Crosslake Days: The Whitefish Chain's Fall Festival

Crosslake Days is the town's annual fall festival, held the last weekend of September on the Whitefish Chain. The 2026 edition ran September 24 through 26, rain or shine, with free activities for all ages. It is the kind of weekend that shows what small-town lake life is actually like in the fall, when the summer crowds thin out and the community gathers on its own terms.

The Hunt for the Lost Chili Pepper

The festival kicks off with three daily clues released at 9 AM each day through the Crosslake App, Chamber member businesses, and the Welcome Center. It is a town-wide scavenger hunt that gets everyone walking the streets and checking the shops, and it is free for anyone who wants to play.

The Chili Cook-Off

Saturday's centerpiece is the chili cook-off, running 12 to 3 PM with free samples at roughly 31 Chamber member businesses around town. Judges hand out the Golden Ladles awards, and the crowd votes for the People's Choice. It is a great way to taste your way across Crosslake's main street in one afternoon.

The Arts and Crafts Fair

The outdoor arts and crafts fair runs Saturday from 9 AM to 4 PM at The Log Church, 37218 County Road 66. Local makers set up under tents on the church lawn, and it is a good place to find the kind of handmade items that make good cabin gifts.

The Rest of the Weekend

Cider and Candlelight Tour: an evening stroll through town.

Knights of Columbus Corn-Hole Tournament: Saturday, with check-in at 11 AM and toss at noon.

Crosslake Street Dance: live music and dancing downtown.

**Live music** at venues like Moonlite Bay and Patrick's Cedar Chest.

**Loon and Lakes Trivia** hosted by WAPOA and the National Loon Center at Up North Social.

More weekend staples: a meat raffle at the American Legion, a Meet the Masters painting event at Kicks the Art Place, an exotic petting zoo, and end-of-season deals at Crosslake Ace Hardware.

Why It Matters to Buyers

A town that fills a late-September weekend with free, family-friendly events is telling you something about year-round life. Crosslake is famous for its summer on the Whitefish Chain, but the community calendar keeps going after the docks come out. For buyers, that is the difference between a place that is lovely in July and a place that feels like home in October.

The Honest Read

Crosslake Days is not a headline event, and that is exactly the point. It is a community gathering built by the chamber, local businesses, and volunteers, and it gives you an honest look at how the town treats its neighbors and visitors. If you are weighing a move to the Whitefish Chain, our Crosslake guide covers the lakes, neighborhoods, and daily rhythm behind the festival.

Thinking about Crosslake? Schedule a conversation or start with our buying guide. Cheers!