[Morsul the Dark]

But of course

The bridge is said to be built by dwarfs. Shire founder. Gandalf is of course connected to both. The final two clues can be connected to both. One clue more directly than the other.

Originally Posted by Morsul the Dark

It was I just looked it up again I was kind of clever in that one. Full disclosure I made this one based on a neat idea but the theme is forced to fit that idea.

1. Plymouth settler of a middling shade but a more common name.
2. Informally myself won’t then again myself seeing the back of a horse man. That’s one way to get over water.
3. A long trek for a soldier followed by the first American note. Akin to Washington or Jefferson.
4. Stretched but replacing the first of orange with the first of apple. With result of monsoons.
5. Take a puppet known for fire but the beginning is seen as the Weasel ‘s baboon foe. This should bring a vision of the answer.

1. GandalF
2. Iant IauR
3. MarchO
4. L*******D
5. IrmO