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The Ultimate Winter Park Summer and Fall Guide

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trail by the woods

The Ultimate Winter Park Summer and Fall Guide

Every day is a new adventure in Winter Park, Colorado, offering ruggedly beautiful landscapes that are verdant and green in the summer and fiery and colorful in the fall. When your journey brings you in our direction for a fall or summer in Winter Park getaway, the only thing that can make your trip better is a stay in one of our Winter Park Escapes vacation sanctuaries! Offering comfort, style, and luxury that will be much appreciated after your day’s explorations, our properties are designed to be an integral part of your Winter Park experience. Because we want to ensure that your time with us is as fun and fulfilling as it possibly can be, we have created this ultimate summer and fall guide to our mountain village!

Your Home Away from Home

The best adventures begin and end in our Winter Park Escapes sanctuaries, and if you are not quite convinced yet, this guide will more than likely provide some gentle encouragement! Every property we offer is designed according to the homeowner’s likes and dislikes, but even though the styles may be vastly different, the sense of home and welcoming will be the same in each property. Offering rustic cabin luxury in some, you will feel comfortable as you follow polished wood floors to rooms that could have come straight out of your dreams.

Kitchens with knotty pine cabinets, tongue and groove paneled ceilings, granite countertops, and stainless steel appliances invite you to create family feasts or whip up batches of homemade cookies to enjoy in nearby dining rooms dominated by sturdy wood tables. Those tables will be where many vacation memories are made as guests play board games, devour meals, or make plans on how to spend their time in Winter Park. Living rooms with plush sofas facing fireplaces made of brick and state-of-the-art televisions allow occupants to keep up with their shows. Because entertainment and relaxation are key to any vacation, our properties offer saunas, hot tubs, game rooms, and access to any and all community amenities!

The bedrooms in our rustic cabins feature soft beds, occasionally facing walls of windows that let in the views while keeping out the weather, fireplaces tucked into corners, and in many cases, en suite baths with deep soaking tubs! These rooms are the perfect place to retreat to after a long day of playing in the beauty that is Winter Park, offering the ultimate luxury for every adult: a night filled with uninterrupted sleep!

hiking trail in woods

Summer in Winter Park

Winter Park is more often thought of as a winter playland, connected as it is to the Winter Park Ski Resort, but we like to think of our mountain town as a four-seasons playground, one that offers a vastly different experience with each change in season! The incredible weather in the summer has guests and residents feeling the urge to get outside, which makes hiking, biking, and horseback riding exceedingly popular activities.

The Fraser River Trail is one of our favorite trails to take, clearly marked, well-groomed, and taking hikers and joggers along the side of the Fraser River; every hike can offer up a different experience! For mountain bikers (if you do not bring your own, you can rent one at Epic Mountain Sports on US 40), you may already know that Winter Park is considered the Mountain Bike Capital of the United States, and as such, you could spend your entire getaway exploring the trails that traverse the area without ever growing tired! The Fraser River Trail is also a popular biking trail, but the Idlewild Trail System is equally adored by all; you can download a complete map of Winter Park trails at PlayWinterPark.

Summer in Winter Park is also known as rodeo season, and the High Country Stampede Rodeo is open on Saturdays beginning July 3 in 2021—what a wonderful way to kick off your Independence Day Weekend! This year, they are proud to announce that they are moving this country rodeo to the next level, having become members of the Cowboys Professional Rodeo Association. Spend your Saturday watching barrel racing, bronc busting, and all the other activities that rodeos feature, and if you are joining us for the Independence Day holiday, be sure to wear your favorite red, white, and blue clothing and accessories to show your love for our nation! If you or your family members cannot get enough of the magnificent steeds working hard at the rodeo, consider a horseback ride through the countryside as another summer activity option in Winter Park! Snow Mountain Stables, located in nearby Granby, offers horseback trail rides as well as wagon, sleigh, and pony rides for the smaller members of your traveling party.

The beauty of the Colorado countryside will make you wish you could pack it in your suitcase and take it home with you, and although that is a bit on the unrealistic side, you CAN take home images of it when you visit some of the art galleries that can be found in town. The most talented artists in the country are drawn to Winter Park, and many spend their lifetimes painting nothing but the scenes they come across every day of their lives! Uptripping in Winter Park offers local and international art and also includes colorful Native American pieces that will add whimsy and flair to your den at home, but there are many more galleries you will want to explore during your stay, including Naked Aspen Designs and Karen Vance Artworks in Fraser. The exhibits and history shown at Cozens Ranch Museum & Gift Shop, also in Fraser, will make a history buff’s heart beat faster as they learn about the trials and tribulations settlers suffered through to help this region become the place it is today.

Love the smooth sounds of jazz music, especially as the notes ring through the trees in an outdoor concert? Jazz Fest has made its way back to Winter Park for 2021, occurring July 17th and 18th, and the lineup promises to excite! Offering performances by your favorite jazz artists—and some new ones that will soon be added to your own playlists at home—tickets are on sale now, so don’t miss out.

marshmallows roasting over campfire

Falling for Winter Park in Fall in Winter Park

As the months fly by and another page is ripped off the calendar, the pace in Winter Park begins to pick up a little, and as more visitors begin to trail into town in this final season before winter, the colors of the trees in the Winter Park landscape begin to turn fiery and brilliant. Cool days lead to colder nights, and the smell of fireplace smoke and pumpkin spice everything wafts through town, leading visitors to spend even more time playing outdoors.

Hiking and biking are still popular Winter Park fall activities, but if you want to see more of what makes our town so special, consider a train ride on the Georgetown Loop Railroad! Located about 30 miles away from your Winter Park Escapes fall sanctuary, the historic steam powered locomotive takes you on a ride through the countryside, giving passengers an up close and personal look at the beauty of the season, pulling out of the station at various times every day of the week. For those who prefer to be in control of the vehicle in which they are riding, the traditional Sunday drive can take place every day of the week on vacation, and the best drives to view the fall colors can be taken along the Trail Ridge Road in Rocky Mountain National Park, Muddy and Rabbit Ear Passes, and the Colorado River Headwaters Scenic and Historic Byway. This last scenic byway is noted as one of the top 25 scenic drives in the state and offers a breathtaking glimpse of the countryside that you will never want to forget!

When the need for taking deep breaths of the clean and fresh Colorado air overtakes you, hiking is also a popular activity in the fall, and the Discovery Loop, also known as the Jim Creek Trail, is one of our favorite places to stretch our legs and marvel in the glory of another perfect fall day in the Winter Park region! Located just three miles south of town, this trail is a seven-mile round trip exploration of exquisite beauty, taking hikers through forests of aspen trees garbed in their autumn finest, past a bubbling creek, and offering views of meadows, more colorful trees, and the majesty of James Peak.

As you can see, there is lots to do outside while in Winter Park for fall, but if you are looking for some indoor activities, there are plenty of those to entertain you as well, especially for traveling families! One of our favorite ways to play, perhaps on a rainy day in the fall, is with a visit to the Foundry Cinema and Bowl, located at 22 Second Street in Fraser. Offering a movie theater that plays the latest releases, eight lanes of bowling, billiards tables, a full restaurant and bar, the Foundry Cinema is a one stop destination for fun!

As you explore the town of Winter Park, discovering new restaurants (we will discuss that more in the next section) and enjoying our small-town charms, spending a few hours involved in a little retail therapy promises to add a little extra sparkle to a getaway that already shines. Gift shops, boutiques, and jewelry stores dot the streets of our Colorado town, offering everything you never knew you needed until you spotted it here. Pick up something for your pet sitter at home, early Christmas presents for your kids, or something sparkly for yourself, just because! Altitude Jewelers, 47 Cooper Creek Way, offers a collection of mountain inspired jewelry that will make beautiful souvenirs of your time in Winter Park.

restaurant with brick wall

The Fresh Air Will Make You Hungry

Even those who do not normally have large appetites will soon discover that all your adventures in the clean fresh air of Colorado will have you craving large meals that stick to your ribs and Winter Park offers more than a few places to fill your stomach as you feed your soul! Dig into a big plate of Veal Milanese at Volarios, 78786 US Highway 40, and don’t forget to save room for their strawberry mint cannoli. Randi’s Grill and Pub offers your favorite Irish and American pub meals along with a large selection of craft beers, smooth wines, and unique handmade cocktails that include a refreshing Blackberry Bourbon Sour created with Jim Beam, blackberry brandy, and muddled blackberries. Breakfast at Waffle Cabin in Winter Park Village is always a special way to start the day, and when you are seeking comfort food for breakfast or lunch, Sharky’s Eatery at 221 Doc Susie Avenue in Fraser offers omelets, and sandwiches, and burgers that will fill all the empty spaces in your stomach!

Once the sun sets on another day of beauty in Winter Park, you may not be quite ready to head to dreamland, and Ullrs Tavern, 78415 US 40, has the late-night entertainment you crave, including live music, pub grub, and pool tables to play at until last call at 1:45 AM. For those who prefer a place that is a little more lowkey, the people at the Basement make newcomers feel like welcome friends who have just been away for a little while, and the beer is always cold! Located at 78295 US 40, pool tables, arcade games, and dart boards offer more ways to have fun at this local hot spot every day of the week!

Come Home to Winter Park

The warm days of summer and the chill days of fall will be made all the better when you choose the comfort and luxury found in our Winter Park Escapes seasonal sanctuaries! Reserve yours today and discover the adventures, the excitement, and the wonders of Winter Park.