8 Things to Know Before You Go to Aspen

The town that inspired John Denver’s 1972 world-famous folk hit “Rocky Mountain High,” Aspen is a year-round, high-end destination that isn’t just reserved for the elite (or singer-songwriters). Colorado accounts for 20 to 25% of ski and snowboard vacations in the US annually, and Aspen gets its fair share of that crowd, thanks to a plethora of annual events like X Games Aspen (Jan. 25 to 28; sports competitions are free to the public) and thrill-seeking adventures like Aspen Snowmass’s Breathtaker, an alpine coaster featuring a drop of more than 400 feet, which opened earlier this winter.

In other words, Aspen does things differently and exudes uniqueness in every possible way. Want proof? There's a chairlift right next to Aspen High School. (If you plan to vacation with your kids, beware of the jealousy factor that may soon follow.)

Here are nine insider tips to make your winter trek more enjoyable, not to mention more affordable.

1. Your Wallet Will Thank You If You Plan Ahead

Aspen isn’t as pricey as you think — if done the right way. Aspen has a reputation for being expensive, and the food there is no exception (and it’s definitely one of the finest parts of the quaint little town). Next time you’re in Aspen, eat like a local and claim a seat at the bar. Almost every restaurant and bar in Aspen offers a slightly condensed menu with dishes that are nearly half the price of a few steps away in the dining room.

Speaking of which, Snowmass celebrates its 50th Anniversary this year and is celebrating the entire 2017-2018 season (in early December, they offered $6.50 lift tickets — the original price on opening day in 1967.)

Other thrifty celebrations include $19.67 and $50 prix fixe menus at participating bars and restaurants and be sure to snag 50th anniversary lodging specials and discounts through the 2017-2018 season.

2. Fall in Love With Walking Around

One of the best things about Aspen is that it’s a walkable town. The best way to embrace any new town is to discover it on foot, so don’t let an onslaught of sleet or powder keep you from all the amazing things the town has to offer. You'll find heated sidewalks here and there around Aspen, but the town also makes it a priority to keep itself plowed and accessible at all times.

Keeping up with Aspen can be affordable if you don’t overlook the brand-new free public transportation, like the Downtowner, which will take you anywhere in town, including the gondola. The Downtowner is an eco-friendly way to maneuver around. Download the app to set pick-up and drop-off locations and enjoy a fun ride in the electric vehicle around town. A car definitely isn’t needed in Aspen, and almost every hotel has a complimentary car service.

3. Aspen Takes Pet-Friendly to New Heights

For travelers who leave their pets behind but still yearn for canine camaraderie, the Aspen Animal Shelter's Rent-a-Pet program allows visitors to spend a day with an eager companion. Don’t be surprised if you end up going home with a new adopted friend (it’s happened more times than they can count). Bonus: Almost every Aspen hotel is pet-friendly.

4. Plan Around Aspen’s Event Calendar

One thing you need to know about Aspen is that there is always something big going on in town. Not only does this increase the number of visitors, it draws the locals as well.

From Jan. 11 to 14, Aspen's annual toast to winter, Wintersköl, dates back to a quiet January in 1951, when local Aspenites decided to celebrate their unique lifestyle with an eclectic weekend of festivities. The four-day celebration features a variety of community events, fireworks and more.

Aspen Gay Ski Week (Jan. 14 to 21) is the oldest annual, weeklong gay ski event in the nation. A model for other gay ski weeks, AGSW offers a unique experience in the scenic and historic mountain town where visitors enjoy four mountains of varied skiing and snowboarding terrain, cross-country skiing, snowshoeing and winter hiking in the Elk Mountains.

Après Ski Cocktail Classic (March 8 to 11) is an annual slope-side celebration blending all things après with craft spirits in an ideal setting at the iconic Little Nell. The four-day event features a grand tasting village and private reserve room of marquee spirits, craft cocktails, seminars by award-winning mixologists, snow parties, various pop-up bars, fireside chats, spirit-paired dinners, on-mountain events and the Great Après Ski Pub Crawl.

Counting down to the end of each year, the 12 Days of Aspen turns the town into a picturesque winter wonderland of holiday cheer with free ice skating, Santa visits, s’more parties and caroling.

5. The Best Party Happens at 11,000 Feet

Access the finest and wildest après ski in North America, but only by ski. If you aren’t a skier (or snowboarder), but desperately want to experience it, find skis fast so you can hit up Cloud Nine at Aspen Highlands to party like it’s 1999. It’s seriously like another world, but perhaps one you may not remember. If you want a table, reservations are highly recommended.

6. Eat (and Drink) Like a Local

Drink like a local at Hotel Jerome’s J-Bar with an Aspen Crud, the bourbon-laced milkshake cocktail that dates back to Prohibition. It’s been written up across the nation and enjoyed by visitors from all walks.

If you’re a breakfast person, don’t miss Breakfast at Bonnie’s (located mid-mountain) where you can delight in pancakes as big as your face that are worth every delicious calorie (then hit the slopes or hike back for that well-balanced life we all strive for). Want a more indigenous food experience? Try Pyramid Bistro, a “nutriatarian” restaurant located inside Explore Booksellers, the local (and only) bookstore in Aspen. Woody Creek Tavern is another must-visit in any season. Treat yourself to a delicious lunch and a handful of their legendary blue-agave margaritas.

During the winter, get there by renting a fat bike down the Rio Grande Trail or grab the bus. In the summer, go for a beautiful hike, ride your bike or get a taxi back.

7. It's Easy to Find World-Class Musical Performances

Bootsy Bellows/Belly Up, Aspen (owned by actor David Arquette and businessmen John Terzian and Brian Toll) is a lounge/nightclub with a pretty impressive rotating calendar of top musicians. The intimate setting will make you feel like you instantly became BFFs with your favorite artist. Order bottle service or a can of cheapish beer and dance like no one can see you. Stay after hours to up your chances to grab a drink with one of the band members.

8. Get Chatty

A tip for pretty much anywhere you travel, but especially in Aspen, everyone has a story. And it’s usually a pretty good one. Embrace the culture and meet the locals and the transplants by chatting it up wherever you go. The stories you’ll hear and insider tips you’ll be privy to will stay with you forever — whether you like it or not!