Family Guides, Venture Out, Winter Itineraries

Long Winter Weekend Itinerary

Another long weekend is ahead of us and it’s going to be a gorgeous one at that with some snow and lots of sun. This long weekend itinerary guide will offer an abundance of suggestions to fill your weekend with adventurous entertainment for everyone! Then on Monday and Tuesday, you can get those soft and sunny turns all to yourself.

Day 0 – Friday

You’re finally on the way to Winter Park, enjoying the drive on highway 40, and the natural beauty of the Continental Divide is mesmerizing. You stop at the top of Berthoud Pass to soak in the never-ending view of the valley and snap a group photo.

You arrive to your slopeside lodge, get settled in, and sit down and relax by the fire after the drive. But that doesn’t last long, the group is ready to get going. There are a few things you can do from here:

  • Make a run to Trail’s End (located in the Village, so it’s walkable!), Fireside Market or Safeway to stock your kitchen with foods and drinks.
  • Twilight Snowshoe Tour offered at the resort. Stroll through the silent winter woods and enjoy the beautiful starlit Colorado sky, then enjoy some tasty s’mores!
  • Enjoy a walk around Winter Park Village. Snap a photo in our larger-than-life postcards, then snag some WP swag from James & Parry’s. Show support for our ski-patrollers and take a gander at our Patrol Clothing Line. Proceeds help fund training for the Winter Park Ski Patrol Dog Team.
  • Order delivery from Doc’s Roadhouse
    • Doc’s new menu is filled with favorites like smothered tater tots, pulled pork and yummy mac & cheese. Plus, get a growler of our limited-edition beer, Mary Jane Ale. They’ll deliver the goods right to your door if you stay at the base!
long weekend itinerary, Long Winter Weekend Itinerary
Enjoying Smores After Twilight Snowshoe Tour

Day 1 – Saturday


First thing’s first, brew a pot of coffee and savor a cup of joe from your balcony while gazing upon the sun-kissed mountains. There’s no better way to start a mountain getaway! Take the morning slow and enjoy time with your group, make a delicious breakfast, and get ready for your afternoon adventures.


After a relaxing morning, enjoy an afternoon activity to see the beauty of Winter Park from a new angle. Some options for you:

  • The Nature Snowshoe Tour provides amusement for the whole family and exceptional views of the Continental Divide.
  • Summit Snowshoe Tour: Traverse the high alpine terrain and experience the road less traveled.
  • Sno Go Bike Tour: For all the adventure seekers, this is for you! Experience sliding down the mountain in a new way.
long weekend itinerary, Long Winter Weekend Itinerary
SnoGo Shred Session


After experiencing some new and different activities over the afternoon, you may be wanting more. If that’s the case, head over to the Winter Park tubing hill for an hour of speed, hollering, and laughing.

For dinner, experience the hustle and bustle of downtown Winter Park and try something new. Here are some places you could try:

  • Pepe Osaka’s is a local favorite that has an Asian/Latin fusion menu that specializes in fish tacos, and don’t forget some of the best margaritas in town!
  • Deno’s Mountain Bistro: The best happy hour in Winter Park! Consists of two different kinds of pizza, two options for tacos, three different flavors of hot wing, and incredible drink specials. Happy hour is 3-6pm daily.
  • Fontenot’s: Craving fish in the mountains? With a New Orleans flare, their scallops, catfish, and cod won’t be beat. They also have steak, pasta, and creative cocktails.

Day 2 – Sunday


Day 1 is under the belt, and more adventures are planned! Lucky for you, you booked one of the tours mentioned above, or, our Intro to Uphill tour. Intro to uphill is learning new ways to explore the mountain, while also getting to ski down!

But before the tours start, food first. Wander around the village to see what food you can find. You stumble upon one of the breakfast places in the village:

  • Goodys: a mountain creperie and pastry shop (plus much more).
  • Mexicali taco: Authentic Mexican cuisine meets breakfast burritos!
  • Waffle Cabin: Sugar Waffles drizzled in chocolate, who wouldn’t like that breakfast!

Whatever the choice, your group will be busy indulging on the tasty food and you’ll be able to enjoy some silence along with your breakfast.


The tour is over, and the group is spent! At this point, there’s a couple of options:

  • Head back to your lodging to stretch, rest, and take some naps, because the next 2 days are ski days 😊.
  • Keep on trying new things and do one of the tours you haven’t done yet.
  • You weren’t able to hit the tubing hill last night, so you decide to go today.
long weekend itinerary, Long Winter Weekend Itinerary
Tubing Hill at Winter Park Resort


Ski days are upon you, so you choose to stay in. You heard from one of the Resort employees that there’s a new food delivery service that delivers to the base and offers a handful of different cuisines, so everyone can get what they want!

  • Doc’s Roadhouse– Comfort food and oh so tasty BBQ!
  • Pizza Pedal’r- Rated as one of the best pizzas, year after year.
  • Lime – Classic Mexican cuisine, can’t go wrong!
  • Vertical – American Bistro-style menu with amazing locally sourced flavors.
  • Goody’s – Didn’t want breakfast? No worries! Goody’s also has savory burgers and sandwiches.

 Day 3 & 4 – Monday and Tuesday

The weekend came and went, and now it’s time to hit the slopes! Make sure to book your rentals, lessons, and lift tickets before to claim your spot and save!

Your morning and afternoons are filled with shredding the mountain, smiling, laughing, and everything else you love about skiing and riding! And lucky for you, your slopeside lodging doubles as a personal warming hut on those cold days.

wolf creek pizza GIF by Elevated Locals

                *Pro-tip – check out our favorite early season laps for a wonderful day on the mountain for all skill levels.*

Don’t forget about all of our new on-mountain grab-and-go options like the pepperoni strombolis at Lunch Rock, Mary Jane Ale at Doc’s, and the worlds-best slopeside truffle french fries at Bradley’s.

In the evenings, you can decide to dive into those activities you haven’t been able to squeeze in yet, or just take it easy and enjoy some very much earned and deserved relaxation!

We hope you find excitement and satisfaction during your long weekend! There are plenty of ways to Venture Out with us, including action-packed activities, grab-and-go food options, and strolls through the village. Take a look at our Deals & Packages to book your long weekend now!

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