Square plays a part in all my favorite Madison activities, it's a great place to pop in on Farmer's Market Saturday or before concerts on the Square. Go here! Buy wine, make friends, you'll love it. You might even learn something too, Andrea and Emily have been trying to teach me for years and while I still can't describe flavors with my words I like to think I have much more discerning taste now.
Square has everything you could possibly need. Something big for my dad who only like cabs? Check. Something funky for when your bougie friends are in town? Double check. Rosé for all day? Triple check (seriously, there are so many rosés.). They also occasionally sponsor arts and crafts events, provided you bring your own arts and crafts. They do have wine though, which everyone knows is the most important ingredient to any DIY.