Events and Things to Do in Oldsmar, FL

Sunday, October 4

Featured

Robin Hood & Little John

OCT

4

2:00 PM

Pioneer Park, 420 Main St, Dunedin, FL

Progressive Arts Theater Presents Robin Hood & Little John — A FREE Theater in the Park Adventure! Sunday, October 4, 2026 at...

Share

Saturday, October 17

Featured

Fall Wine Tasting

OCT

17

7:00 PM

917 Louden Ave, Dunedin, FL

Join us for an evening of fun while we taste wines from around the World! Four regions to include Italy, France, USA and the...

Share

Saturday, October 31

Featured

The Great Westchase 10K, 5K & Fun Run

OCT

31

7:00 AM

9902 Brompton Dr, Westchase, FL

Join over 1,300 runners for the 25th Anniversary of Westchase's favorite race, featuring USATF/RRTC nationally certified...

Share

Sunday, October 4

• Robin Hood & Little John 2:00 pm

  Pioneer Park, 420 Main St, Dunedin

  
  

Monday, October 5

• Oldsmar Historical Collection

  11:00 am

  Oldsmar, FL Calendar, 400 St. Petersburg Drive East, Oldsmar

  
  
• Senior Sit & Fit

  1:00 pm

  Oldsmar, FL Calendar, 650 Pine Avenue North, Oldsmar

  
  
• Indoor Pickleball Clinic - Beginners

  1:30 pm

  Oldsmar, FL Calendar, 650 Pine Avenue North, Oldsmar

  
  
• Indoor Pickleball

  2:30 pm

  Oldsmar, FL Calendar, 650 Pine Avenue North, Oldsmar

  
  
• Zumba

  5:30 pm

  Oldsmar, FL Calendar, 650 Pine Avenue North, Oldsmar

  
  
• OPAL Theater

  6:00 pm

  Oldsmar, FL Calendar, 400 St. Petersburg Drive East, Oldsmar

  
  
• Full Body Fit

  6:00 pm

  Oldsmar, FL Calendar, 650 Pine Avenue North, Oldsmar

  
  
• Volleyball Play & Learn

  6:30 pm

  Oldsmar, FL Calendar, 650 Pine Ave N, Oldsmar

  
  

Saturday, October 17

• Fall Wine Tasting 7:00 pm

  917 Louden Ave, Dunedin

  
  

Friday, October 23

• Broadway After Dark: A Halloween Cabaret 7:30 pm

  1899 San Mateo Dr, Dunedin

  
  

Saturday, October 31

• The Great Westchase 10K, 5K & Fun Run 7:00 am

  9902 Brompton Dr, Westchase