Four days in Aspen of “Feelin’ Alright” with a “Constant Craving” for fun

My friend Jennifer flew in on Thursday for 4 days for a first time Aspen visit, so we wanted to give her a crash course in Aspen summer fun.

That meant hiking, eating, drinking, shopping, and nights of tunes at the Aspen Music Tent.

We started with an arrival dinner on the patio of Cache Cache, our go-to restaurant for anyone visiting Aspen.

With consistently fab food, a great wine list and a super staff, Cache Cache never disappoints, and once again, delivered a great evening.

A bottle of white, a bottle of red, apps, entrées, and a beautiful walk home, and we were set for the weekend’s activities.

Day 1

A start to the day at Aspen Over Easy and then we were ready for a hike.

Since Jennifer lives at sea level, so we decided on hiking trails that would not be too difficult, where she could enjoy the beauty found in and near Aspen.

For day one, we stayed in town for our hike. Heading through the West End, we hiked down Meadows Trail, near Aspen Meadows resort. We then linked up to the Rio Grande Trail, hiking a couple of miles up to the Jenny Adair wetlands, then back to Jennifer’s hotel.

A pretty stroll to the sound of water flowing from Castle Creek & the Roaring Fork River, the 2-3 miles is an easy route shared with cyclists, dogs, strollers and runners in the heart of Aspen.

Dinner that night was at Pacifica.

Pacifica has long been one of our favorite Aspen restaurants and for this evening, we worked our way through an amazing assortment of appetizers, salads and entrées.

The one that stole the show – the sea bass – and it tasted as good as it looked!

Day 2

We headed out to Ashcroft for our hike of the day about mid-morning.

The River Run trail is a beautiful, easy hike within 15 minutes of downtown Aspen. The hike starts at the ghost town of Ashcroft, located 11 miles up Castle Creek Road.  After passing through Ashcroft, the River Run trail begins and runs next to the river. After about a mile following the water, the trail veers slightly to the right and meanders through a meadow, with gorgeous views of the surrounding mountains. At about 1 1/2 miles, you reach the Pine Creek Cookhouse, serving gourmet mountain eats, or a turn around point enabling about a 3 mile roundtrip hike.

No trip to Aspen would be complete without some patio time at Ajax Tavern. We went for a late afternoon happy hour – one of the best summer deals in Aspen. Oysters, beers, burgers and some wine set the stage for the evening’s entertainment.

Next stop, the lawn party at the Benedict Music Tent.

Beverage in hand, we strolled through the pre-concert crowd at the music tent, listening to the sounds of Showarama and munching on bites from the Caribou Club.

Joe Cocker took the stage and delivered a fabulous concert that had the crowd dancing in the aisles and ”Feelin’ Alright!”

Day 3

We decided to take the gondola up Aspen Mountain for our Sunday activities.

When we reached the Sundeck, we headed out on Richmond Ridge.

Richmond Ridge is an easy to moderate five-mile trail off the back of Aspen Mountain. With the entire trail above 11,000 feet, the views are amazing.

At about 1 1/2 miles out, we opted to turn around and head back for lunch, beverages and music awaiting us at the Sundeck.

Following a few hours of afternoon relaxation, it was time to head to one of our favorite watering holes, the J-Bar.

The J-Bar is a saloon favorited by locals and visitors alike located in the historic Hotel Jerome.  The Hotel Jerome is an important part of Aspen’s history, built by Jerome B. Wheeler in 1889 & one of the first buildings west of the Mississippi River to be fully lit by electricity.

The evening was once again spent at the Benedict Music Tent, this time to the incredible sounds of k.d. lang and the Siss Boom Band.  Her spectacular voice delighted the crowd with songs from her new Sing it Loud collection to long-time favorites including a playful version of Miss Chatelaine, the mesmerizing Hallelujah and, of course, a crowd-sing-along to Constant Craving.

Day 4

The hike today – strolling through the shops of Aspen.  

We started at Two Old Hippies, then worked our way through the majority of Aspen’s fine selection of boutiques.

A few hours later, we found a seat at the bar at the Red Onion for a bite and beverage.

How do you end a perfect four days in Aspen?

With an evening at Jimmy’s!

Jimmy’s An American Restaurant & Bar is an Aspen hotspot known for their creative cocktails and delicious steaks.

We nearly always eat in the bar, which offers great views of the surrounding mountains and a lively mix of locals and visitors.

The Citrus Crush cocktail is a refreshing blend of lemon Vodka, soda, lime & mint and was a perfect choice for a summer evening.

More cocktails and steaks cooked to perfection made for a ideal ending to our four days in Aspen with Jennifer!

Article by Kim Hull

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