1. Break out your hiking boots to traverse one of the many trails around the Roaring Fork Valley.
Beginners will be comfortable on the Rio Grande Trail, which starts behind the post office on Puppy Smith Road and follows a paved path most of the way along the Roaring Fork River. An intermediate option is a 1.5-mile trek up Smuggler Mountain Trail, leading to a lookout point with stunning views of Aspen below. Those ready for a challenge can take on the rigorous hike up Aspen Mountain or the Lost Man Loop accessible from Independence Pass. The trailheads in and around nearby Maroon Bells are a quintessential bucket-list item and encompass various difficulty levels. Also, don’t miss an opportunity to view abundant swathes of wildflowers in the summer: The Cathedral Lake and American Lake trails are just two prime spots for amazing color.
Watch a video about Aspen hiking etiquette
2. Catch a music show or live performance at various festivals and venues.
Jazz Aspen Snowmass puts on the annual June Experience and three-day Labor Day Experience, in addition to the JAS Café Summer Series which takes place throughout town. The Aspen Music Festival and School, spanning from late June to late August, is an ode to classical music while providing training to college-age students. Alternatively, head to the Aspen Santa Fe Ballet, Theatre Aspen or Wheeler Opera House for fantastic dance, stage and vocal productions. Concert hot spot Belly Up is also a must-hit for a show in town; past acts have included Snoop Dogg and The Flaming Lips.
3. Hitch a ride on the Silver Queen gondola up Aspen Mountain.
Sweeping views greet those who make the ascent, as well as several free activities with the purchase of a gondola ticket. Breathe in the fresh air and find your zen during a mountaintop yoga class on select days from June through August. Summer weekends bring live music — classical on Saturdays and bluegrass for Sundays — and picnicking. An 18-hole disc golf course is one of the highest official courses in the world. Choose from either the first nine holes if you’re up for a carefree game, the more-challenging back nine, or both for a complete round. Then soak up the sun while grabbing lunch on the patio at the Sundeck, a casual restaurant dishing up American, Asian and Mediterranean cuisine.
4. Indulge in delicious culinary experiences.
Save room in your itinerary to linger al fresco over an expertly prepared meal at one of Aspen’s many amazing restaurants. A farm-to-table approach is emphasized in kitchens across Aspen, and where better to get a sneak peek of local ingredients than at the Aspen Saturday Market? Here vendors supply their best Colorado-grown produce and crafts from mid-June to mid-October. And of course, the mother of epicurean fests happens each June when the FOOD & WINE Classic in Aspen comes to town, offering the chance to rub elbows with celebrity chefs, drop in on cooking demos and sample plenty of great bites.
5. Get a retail therapy fix.
Though downtown Aspen is relatively compact, it manages to fit in more than 200 shops ranging from consignment to eclectic boutiques and designer storefronts. Spend an afternoon strolling the pedestrian malls and browsing vintage apparel, fashion trends, accessories, art, home goods, unique gifts and more.