Ever wish you could text the most stylish people in the world to ask them for their lists of things to do in the places they know best? Here are insider travel tips for those who would never be caught dead in a tourist trap. Bon voyage!
Who
Creatives and hospitality insiders who grew up and/or currently live in the outdoorsy area: Jasmine Dillavou, a mixed-media and performance artist; Ann Alba, vice president and general manager at The Broadmoor hotel; Justin Miller, executive chef at The Broadmoor; Josh Franklin, co-owner of Icons Bar; and Noah Rinsky, the writer behind the Father’s Milk Substack and creator of the Instagram account @oldjewishmen.
What
What to Bring
If you retain just one point from this section, let it be that comfortable shoes are essential to visiting Colorado Springs. Any specific type? “Well that depends on the season, and what you intend to do there,” says Rinsky, who was born and raised in the region. “If you’re going to hang around The Broadmoor hotel in the summer, you won’t need much beyond a pair of good New Balance walking shoes, and flip-flops for the pool.” However, he continues, cross-training sneakers are better suited for hiking near Cheyenne Mountain.
Dillavou, who is professionally based in Colorado Springs, agrees with this point, noting that layers are a smart idea for the area’s fickle weather—the day could start bright and sunny and end with rain, or vice versa. Indeed, as Alba, a resident of nearly four decades, points out: “You can see all four seasons in one day.”
Moreover, Alba continues, the sun is super strong in Colorado Springs, so you should always have UV-protective shades and SPF handy. “Do not forget your sunglasses and sunscreen,” she insists. “Our beautiful blue skies and radiant sunshine are much closer than you would think at our high elevation.”
Because Colorado Springs also has a vibrant downtown with plenty of nightlife, it’s worth bringing at least one look for going out. “Pack for some night life,” advises Dillavou. “Grab something fabulous to wear out for a cocktail crawl, a speakeasy visit, or a late-night concert.”
What to Leave Behind
While it’s smart to have at least one polished look on hand, don’t bother with anything too dressed up or fussy. “In general there is no need to pack formal clothing,” notes Rinsky. “Coloradans are very casual people: Even if you’re eating at a five-star restaurant at the Broadmoor, you probably don’t need to wear a suit.”
The overlook view at Garden of the Gods
Dillavou cosigns this advice, noting that stilettos are essentially a no-go. “You’re going to find yourself doing a bit of walking in Colorado Springs,” she says. “Even on your fanciest date night.”
What to Keep in Mind
“The main reason why people live in Colorado is the outdoors,” says Rinsky. “So they will look at you a little weird if you don’t do at least one thing outside.” Unlike its neighboring regions, though, Colorado Springs is not a ski town—the nearest slopes are roughly two hours away.
“Although our location is not considered ski country, the weather is exciting,” says Alba. “You can enjoy snow one day and blue skies and 50 degrees another.”
Another key part of your consideration, explains Dillavou, should be looking up local haunts and the best times to visit them. “Keep in mind that different parts of Colorado Springs are on different timelines. For instance, Manitou [located between the major attractions of Garden of the Gods and Pikes Peak] closes up pretty early because there are a lot of mom-and-pop shops,” she says, noting that downtown Colorado Springs offers more nightlife.
Where
Where to Stay
Unsurprisingly, every expert began their recommendations with The Broadmoor, a sprawling 107-years-old resort with the distinction of being longest running five-star, five-diamond hotel in the world. Along with its main campus—which includes private houses available for rental, a spa, pool, golf club, and multiple dining choices—the property also offers off-site “Wilderness Experiences” for guests looking to soak up a little more of Colorado Springs’s breathtaking scenery.
The Broadmoor
All that said, there are other noteworthy spots to stay. “ I also suggest The Cliff House [in Manitou Springs],” says Miller, who has lived and worked in Colorado Springs for nearly 25 years. “It has a unique and out-of-the-box experience that offers charm and character in a more nostalgic setting.” Rinsky agrees, describing the location as “a little new-age city inside the city of Colorado Springs.”
The Cliff House
Want to book in the heart of downtown? Rinsky points to The Antlers, while Dillavou endorses Kinship Landing and The Mining Exchange. “These will provide a beautiful experience for you and ensure you leave rested and relaxed,” she says.
Where to Start the Day
If you’re in the city of Colorado Springs, Dillavou says to “start strong with house-made pastries and empanadas at The Exchange on Tejon.” Franklin, a native who opened his popular LGBTQ+ bar downtown in 2020, loves the same spot—but the breakfast skillet is his preferred order.
If you’re a coffee-only person, though, Dillavou calls out Loyal Coffee as one of the best bean roasters in town. “But if you like syrups and sweets and the whole nine yards, get something to sip from Bird Tree Cafe,” she says.
Loyal Coffee
You’ll also want to make time for at least one breakfast at The Broadmoor’s Lake Terrace Dining Room, whether you’re staying there or not. “For regular breakfast, The Broadmoor eggs benedict stands out,” says Alba. “For Sunday brunch, the expansive raw bar is favored.”
The Broadmoor
Where to Eat
For lunch, Alba loves the French onion soup and prime rib at the Broadmoor’s La Taverne restaurant. If you’re in town, though, Dillavou recommends trying the bodega-style sandwiches at Toasted Bunz inside COATI and the buffalo chicken burger at Brakeman's Smashed Burger Bar.
Toasted Bunz
Come dinnertime, try the five-course chef’s tasting menu at Ephemera. “The staff is incredible, the vibe is impeccable, and the food is some of the best in town—just check the restaurant’s long list of accolades,” says Dillavou. “Hot tip: ask for a Fernet to end your dinner.”
Ephemera
Over at the Broadmoor, there are a number of incredible supper options, but the best for special occasions is the recently reopened Penrose Room. “Get the Caesar salad and halibut, followed by baked Alaska served tableside,” says Alba.
Penrose Room
Where to Drink
“Our town houses some amazing cocktail spots,” says Dillavou, whose usual haunts include Chiba Bar, Archives, Cocktails After Dusk, Shrunken Head Tiki, and Bloom Ultra Lounge. “And if you like wine, try Wines of Colorado or The Wine Gallery.”
Franklin shouts out his boisterously fun bar ICONS, where you can enjoy your drinks alongside entertainment that ranges from trivia night to drag shows. But he is also a fan of local establishments Shame & Regret and La Burla Bee.
Shame & Regret
If you happen to be coupling your cocktail hour with dinner at the Broadmoor, Miller says to make time for a “perfectly crafted Manhattan” at The Hotel Bar.
Where to Shop
“I am always a big fan of bringing back something edible or crafted as a souvenir,” says Dillavou. She suggests stocking up on local honey, as well as regional art and handmade jewelry. “Hunt + Gather or Surface Gallery are great spots for those things.”
Surface Gallery
Rinsky, on the other hand, encourages a visit to Manitou Springs for Native American souvenirs and Old Colorado City for saltwater taffy. Franklin shouts out both Cronk Art & Curiosities for its “perfect spooky gifts” and Yobel for its ethical fashion finds.
Where to Enjoy Nature
Because Colorado Springs is such an outdoorsy place, there are more activities to try than one can possibly fit into one trip. But if you want the highlight reel, Rinsky says to start with Pikes Peak mountain and Garden of the Gods, both of which are located near the rustic town of Manitou. It’s also, he says, worth driving to Cheyenne Canyon to check out the lookouts. And if you’re up for it, Miller says this is also a great spot for biking.
Garden of the Gods
Sporty types, says Alba, should hit up Broadmoor Outfitters. “It’s a one-stop shop for all things adventure: geocaching, wild west experience, falconry, white-water rafting, zip-lining—there are experiences for all,” she explains, pointing to Fins Course over Seven Falls Canyon as (in her opinion) the most unique out of all these experiences.
Where to Take in Culture
“Colorado Springs is a big city with many different neighborhoods, so don’t be afraid to explore until you find what fits you,” says Franklin, who counts the Olympic Museum and Wednesday Night live music at Hillside Gardens (during the summer) as a couple of his top recommendations.
Olympic Museum
Dillavou encourages you to try a Local Motive party bus for a bar crawl, or a haunted ghost or lantern tour in Manitou. “They’re all a little silly, and such a blast,” she says.
And if you have a car and some time, Rinsky says you can’t go wrong with a day trip to Denver to see a Rockies game at Coors Stadium.
Coors Field
When
“There is really no bad season to be in Colorado!,” says Rinsky, although he admits that summer might be his favorite time of year to visit. “[The weather is] relatively mild except a few days of very dry heat, but for the most part it’s in the 80s, and rains for 20 minutes in the afternoon.”
Early fall, however, is Miller’s preferred moment to be in town. “It’s an ideal season to witness the changing colors of the trees in our parks and enjoy a blend of outdoor activities and experiences, all with the convenience and charm of a small city,” he says. Plus, as Dillavou points out, October is “Arts Month,” so the city is always buzzing with cultural and creative activations.
Why
While the natural outdoors beauty of Colorado Springs is undeniable, perhaps what makes it most special is its unique mix of breathtaking wilderness and bustling creative energy. “It is a DIY place, and does not function like Boulder, Denver or Aspen—we are our own big-little town,” says Dillavou. “The people here are incredibly genuine, the city always has new and fresh things going on. You will not just go home with a great vacation under your belt, but with refreshed energy!”
