Part 3: 220 Miles on a Stand-up Paddleboard

By Nicky Stimpson
October 29, 2021

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Wednesday, September 1 - Day 6

We knew we were going to be grounded for the day and it was luxurious being able to sleep until 0800. A search for coffee shops turned up a gem: Gordon’s Confectionery. According to the locals, if you wanted to know what was going on in town you went to Gordon’s. Hoping the golf cart was street legal, I drove us into town, and slipped the cart into a spot on the street in front of Gordon’s.

Inside we found a group of men sitting at the back table, take-out orders being placed by folks coming and going, and open stools at the counter. My father has a fondness for sitting at a diner counter and it’s been passed down to me. I enjoy bantering with the wait staff and watching the activity, so we sat down and waited to be served. Eggshells were flying, scrapple was frying, and the three ladies working the grill were cranking out breakfast sandwiches. One of the guys at the back table suggested the fresh sausage and eggs so that’s what we ordered. After finishing up Jay noticed that they served fountain sodas. The authentic kind that is made with syrup and carbonated water. He ordered a small cola which was syrupy and sweet and delicious. Staub ordered a vanilla cola. The waitress explained that the whole town is addicted to these and some people even order them with extra sugar.

With our bellies full, we explored a boatyard where the guys geeked out on old “deadrises” and sailboats. We were invited into the machine shop where they balanced props and did all sorts of metal work. It was a wonderful mess and you could tell that some really amazing things were created there.

After a visit to the local museum we made our way back to the marina, where Ed Wigglesworth, CLC’s president, had arrived by car to take Staub’s place. We drove to the local Food Lion for provisions and the guys spoiled me, stopping at the Smith Island Baking Company for a large Smith Island Cake.

SUP Bay Paddle - Nicky Stimpson
"Ed Wigglesworth, CLC’s president, had arrived to take Staub’s place."


Then it was time for John Staub to head back to civilization and for Jay and me to “break in Ed.” I walked Staub to the car and gave him a big bear hug goodbye. It had been quite an adventure and I was sad to see him go. 

The plan for the afternoon was to motor down to our accommodations on Onancock Creek. I had booked an AirBnB located at the mouth of the creek. It was called “The Boathouse” and I had been keeping my eye on it for a while, so I was excited to check in. Unfortunately, Mother Nature had other plans. Just moving the boat over to the fuel dock was harrowing in the high winds. That’s when we decided it would be unsafe to try to motor CLC’s 21-foot powerboat the 17 miles to Onancock. With a heavy heart I cancelled our accommodations and we remained in Crisfield that night. 

A steak dinner had been planned at our AirBnB in Onancock to celebrate the “over-halfway” mark. Instead we cooked up the steak aboard the chase boat while docked in the marina, using Jay’s ingenious portable galley. We talked about the plan for the following morning. Mary would meet us at the boat at 7am, load her paddleboard, and we’d take a look at conditions in the bay. 


Thursday, Sept 2 - Day 7

When I awoke Thursday morning and looked out the window of my hotel room, a stiff wind had the flags at the marina buzzing and horizontal. But instead of second-guessing our decision I got ready and checked out of my room. At the boat the guys and I were quiet as we loaded Helga on top of the spare Kaholo to accommodate Mary’s board. 

Mary arrived and we got her board and gear squared away. Then we left the dock as I ate my dietary “dust” and applied sunscreen. The always-energetic Mary seemed fired up for the challenge. She had been working hard on the logistics for her crew so I think she was happy to get out and paddle for a change. 

As we left Crisfield’s harbor the wind was whipping the water into a froth and the choppy waves near the shore were two or three feet high. Ed said: “This is the calmest part. It’s only going to get worse from here.” Ed seemed very concerned and I could tell he thought we were crazy to take on open water. As we got further out the waves were at four feet, and the sturdy Steiger Craft chase boat was getting tossed around. Mary seemed confident she could handle the conditions. I think I got caught up in the excitement and continued as if we were really about to jump into the water in these conditions. At one point we even joked about how we made sure not to tell our moms what we had been planning.

SUP Bay Paddle - Nicky Stimpson
"'I don’t want to be responsible for this,' Ed announced."


“I don’t want to be responsible for this,” Ed announced, and I exhaled a sigh of relief. It would have been tough even getting the paddleboards off the racks. It was so rough it was doubtful the chase boat could have even rendered assistance once we were on our SUPs. We’d spend a second day in Crisfield. Mary understood our concerns and took it in stride.

When we got back to the dock, Mary unloaded her board and made plans to sail south to Cape Charles later that day with her crew. We secured our hotel rooms for another night and took the golf cart to breakfast. Ed told us it was his birthday. I said, “Ed! What are you even doing here on your birthday?! I feel terrible, especially since we almost killed you!” Jay and I did our best to make sure Ed had a good birthday.

Friday, September 3 - Day 8

Chesapeake Light Craft SUP Bay Paddle - Nicky Stimpson
Day 8: 42 miles, often in very exposed water.

By Friday morning the storm had abated some, but the winds were still creating three-foot waves with the occasional four-footer. Some of the locals advised us on tracks that would keep us in more protected waters. We motored out of Crisfield and down Broad Creek to the latitude of Tangier Island, smack dab in the middle of Pocomoke Sound. I should have paid attention to the distance of this new route. I ended up paddling about 40 miles that day! 

At first glance the waves looked manageable so we dropped my board into the water. I sat on the swim platform waiting for the right moment to hop on the SUP. In such rough conditions, the only way to transfer from the chase boat to Helga was to jump into the water, then clamber onto the paddleboard . When I go surfing (which is not as often as I like) I have the opportunity to paddle out into the waves to get in a warm-up and get used to the conditions. But that day was like getting dropped into the middle of the ocean. No time for a warm-up. I had to get into the rhythm of the waves and rely on my reflexes to stay upright.

SUP Bay Paddle - Nicky Stimpson
"That day was like getting dropped into the middle of the ocean. No time for a
warm-up. I had to get into the rhythm of the waves and rely on my reflexes
to stay upright." 


I picked my way through the chop in Pocomoke Sound as Jay’s voice crackled over the radio: “Nicky, Nicky, Nicky, no need to respond. Just wanted to let you know that you’re in one of the widest stretches of the Bay.” The western shore was over the horizon, and some of the huge waves overtaking me were so loud that I thought it was an approaching power boat. 

Instead of surfing down waves, I conserved energy and maintained my balance as the wind and tide carried me along towards Cape Charles. Throughout the day Jay would check in over the radio with an update on my distance and the state of the tide. For the most part the long leg was uneventful. Ed caught some great pictures of me sliding down waves.

SUP Bay Paddle - Nicky Stimpson
"Ed caught some great pictures of me sliding down waves."


As we got closer to Cape Charles I told the guys I wanted to land at the town beach where a party was planned for the finish of Bay Paddle. That day the relay teams and remaining solo paddlers had finished the journey and were celebrating in Cape Charles. The remaining solo paddlers were Alessia in her surf ski, and local Annapolis paddlers Brian Meyer and Mark McCulloh, each in outrigger canoes. The three of them got to make up ground the day before because they did not have safety boats and because surf skis and OC-1’s are better suited to rough waters. My goal that day was to land at the beach and join the party! I told Ed and Jay what I wanted to do and they said, “Okay! Let’s go to the beach.”

An endurance trip of this sort is a series of point-to-point legs. Paddle to a waypoint, arrive at that point, then paddle to the next. Just because you can see a waypoint doesn’t mean it’s all that close! At 15 miles out Jay directed me to a point and said, “Cape Charles is just around the corner from there.” It sounded easy enough. So I kept on paddling. After a while Jay was on the radio, “Nicky, Nicky, Nicky no need to respond. You are 10 miles from Cape Charles beach.” The chase boat maneuvered close, and Jay asked if I was okay. I told him that 10 miles was a lot to take on after an already long day. I said I would do as much as I could. 

As I paddled along I would look at the point and then at my watch. I decided to give myself a deadline of 5pm. If I did not make it to the point by 5pm I would shut it down. I paddled on mechanically, using pure muscle memory. Just before 5pm Jay was on the radio again, “Nicky, Nicky, Nicky you are 8 miles out.” That’s when I broke. I dropped down to my knees and tears welled up in my eyes. I tried to compose myself and spoke into the radio, “I’m calling it.” It wasn’t a defeat by any stretch but my emotions got the best of me for a moment. After taking a minute to reflect, I paddled over to the waiting chase boat. As I climbed on board, Ed said, “That was insane.”

We motored into Cape Charles Harbor and docked the boat in a slip at the Cape Charles Town Marina. None of us had been to Cape Charles before and it is a great little town. Since it was Friday night the place was hopping! Jay and Ed went into town to try to find the Bay Paddle party and I stayed back at the boat to just be still for a bit. 

Jay found the party at a park in town, not at the beach. So, it’s just as well I didn’t land on the beach as it would have been a major let down. After I whined about a painful toe, Jay found me a ride and got me to the party. It was great to connect with the other paddlers who told me their stories of paddling under the bridge portion of the Chesapeake Bay Bridge Tunnel and how they saw dolphins and the occasional shark. 

I stayed long enough to chat and grab a quick bite to eat. Then I hobbled back to the Steiger Craft and took some Advil. The next day I had about 20 miles to go in order to complete my journey. Even in my exhausted and almost delirious state I knew I had 20 more miles in me. 


Saturday, September 4 - Day 9


Chesapeake Light Craft SUP Bay Paddle - Nicky Stimpson
Day 9: 28 miles under the Bridge-Tunnel to the finish!

The next morning was chilly as I woke up in the cabin of the Steiger Craft. It was the last day and it was bittersweet to be at the end of this incredible journey. In the weeks and months leading up to this event I would chat with Carleen during our early morning paddles. I would talk about how the word gratitude always came to mind when I thought about my involvement with Bay Paddle. I was grateful that I could physically take on this challenge, grateful that my husband and boys were understanding of the time that had gone into my training and the trip, and grateful that Chesapeake Light Craft, my employer, was not only allowing me but actively supporting me on this epic adventure. Not many people get a chance to do something like this. It was a once-in-a-lifetime opportunity. 

That day my parents and my boys were going to join us on the boat to cheer me on and watch my big finish. We piled everyone on board and motored to the spot where we left off the previous day. Hurricane Ida’s remaining winds had finally dissipated and I had a light tailwind at my back. Some gentle rolling waves pushed me past Cape Charles under overcast skies.

SUP Bay Paddle - Nicky Stimpson
"After taking a break I joked, “Okay, queue the dolphins!” And that’s just what happened."


After a couple of hours Fisherman Island National Wildlife Refuge, or Fisher’s Island, as it’s commonly called, came into view.  Throughout the trip I was always on the lookout for dolphins. I had seen them as far north as Annapolis during one of my training days. I just knew I’d see them at last as I reached the ocean. After taking a break I joked, “Okay, queue the dolphins!” And that’s just what happened. Once I stood up on my board I could see a dorsal fin rise out of the water. There they were! I was excited and nervous as I began to paddle toward a large pod. You always hear stories of dolphins helping people in danger but they are also really big! I was worried one would surface and accidently thump my paddleboard. I got so close I could see air bubbles surfacing just a few feet in front of my board. Then, for some reason, I looked over my right shoulder, braced my blade against the water and saw the most amazing sight. The water had gone clear and, just below the surface, I could see a huge school of fish and something shark-like---perhaps a dogfish---just below my board. And I saw a four-foot shark lurking below the school of fish.

Chris was equivocal as to where the finish would be. But if I was to become The First Woman to Paddle the Entire Length of the Chesapeake Bay on a Stand Up Paddleboard, I wanted to make sure I got to the Atlantic! So I paddled up to and through the bridge. It was the longest stretch I had paddled the entire trip! The amount of water funneling between the bridge and the island was intense. It felt like I was paddling through concrete and I thought I would never get there. 

Once through the bridge I was ejected into calmer water. I decided to paddle out to a buoy about a half-mile away to make it official. That was it, I was done! There were no fireworks or brass bands, but it was a great way to finish my journey. Once back aboard the chase boat, my Mom presented me with a Wonder Woman towel and there were plenty of hugs and high fives to go around. On the way back to Cape Charles we spotted a few more dolphins.

SUP Bay Paddle - Nicky Stimpson
"That was it, I was done! There were no fireworks or brass bands, but it was a great way to finish my journey."

SUP Bay Paddle - Nicky Stimpson
Nicky with her sons at the end of a long journey.


At the dock I was greeted by Chris and some more hugs.We hung out on the boat and ate sandwiches made from a variety of goodies supplied by my Mom. It was nice to have a moment to relax and digest the journey with everyone. Then it was time to say goodbye to my family. I still had to help the guys unload our gear, so my parents took the boys. I would see them the following day. As we were unloading, John Harris arrived in a CLC truck. Cart after cart of gear was rolled up to the truck, and John transferred his own dunnage aboard the Steiger Craft. We left John with the best of our remaining provisions and hopped in the truck for the long drive back to Annapolis. John pointed the boat south for Virginia Beach for a photo shoot rendezvous with his 31-foot proa, Madness, then piloted the Steiger Craft 170 miles back up the Bay to Annapolis. 

Before this journey I worried that having completed such a demanding voyage, I would never get on a paddleboard again. I am happy to report that a week later I was back on my (very tippy) carbon race SUP, paddling with my friends across the Bay from Sandy Point State Park. under the spans of the Chesapeake Bay Bridge. Helga was taking a much needed rest on her rack in my carport as we prepared for the upcoming Bay Bridge Paddle Race. 


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