The annual Holiday Stroll is a cherished tradition with which Whitefish Bay kicks off the holiday season.

Held each year on the Friday following Thanksgiving, the Holiday Stroll features incredible shopping specials and entertainment throughout the evening, including a parade, tree lighting ceremony, food, music, and more. It's the perfect opportunity to enjoy a free pony, train, or trolley ride, visit Santa and his reindeer, and conveniently cross things off your holiday list.

The Holiday Stroll starts the season in a relaxed atmosphere, with scenes from the Nutcracker performed live in store windows and plenty of free family-friendly activities while shops stay open late with holiday specials and complimentary treats.

Revisit refined shopping within our walkable and family-friendly shopping district when you bring your friends and loved ones for a stroll along Silver Spring Drive to kick-off the holiday season during the Whitefish Bay Holiday Stroll.