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Expert Tips for a Winter Escape to Vail

When snowflakes blanket Vail Mountain and the glitter of the holidays light up the night, the most magical time of year arrives — yes, that’s winter in Vail. Whether you’re here to ski perfect corduroy, bask in luxury or even propose, this Colorado winter wonderland will deliver the goods.

Discover Vail caught up with Mark Dubovy, founder and president of Mountain Resort Concierge, for expert tips only a local would know. Explore Dubovy’s “bests” list below, covering everything from “best Vail scenic overlook” to “best Vail ski run for beginners” to the “best place to hold hands” and more.

Mark Dubovy of Mountain Resort Concierge stops to pose on Vail Mountain. He wears a red ski coat, neon yellow ski pants and he holds ski poles and wears skis.
Mark Dubovy, Mountain Resort Concierge

Find your own best moment in Vail this winter:

The Best Places in Vail This Winter, According to Mountain Resort Concierge

Where is Vail’s best scenic overlook for winter?

Dubovy: It’s Mount of the Holy Cross Observation Deck (Eagle’s Nest), across from the top of Eagle Bahn Gondola in Lionshead. It requires only a ski pass or scenic-gondola-ride pass, and it’s only about 100 yards away from the gondola exit. It’s easily walkable and showcases the amazing Mount of the Holy Cross’ 14,000-foot peak as well as a beautiful view looking west down the Vail Valley.

What are the best winter Vail events?

Dubovy: Hands down, the Vail Legacy Weekend in February is the coolest event around, celebrating Vail’s rich history and founding by members of the famed 10th Mountain Division. The highlight of the weekend is the landing of a Black Hawk helicopter on top of Vail Mountain, along with the Legacy parade through Bridge Street in Vail Village at night. Both are sights to behold and an experience you will never forget. Check the calendar for events happening this week in Vail.

Where can you find the best view from a Vail hotel or restaurant?

Cozy sitting space by the fire at Remedy Bar in Vail

Dubovy: If you want to sip a cocktail and treat yourself to a luxury après-ski experience, visit The Remedy Bar at the Four Seasons Resort and Residences Vail, where you can either look out toward Vail Mountain or sit on their outdoor patio by a fire pit and share some laughs. For a more casual experience, visit the outside deck of Los Amigos at the base of Gondola One and watch the skiers take on Pepi’s Face or Head First runs while you enjoy a delicious margarita. Learn about Vail’s après-ski scene.

What’s the best ski run for beginners at Vail Mountain?

Dubovy: Swingsville: It’s easily accessible from the Vail Village gondola (Gondola One) and via Mountaintop Express (Chair 4). It’s very wide, has a mild pitch and often gets a lot of sun in the afternoon. It is also marked as a slow-skiing zone, which makes it less stressful for beginner skiers.

Where’s the best spot in Vail for an annual holiday photo?

The 10th Division Statue commemorates the American ski troops who trained for war at Camp Hale, near Vail, Colorado.

Dubovy: It’s either the 10th Mountain Division solider statue (Ski Trooper) by the Covered Bridge in Vail Village or at the top of Avanti Express (Chair 2) facing the Gore Range on a sunny day. The first is authentic to Vail and its history and overlooks the Gore Greek and the other has stunning views of the mountains and ski trails.

Where’s the best snowshoe trail in Vail?

Dubovy: The best Vail snowshoeing trails, especially for beginners, are accessed from the Vail Nordic Center, with more than 6 miles of expansive trails to explore. It’s easy to go, and they offer full rentals and tips on the best path to follow for your ability. If you want something more challenging or with more views, try the guided snowshoe tours offered by the Walking Mountains Science Center’s Nature Discovery Center on the top of Vail Mountain. They also offer free backcountry and moonlight snowshoe tours, which are breathtaking and once-in-a-lifetime experiences.

Where’s the best, most romantic place to hold hands in Vail?

A couple sits together in the Vail. They wear warm jackets and admire the lights of on the street.

Dubovy: Walk down Bridge Street in Vail at night and take in the sights and sounds of Vail nightlife or take a peaceful stroll along the Gore Creek path and listen to the sounds of rushing water and local wildlife. It will be sure to inspire that one-of-a-kind romantic mountain experience. See a list of Vail’s most romantic things to do.

What’s the best chairlift on Vail Mountain?

Dubovy: For the best view of the back bowls, Orient Express (Chair 21) and Tea Cup Express (Chair 36) are the best to take in the awe of the expansive terrain. However, both tend to be very cold lifts due to their exposure. For a nice scenic ride with consistently short lift lines, try Riva Bahn Express (Chair 6) out of Golden Peak, where you pass through the race area and freestyle parks, and have a choice of getting off at a mid-station or continuing farther to Northwoods. In addition, Highline Express (Chair 10) is often not too crowded and you get to watch the bump pros take on Highline for your enjoyment. Find Vail Mountain lift- and terrain-status updates.

Where is the best place to propose in Vail?

A nighttime, winter photo of the Clocktower in Vail, Colorado. There are lit-up pine trees all around under a dark sky, and a snow-topped Gore Creek Bridge.

Dubovy: Eagle’s Nest [see Dubovy’s tip for Best Scenic Overlook above], Willow Bridge Road (otherwise known as the Vail International Bridge), the Clock Tower view in Vail Village on Gore Creek Drive or the entrance to Vail Village via the Covered Bridge are top choices because of their views of the town and mountain and their iconic foundations in Vail history. If you want something near the water, walk over to the Gore Creek Promenade where you can grab a bench by some trees or walk right up to the Gore Creek and propose under the moonlight. Get ideas for planning a wedding in Vail.

What’s the best off-the-beaten-path winter experience near Vail?

Dubovy: Book a snow coach or snowmobile tour with Nova Guides, located on the former training grounds of [the U.S. Army’s] 10th Mountain Division (now officially known as Camp Hale-Continental Divide National Monument). It features amazing terrain, and you learn about the inspiring history of Vail and the heroic men who were a part of it.

Which only-in-Vail winter activity for families is the best?

A family of four ice skates together in Vail. Two young girls hold hands as they skate in the foreground, and their parents skate in the background.

Dubovy: Depending on your activity level, ice skating at either Vail Village or Lionshead is always a good choice. For a more fun, interactive experience, try bowling at Deca + Bol. For the ultimate mountain winter fantasy, there are a variety of sleigh rides that include a Western, ranch-style dinner from either Bearcat Stables or 4 Eagle Ranch.

Where’s the best place to sip hot cocoa in Vail?

Dubovy: If in town, try the Gorsuch Ski Café in Vail Village, located slopeside near the base of Gondola One. Half ski shop, half coffee shop, it’s a place that hits all your senses. If you want the ultimate hot cocoa, The Remedy Bar at the Four Seasons is the place to be. Served in a porcelain coffee cup and topped with an oversized square marshmallow, this luxe “haute chocolate” will wow you as chocolate and steamed milk are poured over it. Although expensive, at $22 a cup, it is well worth the experience. Find more tantalizing Vail dessert spots.

Where is the best place to eat on Vail Mountain?

A group of people wearing colorful ski jackets and hats sitting around a picnic table in the snow on Vail Mountain.

Dubovy: If it’s a nice day and you feel like grilling your own lunch, head back to Belle’s Camp in Blue Sky Basin for a social, fun vibe and take in the splendor of the Gore Range. For indoor casual dining, Wildwood Smokehouse — located at the top of Wildwood Express (Chair 3) — has excellent affordable options. For ritzy, high-end dining or to enjoy an afternoon cocktail to end your day, make a reservation and head over to The 10th in Mid-Vail. Check out more Vail Mountain decks.

What is an unbeatable culinary experience in Vail?

Dubovy: This is a tough one as almost every restaurant in Vail is top notch. For some of the best authentic Italian, I like La Nonna Ristorante, which offers a variety of delicious pasta dishes in a warm and cozy ambience. The owners are amazing and make everyone feel welcome! For high-end Colorado cuisine, try the Slope Room or Mountain Standard and feast on amazing steak, salmon or pork chops, just to name a few. Check out a full list of Vail restaurants.

What’s the best expert run on Vail Mountain?

Dubovy: Prima or Highline: If you want steep, endless bumps, these are the trails to master. For a more technical challenge, try Prima Cornice or Steep and Deep in Blue Sky Basin, which require steep, narrow turns and sometimes mandatory air. Lover’s Leap is also a fun run, although it loses a few points because, after you make the “leap,” the rest of the run is relatively mellow. If you want to show off for an audience and a crowd, try Look Ma in Mid-Vail or Pepi’s Face and Head First leading right into Vail Village.

More About Mountain Resort Concierge’s Mark Dubovy

Dubovy’s love first for Vail blossomed as a 13-year-old, then he landed a Vail Valley summer internship as a college student. After 14 years in corporate America, Dubovy took the leap and moved to the mountains full time in 2012. To fine-tune his hospitality experience, he worked at Vail Sports and as a ski instructor before launching Mountain Resort Concierge in 2016. An ex-ski racer, Dubovy’s love for sport began early (age 5!); and he’s skied all over the U.S., Canada and Europe.

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Mark Dubovy
Mark Dubovy
Mark Dubovy is a Vail, Colorado, local and founder of Mountain Resort Concierge.