Glitter Gulch, Fat City, Canary City … ah, Aspen. The monikers for this rich-in-history former mining enclave—with its glitz-and-glam reputation thanks to celebrities hiding out on holiday, jaw-dropping real estate, gourmet dining, boutiques that rival Rodeo Drive, five-star resorts, and a world-class arts scene—aren’t far off the mark.

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But thanks to the father of gonzo journalism, Hunter S. Thompson, who lived in the area from 1969 until his death in 2005, there’s an entirely different side to the tony town—one that’s steeped in his counterculture legacy, and helps balance the concept of living the high life. Aspen is also now notorious for having the highest pot shop density of any city in the state; there are six in the downtown core alone. (Snowmass, the resort town next door, has a moratorium on cannabis through October 21, 2018.)

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Whether it’s your first visit since Colorado legalized or you simply want to shake up your standard winter weekend agenda, the following itinerary is curated by a true local to make your time in the high country that much higher.

Aspen has the highest pot shop density of any city in Colorado; there are six stores in the downtown core alone.

Travel

Flying to Aspen has never been easier, with direct flights now offered from Atlanta, Chicago, Dallas, Denver, Houston, Los Angeles, Minneapolis, Phoenix, San Francisco, and Salt Lake City. A cheaper option is to fly to Denver and rent a car or book a seat on a Colorado Mountain Express shuttle.

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Provisions

Purchases at swanky Aspen dispensary Silverpeak are literally presented on a silver platter. (Courtesy of Silverpeak)

Make one or both of our favorite two dispensaries in town your first priority after wheels down. Best Day Ever, owned by longtime local Michael Gurtman, opened as Aspen’s newest retail dispensary last year. And thanks to its organic cultivation facility focusing on heirloom cannabis in Glenwood Springs, it’s already known in town for having the strongest strains ever, along with an expertly curated selection of artisan edibles, designer accessories, and pain-relieving topicals.

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Perfectly in line with Aspen’s luxury-leaning reputation, Silverpeak (named Leafly’s 2017 Best Boutique Dispensary in Colorado) was way ahead of the game, with a gorgeous grand opening when Colorado went first recreational in 2014 that unveiled the country’s first dispensary to look more Barney’s than a basement head shop. Clean lines, natural light, rich woods, and custom cases aside, the entire experience is elevated, with purchases even presented on a silver platter. Here, you’ll also find the industry’s leading lines of accessories, books, and branded souvenirs in a separate boutique space. At a price fitting for a splurge-worthy weekend ($25), check out the top-shelf Purple Dogbud; for a quality gram at less than half the price ($12), ask for the Blueberry.

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Stay

There are still many miles yet to go before you’re smoking a joint at the St. Regis, so as any tourist in a legal city has been frustrated by in the past, the cannabis conundrum remains: You can buy it, but you can’t smoke it. The best option is to book a cannabis-friendly private apartment, condo, or home with listings available on Airbnb (search with the new “smoking allowed” filter).

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Woody Creek Tavern is one of the remaining anti-establishments, where Hunter S. Thompson imbibed nearly every day.

Gear

Aspen is surrounded by four different ski resorts (Aspen Mountain, Highlands, Buttermilk, and Snowmass), making its backyard playground pretty much unparalleled. Lift tickets and rental equipment get pricey, so save a few bucks by purchasing yours in advance directly through Aspen Snowmass.

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Eat

Post-wake-and-bake, hit Spring Café for the Go Green Scramble, perfect fuel for a go-green weekend. (Courtesy of Katie Shapiro)

Chef Chris Lanter is Aspen’s resident cannabis cuisine king, appearing in an episode of Munchies on Vice at Owl Farm and catering infused feasts for high-profile private events like the annual NORML Aspen Legal Seminar. While the law prohibits him from playing with pot in the two restaurants he owns in town, make a reservation at Cache Cache for a special night out, where he’s perfected French bistro fare for nearly 20 years. Hit Home Team BBQ, which he opened last year in partnership with the infamous South Carolina-based crew, for house smoked meats and all of the classic sides. Taking home a T-shirt that’s a spin on the Steal Your Face logo is also a must.

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A 20-minute drive outside of town to Woody Creek Tavern is worth it for lunch or dinner at one of the remaining anti-establishments, where Hunter S. Thompson imbibed nearly every day. Order one of the Mexican dishes on the menu and ask for the Polaroid camera behind the bar to add your own snap to the tchotchke-filled walls. FYI: It’s cash only.

Fuel up for breakfast at Spring Café with a “Go Green Scramble,” packed with farm-raised eggs, kale, broccoli, green onion, and hemp seeds with a fresh pressed juice.

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Imbibe

Carbondale’s award-winning craft distillery has moved up valley with the opening of The Marble Bar Aspen, its sleek second location steps away from Aspen Mountain. With couches and fur throws facing two roaring fireplaces, it’s the coziest spot to warm up après-ski with “The Dude”—a creamy cocktail made with its Moonlight EXpresso, a shave of chocolate, and a mini doughnut as a garnish.

Aspen Brewing Company is Aspen’s only microbrewery and just opened a new and improved tap room downtown where you can enjoy inventive bar fare and craft brew with a view. Its patio is open year-round on a prime downtown corner for people-watching—it’s an excellent place to chill and take the edge off with a brew or a snack after smoking a joint with one of those ultra-potent strains from Best Day Ever.

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Built in 1892, the historic Red Onion is now famed for its original, ornate hand-carved bar, happy hour specials, live music, Mexican-inspired menu and wild late-night scene (yes, there are shot skis).

Find the most epic of session spots on-mountain in the shrines of Aspen Snowmass—sanctuaries in the snow that pay homage to Jerry Garcia, David Bowie, The Beatles, and many more.

Shop

Performance Ski knows their slope style stuff. Here’s you’ll find dreamworthy (and pricey) designer skiwear plus the best of the best in equipment. For a super splurge, grab an Elder Statesman or Made on Grand cashmere sweater embroidered with a pot leaf.

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Only at The Thrift Shop of Aspen will you find like-new discarded designer duds and wares up for thrifting. Proceeds from all sales at this volunteer-run treasure trove benefit the area’s non-profits. Go early, there’s usually a line outside before they open at 10 a.m.

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If you forgot it, Carl’s Pharmacy has it. Much more than a place to fill the Rx’s, it’s also a liquor/convenience/general store where you can head upstairs for “everything you didn’t know you needed” like kitschy souvenirs, housewares, games, toys, sporting goods, and crafting supplies.

More interested in an independent bookstore in a quaint Victorian house? In Aspen, it does still exist at Explore Booksellers, a fantastic place to browse while high. And Ute Mountaineer is the best place to gear up for any of the outdoor adventures you choose to pursue.

Do

(Courtesy of Matt Power)

The Belly Up is Aspen’s best hangout for live music in one of the coolest, intimate venues in the country. The highlight of this season’s concert calendar? LCD Soundsystem, which headlines two nights over X Games weekend.

Get high and take a stroll through the Aspen Art Museum, which presents innovative exhibitions from the international contemporary art scene with admission free of charge. Afterwards, get a green matcha latte at the art museum’s rooftop SO Café, where you take in epic views of Aspen Mountain for as long as you like.

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Find the most epic of session spots on-mountain in the shrines of Aspen Snowmass. Hidden in the trees across all four mountains are sanctuaries in the snow that pay homage to the likes of Jerry Garcia (Aspen Mountain), David Bowie (Aspen Mountain), The Beatles (Aspen Mountain), Hunter S. Thompson (Snowmass), John Denver (Buttermilk), and many more with memorabilia. If you can’t find one on your own, ask a friendly local on the ride up.

If you’re skiing Snowmass for the day, take a ride on the new Breathtaker Coaster between runs (separate ticket required, $49)—a thrilling three-minute ride with speeds up to 28 miles per hour that you can do in your ski boots.

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Additional image credits:

Header: Courtesy of Chamber Resort Association

Flood image 1: Courtesy of Jeremy Swanson

Flood image 2: Courtesy of Woody Creek Tavern

Flood image 3: Courtesy of Aspen Snowmass Shrines