May 23 — 25, 2026
From its humble beginnings, Territory Days has grown from a small neighborhood craft fair into a popular three-day street festival.
Get the most from COS over three, five or seven days
Updated: May 12, 2026
Want to do a little bit of everything during your visit?
Below we’ve broken down recommendations for three, five or seven days in Colorado Springs and the Pikes Peak Region.
If you’re coming to Colorado Springs and only have three days, this one’s for you! Can you do it all in three days? No! But we promise that with this itinerary, you’ll get a well-rounded taste of what our destination has to offer. And afterward, you’ll be inspired to plan your next trip back so you can keep crossing things off your bucket list.
We recommend checking out iconic Colorado Springs lodging options like The Broadmoor or The Mining Exchange, which both have a rich history and are located in proximity to Downtown Colorado Springs and popular attractions. But there are SO many great hotels and resorts in the area, it’s worth taking a deeper look to see what’s the best fit for your budget and needs.
Browse all lodging options and categories here.
With just a few days, you’ll want to get a nice sampling of dining options in the region – and ones that won’t take you too far off the beaten path (you have limited time, after all!).
For breakfast, check out local favorites like Loyal Coffee or Urban Egg. Hit one of the many great lunch spots in Downtown Colorado Springs like Odyssey Gastropub, Red Gravy or The Exchange. For dinner and drinks, community staples include Cerberus Brewing, Edelweiss and The Golden Bee at The Broadmoor.
Browse all dining options and categories here.
AM: Go to Garden of the Gods Park + Visitor & Nature Center
PM: Attend Flying W Ranch’s dinner and chuckwagon show
For your first day, a visit to Garden of the Gods Park is a must for everyone. We don’t make the rules (just the recommendations). But trust us, you don’t want to miss this free city park. It’s a National Natural Landmark with rich geology from ages of erosion and tectonic movement. You can navigate the park by car, bicycle, e-bike, Segway, Jeep, hiking or climbing. The main Central Gardens trail is paved and easily accessible. You’d be remiss not to check out the Garden of the Gods Visitor and Nature Center as well. Not only does its balcony give you an iconic photo op, there’s also a café and gift shop, exhibits and the Geo-Trekker theater – the best way to learn about the history of the park.
After exploring the park to your heart’s desire, get a taste for our Western heritage at Flying W Ranch. The dinner and chuckwagon show runs May through October and includes access to the beautiful grounds the ranch sits on. You can say hello to the many ranch animals, ride on the train, climb Christmas Rock and then head over for a great barbecue dinner and performance by the Flying W Wranglers – the second-oldest Western band in the world.
AM: Take the Broadmoor Manitou & Pikes Peak Cog Railway to the summit of Pikes Peak
PM: Tour the U.S. Olympic & Paralympic Museum
PM: Explore and grab drinks, dinner & dessert in Downtown Colorado Springs
Time to set off and reach new heights – by going up a 14,115-foot mountain first thing in the morning! Don’t worry, you can take the scenic route via The Broadmoor Manitou & Pikes Peak Cog Railway. You’ll pass through different terrain and climate types on the way up, eventually going above tree line to the rocky summit of America’s Mountain. At the top, you can enjoy amenities at the Summit Visitor Center like clean bathrooms, a café (with famous high-elevation donuts!), a gift shop and interactive exhibits to learn about the history of the mountain.
In the afternoon, head to the U.S. Olympic & Paralympic Museum where you can get inspired by learning the history of the Olympic & Paralympic Games – all the way from Ancient Greece to modern times. This museum is one of the most accessible and interactive in the world, so prepare to be impressed.
By now you’ll likely be ready for a break, so take it easy exploring Downtown Colorado Springs. The free shuttle – The ZEB – can take you around from the museum to various stops along the Tejon Corridor, where you will find some great spots to shop and refuel.
AM: Hike The Broadmoor Seven Falls
PM: Take a Rocky Mountain Food Tour
If it’s your last day, make it a great one! Head to The Broadmoor Seven Falls and enjoy majestic views of the surrounding canyon. This attraction is seasonal and typically opens in mid-March, so double check dates as you plan. After taking a free shuttle from the parking area to the falls, prepare for a one-mile hike to the base of the falls or stop at the ticket window for the on-site shuttle ride, then ascend a 224-step staircase to climb alongside the falls. For an accessible alternative, take the Mountain Elevator up to the Eagle’s Nest viewing point.
After shuttling back to your car, get ready for a taste of Colorado Springs with Rocky Mountain Food Tours. This experience is perfect for those who are adventurous eaters and like to experience a variety of local cuisine while visiting.
With a bit more time for your trip, let’s get you off the beaten path! After your first three days getting a feel for what Colorado Springs is all about, head south to Cañon City for day 4 and out to the Eastern Plains for day 5.
AM: Visit the Royal Gorge Bridge & Park
PM: Take the Royal Gorge Route Railroad
PM: Cross Skyline Drive
The Royal Gorge Bridge & Park is famous for America’s highest suspension bridge – 956 feet above the Arkansas River! You can step across the bridge and embark on additional activities like the Skycoaster, zipline, gondolas and Via Ferrata. There are options for all activity levels and ages.
After a couple of hours at the park, take a ride on the nearby Royal Gorge Route Railroad. This scenic train follows the Arkansas River within the canyon. You can even order food and drinks on board to make it a full experience!
Don’t leave Cañon City without crossing Skyline Drive. It can feel scary because it’s a one-way route with steep slopes on either side and a bit like a rollercoaster. But it’s paved and comes with incredible views, thrills and even dinosaur tracks in the surrounding rocks!
AM: Visit Paint Mines Interpretive Park
PM: See the alpacas at Our Red Barn Ranch
Paint Mines Interpretive Park is about 45 minutes east of Colorado Springs in Calhan, CO. It’s known for its colorful clay formations and 750 acres of park to explore. Be sure to stay on trail, as these rock formations are quite fragile, and we want to protect them for future generations to enjoy.
In the afternoon, check out Our Red Barn Ranch. They have alpacas, dorper sheep, angora goats, livestock guardian dogs, cats and kittens, chickens and turkeys! Book an interactive tour to meet all the animals and learn about the on-site fiber processing studio.
If you have a full week, you’re in luck – you’ll have time to explore in almost every direction! After your first five days of exploring, make time for an inspiring and rejuvenating cap to your visit. Consider breaking up your lodging into two spots to enhance your trip. Garden of the Gods Resort & Club is a great, central location with incredible views. The Antlers Hotel downtown is another historic and convenient option.
AM: Visit Rita the Rock Planter troll sculpture
PM: Strike it rich in Cripple Creek
PM: Catch a Green Mountain Falls Skyspace viewing
Time to head to Cripple Creek and Victor! These historic mining towns are ripe with adventure. Start the day visiting Rita the Rock Planter – a larger-than-life wooden troll sculpture made by artist Thomas Dambo. It’s a short hike with great views!
Strike it rich in Cripple Creek at one of the many spots for gaming – Bronco Billy’s, the Golden Nugget, Chamonix and more. Grab lunch at Don Juan’s Cocina while you’re there, too.
On the way back to Colorado Springs, make a stop to view the Green Mountain Falls Skyspace installation – reservations suggested. Designed by artist James Turrell, this kinetic light and color experience will be a treat for your senses.
AM: Explore Old Colorado City
PM: Rejuvenate at SunWater Spa
PM: Dine and grab a brew at Ivywild School
It’s been quite the adventurous week, so spend your last day at a slower pace. We highly recommend exploring Old Colorado City. Back in the day, it was the first capital of the Colorado territory before it officially became a state. Today, it’s a quaint neighborhood with great shopping, restaurants, galleries and events. If you’re here in the summer or fall, check out the neighborhood farmers market in Bancroft Park, which is a local favorite!
In the afternoon, get some much-needed relaxation at SunWater Spa in Manitou Springs. They offer massage and body treatments, plus their cedar soaking tubs are full of mineral water from the nearby springs – all with unparalleled views of the mountains and foothills.
End your trip with a meal and beer at Ivywild School. There are multiple restaurants in this renovated, historic elementary school – plus the award-winning Bristol Brewing and Axe and the Oak Whiskey House. Cheers to a great adventure!
If you’re looking for some fun local happenings to inspire the timing of your trip, check out these signature Pikes Peak Region events!
Looking for even more? Check out these resources to plan additional days in the Pikes Peak Region. And don't forget – you can always use our AI chatbot Penny in the bottom righthand corner to further assist you in your trip planning.
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