"Fall" in Love with Osceola

5 Must-Do Weekend Itineraries


The landscape alone makes the trip to Osceola, WI worth it. A scenic drive that crests small hills and winds along the St. Croix River, with family farms swelling above a rolling sea of golden corn fields eventually giving way to mammoth roadside rock cliffs and forestland painted in an explosion of  color.
Since the steamboat and railroad eras, travelers have sought out Osceola in the fall to admire the deep maroon of sumac and Virginia creeper, the yellows and golds of hackberry, aspen and green ash, and the rich oranges and reds of sugar maples and pin oaks mingling with the ever-green evergreens. But Osceola is so much more than a pretty view. Discover unforgettable things to do and places to eat and stay while you pursue the hues. Don’t forget your camera.

1. Fall color viewing

Primo Peeping!

Fall foliage in the St. Croix Valley is legendary. Variegated hues of red, orange, yellow, green, purple and brown sweep over the highest riverside bluffs, down into the valley and back up through the rolling countryside. The colors hit their peak sometime in late September/early October and create a stupefying spectacle that humbles even the most seasoned leaf peepers.
Fall Colors by Plane: View the entire palette of autumn hues from above on an aerial tour of the region. The panoramic views feature the St. Croix River Valley, inland forests and local lakes. Notice the unique blend of trees that contribute to the rich, vibrant color pattern below.
Fall Colors by Train: Enjoy an excursion through the St. Croix River Valley in autumn splendor in a vintage train ride.Board the train in Osceola. The  “Marine on St. Croix” excursion travels west 90-minutes round-trip winding the bluffs of the St. Croix River Valley and offers amazing scenic views!
Fall Colors by Riverboat: Old-fashioned paddlewheel boats churn through the St. Croix offering guided tours of some of the most scenic vantage points on the river, including uncanny rock formations and the best spots for fall color.
Eat: On select train rides, you can purchase Brunch, Dinner, or Pizza train tickets. Eat on the train or plan for a stop in the Historic Downtown where you’ll find ice cream, coffee houses, burgers and farm to table fare or elegant cuisine in a variety of settings. Taylors Falls Scenic Boat Tours serves up a three-course meal, live music and a full cash bar aboard its dinner cruises, keeping you in the thick of the leaf peeping action while you eat.
Stay: Situated high on the bluffs, the Inn on the St. Croix River masterfully combines charming historical elegance with modern day amenities and comfort. Each of the seven spacious and distinctive rooms features a hydromassage tub, comfy queen bed, a cozy ambiance and an amazing view.


Pumpkin Patches

Small or large, round or oblong, smooth or scarred . . . Bright orange globes dot acres of bucolic fields around Osceola, begging to be picked and turned into jack-o-lanterns, homages to fall, Thanksgiving centerpieces, and tasty pies.
Neumann FarmsFall brings the bounty of the the farm in for all to see. A short distance from Osceola, Neumann Farms has tons of pumpkins, gourds, squash,corn stalks and comes complete with a pick your own pumpkin patch, fully stocked gift shop and farm kitties.
The Pumpkin Express Train & Bash: In late October, the Pumpkin Express departs from the historic Osceola & St. Croix Valley Railroad depot and travels the old SOO Line track through spectacular fall scenery to Dresser, WI where a day of family fun awaits. A hay bale maze, kid-friendly haunted depot, and hand-pump car rides on the train track are among the attractions at this event. Pumpkins are free for children under 15 years old.
Hayride to the Pumpkin Patch: Pleasant Valley Orchard has hundreds of pumpkins in an idyllic fall setting. Pick your favorite from a mound of pre-picked pumpkins or hop on a hayride for a rustic ride to the fields where you can hunt down exactly what you’re looking for. Apples are also ready to pluck. Check out Pleasant Valley’s vast orchard featuring 16 varieties.
Eat: A stone fireplace, spacious patio, and vintage canoe décor gives Tippy Canoes a cabin ambiance from which to enjoy downhome favorites (like the traditional Wisconsin Friday Fish Fry) or try something new (like the Tator Tot Hot Dish Pizza).
Stay: Just down the road from the historic downtown and shopping district (and steps away from Tippy Canoes), River Valley Inn and Suites provides standard hotel rooms and suites with a lobby and staff that represent the unique, welcoming charm of Osceola. The indoor pool and hot tub beckon guests to unwind on a brisk fall day.


Farm Visits

Since the advent of farming, harvest time has been the herald of autumn. Crops are ripe for the picking and ready to be transformed into delicious edibles. With winter lurking just around the corner, fall also produces the last remaining days to frolic comfortably in the outdoors.
The Spoils of Harvest: Visitors to Neumann Farms experience a slice of country living: feeding goats while chickens scurry by, roaming through crop fields and pastureland, exploring an outdoor canning kitchen. Inside the quaint and homey gift shop, the spoils of the farm unfold, including fresh, cage-free eggs, hand-pressed apple cider, seasonal produce, and meats raised on site. For a delightful spin on a classic snack, try the popcorn popped right on the ear.
Eat: The vibe in Osceola is one of remembering the past while looking to the future, and the Watershed Café, named after and built on the site of the headquarters of the sawmill that formed the town, reflects that ideal. Locally sourced, farm-to-table made from scratch cuisine dominates the menu and the outdoor patio overlooks Cascade Falls, a 25-foot high waterfall in the heart of downtown.
Stay: Pleasant Lake Bed & Breakfast is a quiet, family-owned, country lake home framed in forest, offering visitors a peaceful retreat on a private deck or a place to gather and socialize at a fire ring overlooking tranquil Pleasant Lake. Three guest rooms with in-suite bathrooms are each decorated in a comfortable, homespun style with a glimpse of the family’s history.Yummy breakfasts are served up by inn keepers with long time roots in the area.


Wine, Chocolate & Cheese

As the heat of summer subsides and the leaves on the trees dress for cooler weather, endless rows of grapes begin to ripen on the vine. It’s harvest time at the wineries. The St. Croix Valley is an up-and-coming wine region with four award-winning wineries surrounding Osceola. Each vineyard boasts its own unique events, live music and an incredible landscape.
Grape Stomps: In early September, the first grapes of the year come off the vine, ready to be juiced. And so, the wine making season kicks off, along with the shoes of vineyard guests as they trample and tromp, squishing the fruit with their bare feet. Grape stomp events are held annually at Chateau St. Croix, Wild Mountain Winery and Dancing Dragonfly.
Federweisser Festivals: While tavern owners are busy erecting biergartens in preparation for Oktoberfest, WineHaven and Chateau St. Croix set to work producing the young fall wines of Germany for their autumn festivals. Federweisser is made with early white grapes and served when it is just beginning to ferment, giving it sweet, yet refreshing properties. WineHaven also offers the red grape variety, Roter Rauscher.
Wine, Cheese & Chocolate: Quintessential Wisconsin cheese, regional fine chocolates, and locally made wines unite to treat your taste buds to delightful pairings that can only be found in the St. Croix Valley. All four of the area’s wineries (Dancing Dragonfly, Chateau St. Croix, WineHaven, and Wild Mountain) tender their versions of Cheese and Chocolate Weekend in mid-November to coincide with the opening of deer hunting season in Wisconsin, known to the locals as Hunting Widows’ Weekend. You can create your own self-guided tour, or use our itinerary.
Eat: Make a reservation for a prix fixe fall feast in the St. Croix River Inn’s snug and elegant dining room overlooking the river valley. Seasonal, locally sourced, and organic fare headline the five-course meal for a true dining experience.
Stay: After a day of wine tastings and fine dining, relax at the Autumn House Inn, a boutique hotel where comfort and sophistication are top priorities. Indulge in an in-suite massage and breakfast in bed. Try one of the inn’s package deals – Luxurious Spa, Bread & Cheese Banquet, Chocolate Dreams, Wine & Roses or Champagne & Chocolate-Dipped Strawberries – or create your own stay with customized pampering.


Outdoor Fun

Paddle a Canyon of Color: The 7-mile stretch of the St. Croix River between Interstate Park and Osceola Landing is particularly captivating in the fall. The composition of trees that line the river create a medley of vibrant oranges, brilliant yellows and golds, rich, deep reds and lush greens. A leisurely paddle down the waterway leads you between basalt rock walls, past wooded floodplains, and through a kaleidoscope of colors. Fish are plentiful, and dozens of bird species, like eagles and herons, are a common sight. Riverwood Canoe in Osceola provides canoe and kayak rentals, life vests, shuttle service to and from the landings, and free parking, all included in the rental price.
Take a Fall Hike: Between the stifling heat of summer and the icy bite of winter lies the temperate conditions of autumn, an ideal time to hike. Three trailheads originate off Cascade Street, Osceola’s main road, each with distinctively breathtaking features. Eagle Bluff Trail follows switchbacks up the bluff face to an impressive, panoramic view of the valley below. Marked by a statue of Chief Osceola, Cascade Falls Trail descends 135 steps to the base of Cascade Falls where boardwalks alongside Osceola Creek lead to the St. Croix River. Simenstad Trail runs through woodlands cloaked in a blaze of warm tones and past the ruins of the 1867 Geiger Brewery. The Falls Bluff Loop contains all three trails and can be walked in 45 minutes.
Eat: Pop in to the Cascade BP’s deli counter (located at the hiking trailhead and near Osceola Landing) and enjoy a picnic at Gristmill Park overlooking the waterfalls. At dusk, the falls are lit with color-changing LED lights that reflect the season and simulate the light of a full moon.
Stay: Scope out a campsite on the St. Croix River and revel in the fall colors and cooler temperatures right from your home base. There are several primitive campsites accessible from the water and designated by a brown camping sign and metal fire ring.

Plan Your Trip to Osceola, WI


Leaf Watching Tours:
Fall Color Train Rides- MTM
Airplane Tours – Osceola Aerosport
Riverboat Tours – Taylors Falls Scenic Boat Tours
Apple and Pumpkin Fun:
Neumann Farms
Pumpkin Express Train & Bash – Minnesota Transportation Museum
Pumpkin Patch at Pleasant Valley Orchard
Outdoor Adventures:
Riverwood Canoe
Interstate Parks to Osceola Landing – St. Croix National Scenic Riverway
Hiking – Osceola Chamber of Commerce
Riverboat Dinner Cruise – Taylors Falls Scenic Boat Tours
Tippy Canoes
Watershed Café
More recommended restaurants

This article was written by Karen Lawrence and produced by Linda Shober Marketing + Design, a marketing firm located in the St. Croix Valley specializing in providing content, strategy, management, design, and creative for digital and traditional marketing projects. This article originally appeared on the Osceola, WI Mainstreet Chamber of Commerce Website.