1. Hit up the Woody Creek Tavern.
The Woody Creek Tavern was a favorite hangout for eccentric writer Hunter S. Thompson. Need any other reason to go? The walls are plastered with photos, and the ultra cool bar is housed in a building that once served as the post office, gas station and small grocery store. Get yourself a Fresh Squeezed Lime Margarita or two. Or three or four, just to honor Thompson, of course.
2. Settle down outside of Paradise Bakery with one of their legendary cookies and people watch.
The blend of different types of people in Aspen never ceases to amaze. Everyone, from celebrities to locals, are comfortable and in their element. Grab a window seat at the Red Onion Restaurant and Salon and observe. Check out the locals, the ski bums, the hippies, the high school kids, the yuppies, the tourists, Kurt Russell and Goldie Hawn. You might even spot local legend Klaus Obermeyer or Olympic snowboarder and Aspen resident, Gretchen Bleiler.
3. Cozy up with a book at Explore Booksellers.
Explore Booksellers, located in a beautiful Victorian home on Aspen’s Main Street, has been a local favorite for more than 30 years. The first and second floors are filled with current and past titles and the children’s room will make even the most serious adult wish that they were a kid again. Grab lunch at Pyramid Bistro (located inside Explore), then go bury yourself in books once again.
4. Go shopping just so you can realize that Aspen isn’t all Louis Vuitton and Prada.
In fact, dig a little deeper and you’ll find shops carrying just about anything. Don’t miss Pitkin County Dry Goods (Aspen’s original clothing store which opened way back in 1969) and Carl’s Pharmacy (located on Main Street, it has a kick-ass toy section, funky hats and lots of cool and cheap Aspen souvenirs). There are a ton of shops located on the walking mall covering the streets radiating from Hyman Avenue towards the mountain. Make sure to take a pit stop at The Popcorn Wagon, located directly across from the historic Wheeler Opera House, and enjoy some buttery, fluffy popcorn. It should be a goal to find some truly unique item — after all, you’ll get to tell your friends, “Oh this? Just a little something I picked up in Aspen.”
5. Get artsy at the Aspen Art Museum and local galleries.
First things first, it’s free. Try getting that in many other places in Aspen. The Aspen Art Museum organizes exhibitions showcasing cutting-edge international contemporary art. The Aspen Art Museum’s new building, which opened in August of 2014, is a piece of art itself. Designed by famed architect Shigeru Ban, winner of the 2014 Pritzker Prize, architecture’s highest honor, the AAM is his very first building in the entire United States. The museum also offers a Sunday Cinema series, in case you feel like catching a flick.
After exploring the contemporary collections at AAM, head down Hyman Avenue to one of the many local galleries featuring everything from sculpture to modern paintings, Colorado photography, Western Americana pieces and everything in between. Omnibus Gallery, located on the walking mall in downtown, specializes in rare and vintage posters, most dating from the 1800s to 1939. Omnibus is “strong on content, light on fluff,” with prices to reflect the quality of the works (don’t be surprised if you see an original by Henri Toulouse Lautrec) and the location (yes, this is Aspen, meaning that average prices for posters can range from $1,500 to $100,000).
6. Escape to Hallam Lake.
Aspen Center for Environmental Studies, better known as ACES, is a non-profit environmental science education center including Hallam Lake, a 25-acre reserve which takes you through woodland, meadow, pond and marsh communities, to reconnect with nature. In addition to Hallam Lake, ACES has three preserve sites which showcase the Roaring Fork Valley.
7. Comfort food plus boutique shopping means one thing: Boogie’s Diner.
Mac and cheese, burgers, sandwiches, mashed potatoes and shakes are the norm at this 50s diner with Aspen flare. The walls are covered in old-school senior year book photos and Elvis movie posters. Once you’re done with your meal (don’t skip pie!) head downstairs to the boutique to shop for a funky mix of name brand jeans, rock and roll T-shirts and of course Boogie’s merchandise.
8. Catch an intimate live music show at Belly Up.
With around 300 live shows each year, Belly Up is Aspen’s premier live music venue. The resume includes Pitbull and Lynyrd Skynyrd and upcoming performances range from Mac Miller to Dirty Heads, to Lyle Lovett and even Styx. With a capacity for only 450 for general shows, and 325 for seated shows, make sure to get tickets in advance.
9. Drink the local brew at New York Pizza
Ascend the worn staircase to New York Pizza, walls covered with flyers and local announcements, and you’ll discover great pizza is sold by the slice or by the pie. New York Pizza has a prime upstairs location overlooking the walking mall below is perfect for practicing those people watching skills. Open til 2am, and with a number of local Colorado brews available, there’s not a better place to reflect on your busy day of taking in everything Aspen has to offer the non-skier.