Milwaukee

The Walker's Point restaurant that Milwaukee locals claim as their best — and they're right. Small plates built on whatever's at market, a natural wine list that rotates more often than most places rotate menus, and a room that feels like exactly the kind of place you didn't expect to find in Wisconsin. The meal where someone in the group says 'I had no idea Milwaukee had places like this.' They all say it. They're all right.

The Wisconsin supper club tradition at its most theatrical: beer-battered Lake Perch or Walleye, potato pancakes, coleslaw, a New Glarus from the tap, and a polka band that starts at 6pm and takes requests. Lakefront does this every Friday in a room that fits 400 people and fills every one of them. If you're in Milwaukee on a Friday, nothing else is a conversation. Nothing.

Sandy D'Amato's flagship has been Milwaukee's most respected dinner table since 1989 — seasonally driven, impeccably sourced, consistent in a way that only restaurants run by their founding chef can sustain. This is the special occasion dinner on the trip. Make the reservation two weeks out. No shortcuts.

The Bloody Mary has a cheeseburger on the skewer. That's not a gimmick — it's a fully constructed cheeseburger impaled through the drink. Sobelman's became famous for this and stayed famous because the concept actually works. The Bloody Mary bar lets you build your own. The morning after a long night at the supper clubs, this is exactly the right move. Budget an hour.

Milwaukee's most authentic supper club — the relish tray arrives before you order, the Old Fashioned is made with brandy (this is Wisconsin, not Manhattan), and the prime rib has been carved tableside since before anyone in your group was born. The Wisconsin supper club is a dying institution and Buckley's is one of the last genuine ones. Order the brandy Old Fashioned even if you think you don't drink brandy Old Fashioneds.

Walker's Point pizzeria running a wood-burning oven and an all-Italian wine list in a room that could be in Milan if it weren't in Milwaukee. The margherita is the reference point; the rotating specials are what keeps locals coming back. Best late dinner option in the neighborhood when the group doesn't want a production and everyone's tired from two rounds.

Third Ward restaurant from chef Gregory Leon — Iberian and North African influences that you would not expect to find in Wisconsin, and better than they have any right to be. The bacalao croquettes, the lamb meatballs, the sherry list. This is the other meal where someone says 'I had no idea.' Book ahead.

Milwaukee's best craft brewery taproom — East Side location, excellent rotating tap list, and a back patio that fills up fast on warm evenings. The Pastime Pilsner and Urban Noise IPA are the plays. Pub food that's better than pub food needs to be. Right for the evening after Brown Deer when the group wants beer and zero decisions.

Three Milwaukee locations, all of them packed, none of them pretentious. The best Mexican food in the city — proper enchiladas, excellent housemade salsas, strong margaritas. The Brady Street location has the most character. Go for lunch between morning and afternoon rounds, or late dinner when nothing else sounds right.

The North Side deli that Milwaukee Jewish families have been protecting for 70 years. Cash only, tiny, the pastrami is sliced thick, and the chopped liver sandwich is not a joke. Opens at 8am and runs out of things by early afternoon on weekends. Get there early. If the group hasn't had a proper Midwestern Jewish deli experience, this is the one.