Step back in time at the Maidstone Bicentennial Museum for a War of 1812 reenactment, part of a weekend full of diverse events in Windsor. From an adult book fair to a 90s-themed boat cruise, there is something for everyone.
Adult Book Fair at Walkerville Brewery
Remember the excitement of school book fairs? Walkerville Brewery (525 Argyle Rd.) is reviving that nostalgia on Saturday, May 23, from 12 to 5 p.m. Local vendors and independent bookshops will set up shop, offering a curated selection of reads. While browsing, visitors can enjoy a pint from the brewery's craft beer and cider selection. It is a perfect blend of literature and libations for adults.
War of 1812 Reenactment
History enthusiasts can step back to the early 19th century at the Maidstone Bicentennial Museum (1093 Puce Rd.) on Saturday, May 23. Participants from Fort Malden, Provincial Marine Amherstburg, Voyageur, and other groups will demonstrate period cooking, candle making, weaving, and historical weapons. Mini militia activities will engage younger visitors, and Indigenous contributions to the war will be highlighted. Battle skirmishes are scheduled for 11 a.m., 1 p.m., and 3 p.m. Admission is $8, with children age six and under free. The museum gift shop will also be open for souvenirs.
90s-Themed Boat Cruise
Party like it is 1995 aboard Windsor Premiere Cruises' Macassa Bay on Saturday, May 23. Guests are encouraged to don windbreakers, bucket hats, and baggy jeans for a 90s-themed dance party. DJ Chino will spin throwback hits during a four-hour cruise from 6 p.m. to 10 p.m. along the Detroit River. Tickets are $59 and available at windsorpremiercruises.com.
Local Theatre: The Price of Freedom
Arts Collective Theatre presents The Price of Freedom, a play set against the backdrop of the Underground Railroad in the Windsor-Detroit region. The cast includes University of Windsor drama students and community members, telling the story of John Anderson, a freedom seeker whose extradition case became a widely debated legal battle. The show runs at Hatch Studio Theatre (401 Sunset Ave.) on Friday, May 22. Tickets can be purchased at actwindsor.ca/event.
Swimming Showcase
Windsor's International Aquatic and Training Centre (401 Pitt St. W) hosts the 2026 Speedo Canadian Masters Swimming Championships from May 22 to 24. The three-day meet features 748 athletes representing 88 clubs from nine Canadian provinces, as well as swimmers from the United States and Great Britain. Competitions will take place across six sessions of timed finals at the downtown facility.
Family Fun: Leamington Fair and Art Session
The 178th Leamington Fair returns to the fairgrounds May 21 to 24, offering four days of rides, live entertainment, and tradition. Admission is reduced to $7 this year, with ride tickets sold separately. Highlights include a demolition derby, games, concerts, agricultural displays, local vendors, fair food, and a beer tent.
Art Windsor Essex invites families to get creative on Sunday, May 24, from 1 to 4 p.m. Drop in for a hands-on neurographic art session with artist Suela Prendi, where simple lines transform into bold, colourful designs. No registration is needed, and the program is free with gallery admission. All ages are welcome.
