Marketing Minneapolis in winter is tricky business

In today’s newsletter: Urban winter champions take on downtown, Beth Kieffer Leonard passes the baton and it’s Joe Mauer vs. the Timberwolves.

The Minnesota Star Tribune
November 10, 2025 at 12:00PM
Minneapolis Foundation's R.T. Rybak speaks at a Winterapolis news conference on Nov. 3 along with Dayton's Holiday Market producer Mich Berthiaume as Santa Bear, Minneapolis Downtown Council's Adam Duininck and Meet Minneapolis' Melvin Tennant. (Allison Kaplan/The Minnesota Star Tribune)

Good morning and welcome to the very first issue of North Star Insider! We’ve created this newsletter as a place to share ideas and insights that help you plug into Minnesota’s business community. I’m new to the Strib, but I’ve been reporting on business, leadership and innovation for (ahem) many years. It’s a thrill to continue the conversation here — and conversation is exactly what this platform is meant to be, so please weigh in with your ideas, suggestions, and tips.

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R.T. Rybak, Melvin Tennant and Santa Bear rolled up to IDS Center on a bedecked holiday trolley last Monday (this is not a joke) to announce Winterapolis, the latest marketing effort aimed at creating some momentum for winter events in the city. Adam Duininck was there to voice support, on the heels of his Minneapolis Downtown Council pulling the plug on Holidazzle.

What’s new is a Nov. 28 tree lighting event at the IDS Crystal Court, paid for by the Rybak-led Minneapolis Foundation, with support from Xcel Energy and the Pohlad Family Foundation. Rybak, the city’s most relentless optimist, hopes it will illuminate reasons to come downtown this holiday season: a family photo by the Christmas tree and live entertainment, followed by dining and shopping holiday markets on Nicollet.

“There’s this idea that we’re supposed to convince the mythical person from Wayzata who hates downtown to come down,” Rybak said, “but the real holy grail is taking existing trips and expanding them. We’re trying to flood the zone with activities as we head into the hardest part of the year.”

There is some evidence behind the optimism. Last year, the Dayton’s Holiday Market drew 200,000 visitors to Nicollet Mall during its six-week run and generated $2 million in sales — nearly double the prior year — according to market producer Mich Berthiaume (the only downtown booster petite enough to fit inside that vintage Santa Bear costume). The fifth annual Dayton’s Holiday Market opens Thursday with a record 107 local vendors and a popup bar by Northeast distillery Earl Giles. Like the sold-out Dinner Du Nord in September, the Dayton’s market’s success indicates that people will come downtown for special events.

But then there’s January.

Rybak and Tennant, president and CEO of the nonprofit convention and tourism group Meet Minneapolis, acknowledged the city can’t program its way out of a deficit. All the Nutcrackers you can pack onto a holiday calendar won’t fill the empty storefronts along Nicollet.

But with fewer office workers to rely on, events take on increasing importance. Both Rybak and Tennant want to see Nicollet become purely pedestrian (Mayor Jacob Frey agrees, but there’s some opposition), to make it more of an ongoing destination. And if we really want to reanimate the streets more permanently, let’s talk about new uses of street-level spaces beyond retail. Case in point: The Social Lights’ dynamic first level office in the North Loop’s Steelman Exchange building, a spot originally intended for a restaurant. (We’ll save St. Paul for another day.)

Winterapolis isn’t only about downtown, nor is it new. Meet Minneapolis introduced the brand last year as a calendar to aggregate winter events. This year, the group hopes to make it a rallying cry.

And that sounds a lot like another winter festival, the Great Northern. I remember attending a kickoff event in 2017 at the Bachelor Farmer (RIP) where Great Northern board president Eric Dayton outlined an ambition to create the winter version of South x Southwest and Rybak urged Minnesotans to stop apologizing for cold weather.

On Wednesday, the Great Northern will announce its programming for the upcoming winter. Kicking off Jan. 28, the festival will run five days rather than 10. Last year, the festival included more than 50 events across Minneapolis and St. Paul, resulting in $2.1 million of economic activity, according to its 2024 impact report — but also a fair bit of confusion around the what and where. Executive Director Jovan C. Speller Rebollar realized it needed a home base.

This winter, the Great Northern will be rooted in and around St. Anthony Main: climate conversations, documentary films, food demos, an ice bar and the uber-popular sauna village, all taking place along one of the most picturesque streets in the city. Rebollar’s strategy: “Let’s get really clear about what we are, and then go national.”

Exec Moves

Beth Kieffer Leonard, partner-in-charge of Eisner Amper’s Minneapolis office, will pass the baton at the end of the year to Matt Brown, a partner in the business advisory firm’s Minneapolis Tax Advisory Group. Leonard, a champion of the startup community and advocate for women leaders, has led the office since 2008, when it was Lurie LLP. She played a key role in the 2022 merger with New York-based Eisner Amper, a move she said at the time was essential to continue growing with the pace of technology. She plans to remain a partner.

Brown, who worked under Leonard for 18 years, knows he has big shoes to fill. As he said in a statement: “I’m honored to carry forward her legacy: championing our people and clients, serving as a pillar in our community, and continuing to foster and grow the Minneapolis office.”

Former Twins star Joe Mauer, right, plays against the Timberwolves' Donte DiVincenzo during a recent celebrity ping pong fundraising event in Minneapolis. Mauer won the event after defeating Wolves guard Terrence Shannon Jr. (Courtesy of Constellation Fund)

Big Win

Add ping pong champ to Joe Mauer’s career stats. The Twins baseball legend beat Timberwolves guard Terrence Shannon Jr. in the annual celebrity ping pong event hosted by Wolves President of Basketball Operations Tim Connelly and his wife Negah. Each year they pick a Constellation Fund grantee to benefit from the fundraiser. Last week’s event raised more than $60,000 for St. Paul-based Keystone Community Services. Seems ping pong is the new charity chicken dinner.

In the News

Go west: A group of local business leaders, primarily in commercial real estate, are on their way to Denver this morning for a tour orchestrated by the Minneapolis Renaissance Coalition to bring back economic development ideas. Watch for a recap here next week.

Major Merger: Moss & Barnett will become part of Cozen O’Connor as of Jan. 1, adding 50 attorneys to the Philadelphia-based firm’s roster of 1,000 lawyers across 33 offices. This follows a prepandemic wave of high-profile law firm mergers involving Minnesota offices. The Twin Cities’ corporate hub and Moss & Barnett’s expertise in corporate law, real estate finance, energy and public utilities made it appealing to Cozen O’Connor, the firm’s chairman and CEO Michael Heller said.

Wake-Up Call: Sleep Number CEO Linda Findley has a plan to turn around the mattress company, after 11 straight quarters of losses, Patrick Kennedy reports.

about the writer

about the writer

Allison Kaplan

Allison Kaplan is Director of Innovation and Engagement for the Minnesota Star Tribune.

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