North of the Bay Bridge

We started in Rock Hall — not out of nostalgia, but because Dawn was able to get us a room in the Osprey Point Inn, which overlooks lovely Swann Creek, one of the two harbors that serve this quaint old fishing village. Osprey Point is part of a resort marina, with a swimming pool and docks full of high end yachts. Visitors have complementary access to the hotel’s bikes, paddleboards, kayaks and canoes — a fact we would have known if we had read the brochure more closely. 

The hotel also offers fine dining in the fanciest restaurant in town. 

In other words, Osprey Point is technically a little more luxe than we’re accustomed to and definitely outside our usual budget. But Dawn was able to get us a room at off-season rates, less than half what it normally costs. And it was hard to argue with the views from the lawn. 

But this trip wasn’t about laying around the pool and improving our tans. We were there to scope out future adventures and get the lay of the land. In other words, this was a work trip (heh, heh, heh…) 

Although we had vague plans about paddling the local waters and checking out our new (to us) bikes, we knew we’d be spending most of our time in the car. Even on the way to Rock Hall, we took a detour to mosey around historic Chestertown, checking out the handsome main street and the old mansions lining the riverfront. (For the record, this is the most beautiful downtown on the Eastern Shore.) 

And since our room wasn’t available until the afternoon, we explored around Rock Hall, making a special trip down to the Eastern Neck National Wildlife Refuge at the mouth of the Chester. We had read that this was the north Bay’s version of Blackwater NWR down in Dorchester County, so we thought it would be a good place to get on the water. It turned out to be a little too windy when we were there, and the launch spots a little too exposed, for a casual paddle.  

Naturally, we also took advantage of our early arrival to explore Rock Hall itself, scoping out harborside restaurant options on Rock Hall Creek and watching the sun set over the Western Shore from the little neighborhood beach on the bayside. 

Saturday was expedition day. We made the 15-minute drive back to Chestertown to check out the farmers market, nibbling fresh strawberries as we chatted with the vendors and oogled the architecture along High Street. We had planned to eat breakfast at the famous Evergrain Bread Company, but the line to get in was too long. Walking around, though, we discovered The Modern Stone Age Kitchen on Cannon Street, another bakery specializing in breads that use natural leaveners and abstains from refined sweeteners or other artificial ingredients.  

What other small town has two high-quality bakeries within a couple blocks of one another, both of them packed to the gills with customers? But if you want good bread in Chestertown on a sunny Saturday morning in the spring, you better be prepared to wait in line. 

From Chestertown, we took a zigzagging course northward to get a peek at Dawn’s short list of small towns that might be worth a return trip this summer. The Eastern Shore topography north of the Bay Bridge is decidedly more varied than the bottomland and marshes to the south. 

That’s not to say there are no marshes north of the bridge, but the rivers up here are more likely to be overlooked by high bluffs. The roads, too, are different — winding through hills and dales to their destination instead of following the rhumbline.  

And the Bay, of course, is narrower at this latitude. From the mouths of the Sassafras and Elk rivers, the shorelines of Aberdeen Proving Grounds and the Western Shore approaches to Havre de Grace and the Susquahanna seem close enough to swim to.  

Mostly, though, we were focused on quaint towns. Top of our list was Betterton, a charming village at the mouth of the Sassafras River. 

Here, the high bluff is lined with old Victorian homes, some of which served as hotels and roominghouses for the crowds that used to vacation here in the days of steamboats. In the middle of this sleepy village, a gap in the bluffs leads down to the town beach, a wide swath of tan sand bordered on one side by stairs leading to a pavillion at the top of a steep hill, and on the other, by the town pier — doubtless once the wharf for the steamboats that, in the summer, used to fill this small town with tourists. 

When we were planning this trip, we originally thought we would base ourselves Betterton’s Evergreen Knoll Cottages, an old-school cluster of vacation cabins overlooking the river. This quiet little compound has its own tiny beach and the atmosphere of a 1950s summer camp. This was definitely our type of vacation spot. 

Alas, we were never able to reach someone to make a reservation, so we had assumed Evergreen Knoll, like so many small hotels, simply went out of business during the pandemic. Now, though, we’re not so sure. 

While we were in Betterton, we decided to drive past the resort to see what we had missed. To our surprise, the gates were open and it looked like some of the cottages were occupied. But there was no staff to ask if the hotel was still in business, so we’ve made a mental note to check on the status of the property. If it’s still open — and you’re like us and would rather a quirky inn to a modern hotel, this is probably your best choice of places to stay north of the bridge outside of Chestertown and Rock Hall. 

There’s one other advantage to these beach towns at the north end of the Bay: So much freshwater runs into the Bay from these northern rivers that there are rarely any jellyfish or sea nettles. On a hot summer day, that alone is worth the drive to Betterton. 

Some of the other small towns that we visited briefly on this trip were Galena, Georgetown, White Crystal Beach, and Still Pond.  

When we returned to Rock Hall, we took advantage of the longer days to paddle out into Swann Creek and see Osprey Point from the water. The view was so good that we decided to do it again Sunday morning before we left.  

Rising early, we went out to walk the docks while we waited for the hotel restaurant to open. As we headed back across the parking lot to catch the complementary breakfast buffet, we ran into Jerry Messina, the garrulous owner of Osprey Point. The former Philadelphia attorney regaled us with stories about how he bought the property and built the marina and inn. We were delighted when he invited himself to join us for breakfast. 

By the time we finished eating and listening to Jerry’s self-deprecatory jokes about his wife Shirley, nearly two hours had passed. So, we quickly ran up to the room to pack up so we would still have time for a quick paddle in Swann Creek.  

It was nearly a dead calm as we made our way across the creek, startling scores of turtls as we paddled up the long marshy inlet on the far side. On the way back, we sat on our boards mid-creek, admiring the view and concocting schemes to move to Rock Hall. 

That’s always a sign we’ll be back.