I never quite know when the opportunity will arise to check another item off my Florida bucket list.
When the invite came to cycle across the Sunshine State I jumped at the opportunity.
After my epic eight-day kayaking odyssey on the St. Johns River and a multiday trek on the Ocean to Lake Hiking Trail last year, my insatiable itch for adventure needed scratched again.
Kevin Bolton, 36, a friend who works at Adventure Cycling in Winter Springs, texted me around Thanksgiving with the invite to embark on a self-supported ride coast to coast joined by bike mechanic Ben Chalone, 27, who designed the route.
Over several days and 270 miles, we pedaled from St. Pete Beach to Ormond Beach, navigating our way through lush greenery of the Nature Coast and over the ancient sand dunes of Ocala National Forest.
Other than a weeklong bikepacking journey in 2014 from my hometown of Pittsburgh to Washington, D.C., my cycling experiences have been limited to day trips.
Though there is a paved path from coast to coast, this route was set to take us along dirt trails — meaning I would have to outfit my full-suspension mountain bike with bags for camping gear and clothes.
I accomplished this by borrowing equipment from bikepacking enthusiast J.C. Mazza, who works at Kyle’s Bike Shop in Orlando. In addition to securing gear, my cycling legs needed some waking up before attempting this feat. As days counted down to our Feb. 15 departure, I tried to wrestle myself into biking shape by going on rides four days in a row, mostly around 20-25 miles each.
We aimed for a 5:30 a.m. start on that Saturday when we began our journey. A busy week left me no time to sleep on the night before what was supposed to be a 100-mile day.
Day 1: My first century
On the trail: 5:35 a.m.
Set up camp: 5:45 p.m.
Weather: High 83, low 71; mostly sunny and breezy
Mileage: 101
Memorable moment: Jay B. Starkey Wilderness Park, Spirit Tree
Best snack: BBQ brisket sandwich
Biggest gripe: Suncoast Trail
I don’t know where I’d be without energy drinks and the stubborn persistence it took to drag my tired self to Upham Beach Park in St. Pete Beach for a pre-dawn start. I also owe a major kudos to my girlfriend, Karissa, for agreeing to shuttle me there in the middle of the night.
By the light of flashlights, our significant others snapped photos of us looking groggy but determined with the width of Florida in front of us to conquer.
To ensure we truly rode from coast to coast, we wheeled our bikes across the sand to touch the Gulf with our tires. The saltwater made my brakes squeak all morning, but making our start official was worth it.
The first stretch of day one sent us north on the paved Pinellas Trail, which brought countless road crossings on covered bridges requiring us to muscle our way to the top then speed down.
As the sun rose high in the sky, we found a break from heat as we pedaled through Jay B. Starkey Wilderness Park — more than 8,300 acres with plenty of shade. The natural scenery took us away from urban centers and blessed us with full immersion in pine flatwoods.
The next chapter of our day tested us as we battled midday heat on the Suncoast Trail with cars flying past — just a fence separating us from Suncoast Parkway.
As we cycled on, we stopped for a respite under shade from a magnificent live oak named the Spirit Tree. Its wide branches were adorned with hundreds of ornaments and wind chimes, many of which seemed to pay tribute to lost loved ones.
While we weren’t sure exactly what we would eat on a long break in Brooksville, we quickly answered that question — and our voracious appetites — at Florida Cracker Cook Shack. The down-home establishment specialized in brisket sandwiches, which we devoured before sprawling out in the restaurant’s grassy backyard. If we had spent anymore time there we would have fallen asleep.
After grabbing snacks and drinks at a gas station we cruised downhill and onto Good Neighbor Trail, which took us on a 10-mile ride to Withlacoochee State Forest and our impromptu campsite for the night.
We were exhausted as we navigated dirt trails at the end of a more than eight-hour ride but jubilant as we crossed over the 100-mile mark, marking my first century and longest ride ever.
Day 2: Rain on our parade
On the trail: 9 a.m.
Set up camp: 7:45 p.m.
Weather: High 80, low 46; partly cloudy with a brief downpour
Mileage: 60
Memorable moment: Biking through a rainstorm
Best snack: Wings and pizza
Biggest gripe: Feeling cold and wet, tire trouble
After an incredibly long haul on day one, we felt like we had earned the right to have a leisurely start to our second day. Even though we had “only” 60 miles to make that day, time was of the essence.
Around 9 a.m. we departed camp after enjoying coffee warmed by Ben’s small wood-burning stove. Our first miles of the day found us navigating twists and turns of the Croom mountain bike trail system.
A mostly sunny morning on the paved Withlacoochee State Trail gave way to gray clouds. Our group was all too aware of the approaching rainstorm, but we couldn’t quite time our pace to find shelter before we got caught in the weather’s crosshairs. We were stuck on a 10-mile stretch of roadway with cars buzzing past a few feet away.
As rain beat down on us and sent water splashing up from our tires, I tasted the salt dripping down my previously sweaty face.
To add a little extra drama to our already-adventurous circumstances, an RV narrowly missed sideswiping our group.
We longed for the paved trail and sunny skies that blessed us earlier that day but secretly enjoyed this midday plot twist. It kept things interesting, after all.
As we rolled into Ross Prairie Campground, the temperature had dropped almost 15 degrees, leaving us shivering as we looked for cover from rain and lightning.
As soon as the rain subsided we pedaled onto the Cross Florida Greenway Trail, a beautiful stretch of pavement with rolling hills and incredible scenery. This area was once at risk of becoming the Cross Florida Barge Canal, but was instead transformed into a world-class trail system and public green space stretching 110 miles — from the Gulf Coast near Dunnellon to the St. Johns River near Palatka.
Several miles in I couldn’t help but notice a strange bump with each wheel rotation. As we stopped to inspect, Ben located a bubble in my worn-out rear tire.
I called the Santos Bike Shop, which was about to close, and arranged to have them leave a new tire outside the shop so we could fetch it. That turned a tricky afternoon into a solvable situation.
An immaculate dinner option presented itself as we discovered Zella’s Pizzeria & Italian near the bike shop. It felt as if we couldn’t down enough calories to replenish what our bodies spent that day, but we sure tried with greasy garlic parmesan wings, pepperoni rolls and chicken bacon ranch pizza.
After finding a quiet spot in the woods to pitch our tents for the night and building a small fire to dry our damp shoes, Kevin reflected on his company.
“I am thankful to be doing this trip with an outdoorsman like Patrick and a cycling purist like Ben,” he said.
Day 3: Into the wilderness
On the trail: 8:30 a.m.
Set up camp: 7:45 p.m.
Weather: High 68, low 48; mostly sunny and mild
Mileage: 62
Memorable moment: Scrub jay sightings
Best snack: Swamp pizza and brookie
Biggest gripe: Sugar sand
The air felt frigid as I opened my weary eyes for the third day of our two-wheeled march across the state. My legs ached and my posterior was sore from all that time on the saddle as I willed myself to unzip my tent door and face the day.
A morning boost came in the form of a warm shower and hot breakfast at nearby Santos Campground. While getting clean for the first time in days was worth the time, we didn’t start making serious progress until late morning.
After a stretch of roadway and a gas station stop where a Muscle Milk shake helped replenish my sore muscles, we found ourselves again immersed in wild Florida. A dirt trail took us through Marshall Swamp, where we stopped for pictures on a boardwalk in a magnificent cypress dome.
We made good time on pavement before finding ourselves at the edge of Ocala National Forest, a swath of public land encompassing 387,000 acres of the state. We were excited about the immersion in wilderness but our spirits quickly sunk, along with our tires, as we encountered deep sugar sand. The conditions forced us to walk our bikes as we worried about the time this would cost us.
Our fears subsided as we landed on freshly-graded dirt roads which took us through the width of the forest. We flew down ancient sand dunes and muscled our way through the uphills, barely seeing another soul out there.
We stopped for a quick photo op in front of the Navy’s Pinecastle Bombing Range before passing Farles Prairie Recreation Area. It was shortly after that we enjoyed our trip’s first Florida scrub jay sighting.
Our moods were instantly lifted at the sight of Florida’s only endemic bird species in its natural habitat. Smart and social, scrub jays exist in cooperative family units and bury thousands of acorns — which they claim later.
We counted nine or 10 birds in the span of about a mile. They perched to inspect us and sent curious glances our way.
As afternoon stretched on we landed at Sparky’s Place Restaurant in Astor, where we took advantage of the hospitality and “swamp pizza,” which has an Alfredo sauce base, beef, french fries and bacon bits.
With our bellies full and spirits lifted, we rolled into Lake George State Forest after dark using lights to navigate. We made it most of the way through before finding a quiet place to camp for the night.
Day 4: Speeding to the finish
On the trail: 8:20 a.m.
Finished: 3:45 p.m.
Weather: High 68, low 57; partly cloudy and pleasant
Mileage: 47
Memorable moment: DeLeon Springs pancakes, seeing the Atlantic
Best snack: DIY pancakes
Biggest gripe: Headwinds, International Speedway Boulevard
“We’re going to have tailwinds all day,” Kevin proudly announced to the group as we packed up camp. My tailbones were sore and my legs tired after nearly three days of nonstop cycling, and the thought of having the breeze at our backs on our final day boosted my mood.
As I glanced at our route for the day, it dawned upon me we would be passing by De Leon Springs. It had been years since Kevin visited and Ben had never been, so I described the make-your-own pancakes restaurant concept to him.
“So it’s like hibachi pancakes? Aw hell yeah,” he said.
Better yet, it was only about 5 miles to our breakfast destination. That, combined with the fact we would see the Atlantic Ocean that afternoon, proved a powerful motivating force in getting us moving.
We cruised into the state park on a quiet and pleasant Tuesday morning and quickly got seated at the only table on the restaurant’s outdoor screened-in patio. We scarfed down pancakes and enjoyed coffee during a leisurely stop that felt like a fitting reward for three days of hard work.
As morning yielded to afternoon we found ourselves on the shoulder of International Speedway Boulevard in Daytona Beach where we faced headwinds and cursed Kevin’s incorrect weather forecast. We made a quick stop at a brick road that formed one of Florida’s earliest highways before pedaling onward to the gravel roads of Tiger Bay State Forest.
As we found our way back onto pavement and into Ormond Beach traffic we were ecstatic with our increasing proximity to the ocean.
We made a final push to make it to the top of Granada Boulevard Bridge, taking in views of Halifax River on the way, before we sped down toward the beach.
Karissa and her black Lab, Leo, were there to celebrate the finishing moment. Huge grins stretched ear to ear as our tires touched the Atlantic, the sea foam coating our shoes as we lined up for a last group photo.
Cycling across Florida gave me a rare glimpse into stunning scenery, flora and fauna that make up our state.
Though I was uncomfortable at times along the way, I loved the adventure and seeing the Sunshine State in such a unique way. My weary legs were in need of a long rest, but even then, I knew the trip was certainly something I would do again.
Find me @PConnPie on Instagram or send me an email: pconnolly@orlandosentinel.com. Stay up to date with our latest travel, arts and events coverage by subscribing to our newsletters at orlandosentinel.com/newsletters.
Originally Published: April 11, 2025 at 6:00 AM EDT
