Osceola Area Chamber & MainStreet Program
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Hiking

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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. ​


A- Cascade Falls Trail

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 No trail in the Village has as important role in the history of Osceola as the Cascade Falls Trail.  At the top of the deck by Chief Osceola right downtown, head down the steps (all 135 of them!) to reach the breathtaking Cascade Falls. In summer, bring a picnic lunch and enjoy the misty glen while you get up close and dip your toes into the cool water. Then, continue along the stream, across the boardwalks to the St. Croix River. At dusk, the Falls become illuminated with changing colored lighting.  In summer, you'll find fireflies and in winter, the glen becomes a magical place with ice sculptures and glistening waters.
Location: 100 Cascade St. @ the Falls Deck  Osceola, WI

Distance: .3 miles
Level of Difficulty: Vigorous (135 steps)
​


*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

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B- Eagle Bluff Trail

 At the end of the Cascade Falls Trail where you reach the river's edge follow the path south under the Hwy 243 bridge.  Hike or snowshow up the rustic path along switchbacks on the bluff to the top of Eagle Bluff.  Panoramic views of the River Valley from an eagle’s vantage point. 
Location: Trailhead behind Cascade BP 97 Cascade N. Osceola, WI

Distance:  .25 mile
Difficulty Level: Vigorous & Rustic
​
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​C- Simenstad Trail

From behind Cascade BP, head towards 243 along the grass.  The ruins of the Geiger Brewery will be on your right.  Climb the steps to the trail base to find the story of the Picnic Bluff.  Follow the trail as Simenstad Trail loops around the top of Eagle Bluff. Hike or snowshoe this trail, where you can enjoy spectacular panoramic views of the St. Croix River Valley.  A camera is a must!
​Location: Trailhead behind Cascade BP 97 Cascade N. Osceola, WI

Distance: .5 mile
Level of Difficulty: Uplifting
​
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D- HIstoric Village Walk​

Start at the historic RR depot, then stroll north on Cascade St., stopping to take in the architecture of the buildings, each holding the memories of Osceola’s history- from a busy logging town to an industrious steamboat hub to a pastoral farming community. Follow River Street, 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: 1 mile
Level of Difficulty: Easy
​
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Brookside Trail

Behind the St. Croix Art Barn find the trail and bridge to cross Brook Trout stream. When you come to Schillberg Park, take a right and follow the loop through wooded areas, streams and old campgrounds. Cross the wooden covered bridge to find the gurgling Brook Trout stream-a soothing and refreshing loop.
Location: 1040 Oak Ridge Drive, Osceola, WI

Distance: .5 miles
Difficulty level: Easy
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Ridgeview Trail-
​Osceola Loop

Hike through wooded areas, crossing streams and winding down toward the St. Croix River.  Excellent wildlife and bird viewing, as well as flora and fauna exploration opportunities.
Location: 94 County Road S Osceola, WI
Distance: 2 miles
Level of Difficulty: Easy to Moderate ​
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Ridgeview Trail- 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.
​
Location: 94 County Road S Osceola, WI
Distance: 1 mile
Level of Difficulty: Easy to Moderate
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Jeff Meyer Public Fitness Trail

This 8’ wide paved loop provides enough room for leisurely strolls, fast-paced walks and jogging.  The 6 exercise stations provide  additional fitness opportunities and is handicap accessible.
​Location: 2600 65th Ave. Osceola, WI

Distance: .5 miles
Level of Difficulty: Easy
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Standing Cedars - Tewksbury Trail

Hike or snowshoe through a wooded area to find spectacular views of the St. Croix River. The trail continues through prairie areas and historic limestone quarries. Excellent photography, birding and wildlife viewing area.
Location:643 Ridge Road Osceola, WI

Distance: 1.25 miles
Difficulty Level: Easy to Moderate
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Standing Cedars-
​Englewood Trail

​Choose from 3 separate routes to hike or cross-country ski on groomed trails through prairie and wooded areas.  Beautiful wildlife viewing and birding areas.
Location:213 280th St Osceola, WI

Distance: Varies from .7 miles to 3 miles
Difficulty Level: Easy to Moderate
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Regional trails

Other trails for playing outdoors  are 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

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

 

​
Contact Us:
Osceola Area Chamber and Main Street
PO Box 251
Osceola, WI 54020

715-755-3300

Info@myosceolachamber.org
Thank you to our 2021
​Community Champion Partners​

Copyright © 2017 Site Designed and Built by SCVL​
  • Home
  • Business Directory
    • Business by Category
  • Membership
    • Top 10 Reasons to Join
    • Why Belong
    • About Us >
      • Purpose
      • Board of Directors
      • Community Champions
      • Community Champion Investment
      • Advisory Council
      • Ambassador Program >
        • Customer Service Award Nomination
      • Grow Osceola
    • Join
    • Market Your Business
    • Membership FAQs
  • Volunteer
  • News/Events
    • Music on Main St.
    • Osceola Harvest Bazaar
    • Love Your Local
    • Doe on the Go
    • Picnics to Go
    • Osceola Town Calendar
    • Osceola Spring Fling
    • Celebrate Osceola
    • Light Up Osceola
    • Chamber Activities Calendar
    • Ribbon Cuttings
    • Osceola Doc Walks
    • Bird City Celebration
    • E-Newsletter Signup & Archives
  • Visit Osceola
    • Local Attractions
    • Area Attractions
    • Shopping >
      • Shop Small
      • The Looking Glass
      • Wildwood Flowers
      • Studio A Salon and Spa
      • Uptown Gift Boutique
      • Croixland Leather Works
      • Karita's Shoppe
      • Neumann Farms
      • Red Bird Music Store
      • Valley Spirits
      • Osceola Country Store
      • Dick's Fresh Market
      • Bill's Ace Hardware
      • Watershed Cafe
      • Adoray’s Treasures from the Heart
      • Coming Home
      • Style Escape
    • Dining >
      • Lucky Panda
      • Caribou
      • PY's Saloon & Grill
      • Dick's Fresh Market 2
    • Lodging
    • Things to Do >
      • Fall Itineraries
      • Winter Itineraries
      • Family Guide
      • Outdoor Adventures
      • Trails >
        • Hiking
        • Biking
        • Birding
        • Rivertown Trails Coalition
        • Walkable Community
      • Farm to Table
      • Romantic Get-Aways
      • Wine, Cheese & Chocolate Tour
    • Historic Downtown
    • Culture and Heritage
    • Map of the area
    • Remarkable Osceoleans
  • Main Street Community
    • Luminate Downtown Donation
  • Business in Osceola
    • Osceola Overview
    • Relocate Your Business
    • Area Schools
  • New Business/Entrepreneur Toolkit
    • Business ToolKit Table of Contents
    • Utilities Quick Ref Guide
    • ToolKit 1. Self-Assessment
    • ToolKit 2. Do The Market Research
    • ToolKit 3. Consult Experts
    • ToolKit 4. Plan
    • ToolKit 5. Do The Paperwork
    • ToolKit 6. Launch
    • ToolKit 7. Continue Learning
    • ToolKit 8. Enjoy The Challenge
  • Blog
  • Contact Us
    • Volunteer Sign-up
  • Annual Report 2019
  • Postcard
  • Osceola Strong
    • Osceola to GO-Restaurants
    • Osceola to Go-Other Businesses
    • Osceola Strong Donation
    • Tips for Retailers
  • Market & Economic Info
  • 2021 Legilstive Day
  • Memorials