Looking for a book or series where certain locations have personalities

[Shawn]

The book/series is probably at least 10-15 years old.
I know I read the the first book. The only thing that I remember for certain was that there was a bridge who had its own personality and either helped or hindered the main character(s).
I loved the book and I think I was waiting for the next to come out and I lost it.
Any help would be appreciated.

Cheers.
Shawn

[Maggie]

The Ocean at the end of the Lane by Gaiman is coming to mind although personality may be too strong of a word. You'll also find location personalities in Charles de Lint’s books. It’s been ages since I’ve read some of these, so I might be off.

[Cheryl]

Mention of de Lint makes me think of Emma Bull's Finder. It's not the book you're describing, but it's got that vibe. It's part of the Borderland series, and crossing the Border does, apparently*, feel as if one is passing over something that has sentience....

*I've only read Founder, not the others, so I dunno for sure....