Sorry I didn't see this earlier--I live on the Eastern Shore of VA, very near where this ride takes place (about 20 miles from Silver Beach, where it's "centered" at)
First--it's flat, flat, flat. There are a few what we call "hills" but they're really nothing more than little slopes really, raising no more than 20 feet or so. But ones that "high" are few and far between.
There can be wind but that time of year isn't too bad. It's usually blowing about 5mph here all the time anywhere, so I'm used to it. But unless there's a storm, which I'm assuming would cancel the ride, you would probably be looking at nothing stronger than 20mph on a very windy day. Anything higher than that and it's almost assurdly going to be associated with a storm of some sort. So, I would say plan on about 5mph wind, maybe 8mph or so regardless.
BUT, there are PLENTY of trees around here, so you will be riding past lots and lots of natural "wind breaks."
It will be a pretty ride through historic very rural country. The folks here like to call the Eastern Shore "The Land that Time Forgot" and indeed it is. You'll see houses going back to pre-Revolutionary War times, small quaint little villages, beautiful old churches, and meet some great folks! I'm planning on doing the ride myself.
Here's a photo I took back in June of a huge field of sunflowers on one of my rides (this was when I was still pushing my Hybrid before I bought my Trek MSD)--you'll see sights like this and so much more!
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