Most mountain towns tempt summer visitors with a plethora of outdoor adventures, from whitewater rafting and hiking to mountain biking and fly fishing. But Aspen isn’t an average mountain town. In a place where visitors (and residents) fly private, buy bottles of Veuve Clicquot just to spray it (Cloud 9), and drop $1,000 on sushi (Madame Ushi's gold-flaked Chrome Hearts Roll), outdoor adventure can go seriously luxe. 

But mirroring post-pandemic global travel trends, Aspen’s version of luxury outdoor adventure is evolving to emphasize authenticity and depth of experience over opulence and comfort. 

“Most of our Aspen guests come to town regularly and have done the standard activities more than once—they want to connect with locals and see the hidden gems,” says Nomad Inc owner/operator Frank Scotti. “We set up unique, custom experiences. Sometimes this is met with a bit of resistance—for example, they don’t want to leave Aspen or aren’t comfortable with the idea of something new—but if we can get our guests to tap into their inner adventurous spirit, they usually love it.”

With that in mind, we’ve compiled a bucket list of 10 over-the-top outdoor escapes for those who prefer to splurge and let someone else take care of the details, and a handful of DIY versions for those who’d rather adventure mindfully on their own and/or on a budget. 

Lucky for those who recreate here, the rugged mountains cradling Aspen provide ample opportunities for a lifetime of adventuring—perhaps the greatest luxury of all. As Santè Cycling guide and founder Steve Denny puts it: “Recreating in wild places is naturally luxurious.Simply having the time and desire to reinvigorate oneself by stepping away from the human-made finer things is a luxury greater than any other.”

#1 - Heli-Wine Tasting

Colorado’s “Napa Valley” lies just over the Elk Mountains—the Grand Valley and the West Elk wine regions boast some of the highest-elevation vineyards in the world, where warm days, cool nights, and low humidity combine for award-winning Riesling and gewürztraminer, among other varietals. The fastest, most scenic, and most thrilling way to get there? By helicopter. Aspen’s Nomad Inc offers a heli-wine-tasting experience that whisks oenophiles to Paonia, a funky, farm-to-table-focused town 90 miles south of Aspen that’s surrounded by a dozen wineries. Tour vineyards, meet winemakers, and taste everything from dry, crisp whites to robust, meaty reds. And unlike a trip to the actual Napa, you’ll be back in Aspen in time for dinner.

Following a scenic and short flight over the Elks (marvel at the 14ers and rugged topography), you land in Paonia and transfer to a Mercedes Sprinter van that conveys you to sommelier-owned and operated Storm Cellar Winery and Vineyard. Sample the winery’s award-winning dry Riesling from a hillside terrace overlooking the North Fork Valley before heading  to Azura Cellars to sip pinot in an art gallery. Fun fact: The West Elks American Viticultural Area is the only region in Colorado to successfully cultivate pinot noir. 
Other stops along the way might include Western Culture Farmstead and Creamery to sample cheese produced from the seemingly happiest goats in the world, and lunch at Big B’s Delicious Orchards (indulge your inner kid on the swings strung from the huge trees out back) or, if you prefer, an elegant catered meal at the Paonia vineyard of your choice.

THE DEETS: nomadinc.com; starting at $5,000 for a group of four

D.I.Y. #1
Capitol Creek Valley Hike and Picnic
The summer version of après-ski, a post-hike picnic is the perfect way to reward physical exertion in a beautiful setting. And a perfect hike is the Capitol Creek/Capitol Ditch Trail (#1961), a half-day loop around the Capital Creek Valley that offers spectacular views of the namesake 14er as the trail meanders through peaceful aspen groves and high grassy meadows. 
After the hike, savor the best view of the stunningly beautiful valley from (no joke) the trailhead parking lot while snacking on a charcuterie board (no utensils needed) from Boards + Baskets. Local private chef Alex Karlinski works with area producers to source the freshest produce and beautiful seasonal flowers with delicious meats and cheeses. Wash it down with a bottle of Paonia wine, like Peony Lane’s natural chardonnay. “It’s got a uniquely spiced flavor with hints of tropical fruit, and the body and acidity to stand up to bold meats and cheeses,” says Ben Justman, who sells his family’s wine at the Basalt farmer’s market or delivers within the Roaring Fork Valley.

THE DEETS: From Aspen, drive 14 miles west on Highway 82 to Old Snowmass and turn left; continue 2 miles to the T intersection and turn right; after the pavement ends in 5 miles, follow the dirt road for another three miles (the last mile is suitable for high-clearance vehicles only) to the trailhead. Route information: Aspen-Sopris Ranger Station, 970-963-2266; boardsandbaskets.co (from $35 ); peonylanewine.com (from $32 )

#2 - Aspen-Crested Butte Hike & Stay

The hike from Aspen to Crested Butte is a rite of passage for locals and visitors alike. The most luxurious reward for completing the nearly 11-mile, 3,000-vertical trek over 12,500-foot West Maroon Pass is a stay at Eleven’s Scarp Ridge Lodge in downtown Crested Butte. Eleven will coordinate the logistics of the hike over, personalizing the trip for each group and adding whatever amenities are desired. 

The hike starts from Maroon Lake at dawn, to avoid thundershowers, but you’ll feel wide awake as you marvel at the towering Maroon Bells en route to Crater Lake. After a selfie and some steep switchbacks, it’s a gentle, 4-mile downhill hike through a Sound of Music–type landscape, especially from mid-July into August when wildflowers are in full bloom. Following a break for lunch, the hike ends at West Maroon trailhead on the Crested Butte side, 11 miles from town, where a shuttle transports you to your luxe digs for the next two nights.

Scarp Ridge Lodge occupies a 13,500-square-foot, two-story periwinkle Victorian (a former dancing hall and saloon for miners to let loose in the 1800s) two blocks off Elk Avenue. Its large suites feature beds fit for a king, an on-demand oxygen system, built-in sound systems, and rain showers or soaking tubs. Upon your arrival, enjoy an afternoon wellness and massage treatment then a relaxing, in-house, chef-prepared dinner. On your layover day, Eleven’s qualified guides can take you mountain biking, fly fishing, rock climbing (among other offerings), or enjoy Scarp Ridge Lodge’s indoor saltwater pool or rooftop hot tub. Guests can stay in for all meals or head out and experience some of Crested Butte’s restaurants, including Secret Stash, which serves up slices of its famous pizza. On day three, enjoy a hike back (following the same route or taking longer but more moderate East Maroon Pass) or splurge on the heli-charter if you’re in a hurry.

THE DEETS: elevenexperience.com/scarp-ridge-lodge-colorado-summer; from $1,800 per person (includes guided hike, in-field lunch, chef-prepared dinner, and massage), plus lodging (Summer Scarp Ridge Lodge room rates from $1,080 per night based on double occupancy)

#3 - Bike Ride & Dine With The 
Little Nell

After cycling for 24 miles downvalley on the Rio Grande Trail (a paved path that follows the gentle grade of the former Denver & Rio Grande Western Railway) you're ready for an al fresco dinner at Rock Bottom Ranch (RBR), a 113-acre wildlife preserve and educational ranch midway between Basalt and Carbondale.

As Aspen Center for Environmental Studies’ midvalley hub for environmental education, wildlands preservation, and sustainable agriculture, RBR hosts other farm-to-table dinners throughout the summer, but the Nell’s Ride & Dine Dinner Series offers cyclists and locavores a chance to enjoy a farm-to-table dinner at the Ranch prepared by The Little Nell chefs paired with wine from a guest winemaker (the first is on July 18, with Evan Martin of Martin Woods Winery in Oregon's Willamette Valley; at press time the winemaker for the second ride on September 13 was yet to be announced).

“It’s a very special experience, and The Nell makes it exceptional,” says Gordon Silver, who summers in Aspen and started joining Ride & Dine events about five years ago. Silver tries to participate in two Ride & Dine outings every summer for a chance to commune with a wide range of friendly cyclists—both Aspenites and visitors. “It’s an enjoyable ride,” he says, “and a great dinner—which tastes better after the exercise—and the setting is beautiful.”
 Don’t miss a farm tour to explore the gardens and animal paddocks while learning about the complex interaction between agriculture and natural ecosystems along the Roaring Fork River And go ahead and have a second pour of wine: following dessert, The Nell provides return transportation for you and your bike.
THE DEETS: thelittlenell.com; $350 per person, includes tax and gratuity, excludes wine

D.I.Y. #2 - Cycle to Lunch at Pine Creek Cookhouse
Arguably the best all-around road ride near Aspen (longer and more gradual than the ride to the Maroon Bells; less traffic than the ride up Independence Pass), Castle Creek Road climbs nearly 2,000 vertical feet from the roundabout to Ashcroft Ghost Town and Pine Creek Cookhouse over 13 scenic, undulating miles. From Aspen (rent a bike or e-bike from ASPENX or Four Mountain Sports), follow the cycling route along W Hopkins Avenue, then continue on the paved path, past the Marolt housing complex to Castle Creek Road. Enjoy stellar views of the high peaks soaring above Castle Creek Valley, as well as roaring Castle Creek below. One mile past Ashcroft, grab lunch at iconic Pine Creek Cookhouse (reservations are a must; try for the patio with its panorama of 13,000-foot peaks) before descending. This romantic cabin restaurant features “American Alpine” cuisine and uses local ingredients, when possible, like wild game, ruby red rainbow trout, and locally grown produce for its delicious vegetarian and vegan dishes.  

THE DEETS: pinecreekcookhouse.com 

#4 - Saddle Up to Lunch in the Maroon Bells

A newly installed counter recorded nearly 42,000 Maroon Bells bike trips in 2022—a doubling in two-wheeled traffic on Maroon Creek Road from five years ago (mostly due to the rise in popularity of e-bikes). Add to that the shuttle buses running every 15 minutes from 8 a.m. to 5 p.m., and the road to Maroon Bells gets as congested as LA’s I-5. A better way to experience the majesty of the Bells is to bypass the road and go on horseback.  
Saddle up with The Maroon Bells Guide and Outfitters at the T-Lazy-7 Stables on Maroon Creek Road, then ride along Maroon Creek, which originates high in the Elk Mountains and provides water to Aspen. In the saddle for an hour (or 90 minutes or more than two hours) loping along alpine wildflowers, open meadows, and Rocky Mountain wildlife—it’s not unusual to see a bear or a moose, but the horses are used to such surprises.  
At the east portal of the Maroon Bells, you’ll settle in for lunch at a creekside table in a setting that’s cowboy chic. The outfitter’s cook makes a mean steak prepared over an open fire (or a custom menu if desired). It’s BYOB, so pack in your favorite whiskey for cocktails by the fire and a warming red wine for dinner, with music from that  harmonica in your back pocket.

THE DEETS: maroonbellsaspen.com; from $500 per person ($400 on Thursdays), four-person minimum

#5 - Whitewater Rafting  & Cabin Dinner

If you were to design a quintessential adventure-meets-luxury day in the Rocky Mountains, it might look like the private river adventure and high-country dinner offered by Blazing Adventures: Raft a section of the Roaring Fork or Colorado River, then Jeep to a private cabin on Snowmass Mountain for a sunset dinner with music around the bonfire.

Rafting options with the company (which has been guiding in the area for 50 years) include the notorious Slaughterhouse section of the Roaring Fork River just below Aspen, a Class IV whitewater adventure for those 14 years or older; the Upper Roaring Fork, a fun section of Class III whitewater suitable for adventurous families; or the Lower Roaring Fork, which serves up ripples instead of rapids and beautiful scenery. You can also raft through spectacular Glenwood Canyon to a private takeout in West Glenwood.

What could top a half-day, action-packed river adventure like this? An evening Jeep tour and dinner on Snowmass Mountain. Once at the top of Coney Glade, take in the views of the Roaring Fork Valley and enjoy a cocktail before descending to Burlingame Cabin, a historic sheepherder’s cabin tucked in the aspens. Take an extended Jeep tour to a scenic overlook, try your hand at calf roping, toss some horseshoes, or just relax with a cold beverage around the campfire and listen to live music before your guides ring the dinner bell. A BBQ feast is served as the sun sets behind Mt. Daly and shadows begin to dance in the surrounding woods, illuminated by the roaring campfire.

THE DEETS:  blazingadventures.com; from $500 per person

D.I.Y. #3 -Beaver Lake Paddleboard & BBQ
Few things in life are more peaceful than paddling across a high-country lake with snow-capped peaks reflected in the water. One shining example is Marble’s Beaver Lake, which with its spectacular backdrop of mountains and aspens has evolved into a stand-up paddleboard (SUP) mecca. The historic mining town 60 miles southwest of Aspen has lured hikers, ATVers, and anglers for years, but now Marble’s 20-acre lake on the eastern edge of town attracts a flotilla of SUPers every day through the summer. SUP Marble offers rentals seven days a week with hourly, half-day, and full-day rentals. 

Nearby, Slow Groovin’ BBQ is the regional champion of smoked meat and the unofficial social hub of Marble. Sourcing pork from a small farm in Brush, Colorado, Slow Groovin’s St. Louis–style ribs are rubbed with a sweet-spicy dry blend and slow smoked, becoming magnets for its beloved signature sauces. Must try: Hillbilly Nachos (a mountain of pulled pork or smoked chicken and jalapeños smothered with melted cheddar, BBQ sauce, and ranch dressing) and the Unroutine Poutine (a mound of hand-cut fries and brisket and pickled onions slathered with gravy and cheese).

THE DEETS: sup-marble.com, paddleboard rentals from $60 per day; slowgroovinbbq.com

#6 - Aspen Mountain Hike & Dinner

Intimidated by the three-mile, 3,267-vertical-foot hike up Aspen Mountain? You’re not alone. The trek up Ajax is notorious for its unrelenting leg and lung-busting pitch that, according to even locals who hike it regularly, never gets any easier. Enter ASPENX, Aspen Skiing Company’s contemporary rental, retail, and experience brand, which is offering a hike-and-dine outing on Aspen Mountain that makes the journey up a little more approachable and rewarding.

Ascend Aspen Mountain with a skilled guide who knows not only the often-confusing route, but the mountain’s flora and fauna, as well as scenic stops to take a breather while ogling vistas of Aspen, the Roaring Fork Valley, and beyond. Your destination, after an optional summit, is Buckhorn Cabin ( 10,870 feet), which offers views of Mount Hayden, Highland Bowl, and a panorama of peaks. Join your guide for an extra-credit hike up Peanut Butter Ridge to have the landscape further explained. 

Outside the cabin, a swoon-worthy table—styled by ASPENX—awaits with a chef-prepared three-course lunch and a private sommelier serving paired wines. Customization abounds, and not even the sky is the limit, because this is, after all, Aspen.

Don’t even think about hiking down in the dark! A chauffeured ASPENX Audi e-tron SUV will whisk your group back into town in style. 

THE DEETS: aspenx.com; from $15,000 for up to 22 guests

#7 - Hut-to-Hut Gravel Ride

In 2013, Aspen native and professional trail runner Ricky Gates launched the Hut Run Hut, an ultramarathon that links five 10th Mountain Division backcountry huts via singletrack, Jeep roads, and alpine ridges from Aspen to Vail. If just the thought of running and hiking 100 miles makes your knees scream, a brand-new offering from Aspen Expeditions gets you to 10th Mountain huts by bike and lets you try one of cycling’s fastest-growing crazes: gravel biking. This niche sport lies somewhere between road biking and mountain biking and utilizes both dirt and gravel roads and mountain bike trails.

Join a group of cyclists (or book a private trip with your family or friends) and Aspen Expeditions guides to grind on scenic paved, dirt roads, and double track from Eagle to Basalt. You stay one night each at the Peter Estin and Harry Gates 10th Mountain Division huts, with an option to add a third night’s stay at Beyul Retreat, an off-the-grid wellness resort with 13 cabins and a seven-room lodge along the Frying Pan River in Meredith, 44 miles outside of Aspen.

This guided, catered, and supported trip provides everything you’ll need along the route. You’re able to ride for multiple days with little more than a hydration pack on your back while covering 10-25 miles and climbing around 2,500 vertical feet per day, with the option to add or subtract. Another definition of luxury.

THE DEETS:  aspenexpeditions.com; from $1,800 per person for a group of eight or $2,500 per person for a group of four

D.I.Y. #4 - Gran Fondo with the Aspen Cycling Club
The social ride of the summer, this beloved social ride (July 8) starts and ends in Snowmass Village and encompasses some of the Roaring Fork Valley’s most iconic climbs and views. It’s also a chance to witness the inclusive cycling community fostered by the Aspen Cycling Club. Choose 36 miles, 62 miles, or 103 miles, with aid stations at the top of each climb as well as options to add lunch provided by Rolling Fork Food Truck and finish-line food provided by Slow Groovin’ BBQ.  Each distance option builds on the previous, so you can choose your mileage on the fly. Turn the event into a race by chasing Strava segments on each distance option. The fastest times of the day receive prizes.

THE DEETS: aspencyclingclub.org/events/gran-fondo; $100

#8 - Private Water Wade Fishing

The Roaring Fork Valley is known for having some of the state’s highest-quality, public-access fly fishing. So why bother with exclusive private water access? More than 30 years ago, Jon Hollinger, Aspen Outfitting Company’s (AOC) founder and the father of current owner Jarrod Hollinger, recognized that traffic on local public waters was increasing as more and more anglers booked trips to Aspen strictly for fly fishing. Since then, AOC has worked with private property owners near Aspen to maintain several prime sections of the Roaring Fork River for its guests’ exclusive use. Rumor has it the fish feed more readily and aggressively on these private stretches of river.

New anglers benefit from a low-pressure, crowd-free learning environment, while experienced anglers have a chance to slow down and fish every likely piece of holding water, knowing no one is stepping in the river upstream. Families and groups enjoy the private water so they can fish together and not have to spread out along the river. AOC’s private water wade fishing experience includes an expert guide, premium fishing rods, hand-picked flies and Simms waders and boots with an option to add a professional photographer and catered streamside lunch.

THE DEETS: aspenoutfitting.com; half-day starting at $500 per person for a group of two

#9 - Glamping in the Raggeds

Glamping, a luxury camping experience that usually involves decked-out, semi-permanent safari tents with real beds and plush sitting areas, provides the benefits of camping, such as sleeping outdoors (kind of) and reconnecting with nature, without the hassle of finding a campsite, setting up a tent and blowing up a sleeping pad. TOTEM offers all that and more (think battery-powered coffee makers and hot showers), on a 320-acre historic working ranch surrounded by national forest between Carbondale and Paonia—a 90-minute drive from Aspen or a short heli ride. There, you’ll find 10 spacious tents on a plateau overlooking the Raggeds Wilderness with bespoke interiors curated by owner Hart Houston and international clothing designer Jillian Beed of brand Rue Stiic. You can bring your own marbled Wagyu to cook at an outdoor grill area, or arrange through the concierge membership to hire your favorite chef or caterer so you have more time to hike, bike, horseback ride, explore on an ATV, or fish or paddleboard at the nearby Overland Reservoir (where activities are offered through local outfitters). 

THE DEETS: totemglamping.com; from $450 per tent

D.I.Y. #5 - Camping, Elevated
No five-star hotel room in Aspen can compete with a star-filled Rocky Mountain sky. Camping opportunities abound, from reservations-required areas near town to car-camping spots up Independence Pass to backpacking sites, where you’ll pack everything in and out. A few local favorites include the forested, first-come, first-served car camping sites off Lincoln Creek Road, 11 miles up Independence Pass from Aspen; the kid-friendly, lakeside camping at Chapman Campground, about an hour up the Frying Pan from Basalt; and backpacking to Willow Lake, a less-crowded alternative to Snowmass Lake. Food (think pan-seared steak au poivre instead of a boil-a-meal) is the easiest way to elevate your camping game, and the single vessel that will help you do that is a Yeti Tundra 45 Hard Cooler ($325 at yeti.com), which can hold and keep cold enough gourmet overnight camp provisions for four people.

THE DEETS: Chapman Campground sites, from $37, can be reserved at recreation.gov

#10 - Moab Mountain Biking

When Aspenites tire of skiing and want to cycle, they hire Santé Cycling to organize and guide a day trip to Moab, Utah, for a sun-soaked adventure, without the eight-hour round-trip drive.
“There is no better feeling than skiing cold powder one day in March, flying to Moab to ride bikes through the dust and sun in shorts and a T-shirt, then flying back to Aspen and skiing slush bumps the next day,” says Santé founder Steve Denny.  

And even in summer, when Aspen and Snowmass offer hundreds of miles of breathtaking (and lung-sapping) singletrack, sometimes you get a craving for desert slickrock that you just can’t shake. 

Fly from the Aspen airport to Canyonland Fields in Moab, already fueled from breakfast by local favorite Mawa’s Kitchen on the plane. Once in Moab, load into the Coyote Shuttle van and drive 40 minutes to Potash Boat Ramp, where your guide preps your bike before guiding you up Potash Road to Shafer Canyon Road and the most famous part of the White Rim Trail, the Shafer Switchbacks—1,400 vertical feet in 2.5 miles—into Canyonlands National Park.
After lunch at the Shafer overlook, bikes are loaded onto the van and shuttled to the top of the Magnificent Seven Trail System (Mag 7 ), one of Moab’s most famous sections of trail—you’ll find everything from singletrack to drops to steep descents—or loop the classic Jug Handle Loop to a pickup on Potash Road. Fulfilled, you’re ready to return to this side of paradise.

THE DEETS:  santecycling.com; from $2,000 per person for a group of four

 

D.I.Y. #6 - Snowmass Bike Park + Elk Camp Farm-To-Table Dinner
With 25 miles of lift-accessed mountain bike trails—from beginner-friendly, flowing singletrack to adrenaline-inducing descents—the Snowmass Bike Park falls almost 3,000 vertical feet from the top of the Snowmass ski area to Base Village. If you’re in the mood to pedal, load your bike onto the Elk Camp Gondola and then onto Elk Camp Chairlift to start the cross-country ride to Aspen (via the Government Trail) at 11,325 feet with views of dramatic alpine scenery. On Sunset Tuesdays at Elk Camp (5–7:30 p.m. June 28–August, except July 4), bike park hours are extended until dusk,and  the mid-mountain lodge at the top of Elk Camp Gondola thrums with live music on the deck, and cyclists toasting the end of a glorious summer day with farm-to-table fare and libations at Elk Camp Restaurant.

THE DEETS:  aspensnowmass.com; single-day tickets from $54