Friday, November 21, 2025

Eastern Shore Ride Day 1 - Kent Island to Tilghman Island

 My friend Jim and I are going to ride around the Eastern Shore this week. He's going to be in Cambridge for his job on Friday, and we are starting from there. 

I decided to ride to Cambridge from the end of the Bay Bridge, and visit my friends Jim and Mary in Tilghman Island. So today. Debra drove me across the bridge and dropped me off at the Valero in Stevensville,  and I rode to Tilghman. 



I rode 70 miles. Temperatures were in the 40s, It's totally flat, and there was a tailwind much of the way. I meandered around a lot exploring, which meant I only had to ride on the shoulder of US 50 for about 7 miles.

Tilghman Island is pretty remote. It's at the end of a 20 mile road, mostly through nothing. Here I am at the end of the road.



I confess I was befuddled about why Jim and Mary would choose to move to a remote island in the middle of the Chesapeake Bay, with the plan to eventually retire there. I had this vision of them living amongst corn fields and chicken houses. Turns out Tilghman Island is not like that, and it's actually pretty cool. It's basically a resort town for recreational boaters. They have a sailboat.

Historically, Tilghman was the home of watermen. (For folks not from Maryland, a "waterman" makes his living by harvesting seafood from the bay). Watermen have lived on the islands in the bay for centuries, they have a unique culture, and an unintelligible accent. According to Jim, Tilghman once had a much larger population, and had an oyster cannery. Which is now the clubhouse at their yacht club.

The waterman days are pretty much over. Maryland had a very unique approach to regulate the oyster harvest from overfishing. Basically the idea was to make harvesting oysters a complete pain in the butt by requiring that oyster harvesting could only be performed using a wooden sailing ship called a "skipjack". Only watermen are going to do this, because that's how they have harvested oysters since time immemorial. Tilghman was the home of the skipjack fleet. Nonetheless, the oyster population collapsed in the 1990s due to pollution. Jim says there are still a couple skipjacks in Tilghman, and if you want you can pay money to go work on one for a day. Which he did.

Jim sends this additional information about watermen and skipjacks:
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One correction regarding waterman and oystering. It is still a big business here and there are a lot of watermen and boats that go out every morning. They are allowed to harvest the oysters using dredge equipment from power boats, but they have lower quotas. They can (and do sometimes) still use the remaining skipjacks, which are allowed a larger quota. The oyster population has been increasing as of late, but nowhere near what it was back in the day. Here are three skipjacks rafted up at Sandy Point (L-R: Rosie Parks, Thomas Clyde and Rebecca T. Ruark; the last two are based in Tilghman):


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So Tilghman is a quaint small town, with lots of stuff going on all summer, and perfect if you own a sailboat. It's blissfully dark and quiet at night. This may actually be worth living 35 miles from the supermarket. 


To get to Tilghman Island, you have to go through the very fancy town of St. Michaels. There are many shops and restaurants there. There are at least three wine bars. I stopped for lunch at the Carpenter Street Saloon, and had a delicious shaved prime rib sandwich. I figured a "Saloon" would be more likely to tolerate a sweaty guy who rode in on a bike than a "wine bar".


Wandering around on back roads to get to Tilghman Island was really great, although it made the ride take much longer than necessary. This is not the land of chicken houses. It's mostly pine woods, with some farms and estates apparently about duck hunting. It's really beautiful.

Here's the Strava track: 

https://www.strava.com/activities/16508985730




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