((((krazibean))))
In your interaction, it was you who were reticent, you who did not walk up to her and introduce yourself, you who did not offer to show her around the farm. It's OK you were uncertain and reluctant to do these things. It is often confusing about the therapist-client boundaries (I understand completely when you say "it's messed up"), since they are so unique. It sounds like you don't know how much interaction/contact would be appropriate/permitted outside the office. I think your T follows your lead outside of the office. If you had spoken to her, she probably would have too. But I also think you were being respectful, worried you would cross boundaries and initiate more contact than she wanted. I think a talk about this with T would be really helpful.
Maybe your following her car for a half mile was an attempt to connect after the disappointment of the minimal interaction at the farm.
I think I saw my T once at an event I went to that was open to the public. He was standing in the common area, and I was headed to a classroom to attend a seminar. I am not sure it was him, but I think maybe it was. My response was to quickly look away from him (he was engaged in conversation with someone else) and hurry down the hallway to my class. Aaaaackk! You are a lot braver than I was, to even acknowledge your T outside her office. I think it's OK to feel awkward about this.