I finally got to log some miles in 2023! But before I get to that, a quick life update. I left my nearly 17-year career with Delaware State Parks back in February! For the last 10 years, I managed the Indian River Life-Saving Station Museum and all the interpretive programming at Delaware Seashore State Park. Making the decision to leave was hard (I literally went to therapy over it), but it was the right decision. My side-hustle has been growing and I was eager to start the next chapter. But I owe my passion for paddling all to that first summer I interned at the park in 2006, when I led kayak ecotours 4 days/week all summer long.

I’m now totally self-employed and it’s amazing! I make my own schedule and now I have so much more time and flexibility to do things with my family and to do things for ME! Like leaving town for two days to log some serious mileage.

Up until mid-June, I really hadn’t spent ANY time in Kent County, MD, but I took a women’s sea kayaking course in June off the Sassafras River. I spent the weekend in a tiny town called Kennedyville and enjoyed the rolling hills and rural scenery for two days. Spending that weekend inspired me to paddle more legs in the upper Chesapeake, but since it’s nearly 2.5 hours from home, it made more sense to do an overnight trip and paddle several legs, rather than driving up there 3 separate times for day trips.

I was so lucky to have a buddy join me for the non-paddling portions of my trip – my Aunt Margaret Ann (a.k.a. “AMA”). She was so kind to drive over from the western shore to shuttle me between paddles and keep me company at the Airbnb I booked in Chestertown. It was also really fun to catch up – something we don’t do nearly enough!

The first leg I paddled was the longest – a 12 mile stretch between Fairlee Creek and Rock Hall. I go up on Wednesday morning at 4:30 to drive up to Fairlee to launch. I arranged for AMA to meet me in Rock Hall around 11:30 a.m. so I would have a ride back to Fairlee.

I launched just before 7:30 and the winds were totally calm. Paddling up Fairlee Creek was like paddling on a mirror and effortlessly gliding through the water. But as I got closer to the mouth of the creek and into the bay, I noticed the incoming tide was RUSHING through the small inlet. It wasn’t choppy, but I could see some wacky little currents. I powered through with a little moment of panic when I thought I was about to fall in, but the funky currents didn’t last long, and before I knew it, I was in the calm waters of the bay. I glanced behind me at the restaurant at the mouth of the creek and it had a giant sign that said “NO SWIMMING. STRONG CURRENTS.” Yes, that sign would be correct. No way would I go swimming there, paddling was hard enough!

Since Kent County has a bit more elevation than most of the Delmarva peninsula, I was expecting to see some small cliffs most of the way, rather than marshes. While this was accurate, I was also not expecting to see as many beaches as I did! I even pulled over on a beach to take a 30-minute call for work! Yes, it was most definitely private property, but I stayed below the high tide line, so technically I wasn’t trespassing.

Another thing that struck me as interested was the number of cool houses along the way. Lots of variety in architecture, from rustic, overgrown bungalows to giant mansions with manicured lawns. Or as AMA describes them, “conference centers” LOL! I also spotted this cool old watch tower. Not idea what/who would’ve used it, but it was cool looking.

As I closed in on Rock Hall, I felt pretty accomplished. I haven’t paddled many long distances yet this season and I wasn’t even all that tired. I felt like I could’ve kept going on south to Ingleside. But since I made arrangements for AMA to meet me, and there were pop-up thunderstorms predicted for the afternoon, I stuck with the original plan to end in Rock Hall.

Here’s the 12.6-mile path I took:

Once I pulled up on “Ferry Beach“, AMA pulled in shortly after – perfect timing! I loaded my paddle, PFD, and other accessories into her car, and locked my kayak to one of the gazebos on the beach. From there, AMA drove me back to Fairlee Landing so I could take my car back down to Rock Hall to grab my kayak.

We had a leisurely afternoon exploring the Rock Hall area and grabbing some lunch. After that, we headed to Chestertown to check into the Airbnb. It was a newer listing so it was super affordable and the hosts were lovely. AMA and I had the entire upstairs of an 1870s historic home. It was two bedrooms, bathrooms, and sitting area, with a tiny glimpse of the Chester River through the trees, all for $100/night ($180 with airbnb and cleaning fees). Not bad!

See Part 2 for the next leg I completed that evening!