5×5: What to Do in Aspen, CO from Those Who Know

All the best hangouts, in all the best cities, from the locals… 

Nestled in the Rocky Mountains, about 8,000 feet above sea level, there lives a most perfect little mountain town. When the second homeowners and the international visitors jet out, only about 7,000 are left to call this beauty their home. Offering places like Independence Pass, Maroon Bells and the Roaring Fork River, it’s no wonder many who pass through never leave. To get to know more about this backcountry escape we turned to those who’d know best — five locals, from Free People employees to entrepreneurs.

Sammy Steen: Alaskan Commercial Fisherman/Creative Director at ROAM

@sammycam + @thisiswhereiroam

Silver Queen Gondola – 520 E Hyman Ave, Aspen, CO 81611 

The Silver Queen comes straight out of downtown Aspen to 11,212 ft. with panoramic views of the Elk Mountains and White River National Forest. Enjoy your coffee and breakfast burrito from the confines of a cozy box, “our favorite floating living room.” Nothing beats T to B (top to bottom) laps on Ajax during a storm. Warm up, dry off, hang with friends and answer your e-mails, all while getting whisked to the top of one of the most magical mountains in the world.

Roaring Fork River – Jaffee Park, Woody Creek, CO 81656

My favorite stretch of the Roaring Fork, 6 miles downstream from Aspen. There is amazing fishing up and down the Roaring Fork Valle but Jaffee Park, with its unique topography and easy access, makes it my go-to for an afternoon on the river. A free stone river (dams are non-existent) and a catch-and-release policy make this stretch of water tough to beat.

The BLK MKT – 534 E Cooper Ave, Aspen, CO 81611

Artist collective, concept store and gallery. A very unique retail experience and much needed cultural hub in the community. These guys gave Aspen a breath of fresh air with the opening of the shop last winter and are back again with a reiteration in one of the best locations in town (the old Boogie’s location). Not to be missed if you’re looking for something special and a break from the couture, brand-name shops that have eaten up all of the storefronts here. Unique authenticity in a place that can often times feel anything but…

Maroon Bells Maroon Creek Road, Aspen, CO 81611 

This view speaks for itself. The first place I like to take friends who are visiting, to acquaint them with the awe-inspiring nature of Aspen.

Creperie Du Village – 400 E Hopkins Ave, Aspen, CO 81611

An amazing atmosphere and affordable-ish (it’s still Aspen…) menu make this mine and my girlfriend’s favorite date-night place. The ambiance is tough to beat… A cozy downstairs space, revolving around a “community” table and lots of rustic wood decor, is very reminiscent of a European alpine restaurant which is surprisingly difficult to find here. More Aspen than LA, and we like that.

Aspen Art Museum –  637 E Hyman Ave, Aspen, CO 81611 

One of the main draws of Aspen — the metropolitan vibe within the confines of a quaint mountain town. These two paradoxes meet at the Aspen Art Museum. Free entry, world-renowned artists, amazing programming and regular transformations make this a huge asset to the community, not to mention the upstairs cafe which has amazing views of Ajax, wonderful food and a nice, quiet environment for freelancers and young professionals to get their work done. My home away from home.

Mia Sadowsky: Co-Founder of Heir Vintage

@badgalmimii@heir_vintage

Bonnie’s – Aspen Mountain  

Bonnie’s breakfast. The perfect hangover cure. Maybe you had a late night and accidentally took three too many tequila shots right before the bars closed. It’s ok, it happens, and Bonnie’s breakfast is there to help you through the morning struggle. Bonnies is a little family-owned restaurant in the Middle of Ajax Mountain, a ski-in, ski-out joint. If you are able to get there before 10am, what a treat. Take the Gondola up, ski half a run, and indulge on blueberry pancakes, maplewood smoked bacon, hash browns, and everything in between. Bonnie’s interior is small and simple and the views of the mountain are stunning. You’ll feel a sense of accomplishment just getting there before breakfast ends. From Bonnie’s you can either ski all day or cruise down Spar Gultch and still tell people you got on the hill.

Avalanche Ranch – Hwy 133, Redstone, CO 81623

Nestled in a little canyon off Highway 133, outside of Carbondale, lies Avalanche Ranch. The perfect afternoon or early morning natural hot springs hangout. Avalanche Ranch is made up of a few cabins that are available for rent and four soaking pools of different temperatures. Day use is $15$and well worth it. Besides the cabins, which are equipped with all the amenities you would expect in a rental house, there are 4 or 5 cabooses that are available for rent and they are SO. DAMN. CUTE. They are tiny. No bathroom, no kitchen — just a bed and space heater to keep you warm in the winter. If you are on a budget, this is the way to go ($80 a night).

North Star Nature Preserve – Colorado Hwy-82, Aspen, CO 81611

North Star Nature Preserve — a magical place. In the summer it’s gained popularity as the Lazy River, a stretch of water you can float, canoe, or paddle board down on a hot day. The Roaring Fork River slows from its headwaters up Independence Pass and meanders though an unbelievably beautiful part of the valley. Depending on the flow of the river it takes about 1 1/2 hr from start to finish. Because it is a preserve, natures flourishes. Great blue herons nest along the banks in the very top of the tallest cottonwood trees, aspen groves line the left side of the river, and fish — so many fish — scatter as you float by on the crystal clear water. You can experience the stretch of river with a party barge of friends or seek solitude by paddling upstream for an early morning workout.

Cliff House on a Full Moon Buttermilk Mountain

Since I was old enough to carry my own skis or drag a sled behind me, my parents have escorted me to the base of West Buttermilk every full moon during the winter months. Back in the day, small groups of happy mountain people would hike up Buttermilk under the moon’s bright light. We would meet friends in a little warming hut at the top of the mountain that ski patrollers use by day. The door was always unlocked on a full moon. My parents would bring cheese, snacks, caviar and champagne to pop at the top. The venture has now become so popular that the Aspen Skiing Company has opened up the Cliff House,a small restaurant at the mountain top for all the happy mountain people to enjoy a hot meal after a cold hike. It usually turns into one hell of a party, but you’ve got to work for it, which makes it all the more special. It’s a 45-minute to an hour hike up Tiehack, and a 45-minute hike up West Buttermilk (which is much easier). Ski Co doesn’t open the Cliff House every full moon, so be sure to check online for specific dates.

Living Room at the Jerome – 330 E Main St, Aspen, CO 81611

The Living Room at the Jerome is a classy joint. It’s a hot date night kind of spot. Whether you’re looking to cozy up by the fire with a mountain man drinking manhattans, or sitting around a high top with your girlfriends, in your sassy kitten heels and drinking martinis, this is the place. The Jerome is one of the oldest buildings in Aspen, so it’s worth checking out for the interior alone. The decor is alpine chic meets country western, a mix of cowhide-upholstered side tables and deep velvet green tufted chaise lounge chairs. It sounds gaudy but, believe me, looks very eloquent and charming in person. There is a certain warmth and sense of belonging there. The history of the Jerome runs deep and you can feel it the second you walk in.

Hannah Schanfarber: Free People Aspen Stylist/Visuals

@hanasaurus_rex

 Sunset Park – Aspen, CO 81611

This small park has always been a favorite of mine. — just a short drive up the hill from downtown Aspen, and offers great views of the town. It is quiet and relaxing and, in summer, it is my absolute favorite place to picnic. Grab some friends, lay down a blanket at sunset, and you are suddenly filled with a sense of nostalgia for your childhood — where the fruit couldn’t be sweeter, the grass couldn’t be greener, the sun couldn’t be any brighter, and you couldn’t remember ever being happier.

Highlands Bowl199 Prospector Rd, Aspen, CO 81611

Or really, any spot to ski on Highlands or Ajax. Highlands Bowl is a magical place. Located at the top of Highlands Mountain, you have to “earn your turns” by hiking up to a gorgeous snow bowl. When you arrive at the top, you realize you can’t breathe, and you’re not sure if it’s because of the hike or the views around you. Everywhere you turn and look is another snowcapped mountain peak, with clouds majestically swirling around them. The earth feels alive and you suddenly feel connected to it. Often times, you will find a small group of locals up there, enjoying a few beers or just the view.

Red Onion420 E Cooper Ave, Aspen, CO 81611

Aspen’s oldest restaurant established in 1892, the Red Onion is a local’s favorite. With an affordable menu and an environment that is more than welcoming, this is usually our first stop before hitting a night out on the town!

 Tabor Lake/ Independence Pass – Wheat Ridge, CO 80033

Independence Pass is the “shortcut” route to Denver in the summer. However, for locals, it is the best place to explore, with never-ending hiking, biking, fishing, skiing and swimming spots. In the summer, I love to drive and randomly stop along the road to explore. I don’t have a destination — I just keep walking one step at a time; it doesn’t matter where I go, I just want to see what’s around me. My favorite hike is a less-traveled one called Tabor Lake. The trail winds through pine tree forests and then opens up to beautiful meadows with a creek running through it. The trail eventually ends and you then have to bushwhack up the side of a mountain, pushing through brush and trees. But don’t worry, the journey is worth it. At the top, you will discover the most beautiful mountain lake perched in between two peaks. The waters settle into the truest hues of blues, ranging from the ice blues of the Arctic to cerulean and sapphire. Magic.

Ashcroft Ghost Town – 35241-, 36221 CO-82, Aspen, CO 81611

Ashcroft is an old, deserted mining town just outside of Aspen. This is one of my favorite places to camp, as the sites are secluded and quite high in elevation. The road provides access to many 14ers in the area as well as great fishing and biking. In the fall, the aspen trees lining the road glow as they change to vivid shades of crimson orange and yellow, as if somebody took a paintbrush to their leaves.

Melissa Wisenbaker: Public Relations Specialist at Promo Communications

@NeverSacrificeStyle + @AspenCO // Images shot by @redmountainproductions 

Backside of Aspen Mountain– Aspen, CO 81611 

Every summer my boyfriend and I love driving up the front of Aspen Mountain aka Ajax in our Jeep and heading down its backside. Nestled in nature, this area is filled with fields of gorgeous wildflowers and surrounded by hundreds of acres of National Forest service land. I was lucky enough to come up to the backside last summer to enjoy stargazing with an astronomy guide, complete with the finest cheeses, charcuterie and champagne. If you’re looking for some sweet out-of-bounds winter riding, find a friend with a sled or take a powder tour with Aspen Snowmass and experience some of the best secret stashes in the valley!

Woody Creek Distillers– 60 Sunset Drive, Basalt, CO 81621 

In the summer, you can easily bike down to Woody Creek Distillers (WCD) from Aspen via the Rio Grande Trail. The trail is mostly paved and generally downhill. When you first walk into the distillery, you are immediately greeted by the impressive custom carl copper stills. Woody Creek Distillers produces delicious potato vodka (gluten free!), gin and a rye whiskey. All of their spirits are handcrafted, and the entire team is completely hands on. One trend that I think has been touched on but not explored thoroughly is seed–to-bottle, which is the natural successor to the ubiquitous farm-to-table. It’s natural that people will start thinking about their booze as much as they think about the food that they put in their mouth. Woody Creek Distillers personally grows and harvests ingredients for their spirits. WCD does not purchase neutral grain spirits to make any of their spirits and never will. Their potatoes are hand-harvested, trucked in small batches to the Basalt distillery, and processed on-site within days for unparalleled freshness and purity. All of their drinks are delicious, but my favorite currently is the Descent, made with potato vodka, organic pear juice, vanilla syrup, and a hint of coconut infused vodka.   Hint: get a friend to pick you up after, or take the bus!

Castle Creek Road–  Castle Creek Rd, Aspen, CO 81611

This is my favorite road to explore, any time of the year. There are so many hidden gems to pull off and enjoy along the way. In my opinion, it’s one of the best for taking in the fall foliage. In the winter, the road is completely blanketed with snow, which makes you feel as though you’ve been left in a different world. I could spend hours exploring all of its nooks and crannies, and of course taking pictures!

 Cloud NineAspen Highlands, Top of the Cloud Nine Lift, Ski-in ski-out only

Two words: champagne showers. There’s a reason they call it Cloud Nine…Cloud Nine is a cute bistro located on mid mountain on Aspen Highlands. The restaurant is open for lunch with two seating times, at noon and 2pm (you want the book the 2pm)! Once you’re settled in and noshing on fondue and raclette with friends, the restaurant suddenly turns up the music (around 3pm) and everyone immediately jumps on top of the tables and starts blasting champagne.

John Denver Sanctuary– 470 Rio Grande Pl, Aspen, CO 81611

Located just a few blocks from Main Street, the John Denver Sanctuary is a serene park where visitors will not wonder for long where soon learn where “Rocky Mountain High” came from, with Denver’s songs etched into large rocks, snuggled in between the Roaring Fork River and gorgeous wildflowers on end in the summer. There are also many benches hidden within the park, as well as spots where you can bring your four-legged friends to splash around in the water. Luckily the sanctuary is located across the street from my office. My co-workers and I visit often in both summer and fall to find inspiration during team meetings.

April Morlock: Free People Blogger

@amorlock 

Belly Up Aspen– 450 S Galena St, Aspen, CO 81611

The only official music venue in Aspen, the Belly Up is a MUST when visiting. From local bands to artists who sell out Madison Square Garden, there is always someone playing. I love the venue for many reasons: first, because of its intimate setting. The Belly Up only holds 325 guests with a full open seating floor plan, so it allows you to get up close and personal with any artist passing through. A few of my favorite and wicked memory-inducing shows include Matisyahu, Zella Day, Zion I and the Grouch and Chromeo. Second, this venue is actually where I met my now fiancé almost six years ago, so it will always hold a special place in my heart. Don’t forget to stick around after a show — many times you can snag the set list and have the artist sign it for you!!

Conundrum Hot Springs – Castle Creek Road, Aspen, CO 81611

By far one of my favorite hikes in Aspen. With a distance of almost 17 miles round trip, this is one not to miss while in the Rocky Mountains. A moderate to difficult hike due to the distance, most hike with backpacks geared with tents and sleeping bags for an overnight stay. After hiking through fields of wildflowers, hopping across creeks and climbing vertically for what seems like forever, you are rewarded with natural hot spring pools and a breathtaking backdrop. My fiancé and I usually do this as an early morning day trip, waking up with the sun to beat the crowds. We trail run most of it with light packs filled with water and lunch to enjoy at the top. If a 17-mile trail run isn’t for you, look into staying the night with a group of friends for a full conundrum experience!

Ute Trail– Ute Ave, Aspen, CO 81611

This is a great post-work trail, accessible by foot from downtown Aspen. The trailhead starts at the base of Ajax. Take note — this hike is not for the faint of heart. This steep, heavily worn trail ascends 700 feet in just .9 miles. Yet, worth it for views at the point that overlook all of Aspen… If you’re looking for a little more of a workout you can head all the way up, continuing another 2,300 feet to hit the summit of Aspen Mountain. Reward yourself with drinks at the Sundeck and enjoy the backcountry views of the Rocky Mountains. If you’re not looking to head back down on foot, snag a free ride on the Gondola to take you back to town. You can catch many Aspen locals hiking up the Ute daily for a true Aspen workout!

Big Wrap– 520 E Durant Ave #101, Aspen, CO 81611

Talk about burrito heaven!!!! Quite literally a weekly, if not daily lunch spot for all Aspen locals. Big Wrap is more of a grab-and-go kind of vibe with less then ten seats in the whole joint. With burritos named Mr. Potato Head, Wrapzilla and Babs-e-que there is nowhere to go wrong when ordering. This place is cash only, so make sure you stop by an ATM before heading over. Also, if you’re thinking of ordering between 11:30-1pm, expect to wait in line for at least an hour. Calling ahead is always a good idea!! Make sure to say hello to Babs, the owner of this burrito heaven — you can find her there making burritos on the daily, rain or shine.

Leadville – Leadville, Colorado 80461

The ghostly but very much alive neighbor to Aspen. Only accessible from our side of the mountain during summer months, this is the day trip of all day trips. Home to my favorite antique shop, Western Hardware and to some of the best Colorado’s 14’ers, our summers are never complete without at least a dozen trips to Leadville. Leadville will take you back to OG mining days, with blocks of historical architecture. There is always something going on, so make sure you check out the events before heading that way. Even if there isn’t a 100 mile bike race or marathon to catch, the endless trail running and mountain exploring is enough to head over the pass!!

Well, there you have it — all the best spots to hit in Aspen, Colorado. The amazing thing about this mountain town is there are hundreds more locations to explore. From summer to winter, Aspen falls nothing short of one beautiful adventure!

+ Been to Aspen yourself? What are some of your favorite local spots? Share below!! 

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