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As a former (and proud!) Milwaukee resident now living in Chicago, I go back whenever I get a chance. Here's exactly what I hit on my most recent visit before making my way up north for a relaxing getaway.
Lakefront is a must. Its tour is fantastic, and you get lots of samples. If you go up on Friday night, it's the best place in town for a fish fry. Polka, huge communal tables, wholesome Midwestern fun. A lot of people will also recommend you take the free Miller tour, which is very Disneylike in its presentation. Sprecher is another favorite, very relaxed, cool to see the root beer being made!
From Lakefront, I'd suggest you make your way over to the Third Ward area. Lot of shops and galleries. It's also home to the amazing Public Market, which has lots of local meats and cheeses. Definitely worth a stop. Inbetween nibbles, check out the little boutiques there too.
From there I'd head south about a mile to Bay View, my old neighborhood. Along the drive on First Ave. (which turns into Kinnickinnic) there are tons of vintage shops and antique malls.
Good bars in Bay View are Sugar Maple, which is a gastopub-y beer bar, and I'd also recommend drinking at Bernhardts, Palomino (also good for vegan/vegetarian-friendly brunch), Cactus Club, or the best bar ever, At Random. It's my favorite hidden spot in Milwaukee. Trust me. If you only do ONE THING in Milwaukee, it better be this.
Riverwest is turning into another destination neighborhood; great bars there are Foundation, a biker bar turned tiki bar, or Art Bar, a gallery space with a great jukebox and pool and board games.
Downtown is pretty quiet on weekends, which makes it even easier to enjoy the beautiful art museum. From there it’s an easy walk around the East Side. Consider stopping at Beans and Barley, a veggie co-op and restaurant. The Oriental movie theater has been restored to its Art Deco glory, and is a good place to escape. Before you leave town, be sure to go visit Colectivo Lakefront. It's a branch of my local coffee chain housed in an old flushing station on Lake Michigan.
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