A Daycation in Wine Country: The Falls of the Upper Saint Croix River Valley - Minnesota Uncorked™
Osceola, Wisconsin

A Daycation in Wine Country: The Falls of the Upper Saint Croix River Valley

For months I’ve been looking forward to a dinner cruise with Taylor’s Falls Scenic Boat Tours  —  one featuring Winehaven wine and chocolate pairings.  Initially intended to be just a day trip, the morning before the boat tour I found myself peeking on Air B&B on a whim, to see if I could find any available accommodations nearby.  As luck would have it a rental popped up in Saint Croix Falls, WI (just one mile across the river from the boat tour), setting in motion a much needed 24-hour “Daycation”.

Among the reasons the “Falls area” (Saint Croix Falls, WI  and Taylors Falls, MN) is simply one  of my favorite places to go:  its proximity from home — just an hour from the Twin Cities, the majestic river bluffs, tons of outdoor recreation, and small-town charm with great amenities. A 24-hour trip is great, when you’re only traveling an hour from home, but you could easily fill a 5-day itinerary in this area as well!


Osceola, Wisconsin

Cascade Falls in Osceola, WI
Stairs to Cascade Falls

Heading out from the Twin Cities just before last Saturday,  I enacted the “all cell phones OFF” road trip rule, and pulled out a State Highway map.  Road trips are just more enjoyable without Richard constantly telling me I’m going the wrong way — he really doesn’t understand detours, and with it being “road construction season”, I get tired of him constantly telling me to “turn around when possible”.  Richard, by the way, is my GPS — my husband, James often tells me I’m going the wrong way too, but is much more likely to give me the benefit of the doubt.

Rather than heading up 35-E for an “express route”, I selected a more scenic route: take I-94 East from Saint Paul to the first exit in Wisconsin, and wind our way North through Historic downtown Hudson. We arrived in Osceola, WI just in time to explore their Main Street area for lunch.

I’ve been near Osceola dozens of times, when taking Wild Mountain Recreation’s canoe rental service downriver from Taylors Falls. With the canoe trip, you exit on the opposite side of the river from downtown Osceola, so I’ve never actually headed into the city, just hopped the canoe shuttle back up river to my

Cascade Falls Picnic
View of Cascade Falls

car. It would be an easy walk across the bridge from the canoe river exit, and I’m definitely going to pair my next canoe trip with a walk across the bridge for lunch in Osceola the next time I go.

Osceola is an adorable river-way town situated at the crest of the Cascade Falls. If it weren’t for other destinations I had in mind, I could have spent an entire day here: a few close blocks of historic main street buildings filled with intriguing antique shops, ice cream, bakeries, pubs and more — all flaked by hiking trails near Cascade Falls. I did find time to pop down to Cascade Falls, which can be seen easily once you make it down a fairly lengthy staircase (just look to the left of the “Cigar Shop Indian”).   Cascade Falls would have been a great place for a picnic lunch (if I would have known that before hiking down 5-ish flights of stairs, without lunch).


The Artist’s Loft in Saint Croix Falls, WI

Just a few miles North of Osceola is Saint Croix Falls, WI — host city to our accommodations for the night, the “Artist’s Loft”. It was as adorable and cozy as pictured. The attention to detail in this place is incredible, from the most ornate door hinges, to the mosaic tiled bathroom that is almost like a word-find, words such as “relax”, “joy” and more sprinkled throughout the inlaid tile walls.

I had an opportunity to meet with owner Amy the morning of my departure for a peek at the rest of the building — 5,000 sqft currently undergoing renovation, set to transform into a restaurant (and wine bar!! — what are the chances?) which will also include three Air B&B rentals.  Currently, there are two rentals available in the building, the “Artist’s Loft” and “Peacock Room”, which is a modern, recently renovated 1 BR apartment. Amy is also founder of Luminaries Retreats which operates all-inclusive retreats out of the space.  I can’t wait to come back in a year to see this space transformed — or perhaps just to come back for some adventures on the trails guided by Amy/Luminaries Retreats!

The Artist’s loft is located right on Main Street in downtown St Croix Falls and has a number of intriguing sights and shops.  Just two blocks North is Valley Sweets, an old-fashioned ice cream shop with Wisconsin made ice cream (and the world’s best salted caramel ice cream, in my opinion!)  Just one more block North of Valley Sweets, a wonderful park with walking trails, overlooking the top of the dam.

If you haven’t used Air B&B before, it enables private owners to rent spaces — you can find everything from the ordinary to the extraordinary.  I have used it for several trips and always had extraordinary experiences.  Using my code here to book your first stay will give you $35 off (and I’ll make a buck towards my next stay, too) — you don’t have to stay at the Artist’s Loft for the discount, you can book anywhere on Air B&B.


Chateau Saint Croix in St Croix Falls, WI

Chateau Saint Croix Winery

After relaxing at the Artist’s loft for a spell, mid-afternoon I set out to Chateau Saint Croix Winery & Vineyard — also located in Saint Croix Falls, just a few miles north of historic downtown.

Cherubs and gargoyles welcome you to their picturesque grounds, meticulously landscaped and overlooking rolling meadows and wetlands.


Winehaven Wine and Chocolate Pairings
Wine and Chocolate Pairings from Winehaven

 Taylors Falls Scenic Boat Tour

Later that evening, I set sail aboard a paddle boat out of Taylors Falls for a dinner cruise sponsored by Taylors Falls Scenic Boat Tours. A reception on the top deck greeted guests with wine and chocolate pairings from nearby Winehaven Winery. Not only were the wine and chocolate pairings carefully selected — but the chocolates themselves were crafted by a chocolatier in Napa, CA using Winehaven’s wine. Salted caramels made with honeywine, and a dark chocolate truffle infused with Merlot were delightful aperitifs to start the evening.

Taylors Falls Scenic Boat Tours also offer Dinner Cruises featuring wine and cheese pairings with locally made Eichten’s cheese as well.

Dinner was served as the sun set along the river bluffs, and included a hearty three courses Caesar salad, followed by your choice of chicken in mushroom sauce, prime rib, or cheesy manicotti. I had the chicken (very good) and my husband, the prime rib which he enjoyed very much. Though we were already stuffed — we managed to find room for caramel topped cheesecake for dessert.

By the time dinner was over the sun had set and the upper deck was featuring live music by Charlie O — an ironically hilarious, and multi-talented one-man act, skillfully playing piano, guitar and harmonica while singing. He covered hits from Elton John, Billy Joel, Macklemore (believe it or not) and much more. The fact that he was so fantastic and funny, might have been one of the bigger delights of the evening.

About Taylors Falls Scenic Boat Tours

Tours depart daily from downtown Taylors Falls, MN, and there are a variety of trips to choose from:

  • Daily excursions last anywhere from 45 to 80 minutes (no food, but cash bar with wine, beer, soda and light snacks for purchase)
  • Dinner cruises, including the upcoming Leaf Cruise are three hours long and include a three-course meal and live entertainment.
  • A number of other “Specialty” cruises are available such as including Winehaven partnered Wine & Chocolate or Wine & Cheese cruises. Other themed cruises happen throughout the year as well. Keep an eye on their calendar for details!

With fall on its way, the Saint Croix River Valley is one of the most scenic places to experience the fall colors! Enter below for your chance to win a pair daily excursion tickets. The contest is generously sponsored by Taylors Falls Scenic Boat Tours.

Hopping aboard the Taylors Falls Dinner Cruise was just one part of my Daycation in Wine Country, you can read about other highlights in the Upper Saint Croix River Valley, here.

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About The Author

Lauren Voigt

Lauren launched Minnesota Uncorked™ to encourage exploration of wine. When she's not masquerading as a wine writer on the internet, Lauren earns her keep as a marketing specialist in the wine industry. Lauren can be reached at lauren@mnuncorked.com. She is certified in wine through WSET (Level III, Distinction), a Certified Wine Professional (CWP) through Saint Paul College, and a Spanish Wine Scholar (SWS) through Vine Lab Wine & Spirts Academy.
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