Entertainment & Activities
FAWN-DOE-ROSA Wildlife Educational Park
2131 US-8I-Franconia Sculpture Park
29836 St Croix Trail NIt’s free!
If you can’t make a seasonal event, still drop by for locally made and Wisconsin favorite novelties. The Glenna family will even be happy to give you a tour.
Glenna Farms
1333 120th StIf you can’t make a seasonal event, still drop by for locally made and Wisconsin favorite novelties. The Glenna family will even be happy to give you a tour.
Krooked Kreek Golf Course
2448 75th AveOnly 5 minutes away!
Neumann Farms
2277 40th AvenueEnjoy the countryside (especially in autumn) and learn about the area’s history.
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Osceola & St. Croix Valley Railway
114 Depot RdEnjoy the countryside (especially in autumn) and learn about the area’s history.
Osceola Lanes
104 N Cascade StGood ol' fashioned bowling
Osceola State Fish Hatchery
2517 River StCall ahead! Open on Saturday and Sundays.
Pleasant Valley Orchard
17325 Pleasant Valley RdPick your own strawberries and apples
Featured in Discover Wisconsin!
Also the only canoe and kayak rental in the area that will be waiting for you on the beach as you finish paddling. Top notch service!
Riverwood Canoe & Kayak Rental
254 S Cascade StFeatured in Discover Wisconsin!
Also the only canoe and kayak rental in the area that will be waiting for you on the beach as you finish paddling. Top notch service!
St Croix Artbarn
1040 Oak Ridge DrPuts on fantastic shows!
St. Croix Falls Cinema
2179 U.S. 8St, Croix Falls Mini Golf & Go-Karts
1971 US-8St. Croix Valley Hobby Farm LLC
Skiing, snowboarding, tubing, and zip lining—open year round!
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Trollhaugen Outdoor Recreation Area
2232 100th AveSkiing, snowboarding, tubing, and zip lining—open year round!
Imithi Yamanzi
37200 Wild Mountain RdParks & Nature
Check out our FB page where we feature videos of various hiking trails!
The Copper Mine Trail
1124 County Road SThis side of Interstate Park is best for rock climbing, hiking, & discovering glacial potholes.
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Interstate State Park
307 Milltown RdThis side of Interstate Park is best for rock climbing, hiking, & discovering glacial potholes.
Mill Pond Park
202 1st Aveeasy trout fishing
Many village events are hosted here.
Oakey Park
6th AvenueOnly a block away! If the Braves are playing in town, head over to watch our city league.
Osceola Bedrock Glades State Natural Area
County Road SOsceola Landing
Easy boat access and vast picnicking area
Handicap accessible park on OMC grounds—especially great for little tikes who aren’t ready to explore regular playgrounds on their own.
Osceola Medical Center
2600 65th AveHandicap accessible park on OMC grounds—especially great for little tikes who aren’t ready to explore regular playgrounds on their own.
While not as popular as Cascade Falls, but perhaps more rewarding, Buttermilk Falls is tucked away on Buffalo Skull Tract.
Standing Cedars State Natural Area
215 280th StreetWhile not as popular as Cascade Falls, but perhaps more rewarding, Buttermilk Falls is tucked away on Buffalo Skull Tract.
Includes my favorite swimming beach along with hiking, climbing, and excellent views of the St. Croix Riverway
Fun Fact: This is Wisconsin’s oldest state park, but is still newer than our home.
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Wisconsin Interstate State Park
1275 WI-35Includes my favorite swimming beach along with hiking, climbing, and excellent views of the St. Croix Riverway
Fun Fact: This is Wisconsin’s oldest state park, but is still newer than our home.
Wilke Glen neCascade Falls
101 N Cascade StWe have a waterfall in our downtown!
Ipharki yaseWillow River
1034 Co Hwy AShopping
Run by volunteers & supports hospice care.
Bring cash for small purchases.
Adoray's Treasures From The Heart
120 N Cascade StRun by volunteers & supports hospice care.
Bring cash for small purchases.
The Chocolate Gnome
201 3rd AveComing Home
206 N Cascade StMost items sold are from local vendors. This is what Osceola is all about.
Croixland Leather Works
208 2nd AveThe best milk you’ll ever taste. Period. You can also tour the facility to see how such deliciousness gets inside their glass bottles.
Crystal Ball Farms Organic
527 WI-35The best milk you’ll ever taste. Period. You can also tour the facility to see how such deliciousness gets inside their glass bottles.
Friendly and energetic staff; you’ll feel like family as soon as you walk in. Not to mention their product quality is bar none.
Just Ducky® Soap
Friendly and energetic staff; you’ll feel like family as soon as you walk in. Not to mention their product quality is bar none.
The Looking Glass
117 N Cascade StAntiques AND ice cream
Open on Saturdays when the weather is nice (Mayish-Octoberish). You never know what you’ll find!
Pea Pickin Flea Market
1977 U.S. 8Open on Saturdays when the weather is nice (Mayish-Octoberish). You never know what you’ll find!
Treat for you: Pie
Treat for the kids: Free petting zoo
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Pure-n-Simple Farm House Foods
867 US-8Treat for you: Pie
Treat for the kids: Free petting zoo
R M Tack & Apparel
1671 Co Rd ISupport a local ranch and get all your Western wear and gear here!
Warm, welcoming owners with a beautiful gift shop, seasonal activities, & free year-round maple syrup tastings. No one does flavor infused maple syrups better than the Slattengrens!
Slattengren Farms
28776 Saint Croix Trail NorthWarm, welcoming owners with a beautiful gift shop, seasonal activities, & free year-round maple syrup tastings. No one does flavor infused maple syrups better than the Slattengrens!
Style Escape LLC
207 N Cascade StI don’t think there’s any better service downtown than here.
The Staple
102 2nd AveNamed as a nod to the past, The Staple offers gifts, printing, and customization.
Treasure Alley
116 N Cascade StLives up to it’s name. Only open on occasion
The Wild Violette
Florist & boutique
Food scene
All recommendations are locally owned businesses.
Large seating area
Try my personal favorite, the Iced Overlook
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3 Arrows Coffee Company
510 S Vincent StLarge seating area
Try my personal favorite, the Iced Overlook
Be Wild Burgers
Limited hours, unlimited flavor
Cascade Nutrition
201 N Cascade StDalles Restaurant & Lounge
720 S Vincent StTrue Wisconsin supper club vibe
Good ol fashioned burger and shake joint… with mini golf if you wish!
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The Drive In Restaurant
572 Bench StGood ol fashioned burger and shake joint… with mini golf if you wish!
Fiesta Loca
967 WI-35Kennedy's Cafe
260 Main StOur favorite dive when we’re okay with a little extra driving
Lucky Panda
Our Place Cafe
Strictly breakfast and lunch
Poco Loco Mexican Grill
2109 US-8Chipotle’s doppelgänger
Silverbrook Coffee
Drive thru only
Sir Smoke A Lot's BBQ Barn
510 US-8Sometimes sells out, so eat early if you can.
Stella's On 97
7050 Scandia Trail NDate night favorite
Tippy Canoes
1020 N Cascade StVillage Pizzeria of Dresser
101 WI-35Huge portions and extensive menu
Local fare with out-of-this-world deliciousness
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The Watershed Cafe
99 N Cascade StLocal fare with out-of-this-world deliciousness
Za Za's Brickfire
Drinks & Nightlife
Cascade Bar & Grill
Local tip: serves breakfast on the weekends
Chateau St Croix Winery
1998 WI-87Dancing Dragonfly Winery
2013 120th AveDeer Lake Winery
1721 U.S. 8They have the best cheese curds and mini donuts around plus a military discount.
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Loggers Bar & Grill
2071 Glacier DrThey have the best cheese curds and mini donuts around plus a military discount.
There’s nothing more WI than eating bar food in “Little Lambeau.”
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Osceola Lanes
104 N Cascade StThere’s nothing more WI than eating bar food in “Little Lambeau.”
Rustic Roots Winery
20168 St Croix Trail NFantastic burgers and patio has a great view of Cascade Falls
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P Y's Bar
109 N Cascade StFantastic burgers and patio has a great view of Cascade Falls
Winehaven Winery
10020 Deer Garden LnWoodhill Bar & Grill
2394 Wisconsin 35Essentials
Bill's Ace Hardware
202 Chieftain StClosest place to get your specialty coffee...and liquor. Plus, check out the cheese section if you want Wisconsin cheese without traveling to Grantsburg to get it.
Dick's Fresh Market
112 Chieftain StClosest place to get your specialty coffee...and liquor. Plus, check out the cheese section if you want Wisconsin cheese without traveling to Grantsburg to get it.
Osceola Cleaners
201 2nd AvenueOffers cleaning, alterations, and mending with a quick turnaround time.
Studio A Salon Spa
213 1st AveStop in for a quick tanning session, hair style, or to pet Hank, the town’s favorite dog.
Total Image
206 2nd AveStop in for a quick tanning session, hair style, or to pet Hank, the town’s favorite dog.
Valley Spirits
209 Chieftain StValley Spirits
209 Chieftain StOffers same day laundry service, DIY laundry, and car wash & vacuums
Wild River Fitness
2630 65th AveAmacebiso ngesixeko
Amasiko nenkcubeko
Shop on the Weekends
For some touristy businesses, Monday is a Sabbath. Get your downtown shopping done Thursday-Sunday.
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Farmers Market
Farmers Market is 2-6pm at Millpond Park every Friday 2-6pm June-October. Bring cash!
Ukuhamba-hamba
Walk
If you’re able, discover Osceola by walking. There’s so many hidden scenic gems around town that are only accessible by walking.
Ungaphoswa
Butterfly Lane in August
Many butterfly friendly plants are planted along Chieftain Street between 3rd Ave and Mill Pond Park. Enjoy the simple yet enchanting “Butterfly Lane” in August when the plants are in full bloom and the butterflies are in full flight.
Amasiko nenkcubeko
Music on Main Street
Saturdays 2-5pm June-Oct enjoy live music at the Parklet on Cascade and 2nd Ave downtown
Ukuhamba-hamba
Limited Ride Services
Uber, Lyft, & taxis are not readily available in our area. We are happy to personally help get you around if needed. Woodhill Bar & Grill also gives sober rides to customers.