Osceola, WI

Osceola, WI

“Wisconsin’s Cool Little Rivertown”

Friday Favorites: February 12, 2021

Today I’m taking a walk back in time to share the historic and charming river town we used to call home.  Osceola, WI is situated on a bluff above the beautiful St. Croix River and features a quaint downtown, historic buildings and miles of scenic trails. 

Read on to learn about some of my favorite parts of Osceola!

Explore the Landscape and History

River Bluff Trails

Osceola has miles of trails, many of which take you along the banks of the St. Croix River, past Geiger and Cascade Falls, and up along the river bluff.  Start your hike behind The Watershed Café, checking out the small bridge that crosses Osceola Creek and Geiger Falls. Head to the large statue of Chief Osceola then climb down the 135 steps to explore Cascade Falls.  Follow the stream and trail down to the shores of the St. Croix River, then if you’re feeling ambitious continue onto the Eagle Bluff Trail by following the rustic, switchback trail to reach the top of the bluff.  This will link to the Simenstad Trail, leading you back to downtown and taking you by the ruins of the Geiger Brewery.  For details on each trail, visit https://www.myosceolachamber.org/hiking.html

*Note: The 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.

This is also a comprehensive list of trails in the area: https://thestcroixvalley.com/dresser-osceola-hiking-trails/ 

Osceola’s Historic Village Walk

To explore the historic village start at the Railroad Depot and walk along main street, noticing 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.  Turn left on 3rd St. and notice the historic hotel-turned-apartments. Continue by the Methodist Church, turning right on River Street to see beautiful historic homes, views of the St. Croix River at the overlook, then loop back to downtown along Cascade St. 

Osceola & St. Croix Valley Railway

Ride the Rails at the Osceola Depot!  Although it’s still winter I’m already thinking about plans for the spring, and riding the historic train at the Osceola Depot is on my list.  There are two destinations for these day-trips:  Dresser, WI and Marine on St. Croix, MN (check out my guide to Marine on St. Croix here). The Dresser trip is a ten-mile round trip through Wisconsin farmland and the railroading town of Dresser.  The Marine on St. Croix trip is a 20-mile journey along the sandstone bluffs of the St. Croix River.

The Railway offers special trips during the season: leaf viewing and pumpkin rides in autumn, plus a dinner & pizza trip, brunch, or you can even charter your own!  The diesel-powered train features vintage cars and the historic depot has a great little gift shop. 


The train ride to Marine on St. Croix passes a historic building that used to house the famous Bethania Mineral Springs Bottling Works. Learn more about the fascinating history of Bethania Springs of Osceola here.

Shop the Downtown on Cascade Street

Sleepy Thicket

This super sweet children’s boutique opened last year and offers books, clothing, educational activities, and toys for children of a variety of ages, plus a selection of gear and clothing for parents.  Not only are the range of products well-curated, the look and feel of Sleepy Thicket is so charming. From their website: “Brett’s crazy entrepreneurial heart and Nicole’s passion for babies and all things pretty created this “Sleepy Thicket” where people could shop online in a tranquil setting for the little ones in their lives. Coming from sleep deprived parents we thought the name was quite fitting!” I could spend my whole paycheck here buying things for Wrenna.

The Looking Glass

Antiques, a historic building, and ice cream? Sign me up!  The Looking Glass features two levels of handmade items from local crafters, super cool vintage items, furniture, signs, clothing, and much, much more!  One could spend hours exploring rows of books, antiques, artwork, and even a pile of baseball mitts that seems to grow each time I visit!  The Looking Glass can also satisfy your sweet tooth with their ice cream counter; grab a cone and sit in the front shop window or outside (weather-permitting, of course).  The owner, Gwen, hosts a fun, live sale on Facebook each Wednesday, drawing hundreds of viewers, and I hear she’s currently working on installing a vintage tilt-a-whirl in the entrance!

The Staple

I’ve always been a sucker for stationery, boutiques, and great design. Throw in a historic building and bang, you’ve got The Staple!  This printing and design shop was formerly The Copy Shop and was located in St. Croix Falls. The owners, Tanya and Pete, wanted a space that better represented their design and retail efforts, so when this historic corner building in Osceola came available they jumped.  Spending weeks renovating and making the space (which was used as restaurants for the last many years) suitable for a design and print company, they recently opened their doors.  The Staple is chock full of local retail products, beautiful décor, and they even highlight the history of the building on one of their walls. They are also working on a micro-venue in the basement of the late-1800s building, which will include a fireplace and caterer’s kitchen!


The Staple named their business after CH Staples, one of the founding fathers of Osceola. CH built the first drug store in Osceola in 1870 at the site of The Staple. After the original building burned to the ground, his son CW built a stone store (the current Staple building) and stone residence (the Inn on the St. Croix on River Street).  The building has been home to a drug store and soda fountain, a candy store, carpet store, many restaurants, and now The Staple and The Stone Room!

Red Bird Music Store

Get your audio fix at Red Bird Music Store. “A full service shop for all your music needs,” they offer musical instrument sales and repair.  Check out rows of vintage and current records, apparel, jewelry, stickers, and instruments.  They even have a full catalogue of over 2,500 vinyl and cd’s on their website.

Coming Home

I started shopping at Coming Home right after they opened in 2017. We lived in Osceola at the time and I’d get so excited when the “We’re Open!” sandwich board would appear outside their door. This shop is open most weekends and features over 30 vendors.  What started as mainly home décor has expanded to boutique clothing, body products, food, vintage, handmade, and more. 

Bonus: they often have food/beverage samples available!

Eat and Drink

The Watershed Cafe

The Watershed Café is one of our go-to spots for date night or bringing friends from out of town. Their menu is impeccable, locally-sourced, and have you seen their dining igloos??  Our favorite meals are their Risotto Bowl with chicken, the Pot Roast, the Breakfast Flatbread (only available Saturdays).  They are situated next to Geiger Falls and the views are amazing.


During the logging era, Osceola started with a sawmill that was built where lumberjacks floated millions of logs down the St. Croix River. The Watershed Café building is located where the office once stood for the original sawmill called the Osceola Mill.

PY’s Saloon & Grill

Just down main street is PY’s Saloon, a bar with the best french fries ever; they hand-cut potatoes right before frying and they. are. amazing. You can order in a family-size or smaller portion. PY’s also offers a bar menu (their BLT is delicious), occasional live music and open mic nights, plus a nice patio and outdoor bar overlooking Cascade Falls.

Osceola Lanes

Head to Osceola Lanes to enjoy 3 for $5 tacos on Tuesdays and Thursdays or a round of bowling at this quaint bowling alley and bar.  In warmer weather sit at their “Scoreboard Patio Bar” – it’s a great spot to watch a football game and sometimes in the winter they light a bonfire for guests to sit around.

Other places to eat and drink: Cascade Nutrition, Tippy Canoes, Lucky Panda, The Chocolate Gnome, and more!

Osceola is home to a famous viticulturist!  Read more about Elmer Swenson, the Osceolean who helped create some of the world’s best cold-weather grapes.

There are so many more great aspects of Osceola to feature, like the St. Croix Art Barn, Croixland Leather Works, and the Osceola Braves Baseball team. I guess I’ll just have to do another feature in the spring!