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Winter Weekend Escapes: Best Places for Outdoor Enthusiasts in Colder Months

Explore the endless miles of trails for snowshoeing, cross-country skiing, fat tire biking, or hiking this winter

Winter months can feel endless, but we know getting out to enjoy nature can be a refreshing and reenergizing experience. We’ve done the work to find the maps for the best snowshoeing, cross-country skiing, fat-tire biking, or hiking near all 32 of our GrandStay locations. It’s time to plan your next grand winter adventure!

Jump to a Location:

Iowa | Minnesota | North Dakota | Oregon | South Dakota | Wisconsin

Before you go:

  • Check Trail Conditions: Many of these locations provide you with trail condition updates via their website or social media. Some locations remain open for hiking, even if snow is not ideal for winter activities. 
  • Familiarize or Print Trail & Parking Maps: Most links we found provide a map of the trails and parking for your convenience. We recommend printing these maps, just in case.
  • Park Fees: Most of the parks listed are free to enjoy, but fees do apply to some.
  • Bring Hydration: We often forget to consider water in the winter months!
  • Charge Your Phone: Capture nature and memories, and in case of an emergency.
  • Dress in Layers & Wear Comfortable Shoes

Iowa

Iowa offers a variety of ways to enjoy the outdoors during the winter months, from peaceful nature walks to scenic parks and trails. Even without snow, these spaces provide a refreshing way to explore the state’s landscapes and unwind outdoors.

Algona

Ames

Johnston

Rock Valley

 

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Minnesota

With thousands of miles of trails, Minnesota invites winter explorers to slow down and soak in its natural beauty. Whether hiking through snow-dusted forests or gliding along cross-country ski routes, these trails offer peaceful escapes in every corner of the state.

Apple Valley

Becker-Big Lake

Cambridge

Cannon Falls

Delano

Faribault

Glenwood

Hastings

Luverne

Montevideo

Morris

Perham

Pipestone

Silver Bay

St. Cloud

Thief River Falls

Waseca

 

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North Dakota

Nestled along the Sheyenne River, Valley City features several local trails that are enjoyable throughout the winter season, including a portion of the North Country Trail. It’s an easy way to get outside and experience North Dakota’s wide-open scenery at your own pace.

Valley City

 

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Oregon

As you may suspect, the landscape in Sisters, OR, lends itself to stunning hiking and snowshoeing options throughout the area. This list is just the beginning! Keep in mind that these trails offer a variety of difficulty levels. 

Sisters

  • View Top 10 Snowshoeing Trails
    • South Sister Trail
    • Black Crater Trail
    • Peak View
    • Upper Three Creek Sno-Park to Jefferson View Shelter
    • Ray Benson Sno Park Loop
    • Three Creek Lake Trail
    • Maxwell Loop to Mount View Shelter
    • Potato Hill Loop
    • Ray Benson Sno-Park Circle Lake Loop
    • Ray Benson Outer Loop
  • ​All the above are best for snowshoeing or hiking!

 

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South Dakota

From the rugged beauty of the Black Hills near Rapid City to Milbank’s local parks and seasonal ice skating, South Dakota offers winter activities for every pace. It’s an easy way to enjoy the outdoors, whether you’re seeking adventure or simple seasonal fun.

Rapid City

This area is rich with sightseeing, trails, historical landmarks, and beyond! This list is just a taste of the trails to explore near Rapid City! We chose those that are closest to our GrandStay Residential Suites location for your convenience.

Milbank

 

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Wisconsin

Wisconsin is home to an extensive network of trails that are just as inviting in winter as they are in warmer months. Whether you prefer a quiet snowshoe trek, a brisk cross-country ski, high stakes fat tire biking adventure, or a scenic winter hike, you’ll find well-maintained trails surrounded by stunning landscapes.

Kaukauna

Eau Claire

La Crosse

Mount Horeb-Madison

Minocqua-Woodruff

Sheboygan

Waunakee-Madison

 

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We trust that you'll find the winter activity and trail fit for your needs. Whether you add one of these spots to your busy itinerary or make it the reason to go, the comfortable accommodations at GrandStay will welcome you. 

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Looking for Downhill Ski Areas in the Midwest and Oregon? Explore here.