Things to Do Over Labor Day Weekend in Aspen

Things to do over Labor Day Weekend in Aspen

Long weekends carry a gift: an extra edge. A sensation of excitement that arrives with a contrast of experiences and exposure only found in Aspen. Views of exquisite peaks from the morning trail, followed by afternoons of banjo picking and sweet Palisade peaches. Whole, fresh meals at the market and around eloquent tables. And the incredible sunsets and sharp stars are ensued by early mornings to rise and do it all over again.

This holiday, the Valley will help you fill your soul’s adventure needs. The Little Nell will take care of the rest. To stir your excitement, here are things to do over Labor Day weekend in Aspen—but remember to leave gaps for spontaneity.

Bluegrass Sunday

Based in Carbondale, CO, the Hell Roaring String Band will take the stage and deliver a blues-rock-bluegrass fusion of toe-tapping, hand-clapping strums. The five-piece collective performs both creative originals and diverse covers. Catch them on Aspen Mountain’s Sundeck from noon to 3 pm.

Rocky Mountain Oyster Festival

Rocky Mountain Oyster Fest

Replenish at the raw bar. Sprinkle in decadence with BBQ favorites and desserts. The 6th Annual Oyster Festival at Ajax Tavern does not disappoint and features excellent food plus wine, brews, and live tunes.

Jazz Aspen Snowmass

Don your dancing shoes, pack the blankets, and bring the lawn chairs: this three-day showdown will keep you bustling your feet or resting up for the next song. Tickets are already sold out for several shows, so we recommend snagging yours before they go including performances from Keith Urban, Nathaniel Rateliff & The Night Sweats, St. Paul & The Broken Bones, Daryl Hall & John Oates, and Lake Street Dive.

Cycle Independence Pass

Cycling up Independence Pass

Two words: biker’s high. This bucket-list ride delivers a burning climb—from 8,000 feet to 12,000 feet over the course of 18 miles—for the reward of thin (and clear) air plus stunning views. Read our recent Independence Pass cycling guide and if you need a bike rental, we can help with the accommodations.

Farmers Market

Agriculturally rich, culturally diverse. The Aspen Saturday Market is home to an array of produce and creations that are made and grown only in the Centennial State. There should still be a bounty of Palisade peaches over Labor Day Weekend; don’t leave without a taste.

Jeep Tours

Aspen Adventures, Jeep Tour

Sit back and soak up the vista—but also be ready to grab a hold of your seat at some point during a rumbling ride! Select a morning or afternoon half-day tour, or opt for an all-day rendezvous or a backcountry sunset dinner. Four wheels is one awesome way to access the spectacular landscape that surrounds Aspen.

Mountain Biking

It’s no surprise that Aspen is chock-full of incredible mountain biking trails—and the valley’s rising walls come with a cost for the quads. Be ready for the lung-busting ascents—and thrilling descents—from the valley floor and up to high elevations. Pack plenty of hydration and snacks, and prepare to gawk at the incredible scenery.

Maroon Bells

maroon bells

A trip to the Roaring Fork Valley should not end without a close-up glimpse of the Maroon Bells. Maroon and North Maroon Peak are arguably the most photographed mountain duo in all of North America, though their reflection in Maroon Lake is certainly one of the most iconic. The Maroon-Snowmass Trailhead is close to a 20-minute drive from town, and the water’s surface is an even shorter 5-minute stroll from the lot. Go early to catch the calmest photographic conditions. If you enjoy hiking, don’t forget your boots for the 4-mile out-and-back trail through Aspen trees up to Crater Lake.

If you’re looking for things to do over Labor Day weekend in Aspen, plus a true experience, stay at The Little Nell. All of the weekend’s events and adventures are right outside your door.