. | Camping World Stadium | $129+ | This internationally recognized Kpop band will take the stage to "[dominATE ORLANDO].”
An Evening with Heart | Friday, June 27 | 7 p.m. | Kia Center | $77+ | All we wanna do is be in the crowd for this rock band’s performance.
Dillon Francis | Friday, June 27-Saturday, June 28 | 10 p.m. | The Vanguard | $37+ | Catch a set by this producer + DJ, and upgrade your ticket for VIP bar access.
Don’t miss the final two shows in the 24/25 AdventHealth Broadway in Orlando season.
Photo by Elisfkc via Wikimedia Commons
Theater + comedy
Nikki Glaser | Thursday, June 5-Friday, June 6 | Times vary | Hard Rock Cafe | $39.75+ | The queen of roasts stops at CityWalk on her “Alive and Unwell” comedy tour — grab tickets before they sell out.
“Stomp” | Friday, June 6-Saturday, June 7 | Times vary | Dr. Phillips Center for the Performing Arts | $40+ | See what all the noise is about at this dynamic stage show that blends music, dance, and theater.
Leanne Morgan | Saturday, June 14 | 7-9 p.m. | Addition Financial Arena | $50+ | Fresh off a critically acclaimed Netflix special, this comedian adds an Orlando stop to her “Just Getting Started” tour.
8th Annual Florida Festival of New Musicals | Thursday, June 19-Sunday, June 22 | Times vary | The Winter Park Playhouse, Winter Park | $10 | Writers + composers from around the country will present one act of their musicals that have yet to see the spotlight.
“Shucked” | Tuesday, June 24-Sunday, June 29 | Times vary | Dr. Phillips Center for the Performing Arts | $45+ | This Tony Award-winning musical comedy is sure to tickle your (corn) ribs.
Tip “T.I.” Harris featuring the HaHa Mafia | Friday, June 27-Saturday, June 28 | Times vary | Funny Bone Comedy Club | $55+ | Make it a date night with dinner at this Grammy Award winner’s hilarious comedy show.
Active + sports
Annual CommUNITY Rainbow Run | Saturday, June 7 | 6-10 a.m. | City Hall Plaza | $49 | Join this 4.9K run to honor Orlando’s resilience and raise funds for a future Pulse Memorial.
FIFA Club World Cup M11: Ulsan HD v. Mamelodi Sundowns FC | Tuesday, June 17 | 6 p.m. | INTER&Co Stadium | $33+ | Cheer on these teams from South Korea and South Africa as they compete for the national title, or catch another Club World Cup game.
Pride in our City - Orlando City SC v FC Cincinnati | Saturday, June 28 | 7:30 p.m. | INTER&Co Stadium | $12+ | Pride Month comes to the stadium for this celebratory game.
Seasonal events
Central Florida Orchid Society Show & Sale | Friday, June 6-Sunday, June 8 | Times vary | Florida National Armory | $5+ | No orchid-ding around — see award-winning flower displays, shop a variety of orchids, and join informational classes.
Adopt-A-Tree | Saturday, June 7 | 8 a.m.-12 p.m. | Barnett Park | Free | Bring proof of Orange County residency to receive two trees to plant at home.
Central Florida Juneteenth Black History Bus Tour | Saturday, June 14 | 8 a.m.-5 p.m. | Shiloh Baptist Church of Orlando | $50+ | Take a tour through local historical areas and learn about the past from politicians, historians, and social justice advocates.
Jazz & Jubilee: A Night Under the Stars | Thursday, June 19 | 5-10 p.m. | Shady Park, Winter Park | Free+ | The Alvin Giles Band headlines this Juneteenth celebration featuring local bands, dancers, and entrepreneurs.
For the fam
Luminary Market and KaleidoScope 360° Movie Night | Wednesday, June 4 | 5:30-9 p.m. | Luminary Green Park | Free+ | Shop from up to 25 local vendors to support the Creative Village, and stick around for the outdoor film screening.
Movie Night | Friday, June 6 | 8:30 p.m. | Harry P. Leu Gardens | $6+ | Pack a picnic and lawn chairs for an outdoor screening of “Toy Story.”
Dad Games 2025 | Sunday, June 15 | 11 a.m.-2 p.m. | Dave & Buster’s | $31.93+ | Families can go head-to-head in this arcade competition — a photo of the winner will be displayed at D&B’s for a full year.
Caribbean Culture Celebration | Saturday, June 28 | 2-5 p.m. | Hiawassee Branch Library | Free | In honor of Caribbean American Heritage Month, enjoy a parade, food tastings, and family festivities.
Get social
Florida Fashion Shows Presents: Porsche of South 2025 | Friday, June 6 | 7-10 p.m. | Porsche South Orlando | $87 | Mix + mingle with designers at this show where fashion meets the fast lane.
Pride and Proud Pub Crawl | Saturday, June 14 | 6-11:30 p.m. | The Retro Room | $20+ | Celebrate Pride Month with a crawl through the Thornton Park neighborhood featuring entertainment at The Retro Room and Dust.
The Official Pride Bar Crawl | Saturday, June 21 | 4-11:59 p.m. | Underground Public House | $13+ | Tickets to this crawl include up to three drinks, free drag show cover, and afterparty access.