Milwaukee upgrades visitor planning with AI-driven tools and guides

AI guide across town

Originally launched in 2025 as a tool primarily for meeting planners, Ask LeRoy now adds a new layer of trip-planning expertise for travelers of all kinds. Visitors scan a QR code, no app required, to interact with an avatar of digital Packers legend, NFL Pro Football Hall of Famer, and longtime Milwaukeean LeRoy Butler. They then receive real-time recommendations on what to do, where to eat and what is nearby, all powered by Visit Milwaukee’s content.

Visitors can find Ask LeRoy at 3rd Street Market Hall, ThriveOn, Sherman Phoenix, Visit Milwaukee’s visitor information center located within Baird Center, Visit Milwaukee’s offices in the Enerpac Building, as well as Visit Milwaukee’s airport welcome kiosk in the baggage claim area at Milwaukee Mitchell International Airport.

The 2026 Official Visitors Guide will soon be available at more than 125 welcome centers and kiosks across Wisconsin and northern Illinois, as well as in mailboxes and on digital devices worldwide. The guide highlights Milwaukee’s flavor through stories about its accessible lakefront beaches, its reputation as the City of Festivals, thanks to an ever-expanding lineup that includes the new Freshwater Food & Wine Festival, and ways to explore popular classics, like creating a personalized custard trail or Miller High Life trail. The guide also showcases a thriving maker scene shaped by artisans, vintage curators and independent shops like All Goods and Refresh Vintage.

The 2026 Visitor Map features 200 local businesses, attractions, neighborhoods, dining districts and visitor amenities. These are located across Milwaukee and Wauwatosa. The map serves as an easy companion for navigating Milwaukee, no matter the mode of transit.

Map King, the digital foundation for Visit Milwaukee’s visitor experience, has been significantly enhanced for 2026. Updates include a new promotions tab that comes preloaded with all Hotel Month partner deals.

Promotions and guides now appear within individual partner placemarks, helping users move from inspiration to action without leaving the platform. This year, Map King is introducing an expanded map of 3rd Street Market Hall, including detailed vendor information and wayfinding to help visitors navigate the food hall. This is just the first live digital map from the geo-spatial tech company, with more detailed partner maps planned for the coming year.