Do you think it possible that hester would feel a twinge of regret at the thought of leaving the scene of her humiliation and banishment?

Yes, I believe It is very possible that she would regret leaving the town. B

The Scarlett Area made her really famous around that area, and there is no area of the town where she's not becoming the topic of conversation.

Even though it's all considered as negative attention, It still make her life somewhat more colorful compared to others.