Tempest Oyster Bar
On my most recent visit to Madison, I discovered something wonderful that we're missing in Chicago: happy hour. How I’d missed it on prior visits, I don’t know, but you’ll want to spend a couple hours at Tempest Oyster Bar (120 E Wilson St). Monday through Friday from 4-7pm, get oysters for $1.50, shrimp cocktail for $2, plus other snacks, and $1 off tap beer, $3.50 rail drinks and $6 specialty cocktails.
Merchant
Merchant (121 S Pinckney St), a much-lauded place for cocktails in downtown Madison, is another happy hour option. From 3–6pm Monday through Friday, you’ll get $2 off well-made classic cocktails and craft beers, which translates to a $7 sazerac, $6 old fashioned and beers that cost just a few dollars. You can snack, too, with fried cheese curds, charcuterie from Underground Meats and a burger available all afternoon.
Heritage Tavern
You'll find two former Chicagoans at the new Heritage Tavern (131 E Mifflin St): chef/owner Dan Fox (Everest, Spring) and bartender Grant Hurless (Drawing Room), who’s responsible for the Malört Thing, a daily changing Jeppson’s Malört cocktail. The menu also includes the Drawing Room Manhattan. If you’re on vacation to escape Chicago, try the Angostura Sour, a frothy angostura-heavy cocktail made with egg, two dashes of Smith & Cross rum and lime.
Ale Asylum
The brewery (2002 Pankratz St), which expanded in 2012, has a big two-floor taproom, so grab seats and order a flight. For $15, you can sample six beers. Some of Ale Asylum’s brews are available in Chicago, but there are many more you can only try at the taproom. I like the Satisfaction Jacksin, a hugely hoppy double IPA, and Happy Ending, a Belgian Abbey Ale, one of the stronger beers at 7.7% ABV.
Genna's Lounge
When you need a last drink before heading back to your hotel, go to Genna’s (105 W Main St). The dive, which is cluttered with Wisconsin décor, is open for happy hour from 4:30-6:30pm Monday through Friday, when you can get 40 percent off rail drinks and selected tap beers, but it’s even livelier at night, when there are occasional DJs. You’re only in Wisconsin for a brief time: You'd better order a New Glarus.