8 Great, Unexpected Trips To Take With Your Friends

Buddy trips are transformative, funny, revitalizing, sometimes hazardous, and necessary. Good ones will put you through a lot, and that's the point. To form deep, lasting friendships with someone, you need to cross over some terrain together. It's a concept that Aristotle called "shared salt." That's why you and the college roommates with whom you threw rent parties and survived bar fights are still friends. As we get older, we have less time and more to lose; we can't be reckless, but we have to find time for friends, lest we become repressed, boring, miserable, irritable, and by extension, toxic to our spouses and kids. (This is the plot of City Slickers, The Trip, and every other excellent buddy movie, by the way).

A few years ago, I started organizing trips with people I've met around town at the cafe, on creative projects, or at kiddy parties. The first of these was an ice fishing trip to North Hero, VT, with three fellow non-fishermen. I stoked everyone's imaginations with tales of the "water wolf" (a variety of pike) and "Champ," Lake Champlain's own mythical "Nessie"-type creature. We drove up there from the Hudson Valley in the worst blizzard of the year, listening primarily to nineties gangster rap. We had a thoughtful discussion about our fathers; a political argument almost led to one passenger's ouster from the car. The singer in the group mounted a passionate defense of Alanis Morissette. In Vermont, we continued our antics in a shanty on ice, freezing and passing a bottle of Wild Turkey to stay warm. We caught almost nothing, and it was brilliant. We returned home as better friends.

These are the kinds of trips I'm advocating. Don't gamble away your wedding ring or wind up in an Atlantic City drunk tank, but plot a course and try something new; it can be as mild as you want. If there is an element of *moderate* challenge or risk, though, however arbitrary, it will improve your friendship. Here are some ideas.

1. A Golf Weekend In Arizona

I've played precisely two rounds of golf in my life, and it wasn't as easy as I thought, but cruising around a vast rolling green that's been manicured expressly for the world's most gigantic game of ball — that's fun even if your thwacks aren't so accurate.

Arizona is ideal for a long golf weekend, regardless of your skill level. It is always sunny and dry, the surrounding desert and mountain landscapes are beautiful, and there are over 300 courses. It strikes me that watering a golf course worth of grass in the middle of a desert every day is frivolous, considering the imminent climate disaster we face. Still, one of Arizona's most famous courses, TPC Scottsdale in the Sonoran desert, claims to host the world's largest zero-waste sporting event, the WM Phoenix Open. You can golf there in good conscience with a view of the surrounding McDowell Mountains.

Alternatively, in Tucson, you can find slightly cooler temperatures and inexpensive municipal courses that date back to the twenties and thirties. When you aren't golfing, try Sonoran food like Sonoran Burritos, Burros Percherónes, Sonoran Hot Dogs, and Caldo de Queso.

2. A Fishing Trip In Montana

In 1992, the film version of Norman Maclean's novel A River Runs Through It was released, and tourism to the Big Sky State shot up by 120%. If you were more than ten years old at the time and had a soul, then the movie caused you to fall in love with the idea of fly fishing and the state of Montana. Those Montana streams are still pulsing along with an abundance of native trout.

There is so much good fishing in Montana that you could be air dropped anywhere and survive on wild trout indefinitely. However, you'd be better off landing in Bozeman near Gallatin and Yellowstone Rivers. It has a buzzing bar and restaurant scene, and you'll appreciate a good drink at the end of the day, especially if you spend most of your fishing time untangling things. Revelry in Downtown Bozeman has fantastic beer, wine, and cider lists, wood-fired pizza, and a Montana lake trout dish that would be a good consolation prize. If you are looking for a sleepier town, stay just east in Livingston. There are several options for food, drink, and lodging, but you should stay at the storied Murray Hotel. You’ll have late Montana author Jim Harrison’s watering hole, the Murray Bar just downstairs, and two delightful restaurants: 2nd Street Bistro and Stella’s Gourmet Kitchen.

A quick search turns up dozens of five-star-rated fishing guides in the area, so you'll have no problem finding equipment rentals or an outfitter who can fully customize a multi-day trip. Montana Angling Company receives incredibly high praise. They haven’t had a single bad review on Google.

Note: you'll need a conservation license, a base fishing license, and an angler aquatic invasive species prevention pass. All of the licensing information is available here.

3. A Canoe Camping Adventure in the Ozarks

Golfing, fishing, and hunting are ideal activities to do with friends because they provide an ostensible goal or competition to focus on while you're hanging out—some of which require silence (even better!). Camping, as a buddy trip, can be a little open-ended, but if you make it a canoe camping trip or a backcountry hiking trip, all of a sudden, you are on an expedition.

The Ozarks (in addition to being a fictional backwoods gangland) is ideal for both. Paddling or hiking along the 100-mile Current River and its tributary, the Jacks Fork, you'll pass caves, freshwater springs, limestone bluffs, "hollers" (hollows), sawmills, and shut-ins. For free, you can camp on any of the river's gravel bars on public land, and there are primitive campsites available at $5 a night. The Harvey's Alley website lists these campgrounds, helpful tips for riverside camping, and just about everything you'll need for the trip.

4. A Classic Car Tour of Wine (or Cider) Country

I often dream of cruising through wine country in a vintage 66 Lamborghini Miura or a 72 Citroën Maserati (like famous friends Eric Ripert and the late Anthony Bourdain once did) picnicking along the way with several bottles of great wine and a platter of expensive charcuterie.

There are dozens of enticing American routes. In the east, you could do a Hudson Valley cider tour or try out the world-class Rieslings of New York's finger lakes; in the west, there's Napa, Santa Barbara, Sonoma, and more throughout Washington and Oregon. The idea is simple: you take turns driving a magnificent car over a breathtaking landscape and then stop occasionally to eat and drink lavishly (and safely, of course).

The most significant challenge is finding the car. I spend hours on eBay and Craigslist looking for the right vehicle. Buying one, however, is a mistake. Old cars have weird problems. (Have you ever heard of "witches' hair"? Unfortunately, I have.)

Anyway, leave those problems for other people to deal with and just rent your dream car from a company like Drive Share (there are others, but it appears to be the most legit). Right now on the site, stylish 60's and 70's Mustangs, Porches, and Datsun 240zs abound. If something goes wrong, there is a roadside service, and the owner is responsible for fixing the problem.

5. A Southern Gas Station Fried Chicken Tour

Where I’m from, upstate New York, gas station food is disgusting (Stewart’s ice cream being the exception). Mustard and ketchup packets can’t fix those week-old hot dogs from a metal roller in a bun that is somehow both soggy and stale. In the south, though, there is a long tradition of serving good fresh roadside food from gas stations, particularly fried chicken. The notion of fried chicken as a traveler’s food has its roots in the “shoebox lunches” or “chicken boxes” that African-Americans packed when driving dangerous routes out of the south. Soon, gas stations and road stops were known for serving all travelers crispy and juicy legs and thighs. Even our most famous fried chicken chain, KFC, started at a Shell station. Some of the country’s best fried chicken is still being served from gas stations today.

Here are a few I can vouch for: Quick Stop in Milton, DE, Royal Farms (throughout Maryland), Mac's Country Store in Roseland, VA, Browns in Charlottesville, VA, Quick Shoppe in Charlotte, NC, Roy's Grille in Lexington, SC, Krispy Krunchy (throughout GA and beyond), Lawhon's Grocery in Ft. Myers, FL and Joe's Chicken & More in Melbourne, FL.

For most people, this trip works best if you already have some other reason to drive through the south— maybe you're headed that direction for a bowl game, or perhaps you didn't listen to me, and you are picking up a craigslist car. In that case, eating at your fuel stops would be efficient anyway. But if you love chicken like I do, then you might want to make a special trip. If you need something to drink along the way, each town has great breweries (starting with Dogfish Head in Milton, DE), some of which offer camping (like Devil’s Backbone in Roseland, VA).

One caveat: I did this, and the fried chicken was delicious, but my stomach wasn't ready. Bring Tums, Omeprazole, Famotidine, apples, carrots, bananas, those little yogurt drinks, anything to bring peace to the ole microbiome.

6. A Mississippi American Roots Music Tour

Is the blues dead? I don’t listen to much past Muddy Waters. The same goes for country music; I stop somewhere before Gram Parsons. Roots music is hotter when you’re close to the initial spark. Still, the lore of American blues music is irresistible; if someone suggested a trip to the crossroads to see what ghosts are lurking, you'd have to hop in the truck.

The Mississippi Blues Trail includes over 200 blues-related historical markers primarily throughout Mississippi (a few are out of state), on city streets, train depots, farms, cemeteries, and outside foundational blues and country joints like the 100 Men Hall in Bay St. Louis. Historical locations like The Riverside Motel — where Bessie Smith died, and Sonny Boy Williamson II lived — still rent rooms. You can grab a plate of food and a show at one of many legendary clubs. One of the oldest and most charming is the Blue Front Cafe in Bentonia. Even if all the authentic blues and country originators are dead and gone, you'll hear many talented musicians who have devoted their lives to preserving their music. After a few drinks, it may be hard to tell the difference.

7. Renting An Ice Fishing Shanty In Vermont

We covered Type 2 fun in a recent issue: the measured misery that leads to fulfillment and deeper relationships (think the polar bear club). Ice fishing is great because you get to take your suffering sitting down (though you do have to leave your shanty to check on the tip-ups set over holes outside). As I mentioned, three friends and I went ice fishing a few years ago. The cold and the relentless snow were indeed miserable, and that seemed to be enough to trigger the bonding effects of type 2 fun. Without a shanty, it would have been too awful, though.

Find an outfitter who will set you up with one, drill holes for you, provide tip-ups, rods, and bait, and give you a snowmobile ride to your spot on the ice. Lake View Lodge (Formerly Harmony Harbor Lodge) in North Hero, VT, on Lake Champlain, took care of all this for us amid a blizzard and kept us stocked with wood for the shanty wood stove. Their main lodge and the adjoining motel rooms have all the wood paneling, taxidermy, and fishing-related newspaper clippings to keep the rustic vibe in check. In addition, North Hero is only an hour from Burlington and Montreal if you want to tack a fine dining experience on to the end of your trip.

8. A Weekend At Saratoga Racetrack

A weekend at the races always feels like a throwback, and it can be safe fun, provided you bring a friend along to hold you to spending limits (make sure you have those). Depending on your sensibilities, you might want to find a place that approximates gritty LA tracks Bukowski used to write about or the posh Kentucky Derby of the '20s. We recommend a weekend at Saratoga, just south of the Adirondacks in upstate New York, a storied track that offers both divey and glamorous atmospheres. Men in suits and women in big hats and mint juleps cheer in the stands while the ones who mean business, the leathery folks with gold Rolexes, sunspots, and newspapers under their arms, are in the video viewing area, watching the screen through a cloud of cigar smoke.

Hang around and place bets over two or three days, and you’ll start learning the lingo. You may even come out ahead. Afterward, join the lively crowds of bettors and jockeys for drinks in town.

While there, you can visit Hamlet and Ghost for cocktails or head to one of the dozens of nightclubs. Or, for a calmer night, go to Cafe Lena, the longest-operating folk music venue in the United States (Bob Dylan used to headline). For lodging, stay at the Adelphi, which houses Salt & Char, one of the city's most popular restaurants, and start the following day slowly with fried chicken and waffles at Hattie’s.