The Round Island Walk

By Jake Ludemann with Sam Evans and Will Kelly
August 20, 2017

We had never heard of anyone doing it successfully. In fact, the one attempt we knew the most about was waylaid and abandoned after the discovery of a corpse half buried in the sand on the beach off of the 18th tee box at the Big Club. Now I have to give credit to Ted Ahrens and Crosby Cook for starting it off. They completed the North side, paved the way, and gave us the inspiration to attempt a hike that many have thought about, but none have (to our knowledge) completed in one day: The Round Island Walk.

I was at the Pequot one July night with my good friend Will Kelly. Over a few rounds we talked about doing the full round island hike. As the Guinness kept flowing, the subject kept reemerging. But like most ideas that are born in the waning hours at the Pequot Inn, the morning erased the exuberance and commitment we had felt the night before. The idea sat idle in the back of my mind for a few weeks. It probably would have stayed there if not for Will. He revisited the subject and asked if I was serious. Not one to back down from a challenge I decided, “Well why not, can’t be that hard right?”

And so we started planning. We studied the island on GoogleEarth, gathered all the information we could from Ted and Crosby, and examined tide charts to find the best day to embark on our journey. Ideally we would want to start on a mid outgoing tide so there would be more land to walk on on the North Side. About a week prior we drafted Sam Evans into doing the hike with us. Three was a good number, four would be a crowd. Sam had walked the South Side of the island before. This, coupled with Ted and Crosby’s knowledge of the North Side gave us a pretty good picture of what we were up against.

Will, Sam and Jake

So the planning went on and on. Our group was diverse in their perception of the difficulty of the trip. Sam thought it would be a breeze and didn’t really see the need for our detailed planning. When asked what he was going to wear on the trip, he looked confused and said, “You don’t think I can just wear flip flops?” I was prepared for the worst. I packed a med kit and made everyone carry chem lights and headlamps. Will, not being from Fishers, didn’t really know what he was getting himself into. Our predictions on the amount of time it would take reflect this and are as follows. Sam: 12 hours, Will: 10 hours, me: 14 hours, and we would be walking home in the dark. Finally it was go time. I arrived on island early the day prior to do water bottle drops around the island. We knew drinking water was going to be a problem. The water drops were planned fairly well, evenly spread out to make sure we were always flush. With the drops set, we were good to go.

We had a few beers at the Quot on the eve of our walk and I went to bed around 10 pm, alarms set for 5 am wake-up with the coffee ready. I awoke to the faint beep of my alarm being drowned out by the sound of torrential rain and claps of thunder. Not willing to give up before we had even started, we pushed our start time by an hour, and hoped the storm would pass.

When I awoke the second time the sky was gray and there were intermittent drizzles, so the plan was a go. Parked at the Evans’ house, Sam, Will and I made our starting trek out to the first entrance of South Beach. August 12, 2017, 6:45 am on the dot, we were on the coast and cruising west. After rounding Race Point and heading east, the first few hours we were hammering, brimming with confidence and looking at each other with expressions of “we’re going to crush this”.

We knew the North side was going to be the challenge. It was a steady pace until the Hay Harbor crossing. Due to our late start time, we missed low at HHC. We had to swim the channel instead of a chest high stroll across. Will had the good sense to pack some garbage bags. He swam across the channel, bag and shoes waterproofed in the garbage bag. Once his gear was dry and secure on a rock he swam back for us to do the same. Once we were all across we trekked onwards and eastbound.

Island views

The Island is spectacular. The views are just stunning and every time we stopped to take a breather we could enjoy them. But when we were on the move, our eyes had to be trained on our feet. Be it boulder hopping, or traversing slippery and loose cobble, a misstep could have meant a twisted ankle or worse, which would have ended the journey. I’ve fished this island up and down (mostly at night) but some of these views during daylight are just breathtaking.

15+ miles done…

A few more hours in we started to realize what we had really got ourselves into. Between swims, dense growth, boulders and loose rock, the North side was a challenge. We were headstrong and dedicated; we wanted to be the first. Our last water drop by the castle was a welcomed break. We took our shoes off, changed our socks and made a bagel with peanut butter, knowing the entire South side still loomed in front of us. 15.2 miles down and still the South side ahead of us. By this point, we were all feeling it. All conversation and banter had long since been replaced by silence. Everyone hurt. We became aware of things that we hadn’t thought of during planning. Little things, like the fact that because we were walking the same way the whole trip, your right foot would always be on the top of the slant of land that headed towards the ocean. As a result, everyone’s’ right ankle was aching by the time we had made it halfway.

While at the castle. I remember a distinct feeling of, “The worst Is over, the South side is boulder and beach, it should be a breeze”, and I could see Sam and Will thought the same. I don’t know if this is what I really thought, but I think we all needed some hope – motivation to keep going.

We turned the corner. A foggy, cloud covered, boulder strewn South side lay before us.

Now the South Side and North Side are vastly different terrain-wise. The North seems to be a ton more sand, vegetation, mud, reeds and smaller rock. It also is composed of coves, hundreds of them it seemed to us. The Island is seven miles from point to point, but the coves made it more than double that distance.

We pushed on. Already 15+ miles in, it seemed like the finish line was getting closer. The one thing you don’t account for are the many inlets and points. You pass one and think you are way closer than you are. Around every point we’d think, “Oh, Choc must be next.” And then you turn that point and see a stretch of boulders you’ve never seen before or, if you’re lucky, a small spit of sand to walk on. This seemed to go on for ages. Every time you were closer, but by this time we were all drained and the end seemed farther and farther away.

We finally made it to Chocomount. A group of good friends were diligently waiting to check up on us. They offered us beers and Sam took them up on an ice cold PBR to soothe some leg pain. At that point I didn’t blame him. We pushed on in silence, all just set on finishing and getting it over with. Don’t get me wrong, we were all still in good spirits, just exhausted, with many miles to go. Izzy (Isabella Beach) was the next waypoint. Izzy was also the last water drop point. When we made it, we didn’t even stop for water, knowing that sitting down carried the inherent risk of not being willing or able to get back up again. Our only thoughts as we left Isabella were just putting one foot in front of the other. You think about every step when every step hurts.

We were hell-bound to make the finish before dark. Finally, South Beach was in sight. A welcomed one at that – our last push. It was foggy. There was heavy cloud cover and hard sand as we made our way to our round island starting point. To our surprise, a cocktail party at the Rogers’ gave us a thunderous applause and cheers as we passed by their view, we all looked at each other and I could see the smiles on Sam’s and Will’s faces. I can’t lie, it was a great feeling and I think we walked a little taller and faster as we approached the finish line. We each touched the brown pylon that marks the first entrance of South Beach, our exact starting point. Almost immediately after that we were all on our butts, shoes off, unwilling to make the small walk back to the Evans’  and the car. Exhausted, legs cramping, and most likely dehydrated.

We finished. 23.19 miles. 12:26:27 hours.

“We were all on our butts…” Jake, Sam and Will back where they began. Photo credit Jane Crary

Now, when you think of a round island stroll, it seems like a relaxing thought. A weekend jaunt, great views, good friends relaxing, and sunshine. That’s what we thought, and we were mistaken. There were times we were all miserable, (and I can’t speak for everyone, but walking became a much harder task in the ensuing days). But with all the soreness, the aches, the poison ivy, the ticks, the bee stings, came a sense of accomplishment. We had completed the task we had set out to do, and that felt great!

Check Also

Thanksgiving Weekend ~ Fishers Island Style

Don't miss a thing!