Choptank River Adventures – Upper Eastern Chesapeake Bay: Great Loop Cruising

After our highly social visit to Solomon’s Island after cruising back down the Potomac River concluding our adventure packed 40-nights in DC – we were now officially in the Upper Chesapeake Bay.

And we had a choice.

We could either continue up the Chesapeake Bay to explore Annapolis and Baltimore – or we could cross the bay for more time in quaint smaller towns.

With a delightful weather window ahead of us, and a shorter crossing than in the lower Chesapeake Bay, we opted for ice cream.. err.. I mean smaller towns.

This post covers our adventures from August 9-19, 2025, and as always there’s a video version if you prefer (warning: this video contains explicit images of ice cream which may trigger cravings):

Stop 1: Hudson Creek Casson Point Anchorage – Little Choptank River

After leaving Solomons Island on a lovely calm day, we headed across the Chesapeake Bay to the Little Choptank River.

We found a delightful secluded anchorage at the entrance to Hudson Creek and dropped the hook.

It was wonderful to get some downtime on our own. There was paddleboarding, preparing a meal onboard, hot tubbing, a beautiful sunset and just relaxing.

Sometimes, you just need to pad in days like this in-between other adventures. To really enjoy the natural beauty around us.

Stop 2: San Domingo Creek Anchorage – St. Michaels, MD

After some rest and recharge on the Little Choptank, we relocated to begin our explorations of the Choptank River.

First up – St. Michaels, a town we had gotten countless recommendations for.

We puttered up the San Domingo Creek where there is ample protected anchorage space. With a town dock on the southside of town, this is affectionally known as the ‘St. Michaels’ Backdoor’.

Most boaters visit from the north side off of Eastern Bay, where there are marinas and services.

We absolutely adored this little town with lots of dining options, cute stores, a brewery, winery, distillery and of course, a maritime museum. And not one, but two locally made ice cream shops.

There’s also a short rails to trails nature trail, that we used often to get our running and walking in (gotta counteract all this ice cream!).

We ended up staying 4 nights here, soaking the charm in.

Stop 3: Cambridge Town Wall – Cambridge, MD

Next stop along the Choptank River, was Cambridge, MD.

There are years of abundant inclusions in cruising guides and reviews of the amazing town wall that welcomed boaters with 72-hours of free dockage. We happened to spot one… and only one.. mention in a review of a very recent change to 24-hours as we were making our final approach.

And sure enough, the signs posted are clear – 24-hours only, otherwise – GO TO A MARINA!

The anchorage options in Cambridge are quite limited – perhaps one boat can anchor off the wall. We tried, but it felt that we’d be in the way of other boats coming/going. We also tried anchoring out on the river itself, but it was a bit more rough than was comfortable with the wake.

So our hoped for weekend in Cambridge would just be an overnight, unless we wanted to spring for a marina. We kept that option open if we felt a calling.

We ventured out for a late lunch – enjoyed the meal. But were shocked when the bill came and each dish was charged nearly 20% more than the listed menu price. The owner only apologized, noting a fine print mention on the menu that prices might change (we hadn’t noticed it) – and that they had recent cost increases and hadn’t updated their menu yet to reflect it.

We get it.. running a restaurant in this economy is rough. Costs are increasing for all of us. We begrudgingly paid the bill.

But the surprise increase just left a bad taste in our mouths.

Later that evening, we grabbed drinks at the local brewery/bar .. which were quite tasty.

But after a morning run, we didn’t feel called to head to a marina to stick around for the weekend and further explore. So we pulled away.

(We posted this to our Facebook page, and the restaurant did apologize again and stated they would make the price increases more clear. And several locals chimed in not in support of the town wall free dockage change.)

Stop 4: Martin Point Anchorage – Trappe, MD

After our less than 24-hour stay in Cambridge, MD – we moved on back down the Choptank River and selected a lovely secluded feeling anchorage at the entrance to the La Trappe Creek.

Martin Point was absolutely lovely and tranquil, and perfect to get in some paddle boarding.

Stop 5: Oxford Yacht Agency – Oxford, MD

“Oxford has the Best Ice Cream!”

That’s what we had heard multiple times throughout the summer from other cruisers we’ve crossed paths with along the Chesapeake Bay.

And we have had some pretty incredible locally made ice cream in Urbanna, St. Michaels and Pocomoke City so far. So Oxford was definitely on our list!

We saved it for our last stop as we explored the Choptank River.

As we were in need of catching up on laundry, and wanted to get the bikes on the ground for some exploring – we opted for a marina stay for a couple nights instead of the nicely protected anchorage with town dinghy dock access.

We found Oxford Yacht Agency to have the cheapest rates ($1.50/ft on weekends, $1/ft on weekdays) and TXTd the owner to secure a spot. Super informal and small marina, but just a block from the fabled ice cream.

And OMG… Scottish Highland Creamery lived up to every expectation. Their location ‘downtown’ features about 20 hard packed small batch flavors that rotate daily. Their original location down the street is open on weekends, and features 4 soft serve flavors. And both were amazing!

We won’t share how many times we indulged (or how many quarts are now in our freezer)… but let’s just say we’re not quite sure the multiple 5k runs and the 30 mile bike ride (via the in town ferry, and then over to Easton and back) we did quite offset the calories.

We also did dine at Doc’s, one of the town’s only restaurants – which was quite yummy.

Oxford is otherwise a quaint, welcoming and pleasant town to stroll around.

But the real draw.. the ice cream.

Real Time Update

Oof, I’m falling behind on the blog again. But I think just two more posts will complete our cruising season – which is soon coming to an end as winter approaches.

We’re currently docked in Baltimore, MD for a couple more weeks, and then we’ll head off for our winter storage arrangements, and shift back to van life.

Our intentions are to visit Florida for the holidays and then get back to Zephyr in Arizona (hmm.. seems familiar from last year?).