Information Overview

This 5k open water swim across West Penobscot Bay from the Point Lookout Resort Beach (Lincolnville Beach) on the mainland to the island community of Islesboro, illustrates the challenge of providing emergency medical care to Maine's remote communities, including those bound by water. 

It’s not a race, although you can certainly choose to time yourself and compete with your friends-- and you'll find plenty of fast swimmers here to chase!

With a heartwarming spirit, inspiring stories, and a hero's welcome on Islesboro, it's easy to understand why this ocean swim event has grown by leaps and bounds since its inception. A dinner for swimmers the night before, a party at the finish, great giveaways, excellent fundraising incentives, and other perks round out this first class event.

Whether you're here for the physical achievement, the emotional challenge, or the cause, the Islesboro Crossing will hold a special place in your heart and one you'll never forget.

Islesboro Crossing Highlights

  • Saturday afternoon kayak dropoff and packet pickup.
  • Gift bags, T-shirts, and great fundraising prizes.
  • Celebration Dinner at Point Lookout Resort (overlooking the bay) the evening before the swim--included!
  • Guest tickets will be available for purchase so family and friends can attend dinner. Click here to purchase.
  • Mandatory safety and event briefing immediately following dinner (all swimmers and paddlers are required to attend).
  • Celebration Awards Presenation
  • Early morning continental breakfast (with protein offering) before you take off on Sunday.
  • At the finish on Islesboro, a warm island welcome with food and drink, massage, and a visit from the LifeFlight helicopter.
  • Complimentary ferry or water taxi tickets for swimmers and paddlers.


To participate in this event, we ask that you raise a minimum of $175 that will support LifeFlight, a nonprofit organization and Maine’s only emergency medical helicopter service.

We’ll do everything we can to help you meet or exceed your fundraising goals.  Last year, swimmers raised an average of more than $2,000. You’ll have the option of forming or joining a team with other swimmers, paddlers, volunteers, or any combination thereof.

Swimmer Registration Fee: $75 (non-refundable).

Your registration fee is non-refundable, and it does not count toward your fundraising minimum. All swimmers must be able to swim a mile in 50 minutes or less before the event.

Swimmer Fundraising Minimum: $175

To ensure maximum participation in the event, we request that you notify us by June 1, 2019, if you need to withdraw.

Swimmers who withdraw before June 1 will not be responsible for meeting the fundraising minimum

Swimmer Required Escort/Paddler:

All swimmers are required to have their own escort, an experienced adult in a kayak or on a SUP, to paddle alongside them as they cross the bay. While the bay is sheltered from open-ocean, it’s still subject to wind, currents, and water temps in the 60s, all of which demand caution, respect, and preparedness. The paddler is really the first responder, the initial point person in our very detailed safety plan, and he or she should be competent to handle the boat in wind and chop and to provide assistance to swimmers if needed. Swimmers, please select your paddler with these thoughts in mind. Paddlers, please volunteer for a different job if you don’t feel you’re qualified.

Paddlers do not need to pay a fee, but paddlers need to complete the online registration. Please have your paddler register by July 15 so that we can order the Islesboro Crossing t-shirt. 


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