Every fall, the same list circulates. Ferguson's for the corn maze. The Glass Orchard for something different. Connell's if you want the old-fashioned version. It's a fine list, and it hasn't changed much in years, which is exactly the problem. This year it should.
Three things happened at Chippewa Valley orchards in the past few weeks that don't fit the old script. A 168-year-old family farm started pouring wine for the first time in its history. A well-known u-pick spot quietly dropped its name and picked up a new one. And an orchard best known for weddings and a patented apple just announced a multi-day festival that won't open until next fall. None of these are marketing stunts. They're bets, made by people who've run these places for generations, about what an orchard visit needs to offer now that it isn't 1995 anymore.
The Orchard That Waited 168 Years to Pour a Glass
Connell's Family Orchard has been on the same stretch of County Highway OO in Chippewa Falls since 1858, run by seven generations of the same family. Through all of that, the orchard never sold alcohol. That changed in August 2026, when Connell's released three wines made from its own apples, apple, apple raspberry, and spiced apple, all landing on the sweeter end of the spectrum.
Owner Steve Connell has been candid that this wasn't a long-planned pivot. The family pressed last year's surplus apples into cider over the winter, started experimenting, and ended up with something worth bottling. The family has no plans to turn Connell's into a winery outright, and the wine is available only for guests 21 and older who visit the orchard itself. But the fact that an orchard this old, this rooted in the pick-your-own tradition, decided a second revenue line was worth the trouble tells you something about where the pressure sits in this business. Raspberry season ran through late August this year, with peak apple picking landing around Labor Day and continuing through September, which is a tight window to make a year's living off bushels alone.
The Same Farm, a New Name on the Sign
If you've picked apples at the u-pick orchard off Maple Road south of Eau Claire in past years, you knew it as Leffel Roots. It now operates as Maple Harvest Apple Orchard, same location, same owner, same 10-acre corn maze and pick-your-own rows of Honeycrisp and Cortland. The apple pies haven't changed either. As the farm itself puts it, the recipe and the taste stayed put, only the name moved.
Rebrands like this rarely make headlines, and this one didn't need to. But if you're the kind of local who plans a September weekend around a specific address, it's worth knowing before you type the old name into a search bar and end up confused about whether the place closed. It didn't. It's still there, still family run, and it still donates apples to Feed My People to help stock food banks across the region.
A Festival That Doesn't Open Until 2027, and Why It Matters Now
The biggest change on the horizon belongs to Dixon's Apple Orchard and Autumn Harvest Winery, the Chippewa Falls operation known for its exclusive Champagne apple and its rolling-hills wedding venue. Owner Becky Mullane and her team, in partnership with the Northern Wisconsin State Fair, announced that Applepalooza Chippewa Falls will hold its inaugural run October 8 and 9, 2027, at the Northern Wisconsin State Fairgrounds. It's modeled on Dixon's existing Applepalooza in Duluth, Minnesota, an event now in its fifth year that reportedly draws crowds in the thousands.
"This is home," Mullane said of Chippewa Falls.
The details of vendors and programming are still being worked out, but the intent is clear. Mullane wants Chippewa Falls recognized as the apple capital of western Wisconsin, and she's willing to spend a full year building toward one weekend to make that case. For a reader who lives here, the practical takeaway is smaller and more immediate: this fall is your last "normal" one before the calendar gets a new anchor event. Next year, the second weekend of October will belong to Applepalooza. This year, it's still just you, the orchards, and however you want to spend a Saturday.
What Three Separate Bets Add Up To
Take these three stories together and a pattern shows up that no single one of them proves on its own. A legacy orchard adding alcohol sales. A working farm swapping its public name. A wedding-and-wine operation building a ticketed festival a full year out. None of these are struggling businesses grasping at relevance. They're established operations, some multi-generational, deciding independently and in the same season that the pick-your-own bag of apples isn't the whole draw anymore. The draw now includes a tasting room, a rebrand clean enough to market, or an event big enough to become a destination in its own right.
That's useful to know if you're the kind of person who's visited the same one or two orchards for years out of habit. The reason this year's list looks different isn't that new competitors showed up. It's that the old guard is expanding what an orchard visit is for.
The Season at a Glance
A few dates worth keeping straight if you're planning weekends between now and Halloween:
- September 12: Downtown Eau Claire's Fall Festival, the 37th annual, already came and went along South Barstow Street, drawing over 100 vendors and shutting down a half-mile stretch of downtown for the day.
- September 19-20: Chippewa Falls hosts the 22nd annual Oktoberfest at the Northern Wisconsin State Fairgrounds, following on the heels of a brand-new BBQ Fest the venue held at the start of the month.
- Now through late October: Peak apple picking is winding down toward pumpkin season at most orchards, with several running weekend wagon rides through both months.
- Third week of October: This is typically when fall colors peak across the Chippewa Valley, according to Visit Eau Claire's seasonal guide, making it the sweet spot for a scenic drive alongside your orchard stop.
- October 8-9, 2027: Mark it if you want to say you remember when Applepalooza Chippewa Falls was still a rumor.
If you'd rather not drive yourself between stops, the Chippewa River Trolley Company runs a seasonal Farm & Orchard Tour that hits the Apple Hangar at Dixon's Autumn Harvest Winery and Connell's Family Orchard in the same afternoon, with samples included at each stop. It's a low-effort way to see two ends of this year's story back to back, the orchard that just started pouring wine and the one about to headline a festival built for thousands.
None of this requires you to pick a favorite. Eau Claire's orchard scene has room for the place that's been doing the same thing since 1858 and the place trying something new every season. What's changed is that you can no longer assume the orchard you visited last October is doing the exact same thing this October. This year, more than most, it pays to check first.
Living here means these small shifts are part of what makes the Chippewa Valley worth paying attention to, season after season. Whenever you're ready to talk about what's happening in the local housing market with the same kind of on-the-ground detail, Courtney Kneifl and Luxe Realty are a call away for a free home valuation or a no-pressure consultation.
