Apple picking in Door County Wisconsin in fall

POV: It's Fall in Door County. Here's How We'd Spend It.

September 23, 2026•2 min read

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POV: It's Fall in Door County. Here's How We'd Spend It.

Fall in Door County has a way of sneaking up on you - one weekend it's summer, and the next the leaves are turning and everything shifts. The energy is different. A little slower, a little cozier, and honestly one of our favorite times to be up here.

If you're planning a fall trip - or still on the fence about it - here's how we'd spend it.

Hit the Trails on Horseback

If you're looking for something a little different, this is it. We took the whole family to Door County Horsemanship this past summer - and when I say whole family, I mean everyone from an 8-year-old to a couple of 40-something adults who had no idea what they were getting into. Everyone left happy.

The trail leaders made it easy and genuinely fun, and the horses and ponies have real personalities - the kind where you leave remembering their names. (Ours were Cedar and Sadie.) The trails wind through the woods and out through open prairie grasses, and honestly, we've been thinking ever since about what it would look like in the fall. The changing leaves, the crisp air, the quiet of the woods - we have a feeling it would be something special. We're already planning to go back.

Check out their Guest Rides page for details on booking.


Go Apple Picking

Everyone knows Door County for the cherries. But fall belongs to the apples.

The good news - you don't have to go far. Seaquist Orchards is just two miles north of Sister Bay. They offer pick-your-own on select October Fridays and Saturdays, plus an Apple Festival on September 26th - check their website for the latest details. The market alone is worth a stop, stocked with homemade jams, baked goods, and apple cider donuts.

Also worth the trip - Lautenbach's Orchard Country Market & Winery offers pick-your-own in late September and early October, live music, a market, and they're pet friendly. See their website for hours and dates.

Apple season runs mid-September through October - right when the leaves are at their best. Hard to think of a better way to spend a fall afternoon.


A Note on the 2027 Calendar

We're getting ready to open our 2027 calendar soon, and if you're already thinking ahead - same - you'll want to be the first to know. Dates tend to go faster than you'd expect. Sign up for our newsletter here so you don't miss it when that email drops.


Looking for more local favorites? Visit our Door County Travel Guide for more of our go-to spots up and down the peninsula.

Ready to plan your trip? Check availability at Cottage & Bay.

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