
Hoopers Island is one of those places that I’d seen the sign for many times and had never visited. Until December.
I’d been interested in running at Hoopers Island ever since seeing a photo of the bridge (which I now know is the one that runs between Upper Hooper Island and Middle Hooper Island). My friend Nicole was also interested in running there.
We met up at the Tylers Cove Boat Ramp, which is right before the bridge to Upper Hooper Island, on a cold Saturday morning and headed onto the island. During the first part of the run, there were plenty of houses to see.
The boat ramp is just over an hour drive away from Salisbury, where I live. Hoopers Island is located in Dorchester County, Maryland — in the Chesapeake Bay, with the Honga River to the east.

For some of the island, we were running on a thin strip of land and could see water on both sides. After almost four miles of running, we crossed onto what was basically a road that went through the water, with cold water splashing up on one side.
We continued onto a bridge (which I’m sure is what the road technically is as well) and crossed onto Middle Hooper Island after a little more than five miles. This island was mostly free of houses during the first part of our journey, but there were some as we got further down. We ran to the end of the road, which was nearly nine miles from where we started. There’s another island as well — Lower Hooper Island — but it is not accessible by road.

On the way back, we took some of the side streets to add some mileage to be able to hit 20, also adding some at the end. There were not a ton of businesses open to the public on the island — Old Salty’s, a restaurant, which was closed (it was the day after Christmas — I just checked Facebook and it’s back open), a general store that also had a restaurant, and post offices. But there were seafood companies, and we saw a seafood truck go out and back that we assumed was picking up fresh seafood.
It was a beautiful run, and I’m glad I was able to finally explore this new-to-me area. It was windy, and I was cold (unusual for me), but it was definitely worth it to be able to do this cool route.
I would have thought the island would be spelled Hooper’s Island, but I checked to confirm and it’s actually Hoopers, without the apostrophe. Only grammar nerds like me would probably care about this (and the fire department does spell it with the apostrophe). Learn more about the island chain on the Dorchester County Tourism website.
I think this might be an interesting place to visit next time we go through Maryland. Thanks for letting us know about it.
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