Self Guided Walking Holidays & Cycling Holidays

Please wait …

Marvel at Aspen’s Maroon Bells and Crater Lake, two of Colorado’s most iconic landmarks


  • Explore the wilderness, aspen groves and giant peaks of Colorado’s Rocky Mountain Range
  • Hike West Maroon Pass, a bucket-list traverse connecting Crested Butte to Aspen
  • Marvel at Aspen’s Maroon Bells and Crater Lake, two of Colorado’s most iconic landmarks
  • Discover the wildflower capitals of Colorado for blooming lily, lupine and alpine sunflowers
  • Enjoy the summer festivals, laid-back vibe and lively promenade of downtown Crested Butte

Hike Crested Butte’s spectacular wilderness, past the Maroon Bells and into the town of Aspen, for the ultimate Rocky Mountain hiking adventure.

Officially the wildflower capital of Colorado, Crested Butte is an outdoor haven where Nordic tracks and downhill slopes transform into an invigorating trail network for summer hikers. Enjoy an easy-going hike along the Lower Loop Trail where the prairie meets the mountains. Explore the town, Mount Crested Butte and associated ski resort before a full-day hike up-and-over West Maroon Pass into the renowned ski village of Aspen. Spend three days hiking around the Elk Mountains, exploring the White River National Forest and experiencing a canvas of colors, plentiful sunshine and crisp mountain air.

At night, explore Crested Butte’s laid-back country charm and Aspen’s trendy pedestrian plaza, staying in hand-selected B&Bs and charming inns, for an incredible Colorado backcountry experience.

Day 1: Arrive Crested Butte

Immerse yourself in one of Colorado’s most beloved hiking destinations, the Elk Mountain Range. Upon arrival to Gunnison-Crested Butte Regional Airport, take the shared airport shuttle north through Gunnison National Forest to Crested Butte where cabin life, extreme sports and beautiful open land is just a way of life. Check in to your B&B and head into town where eclectic shops, farmers markets, and energetic eateries intertwine with historic wooden buildings and rural neighborhoods. Choose one of the numerous pubs, pizza shops or organic cafés to celebrate your arrival to southwest Colorado.

Overnight: Crested Butte

Day 2: Hike Lower Loop Trail

From your B&B, walk to the Lower Loop Trailhead located on the western outskirts of town. Starting in dense aspen groves, continue along the dirt path through forest canopy, meadow fields and along the Slate River for stunning views of vibrant wildflowers and Mount Crested Butte. Loop back to town and your B&B for late afternoon wine and cheese admiring the looming peaks, groomed ski resort and surrounding terrain from the veranda.

Hike: Lower Loop Trail: 8 mi. (+325/-348ft.), loop

Overnight: Crested Butte

Day 3: Hike West Maroon Pass

Starting with an early morning shuttle, prep your day pack with plenty of water, snacks and a packed lunch for a full-day through-hike starting from Crested Butte and ending in Aspen. From the trailhead drop-off, follow the well-marked trail up through open meadow to the red-rock switchbacks of West Maroon Pass, enjoying the flora, scree fields and chromatic landscape as you ascend. Soak in the spectacular panoramic views from the top before traversing down the other side of the pass. Descend through willow and tundra for views of the much anticipated Maroon Bells and Crater Lake, Aspen’s most iconic landscape and two of Colorado’s fifty-eight 14’er peaks (Maroon Peak and Maroon Peak North). Admire the glasslike reflection of the Maroon Bells before continuing on through aspen forest to the shuttle bus stop below, and a free transfer to downtown Aspen and your overnight accommodation.

Skip the West Maroon Pass through-hike with a private transfer from Crested Butte to Aspen instead (approx. 3 hours, additional costs apply). Upon arrival, enjoy lunch in downtown Aspen before taking the shuttle bus up to Crater Lake Trailhead for a short hike up to the Maroon Bells and Crater Lake, the same last few miles of the through-hike. For further details, speak to one of our destination specialists during booking about this option.

Hike: West Maroon Pass: 11 mi. (+2021/-2,884ft.), point-to-point

Transfer Option Hike: Crater Lake Trail: 4 mi. (+719/-712ft.), out-and-back

Overnight: Aspen

Day 4: Hike Ajax  Trail

Today, enjoy a short and sweet hike overlooking the town of Aspen. Starting at the Midland Trailhead, located only a few blocks from town, enjoy brief, yet steep, switchbacks up the Ajax Trail where the  path gently levels out for stunning panoramas of downtown Aspen and Smuggler Mountain. Walk over ski trails and under gondola tracks connecting with Little Nell Trail, for switchbacks back down to town. Now positioned at the eastern side of town, stop off at the Gondola Ticket Office to ride the Silver Queen Gondola up Aspen Mountain, or loop back to take the rest of the day to relax, delight in a spa or explore Aspen’s culinary culture and stylish boardwalk.

Hike: Hike Ajax Trail: 3 mi. (+407/-381ft.), loop


Day 5: Hike Hunter Valley Trail

Enjoy this lovely hike on the edge of northern Aspen, where rushing waters, wooden bridges and scattered boulders escort you to the picturesque overlook of the Roaring Fork Valley. Starting at the Hunter Creek Trailhead, enjoy walking alongside the creek noting the old silver mines and abandoned shafts along the way. Join the Hunter Valley North and South Trail down Smuggler Mountain and back to Aspen making this day one of the most beautiful and peaceful high valley hikes. Tonight, head into town for live music and daily festivities in celebration of your Crested Butte and Maroon Bells-Snowmass Wilderness hiking adventure.

Hike: 5.5 mi. (+1027/-948ft.), loop

Overnight: Aspen

Day 6: Onward Travel

Depending on your travel arrangements, enjoy a stroll around town or along the multi-use Rio Grande Trail before departure.


We specifically hand-pick your accommodations in comfortable and charming B&Bs to ensure that you enjoy every minute of your stay while exploring Crested Butte and Aspen. 

All accommodations are conveniently located only a short walking distance to each town’s main plazas and nearby trailheads. Additionally, each offers individual character and welcoming hospitality.

Single Rooms & Solo Travelers

This trip is based on two people sharing a room. If you’d like separate rooms, a single supplement is required.

If you would like to request a twin room (same room with two separate beds), please notify us during booking so we can request this option.

This trip is also available to solo hikers (a solo supplement is required).


Breakfast is included each morning and ranges from buffet to a set menu served family style. Most breakfasts include a hot dish (eggs, pancakes or waffles), yogurt, fruit, baked goods, coffee and tea.

Lunches and dinners are not included in this trip, so you can choose from nearby options. For lunches, you can find markets, cafés or restaurants located within each town for dining out or to purchase a packed lunch to take with you on hikes. For dinner, you can dine at local restaurants all within a short walking distance from your night’s stay.

Extra Nights

You can easily request to add extra nights during this itinerary. For further details, please ask us at the time of booking.



Purple Mountain B&B

The Purple Mountain B&B offers a mix of history and comfort for the ultimate mountain getaway. With cozy rooms, an outdoor hot tub, in-house day spa, daily beer tastings, gourmet breakfasts, free bikes and clear views of Mt. Crested Butte, this B&B serves as the perfect base camp for an unforgettable Crested Butte experience.







Hearthstone House

The Hearthstone House offers guests a charming, intimate setting within the heart of Aspen. This Frank Lloyd Wright-inspired Bed and Breakfast has plush amenities and the finest furnishings, so guests feel comfortable relaxing in the luxurious surroundings of Aspen. Enjoy breakfast alfresco, wine and cheese by the fire, relaxing in the herbal steam room or soaking in the hot tub under the stars.


This trip is available to start on any day of the week from July to August, during the peak summer season. In September, this trip is available to start on a Thursday or Friday only.

Please notify us if you desire to book this trip in June, as snowfall each year varies. As these locations are year-round tourist destinations, we suggest you book as soon as your plans are finalized to ensure availability for specific dates.

Note, due to a heavy snow winter in Colorado, some of the higher elevations hikes for this trip may be impacted by snow into late June, and possible as late as early July. Please call your Macs representative with any questions about the current snow-pack conditions and trip availability. . 

When To Go?

The best time to visit southwest Colorado is July through September for clear skies, warmer temperatures and summer events.

June is also a great month to visit (depending on the winter season), as wildflowers are in full bloom and fall foliage is at its peak.


Navigating is easy using the Macs Adventure Navigation App. Your daily hikes will be mapped in the app with GPX tracks, route notes and turn-by-turn directions. All of these resources are available to download for offline use, which is recommended as cell service can at times be spotty within the Rocky Mountains and when hiking. 

You will be provided with local supplier contact information (accommodations, transfers, etc.) in addition to 24/7 telephone support from Macs Adventure should you require assistance.

Experience, Fitness & Grade

This tour is graded moderate, with four days of hiking and a maximum distance of 11 miles. Daily hikes average around 7 miles (5 hours) along well-signed and well-traveled dirt trails, with steeper ascents/descents, often above 8,000 feet in elevation. The distances and ascents/descents are approximations of the recommended routes.

The majority of the trails are available to hikers only, while a few are also available to mountain bikers. When sharing the trail, expect to see hikers, mountain bikers, dogs and at times, horses. As a rule of thumb, keep a sharp eye and ear out for when others approach and pass.

As weather patterns in the mountains are often unpredictable and can change suddenly, hikers should be prepared for hiking in the rain, mud and on the rare occasion, snow, should there be an early or late snow season that year.


Our pre-departure information pack has detailed advice and a packing list on what to bring. This includes warm and cold hiking gear, hiking boots, rain gear and lots of other specifics.

Please be prepared by packing all the necessary items for a comfortable trip. If you have any questions about what to take, we'd be happy to share our own top tips and advice.  

Travel Insurance

Travel insurance helps protect your travel investment, your belongings and most importantly you, from unforeseen circumstances that may arise before or during your trip. For more information, please visit our travel insurance page by clicking this link.

Getting to Crested Butte

By Air

Gunnison-Crested Butte Regional Airport, located about forty-five minutes from Crested Butte, has flight connections from Denver International Airport via United Airlines.

Upon arrival to Gunnison-Crested Butte Regional Airport, go to the Alpine Express check-in counter, located near the baggage claim, for a shared shuttle to Crested Butte and your overnight accommodation (approx. 1 hour, $38-$45, not included).

Getting from Aspen

By Air

We recommend taking the Epic Mountain Express shared shuttle back to Denver International Airport (approx. 4 hours, $92-120, not included).

If you are flying out of Gunnison-Crested Butte Regional Airport, you can take a shuttle from Aspen and back Crested Butte (approx. 3 hours, $60-$450, not included).

Depending on your travel arrangements, Aspen/Pitkin County Airport has both direct and connecting flights.

If desired, we can easily add-on shuttle transfers, or offer our own travel advice, during booking.

By Rental or Personal Vehicle

Arrival and departure from these regions are also possible by rental car or private vehicle. Please let us know at the time of booking of your preferred plans.

Getting Around

For additional transportation services outside the provided itinerary, such as a taxi to a specific restaurant or location, the host at your evening’s accommodation can help assist you in making the necessary arrangements.


  • 5 Nights at hand-selected charming B&Bs
  • 5 Breakfasts
  • Door-to-door luggage transfers
  • Detailed pre-departure information pack
  • Turn-by-turn route notes
  • Macs Adventures Navigation App for mobile phone
  • 24/7 US telephone support


  • Flights
  • Transfers to Crested Butte
  • Transfers from Aspen
  • Optional transfer from Crested Butte to Aspen
  • Lunches, dinners, drinks and snacks
  • Additional nights before, during or after the trip
  • Personal equipment
  • Travel Insurance
  • Gratuities and tips


  • Extra Nights in Crested Butte and Aspen
  • Single Room Supplement
  • Solo Supplement
  • Room Upgrades (only where applicable)

How far in advance do I need to book?

We suggest you book as soon as your plans are finalized as this destination is popular in the summer months and the lodging that we partner with has limited availability. Please note you can start this tour on any day of the week.

What personal equipment do I need?

You will need good hiking shoes/boots, comfortable walking clothes (non-cotton is advised), waterproof rain gear, a daypack, hiking poles, water bottles and warm layers. We will supply you with our recommending hiking gear and equipment within the pre-departure information pack.

We have chosen hiking trails located close to town, so getting to and from trailheads should be relatively straightforward and close by your overnight accommodations. If you choose to bring your own vehicle, you can park in town or at available parking spots near the trailheads.

What if I become ill during my trip?

This trip allows for plenty of flexibility, so if you're not up for hiking, that's Ok. If you need medical services, you'll find information in your pre-departure information packet or you can ask for assistance at your B&B. As always, 24/7 support from Macs Adventure is only a phone call away.


Enquire Now

Get adventure news, trail guides, new trip updates and destination inspiration by signing up to receive our regular emails. We only send these by email, and we never pass data to third parties for marketing purposes. Please confirm if you are happy to receive this travel inspiration & advice into your email inbox.

Our full data & privacy policy

Book self-guided walking holidays and cycling holidays with Macs Adventure. Explore Europe, the UK and the rest of the world and find out why thousands of people trust us to arrange their perfect self-guided adventure.

Get In Touch

lf you require more information before booking, please contact us on

+44 (0)141 530 5464

+1 -844-858-0740


© 2019

Macs Adventure - Head Office: Skypark 5, 45 Finnieston Street, Glasgow, G3 8JU, UK