For a Happier Wallet Try Happy Hour Instead

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While many of us have been laying low these past two years for health and safety, most of us are ready to get back out there and enjoy some society. Unfortunately, the sticker shock of inflation-ravaged food and drink costs may quickly cool that desire. Looking for a simple solution to stretch your dollar further? Take advantage of happy hour deals at bars and restaurants all around the city. There are many places that offer specials, typically 4-6 p.m., but we’re going to focus on the following four places, the finalists and winner as voted by our readers in the Shepherd Express 2021 Best of Milwaukee contest.

Duke’s on Water (158 E. Juneau Ave.) was our fan-chosen winner for 2021. Sort of a cross between a sports bar and a college hangout, Duke’s is the place to go for amazing drink deals on weekdays from 3-9 p.m. and weekends from 11 a.m.-2 p.m. Meet up with friends and score $1 domestic taps, $5 domestic pitchers, and $2 rail drinks. Loads of bar games like beer pong, dice games, darts and pool are available, as well as seasonal sports on all the TVs. Centrally located to most downtown event sites, Duke’s is a great place to grab a couple of drinks before the show or game and save a few bucks.

One of our 2021 Best of Milwaukee finalists, Mason Street Grill (425 E. Mason St. offers a classy, upscale vibe. From 4-7 p.m. Monday through Friday, you can enjoy a $5 glasses of wine, $5 rail drinks, $4 draft beers and $8 bar snacks. If you’re familiar with the delicious food available on Mason Street Grill’s full menu, you’ll be happy to discover their bar snacks are also excellent. Try the house specialty Fried Surf Clams ($8 during happy hour), perfectly fried and served with tartar sauce. Or go for the ¼ Rack BBQ Baby Back Ribs with French fries ($8 during happy hour). When you head out, you’ll feel like you had a tasty drink and a satisfying light meal. The “happiest” part is that you’ll have saved about $5 per snack and $2-$4 per drink. 

Another finalist, Maxie’s (6732 W. Fairview Ave.) is always a fun place to stop in for happy hour deals. From 4-6 p.m. Monday through Saturday you can fill up on $1 fresh-shucked oysters and $1 off your drink of choice. Standout drinks at Maxie’s include a zippy Jalapeño Margarita ($7 during happy hour) and a wonderful Kentucky Sidecar ($8 during happy hour). The laidback Southern hospitality vibe of Maxie’s is great for raising your spirits and is a wonderful way to begin an evening out. Special note: because it can get busy during that happy hour time frame, take advantage of Maxie’s online reservation service and you’ll thank yourself as you stroll past throngs of folks waiting patiently for a table.

If you’re looking for a friendly Irish pub to kick off your evening visit our final 2021 Best of Milwaukee finalist, Moran’s Pub (912 Milwaukee Ave., South Milwaukee). Offering happy hour specials from 4-6 p.m., Tuesday through Sunday, including $3 pub lagers, $5 Mules, $5 Pimms' Cups and a $1 off everything else. Moran’s is a great place to pull up a stool to catch live soccer games, engage in friendly banter, and enjoy a well-poured Guinness. Special events include trivia nights, an in-house pool league, occasional live music or DJ, and discount nights for educators. So, gather with friends, bend an elbow, all while saving a buck or two during happy hour.