Many, many years ago (early 2019, before I had ever even run 100 miles), I had the thought that while many people did the entire 1200-mile Florida Trail, they were always stuck choosing whether to do the east or the west portion of the trail once they got to central Florida. Almost everyone chooses the East section, as far as I know. Obviously for good reason because there are a lot of road sections on the west, but it is still incredible (it goes through my county and that section is the best section in all of the Florida trail and I am not biased at all).

I searched around, and I couldn’t find any record of someone doing the East & West routes together as a loop. It was then that I started plotting the route. Once I realized it was over 400 miles, I had to hit the breaks on my dreams of doing the route. Instead, I focused on building myself up and doing several multi-day events. However, I’m still not at a place where I can do the route myself, but a friend reached out because I talked about it on the podcast and he wanted to take it on!

Thus, the Bear & Boar 444 was created! This roughly 444-mile route covers the East-West loop of the Florida Trail. I’m very excited as my friend Ary Rochon is raising money for the Florida Trail and will be taking on this ferocious course and establishing a Fastest Known Time on it.

Once completed, he will earn the Bear & Boar 444 belt buckle and go down in history for his awesomeness! I am opening up the ability for people to get Bear & Boar buckle if they also complete the route. In order to do so, you will need to follow the road, supply me with your strava, garmin, coros, etc data and make a $250 donation to the Florida Trail Association.

I have created a Google Map (with suggested crew stops that have mileage on them) and a CalTopo Map for people to follow! Please contact me if you’re interested in the route!