Event Details

Sunday, August 8th 2020, this is a free event, we accept donations, if you are racing your contribution is $25.00

Please come and celebrate the life of Tom O'Connor either c one for the paddle out and share with his family many great memories of this great human and celebrate his life or participate in a volunteer 1 mile open water swim, at Sand Key Park, inter coastal side.

Anyone that knew Tom could tell you how amazing of a person he was. He lived every aspect of his life to the fullest and never took anything for granted. He was so unapologetically authentic and he exuded confidence but somehow never came off arrogant. He had a gravitational pull around him that made you want to be near him. Tom had a way about him that made everyone feel special. He was so honestly himself and that brought out the best in those around him. 

Those of us that knew Thomas can speak to how he touched our lives and while he may no longer be with us, we carry on his legacy. Thomas’ first tattoo was the Tree of Life. The roots and the branches are identical and symbolize no beginning and no end. Around the Tree of Life was a phrase written in Gaelic. Translated it said “together we are alive forever”. While you may not have known Tom, you can carry on his legacy. Treat everyone with respect and kindness, attack everything you do with tenacity and grit but most of all, live your life to the fullest because Thomas wouldn’t do anything less. Live Like Tom.

Registration Deadline

The registration deadline is August 7th AT MIDNIGHT.

Packet Pick Up


Casual. Just show up in time to paddle/swim and pick up your Tom O'Connor swim cap.

Event Schedule 


  • August 8th | 6.50am | Paddle out | Sand Key Park, INTER COASTAL SIDE

  • August 8th | 8am | Tom O'Connor Memorial 1 Mile Open Water Swim | Sand Key Park, INTER COASTAL SIDE

  • after party at Smoke and barrel at 10:00 AM

Event Waiver

In consideration of this entry, I, for myself, my heirs, devises, executors, administrators and assigns hereby waive, release and discharge any and all Claims against OWS Crosstraining with Leo, Pinellas County Parks Dept. Pinellas county, A Political Subdivision of the State of Florida, Pinellas County Sheriffs Dept. or organizations, sponsoring or conducting this event, or their employees, representatives, or successors, for any and all damages or injuries I may suffer.  I hereby grant permission for the free use of my name and picture in any broadcast, brochure or account of this event. INSURANCE DOES NOT COVER THESE ACTIVITIES:  BABY JOGGERS, ANIMALS,IPODS/HEADSETS. By completing this event registration, both you and OWS Crosstraining with Leo, agree that the statutes and laws of the State of Florida, without regard to the conflict of laws principles thereof, will apply to all matters relating to this event registration, this Agreement and Waiver, the Terms of Use or other use of the Florida Race Place sites. You agree that exclusive jurisdiction for any dispute with OWS Crosstraining with Leo, resides in the courts of the State of Florida and you further agree and expressly consent to the exercise of personal jurisdiction in the courts of the State of Florida in connection with any dispute including any claim involving OWS Crosstraining with Leo, or its affiliates, subsidiaries, employees, contractors, officers, directors, telecommunication providers and content providers. Entry fees are non-refundable and non-transferable. I must present a photo I.D. to receive my race packet. The race management team reserves the right to accept or reject all entry forms. OWS Sand Key reserves the right in the event of inclement weather, emergency, or natural disaster to cancel the race or move to a later time. In the event of cancellation, there will be no refund of entry fees.