25 Best & Fun Things to Do in Osceola WI

Osceola, Wisconsin, is a charming small town nestled along the St. Croix River. With its beautiful landscapes and friendly atmosphere, it’s a perfect spot for a fun getaway. From outdoor adventures to unique local shops, there’s something for everyone to enjoy. Whether you are looking for a place to relax or some exciting activities, Osceola has it all.

In this guide, we will be highlighting the top things to do in Osceola. From hiking scenic trails to visiting quaint cafes, you will find plenty of options to make your visit memorable. Let’s get started on all the fun waiting for you in this lovely town!

Things to Do in Osceola WI

1. Visit Cascade Falls

Cascade Falls is a stunning natural landmark located right within Osceola. Standing at 25 feet tall, it showcases water cascading over rocky terrain. This picturesque spot provides a serene escape for visitors looking to relax and take in the beauty of nature.

You can enjoy a peaceful walk along the trails surrounding the falls. The area is well-maintained and offers benches where you can sit and enjoy the scenery. Many visitors come to take photographs, capturing the beauty of the falls in every season.

In the warmer months, you might spot various wildlife, including birds and perhaps a deer. The sound of the flowing water creates a calming atmosphere, making it a perfect spot for meditation or reflection. You can even set up a picnic to enjoy with friends and family.

During the winter, the falls can freeze into spectacular formations, adding a magical touch to the landscape. No matter when you visit, Cascade Falls is a highlight of the Osceola experience.

Be sure to bring your camera and enjoy this natural gem. It’s a local favorite for good reason.

Address: 220 Cascade Avenue, Osceola, WI 54020.

2. Explore Historic Downtown Osceola

Historic Downtown Osceola is a charming area that invites you to explore its unique shops and cafes. The streets are lined with beautiful buildings that showcase local architecture and history. Strolling through downtown feels like stepping back in time.

As you walk, stop by local boutiques and artisan shops that offer one-of-a-kind items. You’ll find everything from handcrafted jewelry to vintage apparel. This makes it an excellent spot for gift shopping or treating yourself to something special.

Additionally, don’t miss out on the cozy cafes and restaurants. Enjoy a cup of coffee or a delicious meal made with local ingredients. Many establishments offer outdoor seating for a pleasant dining experience while soaking in the ambiance.

Throughout the year, the downtown area also hosts community events. Keep an eye out for farmers’ markets, art fairs, and seasonal celebrations that bring locals and visitors together.

Overall, Historic Downtown Osceola provides a delightful blend of shopping, dining, and history, making it a must-visit during your stay.

Address: 100 N. Cascade Ave, Osceola, WI 54020.

3. Take a Ride on the Osceola & St. Croix Valley Railway

Step aboard the Osceola & St. Croix Valley Railway for a delightful journey through the scenic St. Croix Valley. This vintage train ride offers passengers a unique experience, allowing you to see the countryside from a different perspective.

The train travels along beautiful routes, showcasing landscapes that change with the seasons. As you ride, enjoy the lovely sights of lush forests, open fields, and flowing rivers. The relaxing sound of the train’s wheels against the tracks adds to the charm of the experience.

In addition to its regular schedule, the railway often hosts special themed rides. These events include excursions like a wine and cheese train or holiday specials that make for a memorable outing with friends or family.

Friendly and knowledgeable conductors provide commentary, sharing interesting facts about the area’s history. This makes the train ride both fun and educational for all ages.

A visit to the Osceola & St. Croix Valley Railway is not just a trip; it’s a step back in time filled with scenic beauty and fun.

Address: 114 N. Washington St, Osceola, WI 54020.

4. Enjoy St. Croix National Scenic Riverway

The St. Croix National Scenic Riverway is a stunning stretch of water that offers countless opportunities for outdoor adventure. Here, you can paddle along the river in a kayak or canoe, soaking in the natural beauty all around you. The river is known for its crystal-clear waters and picturesque views.

For those who prefer fishing, this riverway is a prime location. Cast your line and try your luck attracting various fish species. Several fishing spots are easily accessible, making it a popular choice for anglers.

If you love hiking, explore the trails that wind through lush forests lining the river. These trails vary in difficulty, so you can choose a hike that fits your level. Don’t forget your camera, as the vistas along the way are breathtaking.

Seasonal activities abound, including picnicking and birdwatching. Many birds inhabit the area, making it a haven for bird enthusiasts. You might even catch a glimpse of a bald eagle soaring overhead.

Visiting the St. Croix National Scenic Riverway is a wonderful way to connect with nature and enjoy the outdoors in Osceola.

Address: 401 S. Washington St, St. Croix Falls, WI 54024.

5. Hike at Standing Cedars State Natural Area

Standing Cedars State Natural Area is a hidden gem just outside Osceola. This protected area features diverse landscapes, including forests, wetlands, and wildlife. Hiking through its trails allows you to experience the beauty of nature up close.

The trails vary in length and difficulty, making it accessible for all hiking levels. As you walk, the towering cedar trees provide shade and create a peaceful atmosphere. The diverse terrain is home to many bird species and other wildlife.

Keep an eye out for interesting plants and flowers along the trails. Many sections of the area are serene and quiet, making it perfect for meditation and relaxation.

The natural area is also ideal for photography enthusiasts. Capture the beauty of the landscapes and the vibrant colors of the changing seasons.

Visiting Standing Cedars is a great way to escape the hustle and bustle. It invites you to reconnect with nature in a tranquil environment.

Address: 2328 Cedar Dr, Osceola, WI 54020.

6. Relax at Millpond Park

Millpond Park is a lovely place to unwind and enjoy the beauty of Osceola. This peaceful park features walking trails and lush greenery surrounding a tranquil pond. It’s an ideal spot for a leisurely stroll or to find a cozy place to read.

The park is well-maintained, with benches scattered along the trails. Take a seat and watch the ducks swim or enjoy the change of seasons. You can often see families having picnics, adding to the park’s welcoming atmosphere.

If you’re seeking an active day, you can bring your bike or rollerblades and make use of the paved paths. The park’s layout makes it easy to explore and enjoy the scenery.

For those looking to socialize, Millpond Park regularly hosts community events, including concerts and movie nights in the summer. These events create a lively and inviting environment for families and friends.

A day at Millpond Park is a perfect way to relax and soak in the natural beauty that Osceola has to offer.

Address: 300 Millpond Rd, Osceola, WI 54020.

7. Have Fun at Troll Haugen Ski Resort

If you’re looking for winter excitement, head to Troll Haugen Ski Resort. This resort offers a variety of winter sports, including skiing and snowboarding. With well-groomed slopes and trails, it’s great for all skill levels.

The resort features ski lessons for beginners, making it accessible for those wanting to try something new. Experienced skiers will enjoy the challenging runs that require skill and confidence.

For those who prefer snowboarding, Troll Haugen has terrain parks with ramps and rails to challenge riders. Additionally, there are options for snow tubing, which is a fun activity for the whole family.

Visitors can warm up in the lodge and enjoy hot meals and drinks. The cozy atmosphere makes every trip to the slopes enjoyable. Don’t forget to check out rental equipment if you don’t have your own.

With its snowy hills and vibrant atmosphere, Troll Haugen Ski Resort is a must-visit for winter lovers in Osceola.

Address: 1935 County Rd. G, Dresser, WI 54009.

8. Discover Interstate Park

Interstate Park is a stunning destination located along the banks of the St. Croix River. This park is known for its breathtaking bluffs and picturesque views of the river gorge. Hiking through the park provides access to scenic overlooks and amazing photo opportunities.

The park features several trails that cater to different skill levels. It’s perfect for both casual walkers and experienced hikers seeking more challenging terrain. Don’t miss the chance to hike to the overlooks, where you can see the river winding between the towering cliffs.

Campsites are available for those interested in an overnight adventure. Sleeping under the stars adds to the park’s charm and peacefulness. Many campgrounds provide access to fire pits for cozy evening gatherings.

Additionally, the park is great for birdwatching, with various species making their homes in the area. Bring binoculars to enjoy the sights and sounds of nature up close.

A visit to Interstate Park offers both adventure and natural beauty, making it a must-see destination in Osceola.

Address: 30790 S. Hwy. 35, St. Croix Falls, WI 54024.

9. Hike the Falls Bluff Loop Trail

The Falls Bluff Loop Trail in Osceola offers a picturesque hiking experience. This scenic trail winds through the forested areas surrounding the bluffs, providing breathtaking views of the St. Croix River.

The trail is well-marked and features varying landscapes, including meadows and dense woods. Hikers can experience the beauty of nature in all forms, with opportunities for wildlife sightings along the path.

As you walk, take in the changing scenery with every step. The tranquil environment allows you to connect with nature and escape the hustle of daily life. Make sure to stop at the overlooks for stunning river vistas.

The loop is manageable for most hikers, making it an excellent choice for families or casual walkers. Pack a picnic to enjoy at one of the scenic spots along the trail.

Overall, the Falls Bluff Loop Trail is a wonderful outdoor experience that combines exercise with natural beauty.

Address: 1104 Morrow St, Osceola, WI 54020.

10. Visit the St. Croix Art Barn

The St. Croix Art Barn is a vibrant cultural hub in Osceola where art and community come together. This gallery features rotating exhibits that showcase local and regional artists’ work. When you visit, you’ll find a diverse range of styles and mediums on display.

Aside from exhibitions, the Art Barn hosts various events and workshops throughout the year. These events give guests a chance to engage creatively while learning new skills. Participating in a class can be a memorable experience, whether you’re an artist or simply curious.

The welcoming atmosphere makes it easy to enjoy art and creativity. Many visitors appreciate the opportunity to meet local artists and learn about their creative processes. It’s interesting to hear the stories behind the art on display.

Make sure to check out their schedule for special events, gallery openings, and more. Spending time at the Art Barn is not just an artistic experience; it also fosters community connections.

If you appreciate art and culture, the St. Croix Art Barn is a delightful stop in Osceola.

Address: 790 250th Ave, Osceola, WI 54020.

11. Visit the Osceola Public Library

The Osceola Public Library is a wonderful community resource that offers more than just books. This inviting space promotes literacy and learning, providing a variety of programs for all ages. Whether you are a child, student, or adult, there’s something for everyone.

Inside, you’ll find a cozy atmosphere perfect for reading or studying. The library hosts regular events, including storytime for young children, book clubs, and informational sessions for residents. These programs help foster a love of reading and community engagement.

The library also provides free access to computers and other resources. Patrons can use the internet for research or personal projects. Additionally, many local events and workshops happen at the library, making it a lively community hub.

If you’re looking for a quiet place to unwind, the Osceola Public Library is an excellent choice. It encourages visitors to explore new ideas and connect with others.

Overall, a visit to the library adds to the rich experience of Osceola.

Address: 106 N. Smith St, Osceola, WI 54020.

12. Attend the Valley Brew Fest

The Valley Brew Fest is a highlight for craft beer lovers in Osceola. This exciting event gathers local breweries to showcase their finest brews and craft beers. Attending the festival is a fun way to explore different flavors and styles of beer.

At the festival, you can sample numerous beers while chatting with brewers about their craft. A communal atmosphere fosters conversation and enjoyment, making it a perfect outing with friends.

In addition to beer tastings, the Brew Fest often features live music. Enjoying great tunes while sipping your favorite local brews creates a lively yet relaxed vibe. Food vendors are also on-site, offering delicious local fare to complement the drinks.

This annual event showcases the best of local brewing culture, and it’s an excellent opportunity to discover new favorites. It’s essential to check the festival dates ahead of time as it’s a popular event that draws many visitors.

Overall, the Valley Brew Fest is a celebration of good beer and community in Osceola.

Address: 200 Osceola St, Osceola, WI 54020.

13. Experience the Osceola Community Fair

The Osceola Community Fair is a beloved annual tradition that brings the community together for fun and festivities. This event is a vibrant celebration of local agriculture, crafts, and culture. Here, you’ll find rides, games, and various activities for all ages.

Visitors can wander through exhibits showcasing local produce, livestock, and handmade crafts. It’s a great way to see what the community has to offer and support local artisans and farmers. Children especially enjoy the carnival rides and games, making it a family-friendly event.

Delicious fair food is always a highlight, with options ranging from classic funnel cakes to barbecued delights. You can enjoy live entertainment throughout the event, featuring local musicians and performers.

The atmosphere is lively and welcoming, encouraging community connections and fun. It’s not just a fair; it’s a treasured experience filled with laughter, smiles, and joy.

Attending the Osceola Community Fair is an enriching experience that captures the spirit of the town.

Address: 201 N. 2nd St, Osceola, WI 54020.

14. Enjoy Osceola Village Park

Osceola Village Park is a lovely recreational area perfect for families and outdoor enthusiasts alike. With playgrounds, sports fields, and picnic areas, there’s something for everyone to enjoy. The park is a great place to spend a warm day with friends or family.

Kids love the playground equipment, which is safe and well-maintained. You can enjoy various outdoor games, including basketball or frisbee on the fields. The splash pad area is also a popular choice in the summer, providing hours of fun in the water.

Pavilions are available for rent, making it an excellent choice for birthday parties and family gatherings. It’s a fantastic way to bring together loved ones in a beautiful setting.

Additionally, the park is often the site of community events and gatherings. From seasonal festivals to summer concerts, there’s always something happening at Osceola Village Park.

A visit to this park offers relaxation, recreation, and community spirit, making it a highlight of Osceola.

Address: 134 N. 3rd St, Osceola, WI 54020.

15. Try Fishing in the St. Croix River

The St. Croix River is a popular spot for fishing enthusiasts. It offers diverse fish species, making it a great location for anglers of all skill levels. You can cast your line and try to catch bass, northern pike, and more in its inviting waters.

The river’s scenic beauty provides a lovely backdrop for your fishing adventure. There are several public fishing spots where you can set up your gear and enjoy a day by the water. Many anglers find that the peaceful environment enhances their fishing experience.

Even if you’re new to fishing, local outfitters can provide rentals and advice. They are happy to help you find the best locations and techniques to increase your chances of a good catch. Pack a lunch and make a day of it, soaking in the sun and enjoying the natural surroundings.

Fishing on the St. Croix River is not just about the sport; it’s a chance to unwind and connect with nature. Whether you’re a seasoned angler or trying it for the first time, the experience is always memorable.

Address: Riverside Ave, Osceola, WI 54020.

16. Dine at The Watershed Cafe

The Watershed Cafe is a must-visit dining spot in Osceola, known for its delicious American cuisine. With a warm and inviting atmosphere, it’s a perfect place for a casual meal or a cozy dinner with friends.

The menu features a variety of options, including fresh salads, hearty sandwiches, and mouthwatering entrees. They use locally sourced ingredients when possible, ensuring that your meal is not only tasty but also supports local farmers.

Breakfast is served all day, featuring delicious options such as pancakes and omelets. Try their signature dishes, which are popular among regulars and newcomers alike.

The cafe also has a selection of desserts and coffee, making it a great place to relax and enjoy a sweet treat. Friendly staff and excellent service contribute to a memorable dining experience.

Whether you’re stopping by for breakfast, lunch, or dinner, The Watershed Cafe is a delightful culinary gem in Osceola.

Address: 104 N. Washington St, Osceola, WI 54020.

17. Feast at Lucky Panda Buffet

For those craving Asian cuisine, Lucky Panda Buffet is a fantastic dining option in Osceola. This buffet-style restaurant offers a wide variety of delicious Chinese and Asian dishes, and the atmosphere is welcoming and colorful.

With numerous food options, there’s something for everyone at the buffet. You can load your plate with favorites like sweet and sour chicken, fried rice, and sushi. Many patrons appreciate the freshness of the dishes and the variety available for each meal.

Additionally, Lucky Panda Buffet is an excellent spot for families, providing a casual dining experience where you can enjoy a spread of different flavors. The kids will love the chance to try new dishes or stick to the familiar favorites.

The restaurant also frequently updates its offerings, ensuring you can discover new favorites with each visit. Be sure to save room for dessert; their selection is a delightful ending to your meal.

Overall, dining at Lucky Panda Buffet is a satisfying experience that leaves you wanting to return.

Address: 2050 10th Ave, Osceola, WI 54020.

18. Chill at Tippy Canoes Sports Pub & Grub

Tippy Canoes Sports Pub & Grub is a casual neighborhood spot that is perfect for unwinding after a long day. Known for its laid-back atmosphere, it’s a great place to grab a drink and enjoy a meal.

The menu features a variety of classic pub fare, including burgers, wings, and shareable appetizers. Visitors love the friendly service and the variety of drinks available, including local beers on tap.

What makes Tippy Canoes special is its community vibe. Often busy with locals, it’s a place where you can catch a game on TV or socialize with friends. There’s also live entertainment on select nights, creating a fun and lively atmosphere.

On beautiful days, take advantage of outdoor seating to enjoy your meal in the fresh air. Whether you’re stopping for lunch, happy hour, or dinner, Tippy Canoes is ready to welcome you.

It’s the perfect spot to relax, chat, and enjoy good food with great company.

Address: 109 N. 2nd St, Osceola, WI 54020.

19. Visit Local Art Exhibits

Osceola is home to various local art exhibits that showcase regional talent and creativity. Exploring these exhibits is a great way to connect with the community and appreciate the artistic expressions of local artists.

The exhibits often rotate, meaning there’s always something new to see. Visit galleries, community centers, and even local businesses that display artwork throughout the year. Each venue offers a unique perspective, adding to the vibrancy of the local art scene.

Art enthusiasts can enjoy a vast array of mediums, from paintings to sculptures and photography. Participation in local art events may present opportunities to meet artists and learn about their creative processes.

Engaging with the art community enriches your visit, encouraging conversations and interactions. Events often include openings, workshops, and art fairs, allowing you to dive deeper into Osceola’s cultural offerings.

Overall, visiting local art exhibits is a rewarding experience, allowing you to appreciate the creativity and talent thriving in Osceola.

Address: Various locations throughout Osceola, WI 54020.

20. Relax at Osceola Mill Pond

The Osceola Mill Pond is a tranquil area perfect for relaxation and enjoying the outdoors. This lovely spot features walking trails around the water, making it ideal for a scenic stroll or a leisurely bike ride.

As you walk along the shore, take in the beautiful views of the pond and surrounding natural areas. It’s common to see wildlife such as ducks and geese, adding charm to the experience.

Many people come to enjoy quiet moments, whether it’s reading a book on a bench or simply taking in the sounds of nature. The peaceful environment encourages relaxation and reflection.

If you’re looking for an active outing, bring a fishing pole, as the pond offers some fishing opportunities. Make sure to check local regulations before casting your line.

The Osceola Mill Pond is a serene escape from the busyness of life, providing a peaceful spot to unwind and connect with nature.

Address: 345 Mill Pond Rd, Osceola, WI 54020.

21. Bike on Local Trails

Osceola boasts many local trails perfect for biking enthusiasts. Whether you’re a casual rider or a more advanced cyclist, the trails provide stunning scenery and varying terrains.

Pack your bike and explore the paths winding through forests, along the river, and through the picturesque countryside. Each ride offers a different experience and a chance to see the area from a new perspective.

The trails are well-marked and maintained, ensuring a safe and enjoyable ride. You’ll find paths suited for families as well as more challenging options for seasoned riders. Don’t forget to check your bike before hitting the trail!

During your ride, you might spot local wildlife or enjoy beautiful views of nature. It’s a rewarding way to exercise while enjoying Osceola’s outdoor spaces.

Overall, biking on local trails is a fantastic way to get outdoor activity and explore the beauty of Osceola.

Address: Trail access points throughout Osceola, WI 54020.

22. Explore Nearby Taylors Falls

A short trip from Osceola leads you to Taylors Falls, a delightful destination with stunning natural beauty. Known for its scenic river views and dramatic cliffs, it’s a perfect day trip for outdoor enthusiasts.

Visit the Taylors Falls Scenic Area, where you can hike along various trails that provide breathtaking views of the St. Croix River. The trails are well-marked and cater to different skill levels, making it accessible for everyone.

During your hike, take a moment to visit the iconic Dalles, a unique rock formation shaped by the river. The area is rich in geological history, and you can learn more about it as you explore.

For those who enjoy water activities, kayaking and canoeing opportunities are available. Paddling along the river allows you to see the natural beauty from a different perspective.

Overall, Taylors Falls is a charming destination that complements your visit to Osceola with its scenic beauty and outdoor adventures.

Address: 312 P. St. Croix Ln, Taylors Falls, MN 55084.

23. Kayak on the Kinnickinnic River

The Kinnickinnic River is a fantastic place for kayaking, providing a beautiful and peaceful setting for paddlers. Whether you’re a beginner or an experienced kayaker, this river offers a rewarding experience.

Launch your kayak at convenient access points along the river and enjoy the gentle currents as you paddle downstream. The calm waters allow you to relax and soak in the stunning scenery along the banks.

As you paddle, keep an eye out for wildlife. The surrounding areas host various birds and animals, making it an exciting outing for nature lovers. You’ll often see herons, eagles, and even river otters as you glide along.

For those looking to extend their adventure, consider a guided tour. Local outfitters offer guided trips, which provide insights about the river ecosystem, history, and local wildlife.

Paddling on the Kinnickinnic River is a refreshing and invigorating way to explore the natural beauty of the area.

Address: 377 River St, River Falls, WI 54022.

24. Visit the Osceola Historical Society Museum

The Osceola Historical Society Museum offers a glimpse into the rich history of the area. This museum showcases artifacts, photographs, and exhibits that tell the story of Osceola and its people over the years.

Visitors can explore fascinating displays that highlight the town’s development, including early settlers’ lives, local industries, and significant events. The museum provides insights into the community’s heritage, making it a valuable educational experience.

Friendly and knowledgeable staff are on hand to answer questions and share stories about the exhibits. You’ll leave with a greater appreciation for the town’s history and culture.

Special events and programs are held at the museum throughout the year, including guest lectures and community gatherings. These events enhance community involvement and engagement.

A visit to the Osceola Historical Society Museum is an enriching experience that connects you to the past while celebrating the future.

Address: 105 N. 3rd St, Osceola, WI 54020.

25. Attend Local Events

Osceola hosts a variety of local events throughout the year, showcasing the town’s community spirit and vibrant culture. These gatherings offer a chance to connect with locals, enjoy activities, and experience what makes Osceola special.

Seasonal festivals feature arts and crafts, local foods, and live performances. You can enjoy mingling, supporting local vendors, and discovering unique handmade items.

Community events also promote various interests—whether it’s a fall harvest festival, winter holiday celebration, or summer farmers’ market. Families love participating in fun and interactive activities that cater to people of all ages.

These events often highlight Osceola’s local talent, featuring musicians, artists, and performers. You might find live entertainment enriching your experience, making each visit memorable.

Overall, attending local events is a great way to engage with the community and enjoy the vibrant culture of Osceola.

Address: Various locations in Osceola, WI 54020.

Final Thoughts

Osceola, Wisconsin, is a charming destination filled with exciting activities and attractions. Whether you’re enjoying nature at the state parks, exploring local dining options, or learning about the town’s history, there’s something for everyone. If you’re looking for more places to visit in Wisconsin, we have you covered with a comprehensive list in this article and information about the best small towns in Wisconsin can be found here.

From outdoor adventures in scenic landscapes to engaging community events, Osceola offers a little bit of everything. As you explore the area, you’ll find friendly faces and a welcoming atmosphere, making it a great place to visit or call home.

As your journey comes to an end, the memories of the stunning vistas, delightful dining, and community spirit will surely draw you back to Osceola. Come and experience the beauty and warmth of this wonderful town!