Events in May in Maitland

• Sat, 02 May, 2026 - 06:00 PM

  12th Annual Kentucky Derby Soirée

  Venue on Lake Lily - Maitland Civic Center

  96+ Interested
• Sat, 02 May, 2026 - 04:30 PM

  Derby on Park (Kentucky Derby Party)

  Mercedes-Benz of Orlando

  420+ Interested
• Fri, 08 May, 2026 - 06:30 PM

  Spring Open House 2026

  Art & History Museums of Maitland

  Free
• Fri, 08 May, 2026 - 06:00 PM

  Cheers to Kindness Gala

  Venue on Lake Lily - Maitland Civic Center

  55+ Interested
• Fri, 29 May, 2026 - 12:30 PM

  14th Annual Diversity Awards

  Sheraton Orlando North Hotel

  67+ Interested
• Thu, 07 May, 2026 - 05:30 PM

  Wine and Cheese

  190 Independence Ln, Maitland, FL 32751-5625, United States

  21+ Interested
• Fri, 01 May, 2026 - 10:00 AM

  Homeschool Day at the Telephone Museum

  Art & History Museums of Maitland

  USD 7
• Sun, 24 May, 2026 - 07:00 PM

  Ultimate Santana Tribute at Good Times Bar & Grill in Maitland, FL

  Good Times Bar & Grill

  USD 22
• Wed, 27 May, 2026 - 05:30 PM

  Music in the Gallery (collab. with Howie Music + CFC2)

  Art & History Museums of Maitland

  Free
• Sun, 03 May, 2026 - 06:00 PM

  CLEARWATER A Tribute to CCR

  Good Times Bar & Grill

  USD 25
• Sat, 02 May, 2026 - 08:00 PM

  SPEED LIMIT 70 Debut at Good Times, 5/2/26

  Good Times Bar & Grill

  137+ Interested
• Sat, 09 May, 2026 - 09:30 AM

  Art Workshop: Inner Terrain: Abstract Landscape

  231 W. Packwood Ave, Maitland, FL, United States, Florida 32751
• Sun, 17 May, 2026 - 03:00 PM

  A&H Book Club: May 2026 Meeting

  Maitland Art Center gallery

  USD 7
• Thu, 21 May, 2026 - 09:30 AM

  Real Producers Playbook: Ask the Expert Agents

  Venue on Lake Lily / Maitland Civic Center

  Free
• Wed, 20 May, 2026 - 10:00 AM

  Home Inspection Strategy 3h CE

  EXIT Global Realty

  Free