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Backside Pillbox Hike (President’s Day)

  • Lanikai Pillbox (Backside) 1148 Kamahele St Kailua, HI, 96734 United States (map)

Skip the crowds on President’s Day and get the best of the Lanikai Pillboxes with us by hiking up the backside! The lesser-known Ka’iwa Ridge Trail is a local treat to see the sweeping views of the windward side without fighting crowds for parking or footholds… it’s a little friendlier to beginner hikers, too, without the exposed ridges popular to the “front side.”

Make sure you map your way to us at the end of Kamahele Street - we’ll start at 7am sharp so make sure you get to us on time so that you don’t miss the pack! Bring some good hiking shoes and maybe a water bottle, too. This is a dog-friendly hike, so if you’ve got a sweet pup they’re more than welcome to join. Add a little extra challenge, if you’d like, by bringing along your own ruck pack or sandbag!

This event will be lead by Tim Connelly, 2023 Oahu Pentathlon record-setting Solo Trek athlete and multiple time Ironman, retired Army General, plus all around good dude. You can contact on the day of the event at (407) 487-6177

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February 16

Flat Island Swim