There are some lovely back roads on the Eastern Shore - -
And it makes a great place to start a cross-country bike trip - -
Except for getting across Chesapeake Bay.
From SE Penna, you can take a couple of bus routes to Cape May,
Then take the ferry across to Cape Henlopen and the great state park there.
So it makes a convenient start for folks from Penna.
I have been in touch with MD DOT for years about the bridge.
Until about 5 years ago there was an Annapolis bus with bike racks.
But they eliminated the route and there are no current shuttles.
There are a number of commuter buses to DC from Kent Island -
But they do not carry bikes, either.
Sad thing is that the commuter buses and the bridge get public funding.
Yet the MD hasn't done squat for cyclists all this time.
You know what they say? That there's a private shuttle for hire.
It costs $6 round-trip for two people in a car at the toll booth -
But the private shuttle costs $30 per person - or $120 for two, r-t.
I do not think that comes remotely close to equitable.
What I'd like to do is get a group of cyclists arrested -
Then sue the hell out of the Bridge Authority and hold up their public funds.
They haven't done a thing in twenty years.
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That said - - there is another option - -
You can stop at the pull-out just before the bridge and hitch.
(It's not a rest area and not a good stopping point)
Or you can hitch from the gas station at Stevensville,
Or you can see if you can hitch a boat ride from the Bridge Bay Marina.
(I've done that at other locations a few times - if you have the time it usually works.)
But the ferry crossing from Crisfield is the easiest and most dependable.
There are multiple ferries from Crisfield to Smith Island and Tangier Island.
From Smith Island you can connect to Point Lookout during peak season:
Smith Island Cruises | St. Mary's County MD Tourism
From Smith Island you can also cross over to the Northern Neck of Virginia:
(Looks like this one is out of business)
And from Tangier to Reedville, VA:
Visit Tangier Island, Va.
The most regular schedule and connection is via Tangier.
Ferry Service
(Except that you have no time on Tangier Island)
If you have the $$$ - a weekday overnight would be nice.