Explore Orlando This May 2025 – Mother’s Day Events, Local Events & More

Looking for the best Orlando events in May 2025? This vibrant month brings perfect weather, world-class theater, quirky festivals, and family-friendly activities in Orlando. As local real estate advisors, we know that May is one of the best times to experience Orlando’s vibrant energy, beautiful weather, and strong sense of community. From Broadway performances and outdoor festivals to family-friendly activities, including special Mother’s Day celebrations this month, gives you the perfect glimpse into life here. Here's your guide to the best events happening in Orlando this May.

Top Orlando Events in May 2025

Disney’s The Lion King at Dr. Phillips Center

Location: Dr. Phillips Center for the Performing Arts, Orlando

Date: Through May 18, 2025

Catch the iconic Broadway show featuring breathtaking costumes, stunning sets, and beloved songs. Get your tickets now on the Dr. Phillips Center website. 

Orlando International Fringe Theatre Festival

Location: Loch Haven Park, Orlando

Date: May 13–26, 2025

Celebrate the arts with live theater, music, dance, and food trucks at the longest-running Fringe Festival in the U.S. Plan your festival experience on the Orlando Fringe website.

Gatorpalooza at Gatorland

Location: Gatorland, Orlando
Date: May 17–18, 2025

Live music, crafts, and Florida’s famous gators make this family-friendly fest a local favorite. Visit Gatorland’s website for event details and tickets.

Cinco de Drinko at Krush Brau Park

Location: Krush Brau Park, 2198 Four Winds Blvd, Kissimmee, FL 34746

Date: May 3, 2025

Celebrate Cinco de Mayo a little early with brews, cocktails, and live music at Krush Brau Park. This free outdoor event is perfect for adults looking for a lively way to kick off the festivities in May. Find event details through Krush Brau Park's event listing.

Tacos & Margs Crawl

Location: Wall Street Cantina, 19 N Orange Ave, Orlando, FL 32801
Date: May 3, 2025

Enjoy a downtown bar crawl featuring taco and margarita pairings, giveaways, and a festive Cinco de Mayo atmosphere. Learn more about the event on the Tacos & Margs Crawl page.

Water Safety Day

Location: Oviedo Aquatic Facility, Oviedo, FL
Date: May 3, 2025

Participate in free water safety activities, educational booths, and family fun in Oviedo. Learn more about the event on the City of Oviedo event page. 

Mother’s Day Events in Orlando This May 

Mother’s Day Brunch at The Alfond Inn

Location: The Alfond Inn, Winter Park, FL
Date: May 11, 2025 

Enjoy a buffet-style Mother's Day brunch in the beautiful Conservatory at The Alfond Inn. Learn more about the event here.

Mamas & Mimosas at Far Reach Ranch

Location: Far Reach Ranch, Mount Dora, FL
Date: May 10–11, 2025

Pick blueberries, sip mimosas, and enjoy live music and family fun at Far Reach Ranch. Learn more about the event on the Far Reach Ranch page.

Mother’s Day Ikebana Workshop at Leu Gardens

Location: Harry P. Leu Gardens, Orlando, FL
Date: May 10, 2025

Create beautiful Japanese floral arrangements in a special Mother’s Day workshop at Leu Gardens. Learn more about the event here.

Mommy & Me Spa Soirée at FACE FOUNDRIÉ

Location: FACE FOUNDRIÉ, Orlando, FL
Date: May 9, 2025

Share a pampering spa evening with your child featuring mini-facials and bonding time. Learn more about the event here.

FAQs About Orlando Events in May 2025

What major festivals and celebrations are happening in Orlando this May?
May brings an exciting mix of events to Orlando, from the colorful Orlando Fringe Theatre Festival to family favorites like Gatorpalooza at Gatorland. Special Mother's Day celebrations, foodie festivals, and Cinco de Mayo events add even more variety, making it one of the best months to experience the city's lively culture.

Are there outdoor events and family-friendly activities this May in Orlando?
Absolutely. Events like Water Safety Day, Gatorpalooza, and the Mother's Day outings at Far Reach Ranch offer fun for all ages. Plus, outdoor markets, concerts, and farm festivals make it a great time to enjoy Orlando’s parks, lakes, and family-friendly communities.

Is May a good month to explore Orlando neighborhoods?
Yes! With warm but manageable weather, May is ideal for visiting neighborhoods like Winter Park, Baldwin Park, Horizon West, and Windermere. Many community events, farmers markets, and open houses allow you to experience the lifestyle firsthand while exploring your future neighborhood.

Can attending events in May help me decide where to live in Orlando?
Definitely, from the vibrant arts scene at the Fringe Festival to family activities around Oviedo and Winter Garden, May events showcase Orlando’s diversity. Exploring during this time gives you a real feel for the energy, amenities, and community vibe that each area has to offer.

What is the weather typically like in Orlando during May?
Expect warm, sunny days with average highs around 88°F and occasional afternoon showers. It’s perfect weather for enjoying outdoor festivals, water parks, and lakeside outings. Just pack sunscreen, stay hydrated, and plan for light rain if attending outdoor events.

May in Orlando is filled with energy, celebration, and the perfect blend of city life and community charm. Whether you're here to enjoy the festivals, explore local neighborhoods, or plan your next big move, this month gives you a real sense of what living in Orlando is all about. If you're thinking about making Orlando your home, ALIGN Real Estate is ready to help you find the perfect place. With deep local knowledge and a commitment to your lifestyle goals, we’re here to guide you every step of the way.