Itineraries, Winter Itineraries

5 Iconic Days in Winter Park

Want to make the most of your Winter Park vacation? Use our suggested days to Go Beyond the typical itinerary! Go Beyond with these 5 Days at Winter Park Resort.

Jump start your planning with our daily itinerary, built for a Monday thru Fri. Even if you already know that you want to spend all day riding laps on the Super Gauge, you’ll still have downtime between daylight hours, we can help fill the time in between! Let us know if we missed one of your favorite activities! We recommend using this itinerary for a Monday thru Friday schedule.

winter park vacation, 5 Iconic Days in Winter Park


Morning: Get the Lay of the Land

winter park vacation, 5 Iconic Days in Winter Park

If you’re new to Winter Park Resort, or just coming up for your first time this season, why not take a stroll around and explore the base area?  After your drive, you’ll need to stretch your legs anyways. Start at the top of the Village at the Cabriolet and walk all the way to West Portal. On the way, grab a hot chocolate and pop the kiddos in a wagon. Don’t forget to snatch a trail map so you can plan out the days on the mountain! Stop in our new shop James and Parry’s or grab snacks for the week at City Pop.

Midday: Lunch at Rippy’s Mountain Tavern

Beat the ski rush and grab an early lunch. Stop at Rippy’s and warm up with some hot Mac and cheese! Or try a hearty burger and a local brew. Cozy up in this classic ski slope stop and shake off the travel drowsiness. If you’re really looking for a quiet afternoon, settle in with a book or play a game of cards while you sip your beverage of choice!

Afternoon: Hike or Snowshoe

Get adjusted to the altitude and the weather with a little afternoon exploration. If the sunshine on the snowy peaks is beckoning you beyond your cozy spot in Backbowl, then pick up some snowshoes or break out the wool socks and snow boots.   Drive across Highway 40 and you’ll be at the entrance to the Jim Creek Trail. This hiking trail offers gentle terrain with majestic views of the divide. Feel like you’re really getting into the wilderness while still having the resort in eyeshot.

Evening: Dinner and Bowling

For the evening, grab some delicious pizza at Hernando’s.  This family-owned pizzeria is a long time Winter Park staple. Try one of their specialty pizzas like the Bar-B-Que or Mediterranean for something different and delicious. After your fill of pizza, catch a movie or reserve some lanes for bowling. Depending on your group size, you may want to give The Foundry a call ahead of time to reserve your spot. If a couple of games work up an appetite the Homemade Mini Donuts are a must!

Atención, también juego al bowling 🎳

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Morning: Waffle Cabin Breakfast & Guided Ski & Ride Experience 

winter park vacation, 5 Iconic Days in Winter Park

Rise and shine for your first day on the mountain! Lifts start spinning at 9am, so make sure you get there to get some fresh tracks. If you’re an intermediate to expert skier reserve a place for you and a few friends in our Guided Ski & Ride Experience . Get VIP lift access while skiing or boarding the terrain of your choice with the help of a knowledgeable guide! Find powder stashes, the best mogul runs, and whatever else our guides have up their sleeve to give you an awesome morning. Book this in advance for you and up to two friends.  But don’t forget to grab breakfast! Stop at Waffle Cabin and take this handheld deliciousness up your first chairlift ride of the day.

Midday: Lunch at Sunspot

Having an expert guide take you around the mountain means you’ll definitely lose track of time, but your stomach won’t! Pack a snack so you can stay out on the mountain past the end of your guided experience. You’ll have your guide for 3 hours, so plan to head back to Sunspot Mountaintop Lodge for a later lunch around 1pm.  Eat, warm up, and get back out on the mountain to keep shredding based on your guide’s recommendations from the morning. You’ll have plenty of the mountain to continue riding, but remember the Eagle Wind Lift, The Pioneer, and the Pano close before the typical 4pm time, so plan accordingly! Get more details and check trail statuses here.

Afternoon: Tubing

winter park vacation, 5 Iconic Days in Winter Park

Whenever your legs are ready for a break, you can go take a ride at the Coca-Cola Tube Park! Either go in your riding gear, minus the ski boots, or change into some other warm clothes. Then ride the Cab to the top of the Village and you’ll be in for a blast! Enjoy the best hot chocolate in Winter Park while you watch your friends on the live feed video screens inside. Book ahead because this activity does have a number limit. When your hour is up, Five Mountain Tavern is an easily accessible option for dinner.

winter park vacation, 5 Iconic Days in Winter Park

Evening: Broomball

If you aren’t too exhausted from your day on the mountain. Evening broomball takes place on the Village Pond. Bring the whole gang/family down for this snowy classic! The colds now scene will be postcard-worthy, and will inspire a group trip to the hot tub!


Morning: Ride Janeside

Another day of skiing is calling your name! Today go park at the base of the Mary Jane Territory for a tailgate hub. If you’re coming up from the front range, make sure lawn chairs and a grill are on your packing list. You’ll love the party vibe and want to partake in the action. If you don’t have the luxury or popping the grill in your car, no worries! You’ll still have a great time hanging out at the base. Bring a coffee and some breakfast to go, and enjoy the tailgate environment that makes a Winter Park vacation extremely Colorado.

Take a quick walk around the Janebase before hopping on the Super Gauge. Check online to see if the Panoramic lift is open. If it is, that’s your next stop. Ride to the top of the Parsenn Bowl Territory and get first tracks in one of the most scenic ski-scapes in Colorado. We don’t like to brag, but look:

winter park vacation, 5 Iconic Days in Winter Park
See what we mean?

Midday: Lunch at Lunch Rock

Lap the Pano for a bit, and then try a few runs off the Sunnyside Lift (right beside the bottom of the Panoramic). You’ll get a great variety of terrain! Between these two lifts your morning should be set.

winter park vacation, 5 Iconic Days in Winter Park

When you’re looking for a break, either head back down to the car and fire up that grill, or join the party at Lunch Rock. When the sun is out, so are the riders. Pull up a lawn chair (and a bloody mary) and take in the mountain views without a care in the world.

Afternoon: Relax and Warm Up at Club Car 

You’re in a great place to plan out the rest of your afternoon. Start at Lunch Rock and end at Club Car, how you navigate in between is up to you! Once you are back at the Jane base, grab a warm drink and enjoy the cozy atmosphere.

Evening: Campfire Music Series and Drinks at Vertical Happy Hour

Back on the Winter Park side, live music will end the day around the Gazebo fire. If you’d rather relax indoors, hit Happy Hour at Vertical and really get into the Après zone.


Morning: Relax and Treat Yourself

If you felt the pain on Mary Jane, today will be exactly what the mountains ordered. You have 3 different spa options!

Alpenglow in the Winter Park Village is convenient and offers an array of products like their Parry’s Peak Hot Stone Massage or the Steep and Deep Massage. See their full suite of products here.  If you want to spoil yourself, even more, try the Devil’s Thumb Ranch Spa. Get a facial and massage with the Bliss Package!

If you want to mix adventure with your relaxation day, take a drive to Hot Sulfur and try the Hot Sulfur Springs Resort & Spa! Bring a water bottle to make sure you stay hydrated while you slip into the natural hot springs. Hot Sulfur Springs Resort & Spa is a 40-minute drive from Winter Park Resort and includes the natural hot springs and massage deals. Your body will thank you!

Views, Part 2. 🏔 #colorado

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Midday: Lunch in Town

No matter when the morning takes you, stop in town for lunch at Caffe Giocondo. The sunny cafe offers delicious fresh pastries and a nice selection of sandwiches for lunch. This warm spot offers a place to hold on to your morning zen. Indulge in the delicious Prosciutto, Mozzarella, Tomato sandwich with a Cappuccino.

Afternoon: Sleigh Ride

winter park vacation, 5 Iconic Days in Winter Park

Make a reservation for the 3:30pm Hot Cocoa Sleigh Ride at Sombrero Stables at Snow Mountain Ranch. You’ll glide through the snow-covered meadows to a campfire! Dress for the weather, but blankets are provided so you can cozy up while dashing through the snow!

Evening: Drop off the Kids’  and Treat Yourself to Dinner

If you brought the kids along, this is your night to take a break! Grab dinner at Doc’s or Lime, and when you show your receipt for $25 or more from the Village, the kids’ meal and activity are free! More details here. If kids activities don’t apply to you or the Kids’ Night out is all booked for your date, you could also visit downtown and grab appetizers and drinks at Leo’s. If you’re looking to spoil yourself with a delicious cocktail, try a Ditch Margarita, a Hideaway Brewery Local Brew, or an Idlewild Mule! All valley legends.


Morning: Snowmobiling

winter park vacation, 5 Iconic Days in Winter ParkThe last big adventure switches your gravity powered fun to motorized! You’ll have some new views of the Continental Divide to enjoy. And what breathtaking views they are! Get a unique perspective of the Fraser Valley and the endless stretches of rigid mountains with Grand Adventures. They offer both Guided Tours and Unguided Rentals and is conveniently located in the Village of Winter Park Resort. Their tour is the only one in the County that ascends to 12,000 feet!

We advise booking the Local’s Favorite. It’s a 2 hour tour that starts at 8:45am.

Midday: Lunch at Randi’s Irish Pub

Nothing warms you up like a Guinness! (Well, maybe some Irish Whiskey.) And what pairs well with Guinness? Randi’s Rueben! Sit close to the fireplace and chow down in this traditional pub. It’s located in downtown Winter Park and offers a menu with food and drink that will leave you needing nothing more than maybe a good nap.

Christmas is in the air at #randis today! Come grab one of our 12 delicious draft beers and hang out with us by the fire!

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Evening: Cross Country Skiing

We are big on downhill skiing and snowboarding, but we also have plenty of options for trying Cross Country (Nordic) skiing as well! Give it a shot before the sun goes down and enjoy your final day at Winter Park Resort exploring the many locations throughout Grand County!

winter park vacation, 5 Iconic Days in Winter Park

Do more this winter! Winter Park is a place to come for the skiing and snowboarding but stay because of all the fun the resort and the surrounding area has to offer. Even with fewer daylight hours and colder temperatures, we know how to pack in the adventures. What else do you love about Winter Park vacations? Let us know!

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