A Detailed Travel Guide On All The Things To Do (And Not To) In Aspen

(If you want to skim this Aspen Travel Diary, the things in BOLD are my absolute recommendations for your next trip to Aspen.)

It’s no secret people are clamoring for escapes and getaways. Maybe it’s a weekend getaway or maybe you’ve decided to take an extended sabbatical into the mountains. That’s exactly what we did and here’s how we spent 30 days in Aspen this summer.

Day One: Walked around the new neighborhood with our pup Perry and immediately the dog friendly town won him over, though it rained most of the day. Aspen is probably one of the most dog-friendly towns you’ll ever visit. That night we ordered pizza and wings takeout from Brunelleschi’s Pizza and watched UFC in our condo, which is for sale for $1.66 million.

Day Two: Walked/hiked Hunter Creek Trail with Perry. 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. Then we walked around town, and ate lunch at The White House Tavern – I’ve written about their Crispy Chicken Sandwich in every Aspen story I’ve covered. You can expect a lot of visits from us here. To note: there is always a wait since it’s a super small restaurant, but we are almost always lucky enough to snag bar seats. Then we walked a few blocks to Newbury Park, where I read a new book and my boyfriend hung out with Perry. For dinner, we made a reservation at Kenichi, just a few blocks over. Kenichi has been part of the Aspen landscape since 1991, and for good reason.

Day Three: Grabbed a drop-in rate at O2 for a Sculpt class led by Jenna, who is phenomenal. Later I met up with

friends for a cocktail at The W Aspen’s Living Room, followed by delicious and strong margaritas at Mi Chola – one of only two Mexican restaurants in town (there are two more in Snowmass). Their steak quesadillas are a must.

Day Four: Walked to Big Wrap for made-to-order gourmet wraps, known as one of the most affordable meals in Aspen (they are also big enough to split or save for dinner). We got the Rock Your World and Beef Swift Kick. This place is cash only, so be prepared or use their onsite ATM for a fee. Walked through our neighborhood, with trails jutting out on just about every corner with views alongside the Roaring Fork River.

Day Five: Started the morning off with another Sculpt class with Jenna at O2, then went for a hike on Ajax Trail, which is fairly easy and crosses the front side of Aspen Mountain. After the hour hike, went to LOCAL Coffee House & Eatery for an iced latte and Chia Pudding Bowl. Definitely one of the pricier spots in Aspen for a $22 breakfast. Then we had a picnic lunch on the Rio Grande Trail on the river with lots of other dogs. That evening we grabbed a patio seat at Aspen Tap on the corner of Galena and Hopkins, which boast the city’s best people watching. They are known for their beer selection, but they also have rosé. If you’re a fan of the movie Dumb & Dumber, you’ll love their Mary Swanson cocktail, which is basically a grapefruit hard seltzer $7. Then we went

to Kemo Sabe to get our cowboy hats steamed (a free service they offer) and walked out new ones (nothing like shopping with a buzz, right?). Aspen is one of three locations, the other two in Vail and Las Vegas.

Day Six: Had a 9a tee time at Aspen Golf Club, which is Aspen’s only public course. It’s a beautiful course overlooking Buttermilk Mountain, but one of the oddest course designs I’ve seen. Then a late lunch and happy hour at HOPS Culture’s outside patio. We had a delicious burger and a $6 happy hour rosé for $6. This is a great spot for cheap rosé and a huge selection of craft beer, but the food is pretty average bar food.

Day Seven: Had breakfast at Spring Cafe, which usually closes in between seasons! I get the Acai Bowl and Jason gets the Blueberry Pancakes. Then we took the Silver Queen Gondola up Aspen Mountain and hiked around up top (11,212 feet elevation) with Perry. They even have specific dog gondolas, and all the workers love meeting the pups. Aspen Mountain also boasts the world’s highest official disc golf course

We tried to get the most out of our day pass so came back again to read a book and drink rosé on the mountaintop. We had date night at Ellina, which has a 35-page wine list and amazing pasta dishes. And then finished the night with an Espresso Martini, one of the best in Aspen. Our server Martine was phenomenal.

Day Eight: Walked down by Aspen Meadows and picked up the Rio Grande Trail. We walked around and got lost on trails and in neighborhoods, which is one of the highlights of being in Aspen.

Then we had dinner at Jimmy’s for an amazing steak and enjoyed their robust cocktail menu, especially their Espresso Martini. Anyone who has been to Aspen knows about Jimmy’s, which is donned an Aspen institute and been around since 1997.

Day Nine: Shopping in town, one of my favorite things to do. We had a pizza lunch at the new Aspen Pie Shop with frosé. I would not recommend the pizza at all, however it offers some great patio seating and people watching and was one of the only frosé I saw in town.

Day 10: Iced latte and work at one of town’s newest spots, Bear Den, which is quaint and super cute. I just had a latte, but the food smelled delicious, and everything is organic and made from scratch. Then another sculpt class at O2, followed by an evening stroll along John Denver Sanctuary. Then we treated ourselves to happy hour and dinner at Mi Chola with $10 happy hour margaritas.

Day 11: Morning hike up The Ute, which is popular but not easy. That night we tried the pizza at Aspen Tap and their Espresso Martinis, both were great. We also learned you can also add 5mg Hemp CBD to any drink for $5 (which is so Colorado). We had a phenomenal pizza – The White Pizza – garlic cream sauce, shredded mozzarella, roma tomatoes, ricotta cheese and arugula ($16). I could have done without the massive garlic cloves, but it was awesome.

Day 12: Sculpt class at O2, then walked next door to Starbucks, which is locally owned and operated. Drove out to Grotto Trail, which was an easy hike, mostly shaded and beautiful in every direction. Then went to Devil’s Punchbowl where local boys were jumping in the snowmelt ice-cold water. Went walking around town and hit up the o2 Aspen retail sale, with up to 60% off and scored some mew workout clothes.

Day 13: Drove back to The Grottos Trail, which is one of the most popular spots and enjoyed an afternoon of lounging by the river. Read a new book, packed a picnic with Infinite Monkey rosé and enjoyed the beautiful weather. There is no cell signal, which sort of forces you to relax and enjoy the moment. We drove back and walked through town and did the Hunter Creek Trail hike, which is mostly shaded. Then had dinner with friends at Campo de Fiori (locals just call it Campo), which has one of the best Espresso Martinis in town. The mushroom ravioli is out of this world, and one of the best dishes in all of Aspen. We bounced around next-door at Cache Cache (one of town’s most expensive meals), and then upstairs to Jimmy’s for a nightcap.

Day 14: Took it easy and walked around town. Ordered Hickory House for free delivery, which has awesome wings, pulled pork sandwiches, and more.

Day 15: Walked around Aspen Saturday Market, their weekly farmer’s market in the middle of town. It’s a great way to support local and people watch. They have vendors offering pastries, fresh flowers, and more, but no dogs allowed, which is odd for Aspen. Then we hiked Hunter’s Creek all the way up and down Smuggler Mountain (known as “housewives’ hill” which is my least favorite because it’s very steep and rocky, though the views of Aspen are nice). Went to W Aspen WET Deck, which is Aspen’s only public pool located on the 4th floor. The pool is small, but it overlooks Aspen Mountain and the gondola. We walked over to J-Bar inside Hotel Jerome for their “Locally World Famous” burger ($21) for dinner and a glass of rosé and then their Espresso Martini. The 19^th century bar just started doing a rosé of the day ($14), which is a good way to sample some different wines inside the relaxed and casual atmosphere.

Day 16: Started the hike up Aspen Mountain under the gondola and took a left down Ajax Trail, which leads you to the start of The Ute trailhead. Lunch at White House Tavern, inside at the bar, like always. The wait for an outside table, which is dog-friendly, is always 1-2 hours, especially on nice days. Then walked over to Aspen Public House, which is inside the historic Wheeler Opera House and sat outside by the fountains. Jason had a Wild Brewing Company IPA and I went for a classic Espresso Martini.

Day 17: Went for a hike on Meadows Trail behind Aspen Meadows Resort, which is a quick .57 easy

hike that leads to Rio Grande Trail. Went to Clark’s to check out their happy hour menu for some oysters and $8 martinis (though smaller than most). This place has another location in Austin and boasts a coastal and casual vibe. The Shrimp Cocktail was amazing ($20) featuring large with fresh horseradish.

Day 18: Spent the day walking around to enjoy the fresh air and scenes.

Day 19: Drove to Maroon Bells, which are the most photographed mountains in North America. Note that reservations are required (not recommended, required). Scenic views aside, there are six hiking trails of various lengths and difficulties to choose from, plus bike trails, campsites, and more. We hiked to Crater Lake, which is a 3.8 mile out and back hike probably not recommended for a french bulldog, but a fairly easy hike to the lake. For dinner, we went back to Campo, which quickly became one of our favorites. Then we headed downstairs to Hooch Craft Cocktail Bar, which is in the basement of Meat and Cheese, and offers

a sexy speakeasy vibe without the nuisance or embarrassment of having to know a password. Even though the cinnamon-loaded Espresso Martinis are $20, glasses of rosé are surprisingly only $8/glass. That’s about as cheap as you’ll find in Aspen (or $30/bottle of “Gris de Gris”). Then to Silver City to try their Aperclaw (like an Aperol Spritz, but this one has Aperol, Cointreau, Black Cherry White Claw and Orange Juice), and was the perfectly refreshing drink in the summer.

Day 20: Went to Victoria’s for one of my favorite Iced Soy Lattes and we got two Ham and Cheese Croissants for breakfast (drinks are recommended, not so much the food). Then we rented e-bikes at Aspen Velo on the corner of Mill and Puppy Smith. There are plenty of bike rentals in Aspen, but this one has the most e-bikes to choose from, and on weekends, they can easily sell out. We rode along the Rio Grande Trail all the way to Woody Creek Tavern, which is fun and easy, and a must while in Aspen. Woody Creek Tavern is nearly world famous. They have decent food, great margaritas, and there are always taxis waiting to take the walkers and riders back if needed, since the trek can be a bit daunting for visitors. This spot is cash only. We rode back via Cemetery Lane and followed signs towards downtown Aspen for a different route.

Day 21: It was a beautiful day for a hike on Sunnyside Trail, which has a path off the Rio Grande or you can type it in your maps to start at the base of the trail where there is parking. Hence the name, this trail up Red Mountain is 100% in the sun, so avoid hot days or the peak of the afternoon if you can. Took an Uber (which didn’t used to be a thing in Aspen, but is more so now) to Home Team, inside The Inn at Aspen located at the base of Buttermilk, where the X Games are held. Home Team has a Frozen Irish Coffee locals love (small $11 and large $13) and a $9 glass of rosé, which is cheap for Aspen.

Day 22: Went to the Aspen Saturday Market to stock up at some of our favorites, and after walking

around, went to Spring Cafe for a Smoothie ($9) and Iced Coffee. We spent the beautiful afternoon at W Aspen Wet Deck for $28 pitcher of strong margaritas, which is such a bargain anywhere, especially Aspen. Then we took a RFTA (Aspen’s bus system is always free and has been touted as one of the best in the country for years) to The Highlands for a night of pizza and beer at Highlands Alehouse. They have tons of beer, pizza, and more to choose from, and although they don’t offer it by the glass, a bottle of rosé is only $33.

Day 23: Walked around some easy trails and streets with Perry. Drove down to Basalt to Butch’s Lobster Shack to avoid paying $38 for a lobster roll in town at Clark’s. In hindsight, I would have rather paid $38 for a delicious lobster roll, then $21 for one lacking in flavor. Then we took a walk on East of Aspen Trail, on the side of Highway 82 headed towards Independence Pass. We walked to the North Star River Access, which is a popular spot to jump off the bridge or put in your paddleboard, and the hike was the easiest in town. Ended the night with an Espresso Martini at The White House Tavern, which was beyond delicious and the perfect balance of sweet and coffee.

Day 24: Did another O2 class, then hiked up The Ute around to Ajax Trail (we did not climb the mountain). Opted for Happy Hour at Jing for $7 glasses of wine (no rosé) and a handful of $7 sushi rolls (or $12 for specialty rolls). Then we sat outside at Creperie’s lounge (real name is French Alpine Bistro, but locals call is Creperie), which has an adorable patio setup on the corner of Hopkins and Mill for an Espresso Martini. They also offer an epic rosé happy hour for buy one get one free bottles, from 3-6.

Day 25: Drove to the top of Aspen Mountain, then walked to breakfast at Aspen Over Easy, which is on the 2^nd floor of Scarlett’s and boasts the largest breakfast menu in Aspen and has seating inside and on the sun deck. They offer three variations of a Bloody Mary (each $10) and have signature cocktails like the Hangover Easy ($10). Then we went over to Hunter’s Creek Trail for an afternoon hike with the pup. We made dinner reservations at Monarch, which is attached to Dancing Bear for a chic steak dinner, where they also specialize in Monarch Manhattans ($17-27). The ambiance was great, but the steak wasn’t anything like you’d find in Texas. Next we stumbled upon Betula, which has the ultimate cocktail scene in Aspen, along with an incredible DJ in the cocktail room. The cocktail room is like an actual living room with huge windows, books on the shelf mixed in with actual family photos. The cozy chic experience was probably the most fun (and most expensive) scene we had during our month stay.

Day 26: Drove to Difficult Creek Trail and parked in day use, not the campground parking. The entire hike is 9.8 miles, but is much easier than the name would indicate. Then we drove out to Snowmass for lunch at Base Camp Bar & Grill, which has a pretty expansive beer list and also rosé by the glass. We sat outside near the base of the gondola, but is not a place I would recommend based on the service and subpar food. Somehow we managed to snag a hard-to-find dinner reservation at Betula, and sat at the bar because reservations fill up quickly.

Day 27: Enjoyed a morning hike/walk around town and John Denver Sanctuary, which is perfect for mediation, picnics with the family, or just relaxing. We headed over for a pool day at W Aspen’s Wet Deck for those pitchers of margaritas. Then we walked and shopped around town (mostly window shopping), and had dinner at Mezzaluna, which is fairly inexpensive and solid (wood fired pizzas, pasta and $9 glasses of rosé). They also have a great happy hour with $10 pizzas, $6 glasses of wine, and $6 margaritas.

Day 28: Breakfast at Spring Cafe for their amazing pancakes and french toast, and of course an iced soy latte! Then we grabbed beers by The St. Regis Aspen Resort pool before enjoying my 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. It’s not a pretentious spa, but it has all the luxuries and modalities you need after a month in Aspen. After that we headed to their lobby restaurant, Mountain Social for a quality Espresso Martini, and had the bonus of watching their daily champagne sabering where guests and non-guests can gather around. During the summer this takes place at 5:15pm and in the winter it’s at 4:45pm. We walked across the street for more

shopping at O2, which offers the best brands for athleisure wear and more. Then we went to Hops patio for drinks, and made our way around to Aspen Public House for dinner and Espresso Martinis at 7908, which they have on tap (nitro), and are only one of two places in the world that offer this. This is Aspen’s first supper club offering “elevated comfort food,” dancing, a DJ, and an ultra-high end bottle list.

Day 29: A day after too many Espresso Martinis and visiting some of our favorite spots including

Kemo Sabe, lunch at White House Tavern, drinks outside at Aspen Public House, then Mi Chola and Silver City, followed by dinner at Campo.

Day 30: Our last day, so we walked around our neighborhood trails looking at all the beautiful houses, then one final breakfast at Spring Café, before heading back out.