5 ‘Manventures’ Every Chicago Gent Should Take This Summer

Gather the fellas. Boys weekend cometh.

By Walker Loetscher

5 ‘Manventures’ Every Chicago Gent Should Take This Summer
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22 May 2018

This is but one installment of 37 Things a Man's Gotta Do This Summer, our annual compendium of everything worth seeing, doing, eating, drinking and generally making time for in your neck of the woods between now and September. Stay tuned all month for more.


The biggest crisis facing American men isn’t smoking or obesity. It’s loneliness.

And according to a study out of Oxford University, there’s one very simple way to fix this: spend more time with your friends.

So we compiled five superlative boys weekends near Chicago, engineered to satisfy every budget and preferred method of fraternizing.

Want to hike to a secret campsite with a pack full of brisket? Play four courses in three days? Sample some local whiskey on an overnight canoe trip?

It’s all in there. Howling at the moon optional — though certainly encouraged.

The Shoestring: Sand Ridge State Forest, IL

Before skipping town, be sure you’ve got all your camping essentials taken care of. This checklist from local outdoor guru Aaron Wolf will help with that … As for your provisions? Try 3 Greens Market, and be sure to get the pastrami, pulled pork and smoked salmon ... Then it’s a few hours southwest, just past Peoria, to Sand Ridge State Forest, where you’ll find 55 miles of backcountry trails, including some that lead to 12 primitive hike-in campsites. That’s where you’re headed. Expect a total loop of 5-14 miles, with sandy terrain throughout that can make the going a little tougher than your average flatland circuit.

The Post-Grad: Glenmont, OH

Six hours of fart jokes and full-bore sing-a-longs will be worth it when you arrive at The Mohicans, a bucolic colony of cabins (4) and treehouses (6) that sleep anywhere from 2-15 people. We like Moonlight, a stunning two-story treehouse built from reclaimed barn wood … By day, hike in nearby Mohican State Park; Hemlock Gorge is a breezy two-miler that passes a pair waterfalls … Prefer the view from above? Tree Frog Canopy Tours runs some ziplines that may interest you … And for eats, the proudly local Malabar Farm Restaurant is more than worth the half-hour drive.

The Rainy-Day Fund: Madison and Baraboo, WI

Expect Wes Anderson-ian furnishings (flamingo paintings; vintage tennis racquets) and handpies in the lobby at the college town-appropriate Graduate Hotel … For dinner, pass on the cheese curds for something a little lighter, like, say, the Pan-Asian favorites at buzzy noodle house Sujeo … Then grab some top-shelf meats at The Underground Butcher and head an hour northwest, to Baraboo … New day, new digs: the Inn at Wawanissee Port is home to bucolic digs and a daily wine-and-cheese hour, and they’ll also cut you a discount at nearby Driftless Glen Distillery and Restaurant … Speaking of Driftless, the name seems to be a theme in these parts: Driftless Paddling Guides will take you on your very own Deliverance tour down the Wisconsin River, with single-day or overnight trips available.

The Splurge: Ozark Mountains, MO

It’s not Pebble Beach (yet), but Big Cedar Lodge is well on the way. A no-holds-barred “wilderness resort” best known for its extensive fishing, boating and hunting offerings (owner Johnny Morris is also the CEO of Bass Pro Shops), Big Cedar is primed to join the ranks of golfing’s elite this year. Why? The additions of a Bill Coore and Ben Crenshaw-designed 18-hole course and Gary Player-authored 13-hole Par 3, which will supplement existing options from Jack Nicklaus and Tom Fazio. Fast forward to next year, though, and the fun really starts: that’s when Tiger Woods’s first 18-hole public-access course will come into the fold. And did we mention the six different lodging options and 100-year-old mahogany bar?

The Blank Check: Washington, DC

Think you can round up 5-30 friends who like opulence and live sports? Meet Big Game Air, the same-day jet service that ferries Chicagoans back and forth from the country’s premier sporting and cultural events (the Super Bowl, Coachella, The Masters, etc.) … Why not head to the MLB All-Star Game, which hits D.C. this year? The Home Run Derby is an excellent opportunity to snag that souvenir ball you’ve been waiting for your entire life — or drop it … Stay at the Darcy, a newish boutique from Hilton that slings gin drinks in the lobby, carts cocktails to guests’ rooms and boasts an on-site haberdasher from menswear company Read Wall … As for where to nosh? Well, Spanish Chef José Andrés’s legendary Jaleo, if you had to foresight to book a table. If not, just stroll the stalls at The Wharf, where you can hop between bars and eat lobster and crawfish straight off the boats that caught them.

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