An itinerary that stands the test of time
Updated: June 4, 2026
A 2025 survey by the Family Travel Association showed that 57% of parents plan to travel with both their parents and children – a number that continues to grow.
A vacation spanning three or more generations can be fun but can also pose challenges in choosing activities that are both enjoyable and accessible for the entire group. Where can you go that mom, dad, grandma, grandpa, big brother, little brother and little sister are all going to rave about? Let this itinerary be your guide for a successful multi-generational trip in the Pikes Peak Region.
For resorts that are accessible for seniors and fun for kids, we recommend Hotel Polaris and Flying Horse Resort & Club. Hotel Polaris was built in 2024 and is situated right outside of the North Gate of the U.S. Air Force Academy. It’s full of nostalgia through its mid-century modern design and dining concepts like Doolies – on modern take on a retro soda shop. Kids also love the little touches like the branded teddy bears in each room, aviation-centric art and family-friendly pool. Flying Horse Resort & Club is another fantastic property for those of all ages to enjoy. It has a beautiful golf course, spa, several restaurant concepts, a Kids’ Cabin, pickleball courts and a pool that includes a children’s splash pad.
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Whether or not you’re staying at Hotel Polaris, both Pamela’s and Doolies are fun spots for everyone to enjoy classic Americana fare. The Airplane Restaurant, located in the Southeast area of Colorado Springs, is another favorite for parents, grandparents and little ones. There’s an option to dine in a historic Boeing KC-97 tanker, and guests can also browse the hundreds of pictures, memorabilia and rare artifacts from aviation history. We’d also urge you to add the Omelette Parlor to your list. The house was originally the home of Ruth Etting, a popular singer from the late 1920s. Now it’s a favorite breakfast and brunch spot.
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AM: Tour the Hosmer Visitor Center
AM: Explore the Western Museum of Mining & Industry
PM: Garden of the Gods Park + Trading Post
Make your first stop the Hosmer Visitor Center, located outside of the U.S. Air Force Academy’s North Gate – directly across from Hotel Polaris. It includes interactive and immersive exhibits that help visitors understand the 47-month journey of a cadet. It’s also a great place to learn more about the Pikes Peak Region and its strong ties to the Air Force and military community.
Nearby is the Western Museum of Mining & Industry, which has been an engaging stop for those of all ages since it opened in 1970. Here you’ll find exhibits on the rich mining history of the American West, including a walk-through mine drift, 1895 Corliss steam engine and Colorado’s largest collection of fluorescent minerals. The museum also hosts many events throughout the year, including the annual fall Miners Pumpkin Patch.
Wrap up your first day in town with a classic stop – Garden of the Gods Park! The main Central Gardens trail is paved and accessible for strollers and wheelchairs, with incredible views of the large red rock formations. As you traverse the park further, don’t forget to stop at the Garden of the Gods Trading Post. It has a restaurant and souvenirs, many of which are locally crafted. Plus, homemade fudge which, let’s be honest, has no age limits or calories (that count).
AM: Visit the Edward C. Rochette Money Museum
PM: Stop by the Rocky Mountain Motorcycle Museum and Hall of Fame
PM: Shop and dine around Downtown Colorado Springs
Ever wonder how money has evolved over the years? Even if you haven’t, you’ll be fascinated by the history uncovered at the Money Museum on the north end of Downtown Colorado Springs. Bring the family to see this hidden gem, which is America’s largest museum dedicated to numismatics. Kids 12 and under get free admission, and there’s a senior and military discount.
After, head to the heart of Downtown Colorado Springs where you’ll find the Rocky Mountain Motorcycle Museum and Hall of Fame – a fully free experience. Open Wednesday through Saturday, this spot preserves antique and classic motorcycles from the early 1900s through the 1970s.
Spend the afternoon exploring Downtown Colorado Springs. If your party needs transportation support, consider the free downtown shuttle known as “The Zeb.” It takes people up and down the main Tejon Corridor and is wheelchair accessible. Some favorite spots for families to frequent include Poor Richard’s Bookstore and Toy Store, Cacao Chemistry, Lolley’s Ice Cream, Terra Verde Boutique, Hunt + Gather and Pikes Peak Lemonade.
AM: Tour the U.S. Olympic & Paralympic Museum
PM: See where athletes train at the U.S. Olympic & Paralympic Training Center
For day 3, take your crew for an Olympic City USA excursion! The first stop is the U.S. Olympic & Paralympic Museum – one of the most accessible and interactive museums in the world. Its universal design includes multi-sensory exhibits so every visitor – no matter their age or ability – can explore, learn and feel welcome. That means people can choose audio descriptions where a tactile floor strip triggers the sound upon entering each gallery, enjoy wheelchair accessible digital displays, view open captioning and American Sign Language on all video content throughout the museum and request options for low-sensory experiences. Visitors will get inspired by the stories of Olympic & Paralympic athletes over the years – from ancient Greece through present day.
After the museum, head to the U.S. Olympic & Paralympic Training Center to get a tour and maybe even catch some athletes training in real time! This flagship training center includes state-of-the-art facilities that visitors can explore while learning about athlete programs ranging from exercise and nutrition to sports medicine and performance.
AM: Pikes Peak Trolley Museum
PM: Dinner and a show at Flying W Ranch
Open Wednesday through Saturday, the Pikes Peak Trolley Museum is one of the best multi-generational family attractions (in our humble opinion)! Set in an 1888 Roundhouse, visitors can learn the story of Colorado Springs streetcars through photos, maps and restored vessels. Kids love ringing the trolley bells and playing with the wooden train sets. You can even take a short trolley ride on a PCC car! Oftentimes, there are current restoration projects in the works at the shop to learn about and peek at.
End your trip with a quintessential Colorado Springs experience – a chuckwagon dinner and Western music show at the Flying W Ranch! This family-owned and operated business has been running since the 1950s. Set on the beautiful working ranch property, guests can visit with the animals and participate in many activities ahead of dinner – including climbing to the top of Christmas Rock and riding a fun train! When the dinner bell rings, a cowboy-style barbecue feast is served, complete with all the fixins’. Eat while listening to the lovely tunes of the Flying W Wranglers, the second-oldest Western band in the world.
If you’re looking for some fun local happenings to inspire the timing of your trip, check out these signature Pikes Peak Region events!
July 14 — 18, 2026
Saddle up for five days of cowboy fun!
June 17, 2026
Wake up early and bring your appetite! It’s time for one of Colorado Springs’ most beloved traditions.
August 22, 2026
Experience the flavors of the Americas and sample cuisine from Puerto Rico, Cuba, Argentina, Peru, El Salvador, Honduras, Spain, United…
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.
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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