Ashland's Fall Run: Four Event Weekends Alongside Bayfield's Apple Festival

Every fall, thousands of cars point north out of Ashland toward Bayfield's Apple Festival, and there's a reason for that. The festival draws more than 50,000 visitors from across the Midwest over its three days, with orchard tours, a Grand Parade, and enough cider and craft vendors to fill Bayfield's small downtown to the edges. Ashland also has its own fall events on the calendar.

This year, on that same weekend, Ashland is also running an event three and a half miles south of town.

On October 2 and 3, ABC Raceway hosts the 51st Annual Red Clay Classic, powered by Enbridge, with Late Models, Modifieds, Super Stocks, and Mid-West Modifieds tearing up the dirt track on Butterworth Road. Hot laps start at 6:30 p.m. both nights. It's a fixture that's been running for over half a century, and it lands on the calendar the same week Bayfield fills its parking lots.

That overlap is one feature of Ashland's fall calendar. It fills four of its own fall weekends, from the second week of September through the middle of October, and gives residents other local events to attend alongside Bayfield's festival.

The Weekend That Splits Downtown in Two

The run starts on September 12, and it starts with a scheduling collision of its own. Mural Fest and Car Show takes over Downtown Ashland the same day the Chick-uamegon 5K and 10K sends runners through the streets. One event wants you parked and looking at painted walls and restored engines. The other wants you laced up before the pavement gets crowded with lawn chairs and folding tables for the car show. Locals who've done this before know to pick a lane early, either running before the crowds build or arriving downtown once the race has cleared out.

It's a small thing, but it gives the fall calendar an active start, with more events still to come in October.

The Weekend You Have to Choose

Three weeks later, the choice gets bigger. October 2 and 3 puts the Red Clay Classic in direct competition with the last two days of Bayfield's 64th Annual Apple Festival, which runs October 2 through 4 with more than 150 food and craft vendors and fourteen orchards open for picking. Bayfield's event is the one that shows up in Chicago Tribune roundups and USA Today's fall festival lists. It's built for visitors, and it draws them.

The Red Clay Classic brings Late Models and Super Stocks to the dirt track at ABC Raceway on Butterworth Road. Choosing between it and the Apple Festival isn't really about which is objectively better. It's about which kind of Saturday night you want, a crowded harvest festival up the shore or a loud, local dirt track.

The Marathon Weekend

October 10 brings the Tamarack Health WhistleStop Marathon, along with its half-marathon, 5K, and 10K options, through Ashland. It's the kind of event that closes streets and reroutes morning errands, and longtime residents plan around it the way they'd plan around any predictable disruption, by checking the route ahead of time and giving themselves extra minutes to get across town.

That makes October 10 a race-focused stop between the Red Clay Classic and Harvest Fest.

The Weekend That Stays Home

The stretch closes on October 17 with the City of Ashland's Annual Harvest Fest at Hodgkins Park, running from 11 a.m. to 10 p.m. It's billed as celebrating community on Ashland's East End, and the details back that up. Vendor fees are waived for non-profits and informational booths. The Great Harvest Bake Off is free to enter, split into professional and amateur categories. There's a Chowder Cook-Off and tractor rides alongside the food trucks and beer garden.

The live music lineup under the heated tent reads like a night built for people who plan to stay until the last set:

• Marlee Paine with Michael Pilhofer
• Barn dancing with Sarah York
• Silver Horizons
• Joyann Parker & The Joyann Parker Band

Harvest Fest offers an evening of activities at Hodgkins Park.

Four Event Weekends on the Calendar

Put the four event weekends next to each other and the shape becomes clear. September 12 brings runners and car enthusiasts downtown. October 2 and 3 offers Ashland's own dirt track alongside Bayfield's regional draw. October 10 brings runners into town for a morning. October 17 closes the stretch with an event celebrating community on Ashland's East End.

Ashland's fall calendar includes Mural Fest and Car Show and the Chick-uamegon 5K and 10K on September 12, the Red Clay Classic on October 2 and 3, the WhistleStop on October 10, and Harvest Fest on October 17.

If you're new to the area, or you've lived here long enough that the fall calendar has started to blur together, it's worth marking these dates now, before these fall events take place.

For anyone thinking about where in Northern Wisconsin they'd actually want to spend those fall weekends every year, not just visit once, Matt Schultz and the team at United Country Northern Wisconsin Lifestyle Properties know this stretch of the calendar as well as they know the shoreline and the timber stands around it. If Ashland's rhythm is starting to feel like home, they're worth a call to schedule a consultation and talk through what ownership here actually looks like.