I've got a new logo in the works and I think I'm on to something. I'm not 100% confident in it yet, but I'm happy with my start. The "W" is supposed to give the impression of the dog's front legs (hopefully that is conveyed well). I added a wagging tail for extra cuteness/clarification.
Any and all comments are welcome! This design was partially inspired by ijoshua's "Puppy Website" logo on logopond.com
Of course I've been playing around with font and things like that. Right now it does look pretty bland... I feel like maybe it could use a drop shaddow or something behind/under "Westport".