Autumn, A Magical Time in Door County and at Olson Cottages

While we're in our final week of the 2025 season, its never too early to start thinking about next year. If you’re considering Olson Cottages in early fall, you’ll be in the perfect spot. Door County’s shores, wooded hills, and charming towns transform during September and October into a wonderland of color, cozy flavors, and festive energy. Here’s a curated guide to help you enjoy the very best of Door County in fall.
When to Visit for Peak Color & Quiet Charm

• Best time for colors: Late September through mid-October is typically prime for fall foliage in Door County.
• Off-peak advantage: After Labor Day, crowds thin, parking frees up, and the peninsula feels more relaxed.
• Layering is key: Calm, crisp mornings often give way to mild afternoons — advise guests to pack layers and a light rain jacket just in case.

​Top Things to Do In The Fall in Door County
1. Walk our Beautiful Beach
It's always a great time to spend time on our beautiful sand beach on Lake Michigan and Fall is no exception.  Sure, the water is a bit cooler and swimming might be a bit more challenging temperature-wise, but the walks are still great and warm days still provide wonderful moments on the beach and on our decks.

2. Drive the Door County Coastal Byway
This 66-mile loop (Highways 42 & 57) winds past lakeshore bluffs, orchards, and quaint towns — ideal for leaf peeping and scenic stops.

3.  Hikes, Lookouts & Park Trails

• Peninsula State Park: Hike the Sentinel Trail or climb Eagle Tower for sweeping views of the foliage.
• Whitefish Dunes / Cave Point County Park: The limestone cliffs at Cave Point are especially striking when framed with fiery leaves.
• The Ridges Sanctuary: Quiet woodland trails with interpretive signs and hidden corners that reward those who wander.

4. Savor Local Flavors & Harvest Traditions

• Fish boils: A Door County tradition still active through October — dramatic, tasty, and unforgettable.
• Apple orchards & cideries: Guests can pick apples, sip warm cider, and shop local preserves.
• Trolley & orchard tours: The Door County trolley stops at spots like Lautenbach’s Orchard to combine color, food, and local charm.

5. Festivals, Events & Seasonal Celebrations

• Sister Bay Fall Fest (Oct 16-18, 2026) — parade, arts & crafts, kids’ carnival, Lion’s Club fish boil, and more.
• Egg Harbor Pumpkin Patch Festival (Oct 10–13, 2026) — live music, pumpkins, carnival rides, and fall treats.
• Baileys Harbor Autumn Fest & Classic Auto Show (Sept 12, 2026 – to be confirmed) — vintage cars, live music, vendors, and fall flair.
• Sturgeon Bay Harvest Fest & Street Art Auction (Sept 19, 2026 – to be confirmed) — food, crafts, street art, and community vibes.
• Door County Fall Lighthouse Festival (Oct 2–6, 2026 – to be confirmed) — special tours (boat and land) to lighthouses that are often closed the rest of the year.

6.  Off-the-beaten-path & Relaxing Moments

• Ferry to Washington Island: Explore quieter scenery, small shops, and fall vistas.
• Lighthouse tours & hidden coves: Enjoy unique vantage points where fall colors meet water, especially in afternoons.
• Sturgeon Bay Bridge Walk: A scenic stroll over both Michigan and Oregon Street Bridges with water views and changing trees.
• Farm markets & shopping local: Fall produce, crafts, and regional goodies are abundant in towns across the peninsula. 

September and October offer the same opportunities as peak season in Door County at a more relaxed pace.  Consider Olson Cottages for your next Fall getaway.  New reservations for 2026 begin in February, 2026.