Recently, we went on another Milwaukee adventure – AKA we caroused Cream City – and spent UNDER $20.

What is a “Milwaukee adventure?” We define it as an afternoon or evening we visit two different places on a single Jackson. It’s a challenge, but the goal is to present cheap outing itineraries you might not have considered.  

Last time, we suggested gardens and sushi in Greenfield, and now we’re bringing it back to the East Side with coffee and games. The beauty of this Milwaukee adventure is it doesn’t require planning ahead, just spontaneously grab a pal any afternoon and head over to Downer Avenue for a delightfully cheap thrill. 

Stop 1: Valentine Coffee Rosters
3126 N. Downer Ave., (414) 398-0220
valentinecoffeeco.com
Hours: Daily from 6 a.m. to 6 p.m.
Cost: $5-$10
This is Valentine’s newest space. Grab a drink and perhaps a snack of your choice “to go” from the locally owned Valentine Coffee. Lunch and early dinner items are also available. Head over to Old Guard Games, located one door to the north.

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Step 2: Old Guard Games
3132 N. Downer Ave., (414) 988-0161
facebook.com/OldGuardMKE
Hours: Monday-Wednesday, 10 a.m. to 10 p.m.; Thursday-Saturday, 10 a.m. to 11 p.m.; Sunday 10 a.m. to 6 p.m.
Cost: Free
Leave your license at the front desk and borrow a tabletop game for as long as desired. Cribbage, chess, checkers and more are available – or spend a little extra and buy one of the many card games available in the shop. Take your game and your Valentine Coffee drinks to Old Guard’s outdoor cafe and enjoy the afternoon!

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