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SO YOU’VE DECIDED TO TAKE AN EXTENDED SABBATICAL with your pup INTO THE MOUNTAINS. Not only is Aspen one of the most dog-friendly towns you’ll ever visit, it’s also the perfect place to social distance outside in the high altitude and get some much-needed fresh air.
These are the best ways to safely enjoy Aspen right now.
Take a hike (and, yes, you can bring your dog).
Hunter Creek Trail. This is probably one of the most popular and easy hiking trails in Aspen, consisting mostly of dirt and gravel with public parking at the trailhead. Afterward you’ll want walk around town and eat lunch outside at The White House Tavern—I've raved about their crispy chicken sandwich before. You can then walk a few blocks to Newbury Park, a perfect spot to post up with a book. If you make it a full day, book a table outside at sushi spot Kenichi a few blocks over for dinner. It’s been a vital part of the Aspen landscape since 1991.
Ajax Trail. Fairly easy and crossing the front side of Aspen Mountain, this hike is about an hour long. Do pack a picnic lunch to have on the Rio Grande Trail, set along the river and truly dog-friendly. Then grab a patio seat at Aspen Tap, which boasts the city's best people watching, on the corner of Galena and Hopkins. They’re known for their beer selection, but they also have rosé and—for fans of Dumb and Dumber—a Mary Swanson cocktail, which is basically a grapefruit hard seltzer. You can also get your cowboy hats steamed at nearby Kemo Sabe (and it’s free!) or walk out with new ones (nothing like shopping with a buzz). Aspen is home to one of the shop's three locations (Kemo Sabe can also be found in Vail and Las Vegas).
The Ute. It's popular but not easy. Start under the gondola and take a left on the Ajax Trail, which leads you to the start of The Ute trailhead. It’s all uphill from there (with incredible views) until you wish to turn back. Grab a pizza at Aspen Tap afterward—you can add 5 mg of Hemp CBD to any drink for $5 (which is so Colorado).
“Housewives Hill.” The climb up and down Smuggler Mountain (known as “Housewives Hill”) is steep and rocky, but the views of Aspen are incredible. After the hard work you might want to relax at the W Aspen WET Deck, Aspen’s only public pool, located on the fourth floor of the W Aspen. The pool is small, but it overlooks Aspen Mountain and the gondola, and it has $28 pitchers of margaritas.
Meadows Trail. Behind Aspen Meadows Resort lies a quick, easy hike (just over half a mile) that leads to the Rio Grande Trail. Later, head to Clark’s to check out their happy hour menu—oysters, $8 martinis (on the smaller side), and an amazing shrimp cocktail. Clark’s has another location in Austin, so you might already be familiar with its coastal cuisine and casual vibe.
Sunnyside Trail. This trek up Red Mountain is 100 percent in the sun—hence the name—so avoid hot days or the peak of the afternoon if you can. The path is just off the Rio Grande, and you can type it in your maps app to start at the base of the trail where there’s parking.
East of Aspen Trail. On the side of Highway 82, headed toward Independence Pass, you can hike to the North Star River Access, which is a popular spot to jump off the bridge or float around on your paddle board, and the hike is the easiest in town.
Maroon Bells. These are the most photographed mountains in North America, about 30 minutes from Aspen—reservations are required (not recommended, required)—with scenic views; six hiking trails of various lengths and difficulties to choose from; bike trails; campsites; and more. We hiked to Crater Lake, which is a 3.8-mile-out-and-back hike that's probably not recommended for our French bulldog, Perry, but a fairly easy hike none the less.
Difficult Creek Trail. Be sure to park in the day-use area, not the campground parking. The entire hike is 9.8 miles, but is much easier than the name would indicate.
The Grottos Trail. It's an easy hike, mostly shady and beautiful in every direction. There’s no cell signal, which sort of forces you to relax and enjoy the moment—pack a picnic, bring a book, and relax along the river. From the Grottos day-use area, you can also access the Devil’s Punchbowl swimming hole, where locals love to cliff jump and plunge into the ice-cold snowmelt water below.
Tee off at Aspen Golf Club.
The beautiful course, which is Aspen's only public golf course, overlooks Buttermilk Mountain, and has one of the oddest course designs I’ve ever seen. When you're done, HOPS Culture has an outside patio and is a great spot for cheap rosé ($6 at happy hour) and a huge selection of craft beer and bar food, including a delicious burger.
Ride the dog gondola.
You can take the Silver Queen Gondola up Aspen Mountain and hike around up top (at 11,212 feet elevation) with your four-legged friend. They have specific gondolas for folks visiting with their dogs, and all the workers love meeting the pups. Aspen Mountain also boasts the world's highest official disc golf course.
Rent e-bikes at Aspen Velo.
There are plenty of bike rentals in Aspen, but this one, on the corner of Mill and Puppy Smith, has the most e-bikes to choose from. On weekends they do sell out, so ride during the week. The Rio Grande Trail makes for an easy route to Woody Creek Tavern—a must visit in Aspen with great food and margaritas (although it's cash only). Plus, you can always take a taxi back if needed, since the trek can be a bit daunting for first-time visitors. We rode back via Cemetery Lane and followed signs toward downtown Aspen for a different route.
Mosey around the Aspen Saturday Market.
This weekly farmers market is in the middle of town, and it's a great way to people-watch and support local vendors offering pastries, fresh flowers, and more. Dogs are now allowed, too.
Relax at the John Denver Sanctuary.
This 4.5-acre city park (and memorial for the late songwriter and environmentalist John Denver, who lived in Aspen) is the perfect spot for meditation, picnics with the family, or just relaxing. It's also dog-friendly and connects to many popular trails.
Book a CBD healing massage at Remède Spa.
The spa also has an oxygen bar and serves you a complimentary glass of champagne when your treatment is finished. You can also grab beers before or after at The St. Regis Aspen Resort pool and maybe even catch the daily champagne sabering in the lobby restaurant, Mountain Social (5:15 p.m. in summer or 4:45 p.m. in winter), which has outdoor seating and even its own pup-in-residence.
Unwind with all the best takeout and patios.
Big Wrap offers made-to-order gourmet wraps—try the Rock Your World and Beef Swift Kick (cash only)—for takeout only. Hickory House has free delivery for its awesome wings and pulled pork sandwiches, or if you prefer pizza with your wings, try Brunelleschi’s Pizza. The adorable patio setup at Creperie’s lounge (the restaurant’s real name is French Alpine Bistro, but locals call it “Creperie”) is a must for happy hour (buy-one, get-one-free bottles from 3–6 p.m.), on the corner of Hopkins and Mill. Aspen Over Easy boasts the largest breakfast menu in town and offers seating on its sun deck. They have three variations of a Bloody Mary.