At 4 a.m., I am jolted awake by the sound of waves crashing close to my head. The tent fly is flapping against the wind. I sit up and my first sensation is grit in my teeth. Rubbing my eyes, I discover my face, hair and body are coated in fine sand. Not the way I wanted to start my day. I brush myself off and fall back to sleep.

In the morning, the wind is still howling. The waves are three feet high and tightly spaced. Every few sets, a wave crashes against the riprap flinging spray over the seawall. It’s the sixth day of my Chesapeake Bay tour and I’m trying to figure out if this is the dream adventure I’d planned for my 50th birthday.

Chesapeake Bay Birthday: Angler Celebrates with Trip of a Lifetime

fishing kayak sits on the banks of the Chesapeake Bay during John Hostalka's birthday tour
The best gift ever. | Feature photo: John Hostalka

Background Check

I got into kayak fishing 10 years ago. When I bought my first kayak, I looked at a map of Chesapeake Bay and imagined the cool places I’d discover in my new boat. After fishing from the bank for years, I couldn’t wait to explore creeks, rivers, bays, points and islands on this treasure map.

After a decade of exploring the bay, there were still isolated locations too distant to reach on a day trip or weekend camp. To see the unexplored stretches of the bay, I dreamed of kayaking from one end of the bay’s eastern shore to the other. When I turned 50 years old, I figured it was now or never.

map of the John Hostalka's Chesapeake Bay kayak fishing tour

Treasure Map

The Chesapeake Bay is 250 miles long from the Susquehanna River to the Atlantic Ocean. The eastern shore forms a three-state peninsula between the bay and the ocean.

The Chesapeake drains 64,000 square miles of land from Virginia to New York. Nineteen rivers and 400 creeks empty into the bay. The total shoreline is 11,000 miles long.

The bay water is salty in the south and fresh in the north; the first part of my trip focused on redfish, speckled trout and striped bass, transitioning to largemouth bass and snakehead.

In summer, the wind primarily comes from the south. I planned to launch near Cape Charles at the mouth of the bay and pedal north with the wind. In early July, after receiving blessings from my family and taking off work, a friend shuttled me and my gear to the starting point.

The Routine

Once I was underway, the rhythm of days on the water fell into a regular pattern. In the morning I packed my tent, rolled up my sleeping pad and sleeping bag and organized my gear.

The tent and sleeping stuff went in drybags jammed inside the front hatch of my Hobie Outback. With a cold cup of instant coffee in my cupholder, I pushed off and turned north.

I spent the rest of the day in my kayak. I ate breakfast, lunch and occasionally dinner in the kayak.

I pedaled two to three miles per hour while trolling with two rods. I followed the Eastern Shore working my way north to the Pocomoke Sound.

From there my route took a hard left, crossing open water at Watts Island to Tangier Island and island hopping from Smith Island to Hoopers and Taylors Island into Maryland.

On average, I made about 25 miles a day. There were a few days with perfect conditions where I completed more than 30 miles. When the fishing was good, I might only make 10 miles in a day.

By late afternoon, I began scouting for a sandy beach where I could camp. I chose spots away from houses, without trespassing or wildlife refuge signs.

man drags fishing kayak over a white sandbar
The daily grind. | Photo: John Hostalka

Fishing the Chesapeake

Covering an area seven times larger than New Hampshire, the Chesapeake Bay watershed is massive and diverse. Speckled trout, redfish and striped bass in the south and largemouth bass, snakehead and striped bass in the north.

With a mixed card on the roster, my most valuable player was a soft plastic jig. I used the all-purpose lure to catch redfish, cobia, trout and striped bass.

For most of the trip, as I pedaled north, I trolled a five-inch, weedless soft plastic on one side of the kayak and a four-inch on the other. When the water depth changed, I’d use Tactical Anglers clips to switch to a heavier or lighter lure.

In addition to trolling soft plastics, I kept a topwater lure rigged and ready for surface action. During prime fishing times in the morning and evening, I switched to working topwater lures over grass edges, tree stumps or snags, creek mouths, points, riprap and current seams.

a fishing kayak floats by the shore of the Chesapeake Bay
Unexplored honey holes. | Photo: John Hostalka


On the third day I lost my spool of light leader material. Luckily, I found a few feet of 60-pound leader in the bottom of my kayak. Without a tackle shop on the way, I had to improvise.

I used the 60-pound on my light rods and caught a 27-inch trout, the biggest trout of the trip. Along the way, I met several generous anglers who donated their leader line.

Eating Out

There were no grocery stores to restock food, so I cached food in waterproof containers at four-day intervals. In the weeks leading up to the trip, I paddled out to drop locations and stashed the provisions and jugs of water.

To maximize time for pedaling, I skipped cooking entirely. My ready-to-eat meals included canned soup, granola bars, trail mix and precooked rice packets.

a colorful outbuilding sits on a pier
Small towns were rare, so Hostalka stashed supplies along his route. | Photo: John Hostalka


Most of the Lower Chesapeake is a cellular dead zone. In the first days of the trip, I suffered technology withdrawal. I was forced to live in the moment. Regardless of the weather, I had to get up every day and go to work, moving my kayak farther up the bay.

When it was hot, I dealt with the heat. When it was windy, I dealt with the wind. If the bugs drove me mad, I dealt with them, too. I had to push forward. I became at ease with the unknown and learned to trust my instincts and read what nature was telling me.

Favorable weather for the first week got me halfway up the bay. From there I ran into a big thunderstorm near Smith Island, and then the weather switched to more overcast and cloudy days.

There were windy patches that forced me to cautiously move forward. I had to adapt my expectations to the weather at hand.

a beach campsite with campfire during John Hostalka's Chesapeake Bay tour
Home sweet home for the night. | Photo: John Hostalka


As I traveled, redfish and speckled trout catches were replaced by striped bass and white perch. Shorelines changed from beaches and low, marshy islands to high clay bluffs.

The effects of shoreline erosion were apparent. Jetties and seawalls lined almost every inhabited shoreline. In some areas, acres of trees were standing in the water; is this a sign of rising sea level?

As I neared my home water, familiar landmarks came into view. The water changed from green and transparent to turbid and brown. Shorelines crowded with houses preceded a decline in water quality.

a waterside building collapses into Chesapeake Bay in signs of shoreline erosion
Signs of shoreline erosion. | Photo: John Hostalka

Finish Line

On the last day, I made an early morning crossing near Howell Point and followed the western shoreline past Aberdeen Proving Ground.

kayak at boat ramp after a Chesapeake Bay fishing tour
The end of the trip is bittersweet. | Photo: John Hostalka

As the day drew to a close, I made my way toward my final destination, Havre de Grace. The south winds and low, dark clouds increased as I neared the last stretch of my journey.

I took a few hours to explore some remote snakehead spots I’d always wanted to check out. I caught a few fish and missed a few more.

Within sight of the Jean S. Roberts boat ramp, the storm hit. The first gusts of wind nearly knocked me off the kayak. To avoid a lightning strike, I pulled my fishing rods out of my crate and laid them behind me

I stayed calm and pedaled for cover. Lightning cracked all around. I was in the last hour of an epic adventure and nature was going to test my mettle.

The first sheets of rain came in sideways and stung my face. I put all I had into the pedals, finally pulling under an old railroad bridge. I clung to a stone abutment to block the wind.

Despite the raging storm, I couldn’t help but laugh. I realized a decade-long dream and kayak fished the length of the Chesapeake Bay. After the storm passed, I covered the last mile and made it home.

Cover of Kayak Angler Magazine Issue 50, Fall 2023This article was first published in the Fall 2023 issue of Kayak Angler Magazine. Subscribe to Kayak Angler Magazine’s print and digital editions, or browse the archives.

The best gift ever. | Feature photo: John Hostalka




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