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There is nothing we love more than a good rainstorm here in Winter Park—except maybe a good snowstorm—and when the skies turn a gloomy gray and that wet stuff falls from the clouds during your Winter Park vacation, we can promise that you too will soon feel the same way! Yes, even if it dares to rain during YOUR vacation, these fun activities in Winter Park will keep you warm, dry, and entertained as you shop, explore, and dash between the raindrops as you come in and out of museums, restaurants, and whatever else we find for to do. This guide to rainy day activities in Winter Park in our favorite mountain village will ensure that EVERY minute of your getaway, not just the dry ones, will be even better than you imagined!

A Step Back in Time

As the rains fall, you will stay dry as you spend the hours exploring the Cozens Ranch Museum, 77849 US-40, learning how life was so much different for the early settlers who made their home in this area. Times were rough, especially during the winter, but when Cozens Ranch Museum was simply another stop on the stage coach trail, visitors could always count on a hot meal and a warm place to relax before continuing on with their travels. Today, the buildings that make up the museum have been restored to their former glory, bringing to life the days when travel was by stagecoach, heat was provided by fireplaces, and air conditioning wasn’t even a glimmer in anyone’s eyes. Take a step back in time and enjoy the simpler life for a few quiet hours during your Colorado vacation.

The Heart of Downtown

Serious shoppers never let anything like a few raindrops interfere with their habit—er, we mean hobby—and the downtown area of Winter Park will definitely be your new happy place, rain or shine! Pick up a new tee shirt or some cool souvenirs at Moose Hollow Trading Company in Cooper Creek Square or find a sweet gift for your sweet mom who is babysitting her sweet grand puppies at the General Store, also in Cooper Creek Square. Your children are being relative angels as they splash in mud puddles while you rush them from store to store, so we think a stop at Imaginations would be a worthy reward. Also located in Cooper Creek Square, this fun toy store has a great collection of board games, so pick up a few of your favorites and get competitive in your Visit Winter Park Lodging rainy day sanctuary after you have finished with your shopping expedition! Looking for some winter clothing, ski gear, or other outdoor accessories but don’t think you will use them enough to pay full price? Winter Park Trading has a fantastic selection of gently used clothing and equipment that won’t break your bank and is located next to Cooper Creek Square!

Taste-FULL Adventures

Our favorite part of any vacation is the food; being able to try out new restaurants, new foods, and yes, new beverages makes our hearts beat a little faster, and on a rainy Colorado day, trying out a new restaurant can be a great way to stay dry! Sip and snack at Adventures Decanted, where wine, cocktails, charcuterie boards, pastries, and small plates will make you forget about the dreary weather outside. Located in Cooper Creek Square, their menu changes with the seasons, but is surprisingly well rounded for an establishment that is mainly there for the wine! Paella’s Restaurant and Bakery has a fantastic seafood selection, but we want to be 100% honest with you: We go there for the bakery treats, because how can you go wrong with chocolate and ice cream and sweet cakes? Although we have had a simply wonderful time in Cooper Creek Square, it is time to venture out of its boundaries as we choose a nice Italian dinner from Volario’s, located at 78786 US Highway 40. Offering the best of Northern Italy cuisine, you could spend hours here, sipping red wine and enjoying your favorite dishes; pizza, pasta, and veal Milanese are what’s on their menu! Their dessert menu offers a twist to our favorite Italian sweet, serving strawberry mint cannolis and their ricotta cheesecake will make you wonder why every cheesecake isn’t made with ricotta!

Keep It Cozy with Visit Winter Park Lodging

The rainiest of days offer a sweet comfort when spent under the protective roof of our homes and condos, so unwrap the games you just bought, light a fire in the fireplace, and brew yourself a fresh pot of coffee. We can’t predict when the rain is going to stop, but we can predict you will have the time of your life when you choose Visit Winter Park Lodging for your rainy day adventures. Reserve your stay with us today!