Beginning the Border to Border Calendar Year Triple Crown

This morning I woke up at the room around 6am. I was feeling well rested and ready to rip! Everybody packed up and then we got a ride down to the southern most point. When we arrived there was no one else around and the sun was just rising. It was absolutely perfect. We took some photos and then began heading north! Let the border to border calendar year triple crown begin!

At the monument for sunrise!

It was about 4 miles back to the hotel that we had stayed at last night. Which was right on the trail. So we headed in there and regrouped. Then grabbed the rest of our things and continued walking. It’s such a fun surprise to be setting out with so many other hikers. I expected to be alone for most of this year. So any time spent with friends is a real treat and a surprise.

It feels like a dream being here in the keys.

The sun was already high in the sky as we began road walking across the keys. But the weather was truly perfect. 75 and sunny with a light breeze. I couldn’t have asked for anything more! Once we left the room we walked for a while. A few people headed into a store and a few of us kept going. Then after a couple hours we regrouped at a gas station for our first break. I got a couple snacks, an electrolyte drink, and a protein chocolate milk. Everyone sat in the shade and enjoyed. We were already about 10 miles in for the day too! And it was only just after 10:30am. Not too shabby.

A whole herd of hikers alongside the road.

My loose plan for the day is a bit ambitious though. Obviously it’s tough to say what everyone will want to do. But there is a guy named Jeff who offered for me to tent at his property on Big Pine Key. That would be a 31 mile day. But if I can’t make it that far he said that he could come and pick me up. I’ll just have to see what everyone does and how it plays out. Over all though I need to be averaging about 26-28 miles a day. Especially if I want to buy myself future days off. So I’m trying to do whatever mileage I can, so long as I’m feeling good.

Day 1 and I’m obsessed with these ombraz! They are absolutely perfect sunglasses.

When we left the gas station we continued on for another hour or so. The views were incredible all day. The salt breeze in the air smelt so good, and the ocean was as vibrant as I remembered. Memories were flowing back rapidly as I proceeded. It was less than a year ago today that I hiked this path down to the southern most point to complete the ECT. Every sign we walked by brought back a strong memory of my time down here in early January. It’s hard to believe that I’m already back, less than a year later. With plans even more ambitious.

A lil pit stop!

After another hour or so we came across a covered area that made for a perfect break. It seemed like everybody was still feeling good and enjoying the day. I must say my body was holding up better than I could have ever hoped. The shoulder issue that I had been having before was no longer a problem. I hope it can stay that way!

Long Shot and Nana. Hoping to see some key deer up ahead!

From there we were about 6 miles out from Mangrove Mama’s. A classic spot down here in the keys! The gang planned to regroup there for a late lunch/early dinner. I arrived with Long Shot, Lemon, and Matcha. Then the rest of the crew was a little ways behind. We sat and got waters. I got a virgin pina colada because I could not resist. Then got bacon wrapped dates as an appetizer. They were stuffed with jalapeño and drizzled in a balsamic glaze. The description was far too tempting to resist and they were only about $6. I actually would up loving them too.

Once everyone arrived we all ordered a meal and hung out for a while. We were able to charge our devices there too, which was great because I’d drained the heck out of my phone over the course of the day! For dinner I got fried fish tacos which were delicious. I ate every last bite and almost could have gotten more too. I’m hopeful that my hiker hunger is going to come back in full swing very quickly.

This lunch was so dang good. Fish tacos!

We lingered there for a while before continuing along. But after a while it was getting late and we still had 11 miles to go. It looked like we wouldn’t arriving at the camp spot until 9:30pm. Which is super late! But it’s ok. The keys are always a shit shute, especially when it comes to camping and mileage. I’m just happy to have a safe place to spend the night.

The sun setting on the first day of the year.

The next couple of hours flew by pretty quickly. Then we arrived at a gas station and took our next break there. We only had 6 miles to go to Big Pine Key and our spot for the night. But I could tell everyone was fading fast. There was no obligation to hike all the miles, but it’s also a tough position to be in. Because everyone would rather camp somewhere safe probably rather than stealthing. At this point I just have to do the mileage that I have to do. And everyone else can do whatever they would like.

Most of the crew up ahead walking.

The next hour dragged a big. It was dark and we had to cross over the road repeatedly to jump from one side to the one. The bike path would switch sides now and then. And frequently the path was closed so we had to walk along the busy road in the dark. But we all managed. By 9:30pm we were closing in. I reached out to Jeff and he said it was fine that it was late. He would come by and let us in whenever. It was 4 of us together and then the other 3 were a little ways behind because they stopped off for a break. This is a big mileage day so I do feel bad that everyone tired.

The trail path went right by this outlet of water.


I’ve got to say though, my body really held up. I was a bit sore by the end, but nothing concerning. Just the typical feelings after a 31 mile day of road walking. Considering I’ve been off trail for 6-7 weeks I think I did very well. When we got to the property though I was quite excited. Jeff greeted us and was unbelievably kind. There was a bathroom and sink that we could use. Then we headed to the camping area. There was a big covered area and then a whole empty shipping container. I’ve never camped inside of a shipping container so I absolutely could not resist. That was way too cool to pass up.

A hilarious fake cop sign to help with speeding.

The 30 mile marker. Not bad to make it 32 miles on my first day out.

I was so excited to get inside and get comfortable. I laid my pad out to cowboy camp. Then got situated. Once the rest of the group arrived I headed over to open the gate and let them in. They were sore for sure and I felt bad about that. We’ll see how everyone feels tomorrow. But luckily a lot of the gang doesn’t have goals of a continuous footpath north. So if they want to slow down or skip up, then that’s totally ok! Once they got inside I headed back to relax. It felt so good to finally lay down and stretch. But once again, I’m shocked how ok I feel. It was a big day. But I think I’ll be up to crush some more miles tomorrow.

Sleeping in a shipping container! That’s a first for me.

Right around 10:45pm we got a delightful surprise. Another hiker Dirty Mike was passing through and was coordinating with Caboose. They wanted to surprise everyone. So he came and spent the night with us too. I’m so grateful that this amazing stranger allowed us onto his property for the night. I’ll sleep so much better knowing that we are safe and sound and won’t have any issues. Then tomorrow will begin another long day of walking! Hopefully I’ll be feeling just as good as today.

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Comments 16

  • Chris : Jan 2nd

    Off to a great start! I’m surprised, no Key Lime Pie this time?

    Reply
    • Dan Helfrich : Jan 2nd

      Not to worry. There are quite a few KLP spots all along the way through the Keys.

      Reply
    • Holly : Jan 3rd

      I’m so excited for you … I’ve been following you for quite a while now and I’m looking forward to this big adventure!

      Reply
  • Jess : Jan 2nd

    GO PEG LEG! You got this!

    Reply
  • George in NM : Jan 2nd

    Wow, what ambition. I’m finishing up reading your posts on the CDT, as you finish Colorado and come into New Mexico. I have very much enjoyed every one of them reading. Thank you and Ryan for the details, especially your personal experiences, and for the superb photos.

    And thank you for letting us go with you on this year’s adventures. Happy New Year, and happy and safe hiking.

    Reply
    • Kristina : Jan 3rd

      Hello PegLeg! It’s nice to see you’re in South Florida again- I live in Fort Lauderdale & hope to see you on the Florida Trail!

      On Big Pine Key, go behind the Winn Dixie on Key Deer Blvd to see a handful of deer! They hang out in the shade near the back door, waiting for garbage produce to be chucked out!!

      Sweet Savannahs on Marathon has AMAZING fresh baked Key Lime Pie.

      Robert is Here, outside the Everglades, is also a must stop!

      Reply
  • Jenny L : Jan 2nd

    It’s probably smart to take this huge endeavor on so soon after coming off the cdt. You had some rest up and recover time but haven’t had time to lose your trail edge. I admire your fortitude, I sure couldn’t do it. Few could, but like so many others I really believe in you. You got this.

    Reply
  • Old Man Paul : Jan 2nd

    You got this. God Bless you real good 👍
    Be safe. Watch out for alligators.

    Reply
  • Lin : Jan 2nd

    What a great start! 32 miles, a crew of hikers, sleeping in a shipping container and you’re not even sore!! WOW! Way to go my friend ❤️

    Reply
    • Barbara : Jan 3rd

      Really enjoy your upbeat attitude about your trip! I know it must not be that easy many times! Hope the good feelings stay for a long, long time!

      Reply
  • Ronald Mittelman : Jan 3rd

    And so it begins. First day was a great day and wishing you many more along your way. And Key Lime Pie.!!!

    Reply
  • Chris : Jan 3rd

    Oh no walking is so hard to do. I can’t wait to read about how difficult it was

    Reply
  • Michael Cass : Jan 3rd

    Good for you young lady. If by chance you are in need of breakfast when you reach Islmorada be sure to stop in at Mangrove Mike’s. Great breakfast and reasonable prices. I remain amazed that you can manage this physically, mentally and financially. BTW, in addition to the cardboard cutouts of police trying to slow drivers you will come upon old police cruisers that they park in the median strip in places for the same purpose. 29 degrees in Connecticut and Massachusetts this morning. A wild guess that you are not missing that! Smile and God Bless.

    Reply
  • Ken Rex : Jan 3rd

    Keep on trucking Peg and stay safe.

    Reply
  • Michael Stein : Jan 3rd

    Have care Peg Leg. Really cold weather coming, even for Florida, through the middle of the month. One of your best sources for weather info is Mike’s Weather Page (on Facebook, YouTube, instagram, X & tiktok) & spaghettimodels.com . While his specialty is hurricane season, he is currently tracking the severe cold that is heading to Florida & the Southeast US.

    Reply
  • Jim : Jan 10th

    I hike Glacier and started following you as you hiked “my places.” Do you feel that you are physically stronger, faster, better during prolonged hikes, or are you worn out and dragging a lot?

    Reply

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