Weekend Guide for August 21st to 23rd
Summer is still going strong, and there are plenty of Weekend Adventures Near Barrie to enjoy from August 21st to 23rd. This week’s guide features live music and creative experiences in Cookstown, remarkable vintage vehicles in Minesing, an evening market in downtown Orillia and the opening weekend of the CNE in Toronto. Whether you are planning a family outing, meeting friends or exploring somewhere new, these events offer fun ways to connect with the community and make the most of your weekend.
Canadian National Exhibition Opening Weekend
Location: Exhibition Place, Toronto
When: Friday, August 21 to Sunday, August 23 from 10 a.m. to midnight
Celebrate the opening weekend of the Canadian National Exhibition with three lively days of entertainment, midway fun, creative exhibits, live performances, shopping and unforgettable fair food. Visitors of all ages can explore family-friendly attractions such as Kids’ World and The Farm, enjoy exciting shows or spend time discovering something new with friends and neighbours. This beloved Toronto tradition offers a welcoming way for families, couples and groups to share memorable experiences while making the most of a summer weekend together. More info here.
Gussapolooza Music & Arts Festival
Location: Georgian Bay Steam Show Grounds, 4635 15th Line, Cookstown
When: Friday, August 21 to Sunday, August 23
Gussapolooza brings music lovers, families and creators together for three days of live entertainment and artistic discovery. Explore performances from independent musicians across three stages, interactive installations, hands-on workshops, artisan vendors and local food trucks. Younger visitors can enjoy the Kids Zone, while adults can visit the beer garden or wellness area. With camping available and children 12 and under admitted free with a paying adult, this welcoming festival offers plenty of ways to connect, create and celebrate. More info here.
Canadian Festival of Old Cars
Location: Simcoe County Museum, 1151 Highway 26, Minesing
When: Saturday, August 22 and Sunday, August 23 from 10 a.m. to 4 p.m.
Step back into the golden age of motoring at the Canadian Festival of Old Cars, a family-friendly celebration featuring authentic pre-war vehicles from the late 19th and early 20th centuries. Watch these remarkable machines cruise through the museum grounds, admire their century-old engineering and join in special car games. Live music and hands-on history add to the nostalgic atmosphere, making this a memorable weekend outing for automobile enthusiasts, history lovers and curious visitors of all ages. More info here.
Vintage Pop-Up Market – Starry Night Orillia
Location: Orillia Museum of Art & History, Downtown Orillia
When: Saturday, August 22 from 11 a.m. to 10 p.m.
Discover vintage treasures and local creativity during this one-day pop-up market in the heart of downtown Orillia. Carefully selected vendors will offer retro clothing, nostalgic décor, collectibles, stained-glass art, upcycled accessories and other handmade goods. Whether you are searching for a distinctive statement piece, a thoughtful gift or the excitement of finding a hidden gem, the market offers plenty to explore. Visitors can also enjoy the museum and other Starry Night activities happening throughout the downtown core. More info here.
From exciting festivals and nostalgic vehicles to vintage shopping and one of Ontario’s favourite summer traditions, there is something for every interest this weekend. These Weekend Adventures Near Barrie offer opportunities to support artists and local vendors, discover regional history and spend meaningful time with family and friends. Choose an event close to home or plan a day trip and enjoy everything the region has to offer from August 21st to 23rd.
Looking for more things to do in Simcoe County this weekend? Check back each week for our latest local event guide featuring Cookstown, Minesing, Orillia, and surrounding communities.
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