BlackCanary, do you want your T to see you at this event, or do you just want to watch her from unfar, unbeknownst to her that you are there? I think it is interesting to explore this as a fantasy--on your own, with us here, or in session with your T. I think acting on this fantasy would not be a good thing to do. It seems disrespectful to your T, invasive, stalkerish, deliberately provocative. I get a "yuck" feeling in my stomach when I read your plans. I hope you don't do it.

Maybe if you discuss this with your T, she will offer to walk around the block with you during your session so that you can see how she is outside of her office, interact with her there, talk to her, etc. That way you could satisfy your curiosity but yet not intrude on her private life and family.