The 5 ‘Manventures’ Every NY Gent Should Take This Summer

Gather the fellas. Boys' weekend cometh.

By Shari Gab

The 5 ‘Manventures’ Every NY 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 New York, engineered to satisfy every budget and preferred method of fraternizing.

Want to sleep next door to the world’s largest cave system ... for $6 a night? Race some cars? Go full Lord of the Flies on your own private island?

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

Kentucky (3 images)

The Shoestring: Bowling Green, KY
You’re headed to (literal) middle Earth. The Kentucky Mammoth Cave National Park is the world’s longest-known cave system, with 400 miles of stalactites and stalagmites to wander ... There are eight campgrounds sprinkled throughout its acreage; if you didn’t book in advance, opt for Houchin Ferry, a boat-in site that books on a first-come, first-serve basis ... Back in town, you’ll find handsome, non-helmeted affairs, from visiting the National Corvette Museum to taking in a light-hearted Hot Rods game ... En route, stop at the White Squirrel Brewery for a PB&J burger — and brews, of course. And if you’ve got a few extra pennies to spend, The Bistro offers a full-fledged Italian feast. Because post-adventure carb loading is a thing, right?

Orange County New York (3 images)

The Post-Grad: Orange County, NY
Remember when cycling was outdoors? It’s time for that to be a thing again. Put your squad to the test at the Farm to Fork Fondo, where biking meets wine. You’ll embark on an 80-mile ride though the Hudson Valley with chef-prepared bites along the way ... If you can’t get your butt in gear in time, there’s always the Spartan Race this August. It’s West Point, people, so expect grit to rule the day ... After you’ve drained yourself of all accessible adrenaline, the Peekskill Brewery is waiting with chill IPAs and the rustic Bear Mountain Inn is at the ready with a pillow.

Maine (2 images)

The Rainy-Day Fund: Neddick, ME
Drop your bags at the newly refreshed suites at the Cliff House. Of note: the stunning locale’s new Ledges wing has two oceanfront penthouse suite with terrace doors at the ready to swing open … From there, throw on all the non-coordinating patterns you can muster and head over to the nearby Cape Neddick Country Club, with 18 picturesque holes you can book through the hotel’s concierge ... You won’t have to wander far off campus for excellent eats — nor will you want to. But at the very least, hit Flo’s Hot Dogs on your way in or out of town. Their no-nonsense weiners will put those dirty-water dogs you’re driving back to to shame.

Saratoga (3 images)

The Splurge: Saratoga Springs, NY
Even if you’re not the gambling type, there’s something fairly distinguished about putting a few Benjamins down on the ponies. For that, Saratoga Race Track is your huckleberry … Looking for a more visceral type of horsepower? It would behoove one to stop in at the Saratoga Auto Museum and drool all over the vintage Vanderbilt Cup steeds … Feeling inspired to get behind the wheel? The Monticello Motor Club — and its fleet of track-ready supercars — is only two hours away. It’s members only, but they do host occasional track days and private lessons for guests ... If you’re sore from losing, fret not. You’ll be resting your head at the superior Adelphi Hotel. Built in 1877, these luxurious digs just got a revamp complete with two restaurants from David Burke: the solid steakhouse Salt & Char, and the seasonally focused Blue Hen. And do stop off at the in-house Morrissey's Lounge for a nightcap.

Keys (3 images)

The Blank Check: Sunset Key, FL
Why fight through the flocks of weekenders when you could take over your own private island? For that, head to Sunset Key ... Should you tire of the bend-over-backwards staff and catered rum tastings accompanied by lobster-encrusted grouper, Key West is just a ferry ride away. Start by seeking out a couple of the most coveted tables in town at Little Pearl and raw bar Thirsty Mermaid, and if you need a craft cocktail, bully your way into a seat at Nine One Five ... The sportsmen among you would be keen to head there in July for the Hemingway Day Fest’s Drambuie Marlin Fest, where you can try your hand at sport-fishing for $50k in grand prizes ... Then reward thyself for such efforts with a seaplane hop to the Dry Tortugas for a moment of unspoiled beauty unlike any other.

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