This is a great topic. I always look forward to the rollout that Bill from Rushmore Records puts together during Bay View Gallery Night. I also love the bicycle benefits, annual Bike Bingo! Of course, the underwear bike ride is a good time as well. 

Other than that, I like to create my own silly challenges. Wrote this piece last year and would love to plan something similar for this summer. Currently, I'm thinking it would be fun to plan a route that focuses on Italian Sausage. Scardina's to Glorioso's to Tenuta's in Kenosha and then circle back up to Groppi's in Bay View. 

I'd love to go to more this year, though. I have to make some more bike pals. 

Updating my own topic! Awesome guy Nicholas Sideras put this together:

https://www.milwaukeebikerides.com/  

@mitchyd Sorry for the late reply, I've been injured and recovering for a few months. 

I did a ride called the "Donut Roll" last fall where about 8 of us rode to a bunch of different bakeries across the city. Some guys got a donut at each stop, and some of us bought things to take home because you can only eat so many donuts before you want a nap!

@rasterweb excellent resource!!

@rasterweb All good! Donut ride sounds like a blast!

Hey I followed through with that Italian sausage ride!

https://milwaukeerecord.com/food-drink/sunday-sauce-a-98-3-mile-bike-ride-to-chicago-fueled-by-meatballs-pizza-and-italian-beef/

Amazing! And another great MR story.