Walk down Fourth Street in the next few weeks and you'll start noticing them: straw-stuffed figures propped in doorways, dressed in whatever a shop happens to have lying around. A vintage clothing store might send its scarecrow out in a sequined jacket. A dental office might go for something dryly clever. It looks like seasonal decorating, the kind every downtown does once the calendar turns toward October.
It isn't just that. Every one of those scarecrows is on the ballot in a contest that downtown White Bear Lake's own business owners run for themselves, and the business that wins gets the kind of attention no amount of decorating alone would buy. Understanding that changes how you look at Fall Fest weekend, whether you're strolling it for the first time or the tenth.
A Three-Day Stretch, Not One Big Afternoon
Fall Fest isn't a single event with a single start time. It's three separate things happening on the same few blocks over a Thursday-through-Saturday run in late September, and each one rewards a different kind of visit. Last year's version, held September 25 through 27, laid out the pattern:
- Thursday, 5 to 8 p.m. Ladies Night Out sends shoppers through downtown storefronts for an evening built around browsing rather than buying anything in particular.
- Thursday through Saturday, 9 a.m. to 8 p.m. The Scarecrow Stroll runs the full three days. This is the voting window. Stroll the shops, look at what each business built, and cast a vote for your favorite before the tally closes.
- Saturday, noon to 3 p.m. Polka & Pumpkin Painting takes over Railroad Park at Fourth Street and Highway 61, with live polka music and free pumpkin painting for kids while supplies last.
Main Street posts the confirmed dates and times for this year's event on its own site closer to the date, so it's worth a quick check before you plan around it. But the shape holds steady year to year: come only on Saturday afternoon and you'll catch the park event but miss two full days of scarecrow voting. Come Thursday evening for Ladies Night Out and you're seeing the displays before the crowd has had its say. The people who get the most out of the weekend treat it as three separate outings, not one.
The Contest Every Shop Owner Takes Personally
Fall Fest is organized by White Bear Lake Main Street Inc., a nonprofit run by board members who own businesses inside the downtown special service tax district. It's been around since 2018, which makes it younger than a lot of the traditions people assume have been part of White Bear Lake forever. The event was built with a specific goal: give downtown a family-friendly reason to show up in the shoulder season between summer's Marketfest and the holiday rush.
The scarecrow contest is where that goal gets personal. Businesses build their entries with an eye on what will actually win votes, and the shops with retail inventory have an obvious edge. Emily Blake, co-owner of the vintage store Oldies & Goodies, has described the entries as pulling double duty. One year the shop dressed a scarecrow as a Golden Girl. Another year it went Beetlejuice.
"It is always fun to try to think of a different theme for a scarecrow and incorporate some of the vintage clothing of our store. Since we are a clothing store, it is advertising at the same time."
That's the mechanism. A scarecrow in a doorway looks like a seasonal courtesy. For a shop like Oldies & Goodies, it's a free three-day window display voted on by the entire town, with the prize going to whichever business tells its story best without saying a word. The winning business gets bragging rights. Every voter gets entered into a drawing for a "bear basket," a prize pooled from goods donated across downtown, so the contest doubles as a way of routing foot traffic past businesses a shopper might otherwise walk right past.
Where the Pumpkins Actually Come From
The pumpkins used for Saturday's painting activity in Railroad Park aren't sourced from a wholesaler. They're donated by Pine Tree Apple Orchard, a detail easy to miss but worth knowing if you're the kind of resident who likes understanding how a town's small events actually get built. A free kids' activity in a city park still runs on a local supply chain, one orchard's harvest becoming another organization's programming, with neither business paying the other and both getting their name in front of the same crowd.
It's a small thing. It's also the same logic running underneath the entire weekend: nothing about Fall Fest depends on outside vendors or a big-budget production company. It's downtown institutions trading favors and foot traffic with each other, in public, for three days a year.
The Quieter Fall Ritual Two Blocks Away
While the storefronts fill with scarecrows, the White Bear Lake Area Historical Society runs its own calendar out of the White Bear Lake Armory at 2228 Fourth Street. Earlier this year the Society split its long-running Lake Avenue walking tour into two separate guided routes, both departing from the Armory: one heading toward the Boatworks Commons to trace the history of the resorts, boat builders, and summer cottages that once lined that stretch of shore, the other continuing on to Memorial Beach. The two routes weren't chronological, so either one worked as a standalone outing, each running $20 for the general public and $15 for members with a discount code.
The tour worth building a fall Saturday around is the Society's Gangster Bus Tour, a recurring seasonal offering rather than a one-time date. It's a guided ride to the hideouts and hangouts used by Prohibition-era gangsters around White Bear and Bald Eagle Lakes, including a former Mahtomedi speakeasy, with departures from the Armory at 10 a.m. and 11:30 a.m. running about an hour. Tickets run $30 for the general public and $25 for Historical Society members.
None of this is tied to Fall Fest on the calendar. It's simply the other thing White Bear Lake does with autumn: while downtown businesses turn their storefronts into a public vote, a few blocks away a different local institution uses the same season to pull people back into the town's own history. Both are proof that the town's fall calendar isn't one event with everything else as filler. It's several organizations, each running its own version of the same instinct, that the turn of the season is a reason to bring people back downtown.
How to Actually Spend the Weekend
If you're a longtime resident deciding how much of this to actually do, the sequence that gets the most out of three days looks something like this: catch a Gangster Bus Tour on Saturday morning, spend Thursday evening wandering Ladies Night Out with no particular shopping list, and vote on scarecrows any time between Thursday and Saturday before the tally closes. Save Saturday afternoon for Railroad Park, where the polka music and pumpkin painting make a natural stopping point after a morning tour.
None of it requires advance planning beyond knowing the windows. The Scarecrow Stroll voting stays open the whole three days, the historical tours run on their own separate schedule, and Railroad Park's event is a fixed three-hour block on Saturday. You can do all of it in a weekend or pick the one piece that fits your calendar, and either way you'll have seen more of what downtown White Bear Lake actually does with its own fall season than a single festival visit would show you.
What the weekend adds up to is a small but useful lesson about how this town works. The businesses along Fourth Street aren't waiting for the city to program their downtown. They built their own contest, picked their own prize, and turned decorating into marketing without anyone having to say so out loud. That's the kind of detail you only notice once you've lived here long enough to look twice at a scarecrow.
If you're already part of this community, I hope this gives you one more reason to spend a Saturday downtown. And if you're the kind of person who reads local detail like this and starts wondering what it would mean to actually live here, I'd love to talk. You can reach Jen Azure any time, no pressure, just a conversation about what this corner of Minnesota has to offer.
