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For a guys weekend, it’s hard to beat March Madness: An 8-city guide

Updated: Nov 13, 2021


When it comes to excuses for a guys weekend, the NCAA men’s basketball tournament is as good as it gets. We can safely squeeze our heart-to-heart chats into the gaps between shouts at the ref and trips to the bar. And the nonstop game action of the first two rounds is the perfect accompaniment to commiseration over sputtering careers, thinning hairlines and busted brackets.

Las Vegas is the default destination for this sort of thing, which I get. It has gambling, giant TV screens everywhere, gambling, cheap hotels, gambling and, oh yeah, gambling. But I’ve done March Madness Vegas. I’ve wandered from sports book to sports book looking for seats among the herds of pasty dudes (like me) in cargo shorts and size-too-small college T- shirts. It isn’t pretty.

What I recommend is getting a few of your pals together, picking one of the first-round cities and booking a trip. The atmosphere will be festive. The basketball will be good, and possibly great. And you’ll still get actual time with old friends, a precious commodity in an age when “keeping in touch” is too often done sitting alone, staring at a screen.

Each city will host first- and second-round games, played either Thursday and Saturday, or Friday and Sunday. This means that on “off days” in your city, there will be a full slate of games on television.


Friday, March 16, and Sunday, March 18

Hard to argue with the Music City as a destination for tournament watching. It’s a quick flight from Chicago. And the downtown district has more than enough taverns for postgame revelry, with the added benefit of a steady supply of live music if the games get boring.

There are also side trips for music fans, starting with the Grand Ole Opry, of course. And while I’ve only been to the gift shop at the Johnny Cash Museum, it made me want to come back for a deeper look. And my fellow “American Pickers” fans will want to check out their Nashville store.

Pro tip: Try the breakfast at Pancake Pantry. It’s not far from Vanderbilt, which itself isn’t far from downtown.


Thursday, March 15, and Saturday, March 17

This may be the best sleeper choice on the list of first-round cities. There are multiple entertainment districts to choose from for after-game fun, including the Strip District, which is closest to downtown, and the North Shore neighborhood across the river from downtown, near PNC Park. It offers the most Wrigleyville-like sports bar experience, if that’s your thing. It’s also close to Rivers Casino.

Consider staying in the Shadyside neighborhood, not far from the University of Pittsburgh. You’ll be jostling for room at the bar with Pitt grad students, but it has a less-touristy feel and a nice selection of restaurants. An off-beat favorite tavern is Le Mardis Gras. It allows cigar smoking — a guys-weekend plus — but it’s hardly a sports bar. If the weather is good, follow the tourists to one of the “inclines,” either the Monongahela or Duquesne. These funiculars reward riders with spectacular panoramic views of the city and the three rivers that spawned it.

San Diego

March 16 and 18

It’s a long flight from Chicago but worth it if you happen to catch the city on one of the 365 days a year that the weather is perfect. The compact downtown makes it easily walkable, which, along with the weather, makes it a nice place to pub hop. Big hotels abound, but don’t be afraid of some of the off-the-beaten path boutique options like The Pearl, a refurbished, affordable spot near the beach, with an excellent little bar and a hip vibe.


March 16 and 18

Don’t pass on Detroit just because it’s Detroit. The downtown has come a long way. And the new arena, along with Comerica Park and Ford Field, has birthed a robust restaurant and bar scene. When I visited in January, a winter carnival atmosphere was thriving downtown, with pop-up shops and a bustling lodge-style warming tent, complete with a bar and giant versions of games like Jenga and Scrabble. I expect a similar festive atmosphere for the NCAA tournament.

The assembly-line tour of the Ford F-150 plant in suburban Dearborn appeals to most guys. There’s also casino gambling both downtown and across the river in Canada, which will require a passport or other acceptable documentation.

Insider tip: Grab a Lyft to the Cadieux Cafe on the city’s East Side. This Belgian-themed, eighborhood gem boasts an impressive menu of Belgian beers, along with the nation’s only feather bowling lanes (think bocce, but with wooden, wheel-of-cheese-sized balls, played on a concave lane).


March 15 and 17

I have a personal bias against Dallas for the same reason I don’t like Phoenix. Too much shiny glass and too many brassy steakhouses. But don’t listen to me. It’s easy to get to. The sports bar game is strong. And brassy steakhouses usually serve really good steaks. Plus you can rent a car and drive around looking at big things.


March 15 and 17

My trip to the most populous city in Kansas was to report a story on the state’s efforts to make teaching creationism the law, so I didn’t spend much time in sports bars. But it’s the kind of small city that can be perfect for this type of guys trip. Let’s face it. A lot of dudes are simply looking for a comfortable hotel and a sports bar that serves cold beer and chicken wings.

Is there more to do in Wichita? Probably. But if your priorities are the basketball and beery fellowship, this may be a winner.


March 15 and 17

Probably low on the list from a logistical standpoint. But if you can make the flights work, Idaho’s capital has the same small-city advantages as Wichita, with a lot more natural beauty. If you want to really do it right, give your group an extra day or two and drive over to Sun Valley.


March 16 and 18

The busy airport makes this North Carolina city easy to get to. And the folks there are nutty about their college basketball, so the atmosphere will be festive. But the state’s efforts to limit the rights of transgender people might be a deal-breaker for some or all of your posse.

Next rounds …

While the first-round weekend offers the most action as the field of 64 is whittled down to 16, don’t overlook round two. With most of the weak teams eliminated, the action can be even more intense. Second-round host cities this year are Omaha, Los Angeles, Atlanta and Boston. Three of these are prime locations for sports-themed trips. And Omaha is, um, less expensive.

This year’s Final Four is in San Antonio, a great place to visit if you like river walks. Kidding, sort of. Its famed River Walk can be a bit Navy Pier-ish with its tourist-heavy vibe, but this 300-year-old city is an offbeat mix of Tex and Mex that’s a welcome antidote to the bustling braggadocio of Dallas and Houston.

(This article originally appeared in the Chicago Tribune in 2018)



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