The Eastern Shore of Maryland, which I'm defining as specifically the slice of Maryland that runs along the east side of the Chesapeake Bay, except for Ocean City, is one of America's great regional weekend escapes. If you live on America's East Coast, there are certain beach communities associated with certain states. People from Pennsylvania tend to head to the South Jersey shore towns, with some exceptions for Long Beach Island. People from New York City tend to head to the North Jersey shore towns or out to the Hamptons. Maryland's Eastern Shore has elements of these beach vacations but I think a more appropriate comparison may be similar to Philadelphians heading to the Poconos. The Eastern Shore seems to be more about outdoor activities than sitting on a beach. Although the comparison to the Poconos ends when trying to finding equivalents for the Eastern Shore's small towns. St. Michaels. Easton. Chestertown. Oxford. Cambridge. These towns are as much a selling point of the Eastern Shore as the broader natural wonders and outdoor activities.
Forget the adage “the town is so small that if you drove through and blinked, you’d miss it.” Millington is so small that you could drive through, eyes wide open, and still miss it. After nearly an hour-and-a-half of driving, our newest travel companion, Annie, the miniature schnauzer, was due for a stretch and a meal. I intentionally picked Millington Park for it’s small town remoteness. We let Annie eat in the yard in front of a school. I stopped for water (for Annie) at a Dollar General. We were on our way. I don’t want to read to much into a short visit to Millington but I like to imagine that the people who live here love living here. I like to imagine that they’ve seen what the world has to offer and have found their little piece of heaven. Besides the Dollar General, there’s what appears to be a relatively upscale/nice restaurant, and a liquor store. If you have a good internet connection at home, that may be all you need. It was a nice and quiet town. I’ll need to return at some point – a few miles south is Patriot Acres Farm Brewery – a farm/brewery with a 5.0 rating per Google (as if it a place that sounds that awesome, wouldn’t be that awesome).
Next stop, Wye Oak State Park, for what was hopefully going to be an Annie bathroom. Wye Oak was (unfortunately not is) the largest white oak tree in the U.S. The tree was over 400 years old when it was struct by lightning in 2002. A new tree grows near the road but it was a while to go before it’s the next Wye Oak. There’s a monument to Wye Oak further back off the road. It was also a successful bathroom break.
Next stop, Wye Oak State Park, for what was hopefully going to be an Annie bathroom. Wye Oak was (unfortunately not is) the largest white oak tree in the U.S. The tree was over 400 years old when it was struct by lightning in 2002. A new tree grows near the road but it was a while to go before it’s the next Wye Oak. There’s a monument to Wye Oak further back off the road. It was also a successful bathroom break.
Not to knock Millington and Wye Oak but Joyce and I were starving and it was time for our first “real”, non-Annie related, stop. Before leaving, I had a call with a boss from the Annapolis area who is familiar with Maryland’s Chesapeake towns. In Easton, he recommended a stop at the Tidewater Inn. Good call. The Inn’s crab cake sandwich became the crab cake to which all others will now be compared. Their crab soup had chunks, not lumps, of crab meat. Whole chunks of meaty backfin. We drove up, then back down Washington Street, then hopped back on Route 50 to Cambridge.
In Cambridge we made a direct line to the old town area. Cambridge’s old town has seen better days, but it doesn’t disappoint. Front store facades give an indication of the town’s booming past even if the current storefronts are empty. Around the corning of a building on the main street is a Harriet Tubman mural (she was from the area). There’s a microbrewery. There’s a couple of good restaurants. We walked along the town’s waterfront park.
I went into E.G. Webster and Son, a local grocer that’s been serving the neighborhood since 1939. Their operations are notably because the store hasn’t changed much since 1939. It’s glorious “stuck in the past” environment reminded me of Buenos Aires’s Bares Notables.
We made a stop at a liquor store for a National Bohemian twelve-pack. Apologies to beers like Yuengling and Iron City, which have a major regional connection, but Natty B’oh is by far the best regional beer. It’s such a smooth and crisp taste – perfect for hot summer days and pairs perfectly with crabs. I wish it was easier to find in the Philadelphia area.
We made a stop at a liquor store for a National Bohemian twelve-pack. Apologies to beers like Yuengling and Iron City, which have a major regional connection, but Natty B’oh is by far the best regional beer. It’s such a smooth and crisp taste – perfect for hot summer days and pairs perfectly with crabs. I wish it was easier to find in the Philadelphia area.
Forty minutes later, after winding through the Blackwater Refuge, we arrived on Hoopers Island. We unloaded the car, grabbed two crab traps and a fishing pole, and were back in the car. We picked up fishing licenses at the Hoopers Island General Store. Then we dropped the crab traps into the water off a pier just across the island. When we pulled up the traps, to our surprise, we hauled up a few crabs. Not enough to make a meal (or large enough to want to eat) but enough to feel like a Hoopers Island crab catcher for just a moment. Since the catch wasn’t enough for a meal we ordered take out from Old Salty’s, the island only restaurant – the place could use some competition. It would be a great spot for a beer, to eat some fried bar food, and talk to locals – it’s not exactly the spot for a meal after driving all day. In hindsight we should have picked up more groceries in Easton or Cambridge. After the meal we fished from a bridge on the south side of Hoopers Island. Some Natty B’ohs. Time for bed.
The attraction of Hoopers Island is that you come here to escape life. Escape the city. Escape the news. So when you are here, you don’t do much. Or that could be the 90-degree humid weather speaking. Either way, Thursday was a relatively lazy day.
I spent most of my travel time driving through the Blackwater Refuge area which is like if you combine the New Jersey Pine Barrens with the Florida Everglades. If you’ve never been to either of those places, then I’d tell you that there’s a lot of water. There’s water that comes up to the side of the road and you question with so much water, how is there land for there to be the road that I am driving on. You keep your eyes on the road because a look down and the next thing you know your car could be submerge in a swamp. But it’s not a very swampy swamp. The water is clear, albeit dark, hence the Blackwater name, not murky. The water has a flat surface without there being vegetation strewn across. The Pine Barrens feel is that emerging from the swamp or filling in the land areas are tall trees – the loblolly pine line certain roadways and in other areas appear as clumps in the distance. You drive through swamp for one stretch, then forest, then back to swamp.
The stillness of the water and the fact that there is no one else around magnifies the refuge’s serenity. The landscape is beautiful, but not in a traditional sense. It’s not the rugged mountainous vistas or the sunset seascapes that typically define naturally beauty but rather than untamed wild land that won’t succumb to modernity.
I spent most of my travel time driving through the Blackwater Refuge area which is like if you combine the New Jersey Pine Barrens with the Florida Everglades. If you’ve never been to either of those places, then I’d tell you that there’s a lot of water. There’s water that comes up to the side of the road and you question with so much water, how is there land for there to be the road that I am driving on. You keep your eyes on the road because a look down and the next thing you know your car could be submerge in a swamp. But it’s not a very swampy swamp. The water is clear, albeit dark, hence the Blackwater name, not murky. The water has a flat surface without there being vegetation strewn across. The Pine Barrens feel is that emerging from the swamp or filling in the land areas are tall trees – the loblolly pine line certain roadways and in other areas appear as clumps in the distance. You drive through swamp for one stretch, then forest, then back to swamp.
The stillness of the water and the fact that there is no one else around magnifies the refuge’s serenity. The landscape is beautiful, but not in a traditional sense. It’s not the rugged mountainous vistas or the sunset seascapes that typically define naturally beauty but rather than untamed wild land that won’t succumb to modernity.
Key Wallace Bridge is a popular fishing and crabbing section of the refuge. Again, I’m not sure how there’s a road west of the bridge but I guess this is what makes the area such a great fishing location. On the eastern side of the bridge is a kayak rental shop, although, since there’s no trees, you’d want to be careful before heading out for an hour long trek on the Blackwater refuge.
The Blackwater area is the birthplace of Harriet Tubman and was a major route along her Underground Railroad. COVID unfortunately cause the temporary closure of Harriet Tubman National Museum but the more historical sites are available to be seen while driving through the area. Historians best guess is that Harriet Tubman was born on Brodess Farm in the Bucktown area. A placard commemorates the location. Just up the road is the Bucktown General Store where Harriet Tubman was struck in the head with a two-pound weight that a slave owner threw at another slave but hit Tubman instead.
I backtracked from the Bucktown General Store then headed north to Cambridge to pick up a few cooking supplies from Emily’s Produce. On the drive back to Hoopers Island I stopped at the Old Trinity Church, the Woolford Country Store, and picked up lump crab meat from Lindy’s Seafood. It was another beautiful, winding drive back to Hoopers Island.
I began to notice that a definitive feature of the Blackwater Refuge area was small churches - churches that would be large enough to accommodate the local community of 30-50 worshipers and not much more. It reminded me of Iceland, which has a similar small church dotted landscape, where each church is a little distinct and keeps the driving entertaining for what type of church will appear next. The church on the bottom right is Hoopers Island primary place of worship.
Blackwater Refuge driving videos:
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Hoopers Island was the primary draw of this trip and were we spent two nights. What’s the attraction of Hoopers Island? Nothing. That’s why we came here. I went on Airbnb. Search for homes with a filter that allowed pets. I search around water and for a remote location. I “found” Hoopers Island. I had never heard of Hoopers Island before. A little bit of research and moving Google Maps around and there’s not much to know about the island. It’s home to Maryland’s blue crab industry. The original Phillips seafood is based on the island and there’s about a half dozen other crab catching, steaming, and de-shelling operators on the island.
There’s about one hundred homes on the island. There’s one restaurant – Old Salty’s (which I don’t recommended dining at, no offense intended. It’d be a great place to grab a beer and talk with locals. Not so much for a meal after driving all day.) There’s a general store with all the essentials – although only Pepsi and Budweiser are making the beverage runs down here so you are limited to their brands. The nearest supermarket is in Cambridge, about forty minutes north (not counting fruit/vegetable stands).
Hoopers Island felt like Key West meets West Virginia. There’s two small islands connected via a sea bridge sort of thing (that’s the Key West piece) in what is an otherwise remote-off-the-grid location that’s filled with a friendly, working class group of people (that’s the West Virginia piece). My wife and I loved the small community feel and being near the water that we searched Redfin for available homes in the area. The only drawback is the mosquitoes are brutal.
The first photo is the crab we caught. The second photo is the crabs we ate. I consider myself a bit of a crab connoisseur and I'll state that while the Hoopers Island crabs were not the best crabs I've ever had (maybe I expected too much, maybe the environment at another place added to a previous meal) these crabs were near the best. The biggest difference between these crabs, which were caught hours earlier, and those I've eaten in restaurants, is that these crabs were incredibly clean. None of that yellow guts covering the meat. The lungs and intestines were much easier to pull out. The meat was much easier to get to.
The first photo is the crab we caught. The second photo is the crabs we ate. I consider myself a bit of a crab connoisseur and I'll state that while the Hoopers Island crabs were not the best crabs I've ever had (maybe I expected too much, maybe the environment at another place added to a previous meal) these crabs were near the best. The biggest difference between these crabs, which were caught hours earlier, and those I've eaten in restaurants, is that these crabs were incredibly clean. None of that yellow guts covering the meat. The lungs and intestines were much easier to pull out. The meat was much easier to get to.
If I ever met Anthony Bourdain, I’d ask him if he regretted highlight locations that couldn’t handle the limelight and would be overwhelmed by the subsequent attention? And that in highlighting that type of a location, does he ruin it forever? When I look across the Hoopers Island landscape, I hope the place never becomes build up and commercialized. Maybe one more restaurant or a bar but that’s it. Hoopers Island stands out for what it does not have – a lot of other people and commercial activity. Opening the island as a tourist destination would destroy the very reason to visit the island. How do you balance promotion or acknowledgement without destroying the underlying truth that was previously operating in obscurity?
A few driving videos of Hoopers Island - the first video highlights the Key West comparison - a great drive:
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The next morning, we packed the car. Then we drove to Russell Hall seafood for fresh crabs and fish figuring we may as well eat fresh crabs as long as we can. We purchased two coolers and ice at the Hoopers Island General Store, then headed north.
We tried to stop for breakfast at the Robert Morris Inn in Oxford but we didn’t arrive until after ten and their kitchen was closed. Fortunately Oxford was a nice time, although a very, very small town. Small enough that other than the Robert Morris Inn there wasn’t another place to enjoy a meal. Fortunately, Oxford has a ferry that runs a route across the water to Bellevue and from Bellevue, St. Michaels is twenty minutes away. The Oxford/Bellevue ferry is the oldest, continuously operating ferry in the U.S. Ferries have been plying this route since 1683.
We tried to stop for breakfast at the Robert Morris Inn in Oxford but we didn’t arrive until after ten and their kitchen was closed. Fortunately Oxford was a nice time, although a very, very small town. Small enough that other than the Robert Morris Inn there wasn’t another place to enjoy a meal. Fortunately, Oxford has a ferry that runs a route across the water to Bellevue and from Bellevue, St. Michaels is twenty minutes away. The Oxford/Bellevue ferry is the oldest, continuously operating ferry in the U.S. Ferries have been plying this route since 1683.
Ok about St. Michaels. I’ve been wanting to visit St. Michaels ever since I returned to the U.S. in 2015. I wanted to visit a quintessential, small coastal town and by all accounts, St. Michaels is considered one of the best. But see here’s the thing – Easton, Cambridge, Oxford, and Chestertown (visited later) all have bypasses that take drivers around the main commercial street. In St. Michaels, Route 33/Talbot Street is the route that all cars take and the quaint shopping street. On a Friday afternoon the road is non-stop traffic. Maybe it’s different on a Wednesday. Maybe you need to be on the water and not the main street. I don’t know. But I was not a huge fan of St. Michaels.
Final stop: Chestertown. Similar to St. Michaels I’ve been wanting to stop at Chestertown for a while. The town is located along the Chester River upstream from the Chesapeake Bay. Now this is what I wish St. Michaels was like – a quaint and historical shopping district. An old town square. An old court house. All the stuff that makes you feel like you’ve stepped back in time and no need to worry about cars whizzing through town. I have no regrets about not visiting St. Michaels earlier, but I am kicking myself for not making the hour-and-a-half drive to Chestertown earlier. I’ll need to return sometime and spend the night.