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Halloween in Stillwater, Minnesota blends historic streets and riverside charm with a calendar packed full of fall events, nostalgia, and local oddities. As the riverfront starts showing off its autumn color, you’ll find plenty of unique things to do for Halloween 2026, from wrangling the family for a free festival to plotting a more grown-up adventure before winding down at home.
Classic Halloween Events in Stillwater
Start with the unmistakable signs of fall at Harvest Fest, held October 10–11, 2026, at Lowell Park. The giant pumpkin weigh-off draws crowds every year, but it’s the Pumpkin Regatta on Sunday (October 11) at 2:30 PM, real people paddling huge, hollowed-out pumpkins down the St. Croix River, that delivers the purest Stillwater energy. Both events are free to attend and make for some unforgettable photo ops downtown. Find more at the official event site.
If you like your history with a side of ghost story, the Warden’s House Museum (602 Main St N) leans into Victorian spooky season on Friday, October 30 with “Death, Victorians, and Spiritualism” (free, 6–7 PM). For the bold, Flashlight Tours of the old warden’s house on October 9–10 ($35, age-appropriate for adults and older teens) give after-dark chills in the former prison residence. Details at the Washington County Historical Society.
Halloween Adventures for Adults
For grown-ups looking for a night out that’s less pumpkins, more paranormal, board the Haunted History Trolley Tour in downtown Stillwater. On select nights October 9–30, these 60-minute theatrical rides combine true local lore and live costumed storytelling ($51.94; not recommended for kids under 10). Check the official schedule and tickets for dates and details.
If seasonal wine tasting sounds more your speed, Saint Croix Vineyards hosts Wine-O-Ween on Saturday, October 31 (noon–5 PM). Show up in costume to get a free glass of wine with a paid flight, just make sure you’ve got a designated driver or plan to walk.
Celebrate Halloween in Stillwater with Silver Cannabis Co.
For adults planning to unwind at home after the festivities, Silver Cannabis Company Stillwater at 1778 Greeley St S keeps a curated menu of options. Fall favorites this year include the Dogwalkers Bananaconda Pre-Roll 5-Pack (small-format, hybrid) and Good Green EverCrisp Flower 3.5g, the perfect apple-season nod.
Between the pumpkin regatta, haunted history, and grown-up costume parties, Halloween in Stillwater finds a way to charm just about everyone. From family memory-making to a mellow autumn night in, local businesses and events make it easy to shape your Halloween tradition your way.
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