No matter the season, any trip to Aspen should include a day spent experiencing the town and its rich history. From the Hotel Jerome — the first incarnation of the “Aspen Dream” — to the posh West End, make sure to tour the town’s cultural highlights.
To really understand Aspen, it’s important to do a bit of mingling. You may as well start early with a hearty breakfast, and perhaps a Bloody Mary, at the Aspen Over Easy Breakfast Club, a diner that doubles as a social get-together. A full menu of breakfast dishes and cocktails is offered in a setting where you’d have to try pretty hard not make a new friend.
For a quieter and cheaper wake-up, try Spring Cafe. This organic juice bar and restaurant serves a quick breakfast, including scrambles, avocado toast, açai bowls, and, because this is Colorado, epic huevos rancheros. Service is quick and friendly.
The downtown Aspen Art Museum will give you a feel for the town’s bright and colorful artistic flare. Spend a couple of hours perusing exhibits both modern and classic. The artists who created them span the globe, but the selected works are typically tied to Aspen in some way. You’ll spot the building from blocks away, as its boxy, Japanese-inspired exoskeleton makes it an anomaly among the Alpen lodge façades of downtown Aspen. The museum is closed Mondays, and admission is free.
If abstract art tends to elude your interest, opt instead for the Wheeler/Stallard Museum in Aspen’s West End. The museum’s ground level still looks like Aspen patriarch Jerome B. Wheeler had it set up in the late 1800s. The upstairs features a seasonally rotating exhibit showcasing a facet of Aspen’s history as both a mining and ski town.
On the top level of the Aspen Art Museum is SO, among the most innovative kitchens of any North American museum. The weekly changing menu is built from local ingredients prepared in an efficient, lunch-friendly manner. You may find a flank steak torta one week and a tartare the next, paired with high-altitude veggie options and a kid’s selection.
Alternatively, head to The Living Room inside the Hotel Jerome for a craft cocktail and small plates, including the weird but unforgettable scallop mini corn dogs. Opened in the 1880s, the Hotel Jerome is among the town’s most historic buildings. After lunch, inquire at the front desk about the tours they offer.
Starting at the Wheeler/Stallard Museum, work off lunch with a stroll through the exclusively residential neighborhood of the West End, where ultra-rich seasonal residents put their mega-bucks to use on second, third, and fourth homes. Stretching from Main Street north to the Roaring Fork River, the nearly two-square-mile area has tree-lined streets and artfully done houses ranging from small, updated original homes to full-on mansions.
At first, it looks like any other mountain town neighborhood, with overgrown trees, quaint homes with steeply sloped roofs, and walkers and joggers greeting you with friendly smiles. The further you get into the neighborhood, though, the more jaw-dropping the homes become. Though Jack Nicholson sold his home here in 2013, Lance Armstrong is still around.
Each Thursday at 3:30 PM, the Aspen Historical Society leads a pub crawl to three of the town’s most notable drinking establishments. You’ll start at local-favorite The Red Onion and learn about the history of the pub and surrounding Cooper Avenue. Then you’ll have a beer at Aspen Tap and conclude at the J-Bar inside the legendary Hotel Jerome, a favorite of celebrity residents including Hunter S. Thompson and Jack Nicholson. The tour costs $20 and includes a drink at each stop.
Even if you aren’t in town on a Thursday, paying a visit to each pub on your own offers a glimpse into Aspen’s history as a magnet for the free-wheeling and liberal-minded. Alternatively, you can check out a free museum exhibit also operated by the Aspen Historical Society called History Museum at Lift One. You’ll learn that Aspen Ski Company formed in 1947, just over a decade after skiing became “the thing to do” in the valley, and many more details than you ever thought to ask about the history of skiing in Aspen.
Any good ski town has a vibrant scene of local shredders, many of whom moonlight as the stewards of the town’s nightlife scene. The best place to see this at work in Aspen is at Jimmy’s steakhouse. The mixologist crafting your drink likely spends 100 days on the mountain each winter and will undoubtedly have the stories to prove it. Pull up a stool at the bar, order a daily special from the bar menu, and start asking questions. You’re likely to hear heroic tales of high-peak valor and, at the very least, will come away with some insight into the best powder stashes for the next day.
For a lighter and healthier meal, try Pyramid Bistro. Pyramid is the first certified “nutritarian” restaurant, which means that the menu is mostly veggie, gluten-free, and designed to be low salt and low fat. Dishes include sweet potato gnocchi and pad thai rice noodles, with chicken and fish options available as well.