Aspen Essentials

From famous landmarks to quirky local hotspots, find the best things to do in Aspen.
By: Rick Carroll
Related To:

Food and Drink Essentials: Best Places to...


City Market
711 East Cooper Ave.
The only major supermarket chain within 20 miles, City Market is just a block from the base of Aspen Mountain. During the summer and ski seasons, it is not unusual to walk into this grocery store and find it overflowing with hungry tourists crowding the aisles. Locals are advised to make their excursions in the early morning or after 8 p.m. on weeknights. Otherwise, expect difficulty finding a parking spot, and long waits in the checkout lines.

Clark’s Market
300 Puppy Smith St.
For those willing to spend a bit more money on their groceries and avoid lengthy waits in line, Clark’s Market is an alternative to City Market. Clark’s also has an organic-food section and a deli, which serves hot breakfasts and lunches.


Main Street Bakery and Cafe
201 East Main St.
There’s a reason Main Street Bakery and Cafe has waiting lists for breakfast and lunch almost every day of the year. The joint delivers some of the yummiest homemade meals in town. And their lattes are the best way to give your day a jolt.

Paradise Bakery
320 South Galena St.
Colorado averages 300 days of sunshine a year, and the patio outside Paradise is a great place to soak it up. Paradise Bakery offers some of Aspen’s tastiest homemade cookies, brownies and gelato. Their lattes rock, too.


Aspen’s downtown is full of drinking establishments legendary for their apres ski vibe. Here are our three favorites:

Aspen Brewing Company
557 North Mill St.
The Aspen Brewing Company serves six handcrafted ales. Our favorite is the Smuggler Wheat Ale, named after nearby Smuggler Mountain. The brewers are always on hand to give drinkers the skinny on their product and have a sip with them, too.

Bentley’s at the Wheeler
221 South Mill St.
An Aspen institution, Bentley’s at the Wheeler offers a variety of brews on tap, from Guinness to Budweiser, and plenty of pub grub to go with. Its proximity to the historic Wheeler Opera House -- home to numerous concerts, art house films, plays, and other stage performances -- makes it a popular pit stop before or after the show.

330 East Main St.
John Wayne, Gary Cooper and Hunter S. Thompson hung out here, and it’s a locals’ hangout to this day. The J-Bar, in the legendary Hotel Jerome, has domestic and foreign beers on tap, a big screen TV for sports viewing and plenty of comfort food to accompany the suds and wines.


New York Pizza
409 East Hyman Ave.
Proprietors Earl Rodgers and Kevin Jones have been serving up pies for nearly 15 years in Aspen, and they know their crowd. New York Pizza is open until 2 a.m. during high season. So popular is NYP that it’s not uncommon to see a line of people stretching outside the door. These fat slices are worth the wait and easy on the wallet.

Popcorn Wagon
305 South Mill St.
It’s not just popcorn that’s served at this locals’ favorite. There are also gyros, crepes, hotdogs, pretzels and a host of other midnight munchies. The Popcorn Wagon is open until 2 a.m., with a patio for the hungry masses to fill their bellies under the stars.

Entertainment Essentials: Best Places to...


Many newcomers to Aspen get a serious case of sticker-shock when they first move here. Indeed, while the town is known for its exorbitant cost of living, there’s also an abundance of events and activities that are on the house. Here’s a sampling:

Thursday night concerts
Every summer Jazz Aspen Snowmass, a local nonprofit, puts on a free Thursday night concert series in Snowmass Village, 10 miles from Aspen. Past headliners have included Dr. John, Jerry Jeff Walker and the Freddy Jones Band.

Aspen’s art galleries
Aspen’s downtown is dense with world-class art galleries featuring all sorts of art. Openings are common during high season and often artists are on hand. The ArtWalk on the first Thursday of every month is a guided stroll of gallery shows around town.

ESPN Winter X Games
An irresistible attraction for teens (and some parents), the Winter X Games is held every January at Buttermilk Ski Area. Half-pipe skiing, snowmobile jumping -- you name it, the X Games has it. And there’s no admission price, which might explain why the place is packed for days straight.


Downtown Aspen is pedestrian friendly, so if you like to travel by foot you’ll be recognizing faces in no time. Perhaps the most popular meeting places are the coffee shops, but make no mistake, you’re likely to fire up the most fascinating conversations on the chairlifts.

The Silver Queen Gondola
Corner of East Durant Avenue and Hunter Street
This top-to-bottom chairlift at the base of Aspen Mountain is where you’re likely meet the carrier who delivers your mail, your next-door neighbor or even the CEO of a Fortune 500 company. And depending on how the conversation goes, you might end up taking a (ski) run with all of them.

Zele Cafe
121 South Galena Ave.
With its outdoor patio at one of the busiest intersections in downtown Aspen, Zele Cafe is a hotbed for social activity. On sunny days the patio is full of people watchers and conversationalists. Zele is also home to poetry readings and art displays, making it a vibrant venue to meet interesting and eclectic people.


Club Chelsea
415 East Hyman Ave.
A full bar and large dance floor make Club Chelsea the premier Aspen spot for hipsters who want to cut a rug.

The Regal Watering Hole
220 South Galena St.
It’s a cocktail lounge with an attitude. DJs spin nightly, the floors are leather (yes, you read that right), and the music doesn’t stop until 2 a.m.


Aspen Recreation Center
0861 Maroon Creek Road
With a rock-climbing wall, an ice-skating rink, a batting cage, a lap pool, a wading pool, a kid-friendly lazy river and weight room, the Aspen Recreation Center (known as the ARC), has something for everyone. Locals get a near 60 percent discount -- $8 a day instead of the regular $15 per visit -- and there are also family passes available for purchase.

Tree House Kids’ Adventure Center
Spanning 25,000 square feet and two stories, the Tree House Kids' Adventure Center is worth the 10-mile drive from Aspen. It offers multiple activities for kids, and various rooms are designed for different age groups, with an emphasis on introducing youngsters to the outdoors.


39 Degrees
709 East Durant Ave.
Locals hang out at 39 Degrees, the swank lounge in the Sky Bar just two blocks from the gondola. A large fireplace, comfy couches, creative cocktails and delectable cuisine make it a perfect place to meet friends and warm toes after an invigorating day of outdoor activity. An expansive pool area complete with hot tub and outdoor bar make it the hottest place in town to cool off.

The Wine Spot
415 Dean St.
The Wine Spot, in the Hyatt Grand Aspen, is a full-service bar that specializes in wines from around the world. A terrific small-plate and dessert menu and 35 wines by the glass make this luxurious locale a great place for couples to slip away for a quiet evening.


The Thrift Shop
312 East Hyman Ave.
Call it a bargain hunter’s paradise in a millionaire’s backyard. A clearinghouse for secondhand possessions, The Thrift Shop has leftovers with labels from Fendi, Gucci, Louis Vuitton and other fashion stalwarts. The store has the quintessential alternative vibe, and all the proceeds go to charity.

Explore Booksellers
221 East Main St.
Located in a charming Victorian on Aspen’s Main Street, Explore Booksellers is a beloved independent bookstore. It features a large inventory of classic literature, art books, CDs, magazines and best sellers. The staff must pass a literature test before they get hired. Explore also features a coffee shop with organic brews and a vegetarian cafe.

Outdoor Essentials: Best Places to...


Aspen is a legendary ski resort, but there’s a time-worn cliche that says it all: "I came here for the winters but ended up staying for the summers." And how true that is. Be it camping, hiking, biking, running, fishing, or kayaking, Aspen has many warm weather activities thanks to an extensive trail network and the Roaring Fork River, which runs through the heart of town. But perhaps the outdoorsiest thing to do in Aspen does not involve breaking a sweat. The 10-mile drive up to the towering mountains known as the Maroon Bells outside town provides some of the most captivating scenery in the country. Flanking the Bells is Pyramid Peak, just as astounding. It’s not uncommon to see dear, marmots, big horn sheep and other animals roaming the territory.

Smuggler Mountain
It’s known as the playground of Aspen. Hikers, runners and cyclists trek up this 1.6-mile dirt road just a few blocks from downtown. Dog- and kid-friendly, Smuggler Mountain is the gateway to several backcountry trails that lead to some historic mining cabins.


Saying Aspen is a dog-friendly town is like saying Las Vegas is for people who like to gamble. The question isn’t "Where to Take Fido," it’s "Where Not to Take Fido." That’s because pooches are allowed almost everywhere. You’ll see them in banks, newspapers, the airport and cafe patios. They've even been seen in the courthouse and at Aspen City Council meetings. The city of Aspen has a leash law, and on just about every block there are stations with bags to pick up your dogs’ poop.


The higher you go, the better the view. That said, we’re offering two options -- one by foot, the other by car. In either case, the end of each trip will give you jaw-dropping views of downtown Aspen, not to mention the spectacular Elk Mountain Range gracing the background.

Smuggler Mountain
A 1.6-mile climb, which ascends 800 feet, will lead you to a sundeck that offers a captivating look at the charming mountain town below.

Red Mountain
The best way to climb this hill is by driving a vehicle up Red Mountain Road. You’ll pass jaw-dropping mansions on the way up as well a series of overlooks where you can look over the town below. 

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