Make the most of your carefree summer days.
Make the most of your carefree summer days. (Photo: Robert Kohlhuber/Stocksy)

How to Get Outside (and Get Cultured) Every Weekend This Summer

You're going to fill every free day—from Memorial Day through Labor Day—with wild races, delicious food and drink, good music, and an abalone or two

Make the most of your carefree summer days.

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Beautiful, sublime summer is almost here. But it can go by in the blink of an eye, and that means you should never spend a weekend at home just because you didn't know what plans to make. To make the most of your carefree days, we rounded up the most unique outdoor experiences in North America. There's an event or race for every weekend, so keep this calendar handy at all times.

May 29: MB Bike the Drive

Where: Chicago, Illinois
​Cost: From $59

It’s worth the 5:30 a.m. start for this once-a-year chance to cycle a car-free, 30-mile loop on Lakeshore Drive. Start in the historic Bryn Mawr neighborhood and ride south to the half-way-point rest stop on the lawn of the Museum of Science and Industry in the heart of the city. This isn’t a race, but cars are allowed back on the route at 11 a.m. If that’s not reason enough to ride fast, the post-ride pancake feast at Butler Field is.

June 4-5: TX German Bier and Käse Festival

Where: Austin, Texas
Cost: $45

Belly up to Austin’s oldest beer garden, the Saengerrunde, founded in 1867 by German immigrant August Scholz, for this annual artery-clogging festival. Taste German-style beer from 16 breweries and sample mouthwatering Käse, grilled cheese prepared by the best chefs in Austin. Dance it all off to Brave Combo, a homegrown Texas band that plays world beat music. Party and bowl at the Saengerrunde until 10:30 p.m.—or until the food runs out.

June 9-12: Southern Grown Festival

Where: Sea Island, Georgia
Cost: From $950

This four-day festival celebrates southern cooking, music with soul, and stiff bourbon cocktails. Start off with a genteel meat-and-three picnic while playing lawn games along the Black Banks River and listening to Tennessee-based The Black Cadillacs. Get wild on Saturday night with performances by Dumpstaphunk and the Tedeschi Trucks band, followed by the Late-Night Throwdown, a battle into the wee hours to determine which chef-bartender team makes the best crowd-pleasing comfort food and cocktails.

June 17: Spartan Agoge

Where: Pittsfield, Vermont
Cost: $450

In Ancient Greek, the word “Agoge” means “rearing.” That’s gentle terminology for the physical, mental, and emotional extremes this 60-hour, team-based training session will extract from participants. Since Spartan activities are secretive, we can’t give you insider tips other than to aim for the ultimate goal, which is to embrace the unknown and become the “master of yourself.” And make it out of Vermont alive. Packing tip: bring 10,000 calories of MREs (that's Meals-Ready-to-Eat).

June 23: Race to Alaska

Where: Port Townsend, Washington, to Ketchikan, Alaska
Cost: $650 to race, plus $75 per each additional crew member

In the true spirit of Alaskan self-reliance, this 750-mile race has two basic rules: no support and no motors are allowed. For a sense of just how difficult the route through the Inside Passage is, last year 35 teams of sailors, rowers, and paddlers started, and only 15 made it across the finish line. As event organizers like to say, it’s the “Idatarod on water”—minus the dogs, plus the risk of drowning. Be sure to win: The first place prize is $10,000. Second place is a set of steak knives. And even if you're not competing, this one is a blast to watch.

June 26-28: Abalone Camp

Where: Little River, California
Cost: $618, includes gear, two nights lodging, and some meals

Learn how to harvest bivalves from the best freedivers in California at this two-night camp at the peak of the abalone season. Whether a rank beginner or experienced freediver, guests learn how to collect, then clean, cut, and pound the abalone they caught. Camp culminates in a cooking demonstration and, of course, a communal feast on the lawn at the Little River Inn.

July 3: Bluegrass Sundays

Where: Aspen, Colorado
Cost: Free

What says summer more than a high-alpine hike through wildflowers of the Colorado Rockies? One that ends at the top of Aspen’s 11,212-foot-tall Ajax peak with craft brews and bluegrass bands. On this particular Independence day weekend, the picking is provided by Running Out of Road, a five-piece band from Durango. If you’ve had a few too many for the hike down, there’s always the option to ride the gondola.

July 4: Independence Day Celebration

Where: Jackson, Wyoming
Cost: Pancake Breakfast, $10 adults, $5 kids

Celebrate our nation’s independence where the deer and the antelope occasionally roam in downtown Jackson, Wyoming. The party starts with a pancake breakfast on the square and a “Howdy Pardners” parade that includes clowns and classic cars. Take the rest of the day to climb a Teton, but be back by 6 p.m. sharp for the Town Square Shootout, rodeo, and fireworks exploding over Snow King Mountain.

July 9-13: Artist Camp

Where: Labrador, Newfoundland
Cost: $760

This two-night retreat offers guests the chance to craft silver jewelry en plein air while camping on Prisoners Island off the coast of Labrador. The island’s name may sound foreboding, but its misty Atlantic coastline and berry-covered hills provide inspiration. Local artist and kayak guide Pete Barrett provides the instruction. Bonus: There’s also time to hike the mainland’s 4,131-square-mile Mealy Mountains National Park Reserve, Canada’s largest and newest swath of protected beauty.

July 14-17: Northwest String Summit

Where: North Plains, Oregon
Cost: From $225

You may be getting too responsible to spend a summer chasing Railroad Earth in your beater Vanagon, but this event, with its glittery homemade hula hoops, will bring you back to simpler days. The 15th anniversary concert, at a beautiful venue 20 miles northwest of Portland, is the apex of summer bluegrass festivals with a star-studded lineup including Yonder Mountain String Band, Leftover Salmon, the Infamous Stringdusters, Railroad Earth, and many more. There’s even a Kids’ Area for costume-making, board games, and passing down the art of hula-hooping.

July 23-28: Singletrack 6

Where: Kootenay Mountains, British Columbia
Cost: $581

The best of all worlds: An epic six-day stage race that climbs roughly 10,400 feet and traverses 160 miles of sometimes rocky, sometimes flowy singletrack. It also passes through funky small towns like Fernie, Cranbrook, and Golden, which ensures that after three to five hours of riding per day, there will be a delicious hot meal and a comfortable bed in a luxurious inn. End-of-ride brews and music are guaranteed, although the music lineup is still TBD.

July 29-31: Pikes Peak Ultra

Where: Pikes Peak National Forest, Colorado 
Cost: $145

Fun is a relative term, but for some particularly masochistic runner types, this tough 50-mile footrace through Pikes Peak National Forest, which has a total elevation gain of 11,000 feet (and loss of 11,000 feet), might be the best weekend of the summer. There’s no doubt the course, which culminates at the summit of 11,499-foot Mount Rosa, is brutal. But it brings new meaning to the term “runner’s high.”

August 6: Farm to Fork Fondo

Where: Lancaster, Pennsylvania 
Cost: From $125

In the best Italian tradition, this fully supported, 109-mile “Big Ride” brings together the finest things in life: food and bikes. Join 500 cyclists, including pros from the Colavita-Bianchi women’s cycling team, as they climb and descend almost 7,000 feet into the rolling, verdant Pennsylvania Dutch countryside through Amish and Mennonite farming communities. This isn’t a race, but there are timed GPS segments along the route. The faster you go, the more time you have to eat at the post-ride barbecue at the Country Barn, owned by “Farmer Jim,” whose family has been working the soil here for three generations.

August 10-14: Kids Adventure Games

Where: Vail, Colorado
Cost: Adventure race, $180 per team; Mud run, adult $20, kids $10

It’s never too early to get your kids addicted to adventure racing. This two-hour race is a non-intimidating, two-kid-per team, 2.5-to-3.5-mile epic that starts with a ride up the Lionshead gondola (different age groups participate on different days). Kid teams (no parent-assistance allowed) then follow a mapped route down the mountain that includes a low-ropes course, climbing, a zip-line, and a Tarzan swing. It all culminates in a giant slip-n-slide on steep Pepe’s Face to the finish line. The course sounds like so much fun that we’re lobbying event organizers to create a similar one for adults. For more singularly focused kids, who want mom and dad to join in the fun, the entire family can participate in the 5K Mud Run on Saturday.

August 20-21: Folks Festival

Where: Lyons, Colorado
Cost: Three-day festival pass, $150; with on-site camping, $220

This 26-year-old bluegrass festival is the mellow elder statesman of its jamming siblings, like Rocky Grass, which takes place here earlier in the summer. This event is so mellow, in fact, that concert goers can tube the St. Vrain River while listening to Lucinda Williams, The Decemberists, Dougi Mclean, Kathie Mattea, and more from mid-morning to 10 p.m. every night. To move your body beyond opening a beer, Rocky Mountain National Park is a 40-minute drive away, and the 3,000 acres of open space and singletrack trails at Hall Ranch are just a short ride away.

August 27: Peaks and Paws

Where: Village at Squaw Valley, California
Cost: $5

Man’s best friend is the star at this all-day fest that benefits the Humane Society of Truckee-Tahoe, with events like the K9 Kings Ultimate Flying Dog Show, an entertaining display of doggie athleticism. Humans participate, too: join a guided hike up a peak, listen to bluegrass bands like The Cherry Pickers and Dusty Green Bones on the big stage, or walk away with a new four-legged friend. And, yes, there’s even a “Yappy Hour” where you can save $1 on drinks and your pooch can munch on complimentary dog treats.

September 5, Labor Day: Chill Out

Where: Anywhere, USA

For one last blast of summer, one could partake in the Roy Webster Cross-Channel Swim, a rigorous 1.1-mile crossing of the Columbia River that starts with a paddleboat ride, ends in Hood River, and dates back to 1942. But this is Labor Day. Take advantage and get lazy. We suggest reading a few of the 25 essential books for the well read explorer, baking bitter chocolate and sea salt sticky bites (they're healthy enough to take on a run!), then couching it to watch the 10 most underrated adventure movies on Netflix (in our opinion). To avoid going batty by the end of the weekend, school yourself on three simple strength moves that will have you rearing to go for fall races.

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