18 Things to Do in Orlando This Week · May 14–17, 2026

Festivals & Special Events

Orlando International Fringe Theatre Festival

The longest-running Fringe theater festival in the U.S. takes over Loch Haven Park with 100+ shows spanning comedy, drama, and avant-garde performance from around the world.

Friday, May 15, 2026 · Loch Haven Park, Orlando

Weekend Happenings in Orlando: May 20–22

Orlando Magazine's curated roundup of the best events happening across Orlando the weekend of May 20–22.

Friday, May 20, 2026 · Orlando

AltSocial Wellness Event at Ritz Carlton

AltSocial's alcohol-free daytime wellness experience at the Ritz Carlton Orlando features cold plunges, group fitness, live DJs, coffee, and community connection.

Saturday, May 23, 2026 · Ritz Carlton, Orlando

Lionheart Music, Art & Wellness Festival

A full day of music, art displays, and wellness activities at Orlando Amphitheater raising awareness and support for domestic violence victims.

Saturday, June 13, 2026 5:00 PM · Orlando Amphitheater

Arts & Culture

The Stand-Up Comedy Showcase @ Flower Girl

An intimate stand-up comedy showcase held inside the lush Flower Girl Greenhouse in Orlando.

Friday, May 15, 2026 8:00 PM · Flower Girl Greenhouse, Orlando

Unconditionally: The Ultimate Pop Diva Celebration Starring Kayla Fischl

A high-energy pop diva tribute show featuring Kayla Fischl performing at the Goldman Theater as part of the Orlando International Fringe Theatre Festival.

Saturday, May 16, 2026 5:40 PM · The Sig and Marilyn Goldman Theater at Orlando Shakes

Date Night

Thornton Park 2nd Thursday Wine + Art Walk

For $10, get a wristband, wine glass, and map of Thornton Park galleries and shops pouring complimentary wine alongside local artist showcases from 6:30–9:30 PM.

Thursday, May 14, 2026 6:30 PM · Thornton Park, Orlando

The Notebook – Musical at Dr. Phillips Center

The beloved romantic story of Noah and Allie comes to life on stage at Dr. Phillips Center for the Performing Arts in a sweeping musical adaptation.

Friday, May 15, 2026 · Dr. Phillips Center for the Performing Arts, Orlando

Music & Nightlife

Throwback Thursday | All Vinyl Night at 480 N Wine Bar

A free all-vinyl DJ night at Winter Park's 480 N Wine Bar — bring your ears and your nostalgia.

Thursday, May 14, 2026 7:00 PM · 480 N Wine Bar, Winter Park

Modest Mouse at House of Blues Orlando

Indie rock icons Modest Mouse bring their electrifying live show to House of Blues Orlando.

Friday, May 15, 2026 · House of Blues, Orlando

SIDEPIECE – Horny House Tour

The house music duo SIDEPIECE brings their Horny House Tour to Orlando Amphitheater for a late-night dance party running into the early hours.

Saturday, May 23, 2026 9:00 PM · Orlando Amphitheater

Outdoors & Active

Run for Resilience 5K

A community 5K run at Bill Frederick Park open to all participants — a meaningful morning out with purpose.

Saturday, May 16, 2026 8:00 AM · Bill Frederick Park, Orlando

Iron Hour – Free Group Fitness at Ward Park Fitness Trail

A free community group fitness session at Ward Park Fitness Trail — all fitness levels welcome.

Saturday, May 16, 2026 9:00 AM · Ward Park Fitness Trail, Orlando

Free Events

Fridays on the Plaza – Free Live Music

The City of Winter Garden hosts free live music every Friday night at Centennial Plaza Gazebo in downtown Winter Garden.

Friday, May 15, 2026 7:00 PM · Centennial Plaza Gazebo, Winter Garden

Essentrics Stretch & Fruit Picnic at Wadeview Park

A free outdoor Essentrics stretch class paired with a fruit picnic at Wadeview Park — a lovely way to ease into the weekend.

Saturday, May 16, 2026 10:00 AM · Wadeview Park, Orlando

Zumba with Julia

A free Zumba class hosted at Fabletics — a great way to dance your way into the weekend.

Saturday, May 23, 2026 9:00 AM · Fabletics, Orlando

Family-Friendly

Cirque du Soleil's Drawn to Life

A jaw-dropping blend of Disney animation and world-class acrobatics from Cirque du Soleil, performed year-round at Disney Springs.

Friday, May 15, 2026 · Disney Springs, Orlando

EPCOT International Flower & Garden Festival

EPCOT's beloved outdoor festival wraps up June 1 — the final weeks to enjoy blooming topiaries, fresh seasonal outdoor kitchens, and live concerts around World Showcase.

Saturday, May 15, 2026 · EPCOT, Walt Disney World Resort