Fall Itineraries

A Fall Guide Beyond Just the Leaves

Winter Park is home to many authentic Fall experiences (still with the pleasure of a Pumpkin Spice Latte or two), but gazing at the leaves and chasing the changing colors is only a small part of this time of year (check out our leaf-peeping blog). If you missed the peak colors, or you just want to add more to your fall trip, we’re laying out the best of fall in a 4-day guide below.

, A Fall Guide Beyond Just the Leaves

Sweater Weather

Morning: Get Dressed!

I’m sure you have a full fall wardrobe already picked out, but you’re in the mountains now, and that calls for a whole new style. Hit the shops of Cooper Creek Square for morning coffee and a sweet treat from Mountain Grind. Shop for one-of-a-kind gloves, scarves and hats, then pick up a Fleece from Moose Hollow Trading Co. to really keep you warm while lookin’ good! You might be feeling a little antsy for ski season at this point, so you might as well pop into Powder Tools to browse boards, apparel, accessories, and more.

Mid-day: Visit the Strip

, A Fall Guide Beyond Just the Leaves

It’s no big city street or coastal board walk, it’s better. Spend the day wandering the less-than-a-mile main street that hosts everything from cute shops to city parks and small-town entertainment. Stop where you like and mozy where you wish; you’re on mountain time in the fall, and there’s no rush to get anywhere fast.

The Perk is the place to be for afternoon tea. Bring the whole family and share warm drinks in the cozy lounge area. While you sip, get competitive with one of the many board games available for your use.

Maybe even stroll through Rendezvous Event Center to walk along the Fraser River in Confluence Park or wander up Yankee Doodle trail for some broad valley views.

Now that you’ve worked up an appetite, no doubt, indulge in a margarita (how could you say no to in-house-infused-tequila?) and fish tacos at Pepe Osaka’s.

Evening: Cozy Cuddles

, A Fall Guide Beyond Just the Leaves

Check in for your stay at Founders Pointe. These updated condos will have you snuggling in a shared living space, prepping snacks in a cozy kitchen, and warming up next to the fireplace.

, A Fall Guide Beyond Just the Leaves

Hike and Bike

All day: Trail Traipsin’

Explore the plethora of trails in Winter Park and the surrounding area. And man are there plenty to be explored. If you’re looking for a long hike to take up most of your day, try Devil’s Thumb or Byers Peak. Or if pedaling is what you’re after, take a cruise on Serendipity. Chances are there will still be leaves to spot on your adventure, but even if most have already fallen, the views are still incredible.


, A Fall Guide Beyond Just the Leaves

All night: Recover

Eat at Vertical since it’s close to the bed you’ll need after your full day. If you’re up for it, hit the hot tubs located on the rooftop-style lounge of your hotel to soak away any aches and pains. Then hit the hay as early as you wish (we’re not judging).

, A Fall Guide Beyond Just the Leaves

Take a Drive

Morning: Pumpkin Spice Latte

Did you really think we’d create a fall guide without mentioning this famous (or infamous, depending who you ask…) fall drink? We may be far from the city lifestyle, but we still have our favorite caffeine fixes to get us fired up for the day. Try freshly baked goods and high mountain roasted coffee from Rocky Mountain Roastery. Want a more convenient morning stop? Starbucks in the Village is just a short walk from Founders Pointe.

Mid-day: Drive Through Rocky Mountain National Park

, A Fall Guide Beyond Just the Leaves

You already became an honorary Coloradan yesterday when you spent the whole day getting your fill of mountainly adventures. But if you want to brag about your new title with even more pride, you have to reach the top of Trail Ridge Road in Rocky Mountain National Park. This scenic drive offers impressive photo ops, wildlife sightings, souvenirs galore, and even a little a taste of history, all just 36 miles from Winter Park. Not to mention the beautiful valley views and vast mountain lakes you’ll pass before you even get to the park!

Evening: More Fall Spices

On your way back to Winter Park, stop for dinner in the tiny town of Tabernash. The Tabernash Tavern switches up their menu often, which means exquisite entrees that reflect the season in which they’re served. Visit this area-famous restaurant to find something as pumpkin-y as pumpkin bisque or something as anti-pumpkin-y as a juicy steak.

, A Fall Guide Beyond Just the Leaves

Dance for the God of Snow

Morning: Hit the Gym, but Better *Great for Rainy Days*

The Rec Center is the area’s only gym, so it offers loads more than just a few running machines and free weights. On top of a full gym, there’s a basketball court, a gymnastics setup, a play room complete with a ping-pong table, and a swimming pool complete with a water park. While the kids (and kids at heart) hit the water slide, adults can enjoy their time, too… Climb the rock wall, take a yoga class, dance your way through a Zumba session, or float on down the lazy river.

Afternoon: Drink Whiskey

Idlewild makes the best whiskey around right here at 9,000+ feet. Visit their speak-easy style setup and order a fancy drink to get ready for a fun night!

, A Fall Guide Beyond Just the Leaves

Fall is fantastic, but winter is what we live for. Feel free to head out today, but just be prepared to come back in a few weeks. When the snow starts coming, that’s game on for the winter adventures you’ve been waiting for.

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