Winterland brings holiday fun back to Gallagher Way next month

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Wrigleyville's Gallagher Way is bringing holiday cheer back this December with its Winterland event, featuring an array of festive activities for the whole family. 

Winterland kicks off on Dec. 6. The event will run every weekend through Dec. 22, transforming the space near Wrigley Field into a winter wonderland with holiday lights, seasonal markets and cheerful entertainment.

The festivities begin with the Winterland Tree Lighting Ceremony on Dec. 6 at 6 p.m., a community celebration that includes live entertainment, free hot chocolate, and holiday giveaways. Santa’s Workshop will also be open throughout the season, where families, including pets, can take photos with Santa every Thursday through Sunday.

Gallagher Way will also introduce a Winter Market during the first weekend, offering holiday shoppers a variety of vendors selling everything from decorations to gourmet treats. Also debuting is a Winter Carnival, available for the final two weekends, bringing festive rides for visitors. 

Winterland hours

  • Thursday and Friday: 4 p.m. - 9 p.m.
  • Saturday: 11 a.m. - 9 p.m.
  • Sunday: 11 a.m. - 7 p.m.

Guests can take part in wreath-making workshops on Dec. 7-8, holiday Movie Nights and themed pop-ups at nearby venues like Hotel Zachary, Mordecai and Lucky Dorr.

At Hotel Zachary, families can enjoy Teddy Bear Tea on weekends, while the hotel’s Globes on the Terrace offers cozy private spaces with holiday treats and games for groups. Those looking for a festive night out can enjoy holiday-themed cocktails at Mordecai’s Mistletoe Pop-Up Bar or seasonal beers at Lucky Dorr’s Lucky Lodge.

For more details on event hours, tickets, and reservations, visit the Gallagher Way website.