5 Day Aspen Itinerary (Spring + Summer in Aspen, Colorado)

One of my favorite self-care getaways in the US has definitely been visiting Aspen, Colorado. If you are visiting during my favorite time of year (spring and summer) and are trying to figure out exactly what to do, I’ve got your back! Here is a 5-day Aspen itinerary based on an Aspen trip I planned during their Secret Season (May-June).

Aspen has such a great combination of wellness, outdoor, and culinary experiences (my own three pillars of vacation bliss) that you really can’t go wrong with finding amazing things to do in Aspen!

Feel free to print this guide and follow along.

Afternoon: Check in to your Aspen Hotel

Whether you’re driving in or flying, Aspen upon arrival is a sight to see. The mountainous landscape and Aspen trees give a beautiful welcome to your stay in the city of Aspen. You can expect check in time at most lodging options to be around 4pm.

Where to stay in Aspen:

I stayed at the Aspen Meadows Resort which is just outside of downtown Aspen, CO. The Bauhaus-inspired property has 40 acres of land, 98 rooms, and individual access to each room/apartment making for an ideal place to social distance.

There are wellness services onsite (including a pool and hot tub), a restaurant with top-level views, and a free shuttle available to take you downtown and pick you up anytime.

Aspen Itinerary Tip: Get settled into your hotel, explore the property, ask the front desk for their personal recommendations, and get to know the people you’ll be interacting with during your stay (shuttle driver, front desk assistance, fitness center staff, etc.)

Evening: Dine at a renowned Aspen Restaurant, Element 47

Kick off your first night in Aspen celebrating their culinary scene. During my stay we reserved an outdoor table at Element 47, a fine dining establishment at The Little Nell.

What to expect at Element 47:

Expect prix fixe menu options, unique cocktails, excellent service, and a romantic outdoor setting. We ordered the 3-course prix fixe menu for $95 per person (drinks not included) and enjoyed mouth-watering wagyu beef, saffron risotto, octopus, lamb, and more.

Morning: Horseback riding in the Aspen Grove

Try horseback riding in the calm of the morning and explore Aspen’s stunning outdoors. You can book a short ride, a half-day ride with a meal, or even an overnight excursion.

How to go horseback riding in Aspen:

I used Maroon Bells Outfitters’ horseback riding services at the T Lazy 7 Ranch, which is minutes from the Aspen Meadows Resort, where I stayed.

We horseback rode through the Aspen Grove along a snowmelt stream for an hour ($95/person). If you want more mountainous backdrop for photos you’ll have to book a longer ride.

Afternoon: Brunch at Mawa’s + Mountain Activities

Horseback riding requires energy, and you’ll work up a nice appetite by the time you’re done. Grab brunch at Mawa’s Kitchen (a Black, female-owned restaurant and local favorite), then head over to the Buttermilk Summit Express to experience one of Aspen’s fun chairlifts.

Aspen lift sightseeing tip:

Lifts are often seasonal. Buttermilk’s Summit Express is perfect for spring sightseeing; Aspen Mountain’s Silver Queen Gondola or Snowmass’s Elk Camp Gondola and Chair is ideal for summer sightseeing.

Evening: Dinner + Drinks at Mi Chola

There are so many amazing restaurants to choose from in downtown Aspen, and I was torn between Mi Chola and Casa Tua for dinner. Both had beautiful establishments and outdoor seating, but we eventually chose to have dinner at Mi Chola for Mexican fare. The street tacos and cocktails were my favorite on the menu.

Morning: Smuggler Mountain Observation Deck

There’s a plethora of hikes to choose from in Aspen, easily accessible from the city! I chose to hike to the Smuggler Mountain Observation Deck because it was a total of three miles, out and back, and was considered a moderate-level difficulty.

Well, I’m glad I didn’t try anything more strenuous because it was a challenge! After the hike, we visited to the John Denver Sanctuary to wind down.

How to survive the hike to the smuggler mountain observation deck:

This east Aspen trail is mostly switchbacks at first, somewhat rocky terrain, and you’ll see lots of mountain bikers. If you aren’t used to the elevation, take every bit of shade and the endless views as an excuse to catch your breath.

• Bring LOTS of water
• Start your hike on Smuggler’s Road before 9am to avoid heat and high sun (there is very little shade and I regretted starting at 10am)

• Take your time and enjoy the view 🙂

Visit John Denver Sanctuary for Serenity:

After a challenging hike at Smuggler’s, you’ll be glad to know the serene John Denver Sanctuary is right nearby! With four acres of nature, I loved heading over to calm my soul and reflect on the fulfilling hike I’d just completed. There are lots of places to stroll, do yoga, meditate, or just sit by the water listening to its relaxing flow.

Afternoon: Wellness Activities + Lunch with a View at Plato’s

Since my hotel (Aspen Meadows) had an outdoor pool and hot tub, plus 40 acres of grounds to peruse, I was excited to spend the afternoon having lunch with a view and relaxing. I suggest you do this too!

Where to have lunch with a view in Aspen:

Head to one of my favorite spots for lunch with a view a Plato’s Restaurant on the Aspen Meadows Resort property. This was perfect for us because we got to shower and freshen up after our hike, followed by a delicious charcuterie board and lunch with a jaw-dropping landscape for the patio backdrop.

Evening: Dinner at Ajax Tavern, Dessert + Downtown Stroll

After a full day of hiking, meditating, swimming and indulging in more delicious food, a stroll downtown is a fulfilling constitutional walk.

For dinner, I recommend Ajax Tavern, as you’ll have plenty of outdoor seating for sunset, mountainside views, and are right in the thick of the action downtown. If you want dessert elsewhere, follow the crowd to the Paradise Bakery for gelato or homemade cookies (they close at 9pm).

Morning + Afternoon: Hike Maroon Bells!

This was one of my major goals in Aspen: hike around Maroon Bells. This outdoor activity is so popular in Aspen that you will have to reserve your arrival time slot in advance, as there is a 30-minute shuttle that’ll take you there.

There are parking permits available but they were booked two months out by the time I tried to reserve our spots.

My schedule recommendation if you want to hike Maroon Bells:

• Reserve 9:15 am shuttle tickets, get 7:30 am room service delivered to your room for breakfast, and leave the hotel at 8:15 am to arrive at the Aspen Highlands at 8:30 am for check-in (they require 45 minutes advance arrival and leave on time).
• The last shuttle leaves the park at 4 pm (or 5 pm depending; they will let you know), which offers plenty of time to take on a few hikes in one day! Be sure to pack snacks and water; there is a water fountain and bathrooms at the trailhead.

Evening: Meat & cheese Restaurant for dinner 

After a long and satisfying day hiking, you’ll be hungry! Head to the beloved Meat & Cheese Restaurant and Farm Shop for locally sourced, sustainably raised ingredients and an eclectic menu.

FYI: Dinner runs from 5pm-9pm and if you’ve been loving my food recs check out my full Aspen restuarant guide.

Morning + Afternoon: Breakfast at Jour de Fête + Explore Downtown

It’s the last day (sad face), and I like to spend this day making sure my belongings are packed and put together, and then enjoying a nice breakfast followed by some exploration of sites I didn’t get to check out.

Before you leave Aspen, check out the:

• Aspen Art Museum — open Tues-Sun 10 am-6 pm (free admission, people typically spend about 90 minutes here)
• Aspen Farmer’s Market if it’s a Saturday — open June 12 – October 9

→ LEARN MORE: Find more amazing things to do in Aspen year-round at AspenChamber.org and @AspenCO.

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