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Events and Things to do in Maitland, FL this weekend

Looking for things to do in Maitland this weekend? Explore our real-time listings for the best concerts, nightlife, and food and drink experiences. From seasonal festivals and comedy shows to free activities, find your next plan with our constantly updated feed of Maitland's most popular events.

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Things to do around Maitland

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Frequently asked questions about Maitland

What are the best events to attend this weekend in Maitland?

The best events to attend this weekend in Maitland include concerts, nightlife experiences, seasonal events, food and drink tastings, and live entertainment happening across the city. According to Eventbrite, some of the best events this weekend include:
  • Brick Fan Event Orlando – A LEGO® Fan Expo | Dezerland | May 2–3, 2026
  • Fragility of Democracy Session 2 - "Myths, Money, and the Making of Blame"
  • Smooth Sessions at Blue Bamboo with Dee Lucas
  • TheXpos Wedding Expo & Bridal show

    • Which events are currently trending in Maitland?

    Trending weekend events in Maitland often reflect seasonal moments, nightlife demand, and popular neighborhoods, including concerts, parties, and special themed events. The trending searches this month in Maitland are:
  • first friday
  • lake lily
  • free easter egg hunt
  • ribbon cutting orlando

    • Which events are coming up in Maitland this weekend?

    In addition to what's happening right now, there are many upcoming weekend events in Maitland, including live shows, parties, food experiences, and limited-time events. Discover upcoming weekend events you won't want to miss:
  • Curry Duck Curry Competition - 19th Anniverserary
  • Stories in Stone: A Walking Tour of the Maitland Art Center
  • Tai Chi with Tisse: Meditation in Motion
  • Brunch Confessions | Mics, Mimosas and Memories

    • Are there free things to do in Maitland this weekend?

    Yes — there are often free things to do in Maitland this weekend, including live music, cultural events, seasonal activities, and community gatherings. Many events on Eventbrite are free or offer free entry options. These are some free events happening in Maitland this weekend:
  • Free Events this weekend