Eastern Bay & Chester River – Upper Chesapeake Bay Great Loop Cruising

We had explored just about all we could along the Choptank River on the Upper Chesapeake’s Eastern Shore, so it was time to transit to the next bay north.

After some weather moved through, we ventured back out from Oxford (with a couple quarts of ice cream, of course) and passed through Tilgman Narrows.

We saw some of the cheapest marine diesel there, but unfortunately we didn’t have much room in the tanks to take any on.

With a transit up the coast a bit and we were on the Eastern Bay with new adventures awaiting us.

This tale covers August 20 – September 2, 2025.

As always, here’s the video version:

Stop 1: Dividing Creek Anchorage – Wye Island, MD

Wye? Y-Not!

With Hurricane Erin off the coast and predicted to have some higher winds and tidal effects along the Chesapeake, we found a short weather window and puttered over to the Wye River from Oxford.

We selected Dividing Creek to anchor, which was delightfully protected from just about every direction and had plenty of depth if the water got sucked out from under us.

There are dozens and dozens of wonderful anchorages around Wye Island – but we selected this one because there’s a kayak launch at the head of the creek for shore access to explore the island’s many trails.

We spent a mesmerizing 3-nights in near seclusion with barely a nudge on the anchor chain – listening to the eagles, egrets and coyotes, watching the sea nettles swim by, paddle boarding and going ashore for hikes and runs with foxes & deer.

Ahhhh…

Some seek out fancy resorts for relaxation.

But this.. this is our bliss.

Stop 2: Thompson Creek Anchorage – Kent Island, MD

Another boat-up winery?? We’re in.

After the winds died down, we left our protected anchorage off of Wye Island and headed to Kent Island.

Spotting Cascia Vineyards along Cox Creek with a dinghy dock, we verified we could use it with the owners. While you can anchor right in front of the dock, we opted to tuck down around the corner in Thompson Creek for a little more southerly protection.

This is an amazing winery with a great selection of tasty dry French-style wines, with all grapes grown on site. We had a relaxing afternoon sitting under a shade tree sharing a bottle of their Viognier.

After wrapping up a few more bottles to bring aboard for later, we headed down the creek to a town dinghy dock within walking distance of a grocery store to pick up a few items.

With the tides extra high still from Hurricane Erin and a null moon, the dock was underwater – so we came prepared to wade ashore.

Having a drone onboard not only gives us lovely photos & video to share with you – it’s extra handy for scoping things out in advance. That’s why we call our drone ‘Scout’ (Chris just got a new DJi Mavic Air 3 to replace our broken Pro).

Stop 3: Kent Island Yacht Club – Kent Island, MD

After a lovely visit to the winery on Kent Island, we moved over to Kent Island Yacht Club, where we had made a reservation for a couple days.

Our goal was to hit the Cross Island Trail with the bikes, and the club was nicely located along the narrows with access to dining and the trail.

They also give a fabulous discount (1/2 off – just $1/ft!) with our MTOA membership, which includes Yacht Clubs of America reciprocity.

We timed our arrival for slack tide for minimal current – which whips through this channel. But with higher tides than normal thanks to a recent hurricane passing off the coast, there was still an opposing current to the winds. Which made docking trickier than anticipated.

With the help of folks coming over from the tiki bar to help secure lines, we got ourselves docked. And then hit the tiki bar ourselves to make new friends.

The yacht club is very casual and chill – offering a clubhouse, pool and bars. We arrived on a Sunday so only got to briefly experience it before they closed at the start of the week.

We spent the rest of the time crossing the island multiple times by bike and running on the amazing shaded and scenic trail.

And thanks to a local’s tip at the tiki bar – we found Friendlys – a gas station serving amazing Indian food (and a fully stocked liquor store).

We only got to one of the many waterside grills around us (Dockhouse), but heard lots of recommendations for the others. Only so much dining out one can reasonably do on a 2-night stay!

Stop 4: Cacaway Island Anchorage – Langford, MD

We timed our departure from Kent Island Yacht Club for an afternoon slack tide – enjoying swimming some laps in their pool as we waited.

Why? Because the currents rip through Kent Narrows, and we had to pass through a narrow drawbridge. After watching several boats crab through, we decided – what’s the rush?

After we cleared the bridge, we stopped at Piney Narrows marina for a pump out, which was free with fuel – so we topped up the tanks too.

And then we took a right onto the Chester River to explore.

First stop, we veered up Langford Creek to a top rated anchorage off of Cacaway Island.

It was so serene and tranquil midweek that our intended one-night turned into two.

We enjoyed paddleboarding around the island and lovely sunsets. We even got in a little work for our ‘day job’ over at the Mobile Internet Resource Center (that’s Chris hard at work watching a Starship launch while soaking in the hot tub.).

Yup. Life is rough.

Stop 5: Chestertown Anchorage – Chestertown, MD

Labor Day weekend was upon us, and it can sometimes be tricky to find the right place to ride out a holiday weekend for us nomads.

It’s a weekend when recreational RVers and boaters have a chance to come join us for a few days. Which means the waterways can get full of zoomy boats, and we’d prefer to be out of their way.

We selected Chestertown as our destination – located up the Chester River. It’s a smaller town that didn’t seem like it’d be a party central.

There’s a city run marina that offers reasonable rates and a free dinghy dock, and plenty of anchorage space across the way. With the lovely weather, we opted for the anchorage.

We enjoyed exploring around this quaint historic town for a few days – utilizing the lovely rails to trails path for running & walks, an abundant weekend farmer’s market and several locally owned restaurants. There’s even a nicely stocked natural foods store (and a full grocery about 2 miles away).

Our fellow boat & van nomad friends Patti & Steve had also selected Chestertown for the weekend, and it was awesome to catch up with them.

All and all.. a great place to hide out from potential chaos.

Stop 6: Reed Creek Anchorage – Centreville, MD

We left Chestertown early morning on Labor Day to avoid recreational traffic, and it was a lovely cruise back down the river.

We selected Reed Creek near the mouth of the river to drop the hook for the rest of the holiday weekend – which was an absolutely perfect spot to chill overnight.

Lovely and protected, and not a single zoomy boat all day long.

This anchorage can easily fit dozens of boats, but we only had a handful for our stay. Only downside, no easy shore access – otherwise, it would have been tempting to stay longer.

Real Time Update

We just wrapped up a nearly 6-week jam packed stay in Baltimore, and are out for a final few days of cruising around the Upper Chesapeake before we start preps to haul out and winterize. Our next travelogue will wrap up these final adventures of the cruising season.

Blooper, our van, is already awaiting us – thanks to great train access in this region we were able to get her repositioned from Norfolk.

Once we’re moved back into the van and the boat is ready to hand over to the yard – we’ll be starting our southerly migration where we already have a booked calendar of time with friends, family and catching up on doctors appointments.