Aspen Winter Weekend Itinerary (3 Days In One Of Colorado’s Best Winter Towns)

Aspen is one of those places that’s talked about a lot — and honestly, it deserves most of the hype. But what most people don’t realize is how flexible it is as a destination. Yes, it caters to the ultra rich, there’s also nightlife and serious ski culture, but amid all that you can still have a really laid-back, casual winter weekend here if that’s more your speed.

I live in Colorado and love visiting Aspen regularly. There’s always something new to try, and even when I repeat the same activities, it never really gets old. It works whether you want to be outside all day, spend your time eating and wandering around town, or mix a little of everything.

Skiing is obviously the main draw, but this itinerary isn’t built around ski days. There’s plenty to do besides skiing, but you can easily swap anything here with a day on the slopes and keep the rest exactly the same.

This is how I’d plan a winter weekend in Aspen based on multiple trips.

Aspen Winter Weekend Itinerary 

Day 1

Day one is a good mix of getting outside, exploring town, and checking out Aspen’s social scene.

Snowmobiling To The Maroon Bells (T-Lazy-7 Ranch)

If you only pick one “big” winter activity to do in Aspen, I’d make this the one. Snowmobiling to the Maroon Bells through T-Lazy-7 Ranch is one of the coolest experiences in the area. You follow Maroon Creek Road through snow-covered forest and wide-open valleys, and eventually end up near Maroon Lake with some of the best views you’ll see all weekend.

You don’t need any previous snowmobiling experience. The guides walk you through everything before you leave and handle all the logistics, so it’s very beginner-friendly while still feeling like an adventure.

The tour lasts a few hours and leaves from T-Lazy-7 Ranch, just outside town, which makes this an easy half-day plan. 

Winter weekends fill up fast, so book this ahead of time at T-Lazy-7 Ranch. They also offer a longer Independence Pass route that includes lunch if you want to turn this into more of a full-day experience.

Explore Downtown Aspen

Downtown Aspen is small enough to walk end-to-end but packed with plenty to explore. You’ll find a mix of historic buildings housing luxury boutiques, outdoor gear shops, art galleries, and cafes — all with excellent mountain views.

Even if shopping isn’t your main goal, it’s worth spending an hour or two just wandering around. Grab a coffee, pop into a few stores to warm up, take a few photos, and keep moving. It’s a nice low-effort activity for the late afternoon.

Aspen Art Museum (Easy Downtown Add-On)

If you’re already downtown and want to add something different into the mix, the Aspen Art Museum is an easy stop. It’s free to enter, centrally located, and small enough that you don’t have to commit your entire afternoon.

They also have a rooftop cafe and viewing area, which is absolutely worth checking out. Even a quick walkthrough gives you a break from being outside and adds some variety to the day.

Après Ski (Even If You Didn’t Ski)

Après is a big part of Colorado ski culture, especially in Aspen, and you don’t need to ski to enjoy it. Late afternoon is when the whole town shifts gears. People come off the mountains, the music turns up, patios start filling, and everything feels very social.

Some of the best spots are right at the base of the mountains. On Aspen Mountain (Ajax), Ajax Tavern, The Wine Bar, and The Sundeck are all solid options with good views and a fun crowd. Because downtown Aspen sits right at the base of Aspen Mountain, you’ll also find plenty of après spots scattered throughout town.

You don’t need a plan here. Walk around, see what feels fun, grab a drink, and hang out.

Evening: Belly Up Aspen & Nightlife

After après, it’s usually time for food and a quick reset before heading back out. Aspen has a strong restaurant scene, so whether you want something upscale or casual, you’ll have plenty of options. (I listed the best restaurant options a few sections down.)

After dinner, Belly Up Aspen is worth prioritizing if there’s a show while you’re in town. It’s one of the best small music venues in Colorado and regularly hosts well-known artists. The space is intimate, the sound is great, and it’s easy to walk to from most downtown hotels. Shows often sell out on winter weekends, so buying tickets ahead of time is a good idea. Check out upcoming events at Belly Up Aspen Calendar.

If you’re not going to a concert — or want to go out after — Aspen still has plenty of nightlife options. For cocktails and nicer drinks, The J-Bar at Hotel Jerome, Bad Harriet, Stranahan’s Whiskey Lodge, and Hooch Craft Cocktail Bar are all solid picks.

If you want something more relaxed, Aspen Public House, Zane’s Tavern, and Aspen Brewing Company are easy, casual stops.

And if you’re in the mood to stay out late, The Sterling, GALA Aspen, Ponyboy, and Escobar Aspen are some of the main late night spots.

Day 2

For the second day in Aspen, I like starting slow and building into the day. You’ll get another unique winter experience in the early afternoon, followed by a cozy lunch, then an afternoon that’s all about relaxing before your final night.

Snowshoe To Pine Creek Cookhouse

This is one of my favorite winter daytime activities near Aspen — and it’s basically a snowshoe (or sleigh ride) trip to a remote mountain restaurant that isn’t accessible by road in winter. Snowshoeing through the Ashcroft Valley to Pine Creek Cookhouse feels remote and peaceful without being overly difficult. The trail is well-traveled, scenic, and manageable for most people with moderate fitness.

If snowshoeing isn’t your thing, you can also book a horse-drawn sleigh ride instead, which gives you the same experience without the walking.

Either way, the payoff is the same — arriving at a cozy, cabin-style restaurant tucked into the valley, where you can warm up with a real sit-down meal. Getting here is a huge part of the experience, but the food itself is genuinely good too, which makes it even better.

After lunch, it’s worth taking a short walk through Ashcroft Ghost Town, which sits right next to the trailhead. In winter, it’s especially quiet and beautiful, and it doesn’t take long to explore.

Reservations for Pine Creek Cookhouse are required and book out quickly, especially on weekends and holidays. Be sure to check availability in advance at Pine Creek Cookhouse (you can also find tour and sleigh ride information there). You’ll also need to plan transportation to and from the trailhead ahead of time.

Afternoon Options

By this point in the weekend, most people are ready to slow things down a bit — and Aspen makes that very easy. You could lounge in your hotel hot tub, relax at a cafe with a coffee, or browse downtown shops again. But if you want to fully lean into relaxation mode, here are a couple of great optional add-ons.

Option 1: Aspen Spa

Aspen has some excellent spa options, and after a busy weekend of activities, this is the perfect time to book one. Whether you’re getting a massage, booking a hydrating facial, sitting in a steam room, or just hanging out in a quiet lounge space, it’s a great way to warm up and recover before your final night.

A few solid spa options to check out:

• RAKxa Wellness Spa – known for its holistic approach and serene atmosphere.
• Aspen Alps Spa – a cozy retreat with personalized treatments and mountain views.
• Yarrow, Auberge Spa – luxurious, nature-inspired therapies in an elegant setting.
• The Spa at The Little Nell – refined and relaxing, perfect after a long ski day.
• True Nature Healing Arts – ideal for yoga, meditation, and restorative treatments.
• Beyond Massage Aspen – locally loved for its expert therapists and relaxed vibe.

Book ahead during peak season, especially on winter weekends. Many hotel spas allow non-guests to book treatments with advance reservations.

Option 2: Hot Springs In Glenwood Springs

This option takes a bit more planning, but if you can fit it in, it’s well worth it. Glenwood Springs is home to some of the best hot springs in Colorado and is only about a 40 – 50 minute drive from Aspen, making it a great half-day trip.

Soaking in warm mineral water while surrounded by snowy mountains is pretty hard to beat.

Some good options in Glenwood Springs include:

• Glenwood Hot Springs – Open since 1888, it features the world’s largest hot springs pool.
• Iron Mountain Hot Springs – A modern retreat with beautifully landscaped pools of varying temperatures and beautiful river views.
• Yampah Spa & Vapor Caves – A unique underground experience where you can unwind in natural geothermal steam chambers with options to book a private mineral bath.

For more information check out my guide to the Best Hot Springs Near Aspen.

If you choose this option, plan to spend most of your afternoon here and head back to Aspen in the early evening or at night.

Evening: Ice Skating

Depending on how you spent your afternoon, you may be up for one more activity — and ice skating is a great option. It’s an easy, low-effort outing that fits nicely before or after dinner.

There’s an outdoor rink in Silver Circle near the base of Aspen Mountain, with public skate sessions and rentals available on site, so you don’t need to bring any gear.

Even if you don’t feel like skating yourself, it’s still a fun place to stop by, grab a hot chocolate, and people-watch for a bit.

After skating and dinner, you can either head out for another night in town or keep things low-key and rest up for the drive home the next day.

Day 3 (Departure Day)

Brunch Before Heading Out

Finally, wrap up the busy weekend with brunch before hitting the road, the perfect way to slow down, fill up, and ease out of trip mode.

There are plenty of cozy cafes and sit-down brunch spots downtown. I usually prioritize somewhere walkable so I can squeeze in one last stroll around town before leaving.

For sit-down brunch, Origin by Farmer & Chef and Willow Creek Bistro are both solid options. If you’re looking for something quick and casual, Spring Cafe and Paradise Bakery & Cafe are easy for a quick meal.

If you’d rather stop somewhere on your way out of town, Mawa’s Kitchen is a great option right next to the Aspen Airport.

Optional Stop: Glenwood Springs On The Way Home

If you skipped hot springs on Day 2, this is the perfect time to add them in. Glenwood Springs sits right along the route back toward Denver and makes a natural stopping point.

Ending a winter weekend with a soak is one of the best possible ways to wrap up an Aspen trip — relaxed, warm, and not immediately thrown back into real life.

Aspen Restaurants

Eating in Aspen is genuinely part of the experience. For a town with around 6,000 full-time residents, the food scene is extremely strong — strong enough that the Michelin Guide has taken notice. Whether you want a big “night out” dinner or something more relaxed, there’s a lot of variety packed into a small area.

If you’re in the mood for something more upscale, these are some popular standouts:

• Element 47 – Located inside The Little Nell, this is one of Aspen’s go-to fine dining spots. It’s especially popular in winter for its seasonal menus and cozy, polished atmosphere.
• Bosq – A Michelin-starred option if you’re looking for something more intimate and chef-driven. This is a good pick when you want a truly memorable meal.
• PARC Aspen – Refined but approachable, with seasonal dishes and a strong wine list in a stylish dining room.
• Aurum Food & Wine (Snowmass Base Village) – Elevated New American food in a space that feels upscale without being overly formal. A good choice if you’re spending time in Snowmass.
• Velvet Buck (St. Regis Aspen) – Known for its festive winter dinners and comfortable, upscale lodge-style atmosphere.
• Matsuhisa Aspen – Chef Nobu’s Aspen outpost, serving Japanese-Peruvian dishes, sushi, and creative plates inside a historic Victorian house.

Reservations are necessary for these spots — especially on winter weekends and holidays. One tip I always give people: check lunch menus too. Some of these restaurants offer surprisingly good lunch pricing and tend to have better availability during the day.

If you’re looking for something more casual (and a little easier on the budget), White House Tavern, Aspen Public House, Clark’s Oyster Bar, Meat & Cheese, and Aspen Brewing Company are all solid choices. You’ll still get good food without committing to a full fine-dining experience.

Additional Things To Do In Aspen

Skiing and snowboarding are obviously the main draw — and with four resorts in the area (Aspen Mountain/Ajax, Snowmass, Aspen Highlands, and Buttermilk), there’s a huge variety of terrain for every level. Whether you’re brand new or have been skiing for years, Aspen makes it easy to spend full days on the mountain.

That said, there’s plenty to do beyond skiing. If you want to mix things up or fill in downtime between ski days, here are some popular options:

• Ride the Silver Queen Gondola for panoramic views over Aspen.
• Explore Snowmass Village for shopping, dining, and a quieter mountain-town vibe.
• Go snow tubing or sledding for something fun and low-commitment.
• Catch a show at Wheeler Opera House, a historic downtown venue.
• Ride the Breathtaker Alpine Coaster for a quick adrenaline boost.

For a deeper dive, you can check out my full guide on the Best Things To Do in Aspen in Winter & Spring.

It’s also worth checking Aspen’s event calendar before your trip. Winter is packed with festivals and competitions, including highlights like the Toyota U.S. Grand Prix, Aspen Gay Ski Week, and Winter X Games. You can find the full schedule on the Aspen Snowmass Events calendar.

Where To Stay In Aspen

Aspen has a wide range of accommodations, from ultra-luxury resorts to smaller boutique hotels and condo-style stays. This is one of the most expensive resort towns in Colorado and winter is peak season, so prices are high.

If it’s your first visit, I recommend staying near downtown Aspen. Being able to walk to restaurants, après spots, shopping, and nightlife is a huge convenience in winter, especially when roads are snowy and parking is limited.

A few popular places to stay in Aspen include:

• Luxury: The Little Nell — Aspen’s most iconic luxury hotel with ski-in/ski-out access, a top-tier spa, and one of the best dining scenes in town.
• Mid-range: Limelight Hotel Aspen — Modern, comfortable, centrally located, and a favorite for walkability and value relative to location.
• Budget-friendly (by Aspen standards): Tyrolean Lodge — Simpler accommodations with great location, good reviews, and lower nightly rates compared to most downtown properties.

For more hotel options and detailed recommendations, check out my Best Hotels In Aspen guide.

If budget is a factor, Airbnb and VRBO can be good options for groups. For solo travelers or couples, booking far in advance (sometimes up to a year out) gives you the best chance at lower rates — though winter pricing in Aspen is always on the higher end. Visiting midweek instead of weekends can also make a noticeable difference.

Another budget-conscious option is staying outside of Aspen in towns like Carbondale, Basalt, or Glenwood Springs. You’ll have a commute, but the Roaring Fork Valley has excellent public transportation, making this a realistic way to save money.

Aspen Weather

Generally speaking, winters in Aspen are cold but sunny. Snowfall is consistent throughout the season, and bluebird days are common between storms. Temperatures drop significantly at night, but daytime sun can make it feel warmer than you’d expect.

Because Aspen sits at high elevation (just under 8,000 feet), weather can change quickly. It’s not unusual to experience sunshine and a snowstorm in the same weekend.

Here are the average winter temperatures and snowfall in Aspen:

December — 40° / 10°F (High / Low)
Average snowfall: ~ 61” across 14 days 

January — 37° / 7°F
Average snowfall: ~ 54” across 13 days

February — 40° / 10°F
Average snowfall: ~ 62” across 13 days

March — 46° / 18°F
Average snowfall: ~ 71” across 13 days

Peak ski conditions are typically January through March.

What To Wear In Aspen

Winter in Aspen is all about layering. Mornings and evenings are very cold, afternoons can surprisingly warm up in the sun, and you’ll likely be bouncing between outdoor activities and indoor restaurants or shops throughout the day.

Here’s what I recommend packing:

• Warm winter coat — Long, insulated, and weather-resistant.
• Base layers — Thermal tops and leggings make a huge difference if you’re spending extended time outside.
• Waterproof boots with traction — Streets and sidewalks can be snowy or icy, traction really matters.
• Hat, gloves, and scarf — These are especially important when doing excursions, but even on sunny days, mornings and evenings get cold fast.
• Casual dinner outfit — Aspen is stylish but not overly formal. A nice sweater, boots, or a simple winter dress works well. (Visitors tend to dress up much more than locals — for fine dining, dressing up is expected, but you can still lean more “mountain casual.”)
• Sunglasses — Snow glare is real, especially on bright days.
• Swimsuit — If you’re planning hot tub, spa time, or hot springs.

Don’t forget sunscreen — high elevation plus reflective snow can be surprisingly intense. A reusable water bottle is also a good idea. Aspen is very dry in winter, and dehydration sneaks up fast.

For a more detailed break down, check out What To Wear In Colorado In Winter.

Getting To Aspen

Aspen is located in western Colorado and is accessible by both car and plane. From Denver, the drive takes about four hours in good winter conditions, but snowstorms and weekend traffic can add time.

Tip: Always check road conditions before driving in winter. COtrip is great for real-time road updates, and the National Weather Service is helpful for checking specific mountain locations (like Vail Pass, Loveland Pass, etc.). Independence Pass is closed seasonally, so winter routes follow I-70 and funnel through Glenwood Springs.

If you’re flying in, Aspen/Pitkin County Airport (ASE) is the closest option and sits just minutes from downtown. Flights can be more expensive and weather-dependent, but it’s by far the most convenient.

Another popular option is Eagle County Regional Airport (EGE), about 1.5 hours away. It often has more flight availability and (relatively) better pricing during peak ski season.

The nearest major airport is Denver International Airport (DEN), which is about four hours away by car. You can find great flight deals here year-round and there are ample shuttles to Aspen (book in advance) or you can take the Bustang to Glenwood Springs and RFTA to Aspen if you prefer public transit.

Getting Around Aspen

You don’t need a car in Aspen in winter.

Aspen is very walkable if you’re staying downtown. Many hotels, restaurants, shops, and nightlife spots are within easy walking distance of each other.

The town also has an excellent free bus system that connects Aspen, Snowmass, and nearby areas. It’s reliable, easy to use, and one of the best public transit systems in the state.

For destinations not directly connected by bus routes, there are private car services, hotel shuttles, and occasional Uber, Lyft, or taxi availability — though I wouldn’t rely on rideshare as your primary plan.

If you do rent a car, parking at your hotel is usually your best option — even though it often comes with a high price tag. Downtown parking is very limited, street parking has strict limitations including overnight restrictions. If you plan to use a garage, double-check the rules ahead of time (not all allow overnight stays, for example) and expect high parking rates. Because parking is tough here, many visitors choose to park once and rely on walking combined with private or public transportation for the rest of the trip.

Between the scenery, food scene, winter activities, and overall energy of the town, Aspen makes it easy to put together a memorable weekend. Whether you follow this itinerary exactly or swap pieces in and out, the flexibility is what makes Aspen such a strong winter destination.

I hope you’ve found this helpful in planning your trip and have the best time!

Any questions? Please leave a comment below or reach out on social media.

Looking for more information? Below are additional Aspen and Colorado guides!

More Information For Your Winter Vacation In Aspen:

• Top Things To Do In Aspen In Winter & Spring
• Best Hot Springs Near Aspen
• Top Hotels In Aspen, CO
• X Games Aspen: What To Know Before You Go
• Christmas In Aspen: Top Things To Do
• What To Wear In Colorado In Winter (For Mountain Towns & Ski Trips)
• Aspen Vs Vail: Which To Visit?
• All Aspen Guides

More Information For Your Colorado Vacation:

• Best Winter Destinations In Colorado
• Spring Break Destinations In Colorado
• Luxury Mountain Towns In Colorado
• Best Colorado Mountain Towns For First-Time Visitors
• Colorado Travel Guide (how to plan your trip!)
• All Colorado Guides