Royal Oak Holidays 2026: Cookie Crawl, Santa and Grinch Visits, and Three Free December Weekends

Royal Oak Holidays returns for three consecutive weekends from Friday, December 4 through Sunday, December 20, 2026, and the program is free, which makes it one of the most accessible holiday seasons in Oakland County for families with young children. The City of Royal Oak runs the season through its official Royal Oak Holidays program, and the 2026 lineup includes the Cookie Crawl, visits with Santa and the Grinch, horse and wagon rides, holiday markets, ice sculptures, and ice skating at The Rink at Centennial Commons.

The Cookie Crawl takes place Sunday, December 6, from noon to 4 p.m., when families visit downtown Royal Oak businesses to collect 18 locally sourced, handcrafted cookies. Participants buy a Cookie Pass and check in at Stagecrafters at 415 South Lafayette Avenue between 11:30 a.m. and 3 p.m. to pick up a cookie tin, the event map, and the pass itself.

Visits with Santa run all three weekends, on Fridays from 5 to 7 p.m. and Saturdays and Sundays from noon to 4 p.m., at various downtown locations. The Grinch Weekend wraps up the season on Saturday, December 19 and Sunday, December 20, with Grinch visits and activities across the downtown. Horse and wagon rides run on Fridays and Saturdays during the season, on December 5, 11, 12, 18, and 19, from 5 to 9 p.m., with pick up and drop off on Troy Street across from Royal Oak City Hall.

The season also brings back the holiday toy drive and ice sculptures within the December 4 through 20 window, and the official site at royaloakholidays.com is where the exact dates for those two pieces get published as they are set. The holiday markets run all three weekends around Centennial Commons, and The Rink at Centennial Commons opens for the winter, so an afternoon can combine skating, shopping, and a cookie crawl in one walkable downtown trip.

For families considering Royal Oak as a place to live, a free holiday season programmed across three full weekends in the downtown is a practical example of how the city keeps its public spaces active through the winter. Because event details can shift, the official Royal Oak Holidays site at royaloakholidays.com is the page to check before heading out.

Sources: Royal Oak Holidays official website (royaloakholidays.com), Cookie Crawl, Santa, Grinch, and Horse and Wagon Rides pages. Information verified October 20, 2026.