We’re Planning for this October
Barry, my long distance Scottish boyfriend, is coming back to Wisconsin this October, and I’ve officially entered planner mode. We haven’t nailed down the exact dates yet, but one thing’s for sure—we’re heading to Door County for a few days to soak up peak fall foliage.
Fall in Door County is stunning. The leaves are bold, the orchards are full, and cider just tastes better up there. It’s also… not cheap. So I’m putting together a realistic, affordable fall itinerary that still feels intentional and memorable. Think: small-town charm, scenic hikes, cozy coffee shops, and a few spooky seasonal detours.
Whether you’re planning a fall getaway with your partner or just need a long weekend in Wisconsin, here’s what we’re dreaming up.
🍎 Fall in Wisconsin: The Little Things Hit the Hardest
When Barry visits, I try to show him what makes the Midwest feel so magical, and why Wisconsin is America’s best kept secret. This trip, no over-the-top plans—just simple seasonal stuff that makes October feel like nostalgic.
- Visiting a pumpkin patch and apple orchard
- Making fresh apple juice at home
- Carving pumpkins while listening to spooky playlists
- Eating caramel apples like it’s our part-time job
- Haunted tour at Shaker’s Cigar Bar in Milwaukee
- Maybe stopping by the Milwaukee Public Museum (it’s such a great museum that won’t be around much longer, and he’s never been)
But the highlight? Our four-day Door County escape up north.
🛏 Where We’re Staying: Cute, Not Pricey
I did a deep scroll through hotels and Airbnbs, and most of them were sitting at $700–$900 for three nights. Yikes. Then I remembered the Holiday Motel in Sturgeon Bay—not fancy, but clean, super affordable, and actually adorable in a mid-century Americana kind of way.
- 💸 Price: About $317 total
- Vibe: Old-school charm, central location, nothing too flashy—just right
It leaves us more room in the budget for multiple cider tastings, antiquing, and impulse jam purchases.
🍁 Door County Itinerary (3 Nights / 4 Days)
🧳 Day 1: Arrival + Exploring Sturgeon Bay
- Check into the Holiday Motel (around 2–3 PM)
- Take a walk downtown—pop into antique shops and general stores
- Grab a coffee at Lawlss Coffee (my absolute favorite spot)
- Dinner options with gluten-free choices:
- The Gnoshery – sandwiches, soups, cute and casual
- Crate – ramen, sushi, GF-friendly
- Sonny’s – GF/DF pizza and pasta
- The Gnoshery – sandwiches, soups, cute and casual
- Catch the sunset at Sturgeon Bay Ship Canal Pierhead Lighthouse
Laid-back and local. The perfect way to settle in.
🌲 Day 2: Fish Creek, Orchard Stops & Fall Walks
- Morning drive (~30 mins) to Fish Creek
- Stop at Lautenbach’s Orchard Country Winery & Market
- Cider, jams, cute photo ops—and rumor has it, apparently there are gluten-free apple cider donuts?! I’m manifesting that to be true.
- Cider, jams, cute photo ops—and rumor has it, apparently there are gluten-free apple cider donuts?! I’m manifesting that to be true.
- Wander through Founder’s Square Park—charming shops, all decked out for fall
- Brunch: Julie’s Park Café (burgers, pancakes, solid GF options)
- Afternoon exploring Peninsula State Park
- Hike Eagle Trail or bike Sunset Trail
- Climb Eagle Tower for sweeping views of fall colors and the lake
- Hike Eagle Trail or bike Sunset Trail
- Dinner options:
- Blue Bear – gluten- and dairy-free lasagna that blew my mind
- Pelletier’s – classic Door County fish boil experience
- Blue Bear – gluten- and dairy-free lasagna that blew my mind
🏝️ Day 3: Washington Island Adventure
- Early morning departure (leave around 7:30–8:00 AM) for Northport Pier about an hour drive
- Grab coffee + snacks at Sip on the way
- Hop on the Washington Island Ferry ($30 round trip)
- Island highlights:
- The Stavkirke (Viking Church) and the quiet forest prayer path
- Schoolhouse Beach – white unique pebble beach, crystal-clear water
- Climb the Mountain Park Lookout Tower for panoramic island views
- The Stavkirke (Viking Church) and the quiet forest prayer path
- Lunch: Albatross Drive-In – GF burger + fries, classic roadside vibes
- Optional cider tasting at Island Orchard Cider before the ferry back
- Return to Sturgeon Bay for a relaxed dinner at Brick Lot Pub or Get Real Café
Big day, lots of nature, and plenty of opportunities to slow down and take it in.
🎃 Day 4: One Last Cozy Morning
- Grab one last coffee at Lawlss
- Brunch: either Julie’s again or Get Real Café
- Optional stop through Green Bay to say hi to friends or break up the drive
- Head home in the afternoon or early evening—tired, happy, and probably full of donuts
🧣 Little Ways to Make the Trip Extra Cozy
- Dress in layers—fall in Wisconsin is chilly in the morning, warm by noon
- Pack a blanket and thermos for beach breaks or park bench hangs
- Bring your own mugs—it makes roadside cider stops feel intentional
- Stock up at farm stands: cherry preserves, dried apples, fall snacks
- Keep your plans flexible—some of the best moments will be unplanned
Final Thoughts
This trip isn’t about luxury. It’s about being present, enjoying the season, and making sweet little memories without overspending. Door County in October really is something special—and with a bit of planning, you can experience all of its beauty without the hefty price tag.
We’ll carve pumpkins, sip cider, and drive home with a trunk full of fall. Couldn’t ask for much more than that.
The Roaming Rebel 
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