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Osceola WI Tourism, find tourist attractions, things to do, places to shop, places to eat and things to do
  • Discover
  • Experience
    • Local Attractions
    • Area Attractions
    • Shopping >
      • Coming Home
      • The Looking Glass
      • Wildwood Flowers
      • Red Bird Music Store
      • Studio A Salon and Spa
      • Uptown Gifts
      • Karita's Shoppe
      • Neumann Farms
      • Valley Spirits
      • Osceola Country Store
      • Dick's Fresh Market
      • Bill's Ace Hardware
      • The Granary Frame Shop
      • Watershed Cafe
      • Treasure Alley
      • Adoray’s Treasures from the Heart
      • Style Escape
      • Croixland Leather Works
    • Historic Downtown
    • Culture and Heritage
    • Map of the area
    • Remarkable Osceoleans
    • Directory >
      • Business Directory
  • Things to Do
    • Outdoor Adventures
    • Family Guide
    • Choo Choo Specials
    • Hiking Trails >
      • Trail Maps
    • Biking Trails
    • Birding
    • Fall Itineraries
    • Winter Itineraries
    • Farm to Table
    • Romantic Get-Aways
    • Wine, Cheese & Chocolate Tour
  • Places to Eat
    • Where the Locals Eat
  • Places to Stay
    • Lodging
    • Camping
  • Events
    • Rhubarb Fest
    • Music on Main St.
    • Osceola Harvest Bazaar
    • Valley Brew Fest
    • Doe on the Go
    • Wheels and Wings
    • Light Up Osceola
    • Celebrate Osceola
  • Contact Us

Hiking Trails

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Where We Play
With access to over 1000 miles of trails in the area, Osceola makes an ideal basecamp for discovering the great outdoors in all four seasons. So whether you’re a dedicated hiker ready to hit the trail or a nature lover just looking for a reason to get outside, you’ll find miles of trails in playgrounds of beauty and natural surroundings right here and nearby Osceola. ​


CLICK HERE FOR ALL TRAIL MAPS!
Want to Help?
We have a variety of volunteer opportunities for you; one-time trail building days, cutting invasive species like buckthorn, and planning fun events. Plus, you can join the fun group of people who are the Coalition! Additionally, there are opportunities for donations. By making a special gift of any size, you are helping plan and expand trail networks and make trails the center of a healthy and thriving community. As a volunteer, you could give a little time to keep the trails maintained and working great for the many visitors and citizens who use them. And with your help, volunteers can help build more trails- healthier places for healthier people. 

 In Town Hiking Trails

A- Cascade Falls Trail

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At the top of the deck, head down the stairway to reach breathtaking Cascade falls. At dusk, the falls become illuminated. Continue along the stream to the St. Croix River. 
Location: 100 Cascade St. @ the Falls Deck  Osceola, WI

Distance: 0.3 miles
Level of Difficulty: Vigorous (135 steps) 
Features: Cascade Falls, St. Croix River, Osceola Creek


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B- Eagle Bluff Trail

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At the river, steep switchbacks lead up the bluff to the most spectacular views of the valley from an eagle's vantage point. 
Location: Trailhead behind Cascade BP 97 Cascade N. Osceola, WI

Distance:  0.5 mile
Difficulty Level: Vigorous & Rustic
Features: High bluffs, valleys, St. Croix River

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C- Simenstad Trail

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At the top of the bluff, an easy loop trail provides views of the valley and historic village of Osceola. An easier access begins at the trailhead behind the BP station. 
​Location: Trailhead behind Cascade BP 97 Cascade N. Osceola, WI

Distance: 0.8 mile
Level of Difficulty: Easy to Moderate
Features: High bluffs
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*Note: FALLS BLUFF LOOP combines Cascade Falls Trail,  Eagle Bluff Trail and Simenstad Trail that creates a loop that is both challenging and provides diversity. Discover a falls, a river, a creek, the bluffs overlooking the valley, and a natural spring all in a 45 minute walk.

Historic Village Walk​

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Enjoy this stroll from the historic train depot through town and learn some of our amazing history! Follow River Street and stop at the Ladd Overlook for a lovely view of the St. Croix River. Trail uses sidewalks and is handicap accessible. 
Location: Start @ 114 Depot Road Osceola, WI

Distance: 0.6 mile
Level of Difficulty: Easy, ADA accessible 
Features: Local shops, community gatherings, St. Croix River

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Printable pdf for info on our town history
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Brookside Trails

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Starts at the Trailhead next to the St. Croix Artbarn, and leads you through a park that was originally a campground. The trails are being improved but are fun to explore. Don't miss the covered bridge! 
Location: 1040 Oak Ridge Drive, Osceola, WI

Distance: 0.5 miles; Varies by trail
Difficulty level: Easy
Features: Osceola Creek, covered bridge, bridge

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Local Hiking Trails
​Just Outside of Town

Ridgeview Trail-
​Osceola Loop

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Follow the stream all the way to the St. Croix River! Along the way, you'll enjoy wildlife and birding. 
Location: 94 County Road S Osceola, WI
Distance: 2 miles
Level of Difficulty: Easy to Moderate ​
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Ridgeview Trail- Chisago Loop

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Just 0.3mi farther on Co. Rd. S from the Osceola Loop, and you will find the Chisago Loop. Hike or snowshoe up a short incline for fabulous view of the St. Croix River. An easy ascent for birding and photography opportunities.
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Location: 94 County Road S Osceola, WI
Distance: 1 mile
Level of Difficulty: Easy
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Jeff Meyer Public Fitness Trail

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Located by the hospital, this is a paved loop for strolls, walks, and jogging. Includes 6 exercise stations and a fenced inclusive playground.
​Location: 2600 65th Ave. Osceola, WI

Distance: 0.5 miles
Level of Difficulty: Easy, ADA accessible 
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Standing Cedars - Tewksbury Trail

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Rustic trail through woodlands, prairie, and historic limestone quarries. Spectacular view of the St. Croix River. 
Location: 643 Ridge Road Osceola, WI

Distance: 1.25 miles
Difficulty Level: Easy, Uneven Ground
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Standing Cedars-
​Englewood Trail

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Prairie, woodlands, and groomed cross-country trails. 
Location: 213 280th St Osceola, WI

Distance: Varies from 0.7 miles to 3 miles
Difficulty Level: Easy, Uneven Ground

Standing Cedars- Brown Trail

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Wetlands, woodlands, and prairie. 
Location: 2474 65th Ave Osceola, WI
Distance: 1.0 mile 
Difficulty Level: Easy, Uneven Ground

Standing Cedars- Buffalo Skull Trail

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Dry cliffs, oak savanna, ravine, forest, and prairie. Follow the trail to Buttermilk Falls, a beautiful waterfall and scenic overlook.  
Location: 2849 55th Ave Osceola, WI
Distance: 0.7 miles to 3 miles 
Difficulty: Easy, Uneven Ground

Regional Trials
Other trails for playing outdoors are just a short distance away:

Gandy Dancer Trail
7 miles north on Highway 35
 98-mile interstate recreational trail follows RR grade with limestone surface crossing into MN and back again into WI on its way to Superior.

Stower Seven Lakes Trail
6 miles west of Osceola on County Rd. M
14 mile recreational trail follows RR grade limestone surface. Groomed in winter for snowshoe and cross country skiing.

Ice Age National Scenic Trail
7 miles north of Osceola
1000 mile footpath highlights landscape features of the glacial remnants of 120000 years ago as it travels through some of the state’s most beautiful natural areas. 

WI Interstate Park
7 miles north of Osceola on Hiway 35.
12 short trails & scenic views of the steep gorge-Dalles of the St. Croix.

William O’Brian State Park
11 miles across the river from Osceola on Hiway 95
16 miles of trails
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Tips for trail safety & etiquette
• Stay to the right
• Watch and listen for others
• Pass slower traffic with care- give warning
• Trail speed limit is 15 mph
• When cycling wear a helmet
• Do not leave litter on trails
• Keep pets on a leash and pick up waste
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Contact Us:
Osceola Area Chamber and ​Main Street 
PO Box 251
Osceola, WI 54020

715-755-3300
Info@
myosceolachamber.org
We're Closer than You Think
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Visitor Links:
Polk County Information Center
Travel Wisconsin
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  • Discover
  • Experience
    • Local Attractions
    • Area Attractions
    • Shopping >
      • Coming Home
      • The Looking Glass
      • Wildwood Flowers
      • Red Bird Music Store
      • Studio A Salon and Spa
      • Uptown Gifts
      • Karita's Shoppe
      • Neumann Farms
      • Valley Spirits
      • Osceola Country Store
      • Dick's Fresh Market
      • Bill's Ace Hardware
      • The Granary Frame Shop
      • Watershed Cafe
      • Treasure Alley
      • Adoray’s Treasures from the Heart
      • Style Escape
      • Croixland Leather Works
    • Historic Downtown
    • Culture and Heritage
    • Map of the area
    • Remarkable Osceoleans
    • Directory >
      • Business Directory
  • Things to Do
    • Outdoor Adventures
    • Family Guide
    • Choo Choo Specials
    • Hiking Trails >
      • Trail Maps
    • Biking Trails
    • Birding
    • Fall Itineraries
    • Winter Itineraries
    • Farm to Table
    • Romantic Get-Aways
    • Wine, Cheese & Chocolate Tour
  • Places to Eat
    • Where the Locals Eat
  • Places to Stay
    • Lodging
    • Camping
  • Events
    • Rhubarb Fest
    • Music on Main St.
    • Osceola Harvest Bazaar
    • Valley Brew Fest
    • Doe on the Go
    • Wheels and Wings
    • Light Up Osceola
    • Celebrate Osceola
  • Contact Us