Here's a 5-day Colorado route that runs clockwise from Colorado Springs, northwest through the mountains and up to Breckenridge and Aspen, north to Estes Park and then back South to Denver.
Logistics: Plan to do this in summer (mid-May through September) if you want Independence Pass between Breck and Aspen as it's closed roughly November to April. Colorado's ski season generally runs from mid-October through mid-April.
Reservations to lock in early: Rocky Mountain National Park timed-entry permits (required May–October), Maroon Bells shuttle tickets via recreation.gov
WHAT
sightseeing, hiking, driving
WHEN
mid-May through September (summer season)
mid-October through mid-April (ski season)
Duration
>5 days
Day 1 - Colorado Springs
Garden of the Gods take a short hike on Siamese Twins trail or Kissing Camel viewpoint
Cave of the Winds walk inside the historic caves
Broadmoor Seven Falls multi-story waterfalls, steep stairs
Cheyenne Mountain Zoo reservation required
Optional: Drive up to Pike's Peak, but this is a very high view point, normal to feel altitude sickness (14000 ft).
Evening drive towards Nathrop (2hr) or Aspen (4hr) for lodging
Day 2 - Aspen
Independence Pass scenic drive through Colorado Rockies
Maroon Bells Scenic Area reservations required online read more: (https://www.visitmaroonbells.com/)
Evening drive towards Breckenridge (2.5hr) or Frisco (3hr) for lodging
Day 3 - Breckenridge and Vail
Walk around South Main Street in Breckenridge for shops and restaurants
Drive up to Frisco to check out the Sapphire Point Overlook
Drive to Vail to check out the Vail Village
Optional: Stop by Copper Mountain for golf, go karts, coasters, and boat rentals. Check their website to see what is open (seasonal).
Evening drive towards Estes Park RMNP (2.5hr) or Black Hawk (1hr) for lodging.
Day 4 - Estes Park
St. Mary's Glacier is a short, but beautiful trail - semi frozen in May which makes it even cooler. Go early morning or sunset (on your way back from Estes).
Estes Park (need access using Rocky Mt National Park timed pass read more about it from https://estes-park.com/rocky-mountain-national-park-timed-entry-permits/)
Few easy and short trails once you're in:
Bear Lake most famous easy trail, makes a full loop
Emerald Lake famous emerald green lake with surrounded with mountains
Dream Lake offers iconic views of Hallett Peak and Longs Peak, and can be completed in about 1.5 hours
Evening drive back to Denver (1.5hr) or Boulder (1hr) for lodging.
Day 5 - Denver
Visit Denver Botanic Gardens and Red Rocks Park & Amphitheatre.
Like most downtowns, Denver is built more for business and convenience than for living so most people fly in and out of the city but actually reside in surrounding areas like Aurora or Boulder.
(Written 2021, Updated 2026)