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When you walk into Obermeyer outdoor clothing’s Aspen headquarters, you’re not bombarded with wild colors or moody tunes in the reception area. There are pictures and awards dotting the space, sure, but it isn’t attempting to re-create the millennial energy of some dot-com lobby — well, that is until Klaus Obermeyer, the company’s 98-year-young founder and president, walks into the office. Spry and full of light-hearted anecdotes, Obermeyer warms a room with his stories much like his down ski parkas have done for bodies over the past few decades.

“I just swam a half mile today,” he says without a hint of self-importance. Mind you, it’s only 8:45 in the morning. But Obermeyer, a Germany native who’s been in Aspen since 1947, knows a few things about the city — one being that you need an early start if you’re to see everything. And we’re not just talking about in winter, either; with great hiking, fly-fishing and outstanding dining, autumn is an amazing time to enjoy Colorado’s fresh air, too.

Read on for a more in-depth analysis into some of the best outdoor options along with a few gear suggestions to help you reach your goals safely and stylishly.

BEFORE HEADING OUT

Aspen may be small, but it boasts a healthy roster of high-end hotels from which to choose. With Forbes Travel Guide Five-Star The Little Nell and Four-Stars Hotel Jerome and The St. Regis Aspen Resort all within walking distance of each other, the competition for your overnight dollars is fierce.

But while these prime properties duke it out over marble bathrooms and custom paintings, The Gant tiptoes into the conversation with condo rentals that deliver a genuine home-away-from-home experience. Units range from one-bedrooms ideal for a honeymooning couple to four-bedroom spreads that provide 1,750 square feet of space for the family’s gear and children’s games, while still having plenty of room left over for a full kitchen and living area.

Beyond the spacious layouts, though, the property wins over your group with a pool scene straight from an Ansel Adams picture, a friendly staff and a delightful location that nearly rubs elbows with Aspen Mountain on one side and Roaring Fork River on the other.

Gear Guide: Ladies should pack a pair of Lululemon City Trek Trousers, while the gents can’t forget their versatile ABC Joggers. Everyone needs an Obermeyer Carson Down Vest for those brisk Aspen evenings.

THE GREAT OUTDOORS

More than 7,900 feet above sea level, Aspen sits in the southeastern end of the Roaring Fork Valley. Head 10 minutes in almost any direction and you’ll run into rocks, ranges or Klaus Obermeyer-approved rapids. If you’re into fly-fishing (Elk Mountain Anglers) or whitewater rafting (Blazing Adventures), you’ve come to the right place. Conditions are so pleasant in August and September that you can dive right into both.

If you’re not quite sure what you’re into, head to Snowmass, an area famous for its skiing, to have a great time over the coming weeks (daily through September 3; weekends until September 30). Once you take the gondola up the mountain, you’ll be tempted with disc golf, paintball and zip-lining. There are also more than 40 miles of mountain-biking trails to explore. Try any of those activities on your lonesome or connect with a guide for a customized tour on your feet, bike or even a skateboard.

To turn down the adventure knob a few ticks, stop by The Little Nell. A property with sparkling accommodations and amenities, the hotel also stands out when it comes to accelerating the heart rate on two wheels. In fact, Little Nell general manager Jonathan Fillman recently told us that, “cycling is a huge part of our DNA,” and after looking at a hotel program that includes complimentary cruiser bikes, a ride-and-dine series (September 6) and an overnight Clip-In With Christian cycling camp (August 19 to 23, with pros Christian Vande Velde, George Hincapie and Craig Lewis), we’re inclined to believe him.

But Aspen understands that not everyone wants to perspire on their vacation. So, for those guests, the city has a robust late-summer/early-fall calendar — the next few months are filled with everything from great music (Jazz Aspen Snowmass, August 31 to September 2) to cinematic endeavors (Aspen Filmfest, September 25 to 30) — that asks almost nothing of your muscles.

Gear Guide: The go-everywhere Mountain 600 Chelsea boots from Danner and an Igloo Legacy tumbler filled with H2O can transition from the forest to the festival without breaking a sweat.

APRÈS HIKE

Just because Aspen is months from its first snow, don’t think for a second that visitors aren’t still gathering for laughs and libations. Even without the powder, Hotel Jerome’s Living Room is the place to meet. The lively spot evokes an 1800s feel with leather furniture, box beam ceilings, roaring fires and bartenders who pour your local Woody Creek rye with care.

The evening scene at The Limelight is just as welcoming. Though we suggest a refreshing happy hour cocktail after a long day on the trails, this hotel does some of its finest work in the kitchen. During our last visit, we had tremendous truffle fries with shaved asiago and a wood-fired wild mushroom pizza we can’t get out of our minds. Couple those tasty bites with live tunes (every weekend through October 6) and you see why this place is so popular.

Mi Chola, a haven for authentic Mexican fare since its 2016 debut, is another wise choice for winding down. Funky wall art and painted skulls decorate the interior, but Mi Chola’s menu is accentuated with grilled jalapeño poppers, seafood enchiladas and a street-taco roster filled with delicious possibilities. Pair your meal with a seasonal pour from Aspen Brewery for a taste of the border done with a Colorado twist.