Time to finally discover Madison

After living in the Madison area for 20 ish years, I feel its finally time to really get this great city. I have walked all around downtown, but go back to the same places every time. This year is the time I finally realize the greatness of Madison. Wondering if there is a list or at least suggestions of the places, food, drinks, events, people, things I need to do to finally say I know this city. And for year round. I'm a typically summer explorer but that cuts out so much time of the year. Cheers to this great city!!