Labour Day weekend is the perfect way to cap off the summer in Simcoe County. From family picnics and outdoor adventures to live music and late-summer festivals, there’s no shortage of things to do.
We’ve rounded up some of the best events happening across the region to help you make the most of the long weekend.
We’ve rounded up some of the best events happening across the region to help you make the most of the long weekend.
1. Pirate Party – Free (Extras Available for Purchase)
Port of Orillia | August 29 - September 1, 2025
Ahoy, mateys! Set sail for fun at the Pirate Party in Orillia, featuring live entertainment, themed activities, and plenty of food and drinks. Perfect for families and pirate fans of all ages, it’s a great way to bring some swashbuckling adventure to your weekend. Costumes encouraged!
2. Friday Night Live at the Coldwater Mill – By Donation
Coldwater Mill, Coldwater | Friday, August 29
Enjoy a summer evening of live music inside the historic Coldwater Mill. This long-running community series showcases local musicians in an intimate, one-of-a-kind setting. With admission by donation, it’s an affordable way to kick off the Labour Day weekend while supporting local arts and heritage.
3. Sunset Paddle – $45
Wye Marsh Wildlife Centre, Midland | August 29, 2025
Take in the beauty of late summer evenings with a guided sunset paddle through Wye Marsh. This relaxing excursion lets you explore the wetlands by canoe or kayak, while learning about the wildlife that calls the area home. A peaceful and memorable way to spend part of your long weekend.
Friday Harbour Resort, Innisfil | August 31, 2025
Start your morning lakeside with a refreshing pilates class at Friday Harbour. With views of Lake Simcoe as your backdrop, this session is perfect for anyone looking to stay active and recharge before a full day of weekend fun. No experience needed—just bring a mat and enjoy the fresh air.
5. Carnival Barrie – Free
Meridian Place & Downtown Barrie | August 30-31, 2025
Downtown Barrie will come alive with music, dancing, food, and vibrant cultural displays during Carnival Barrie. This free festival celebrates Caribbean culture and community, featuring live performances, kids’ programming, and delicious food vendors. Bring the whole family for an afternoon of sights, sounds, and flavours.
6. Movies in the Park – FreeRotary Aqua Theatre, Orillia | August 30, 2025
Pack a blanket, bring some popcorn, and enjoy an outdoor movie under the stars. Movies in the Park is a community favourite, offering a fun, free evening for families and friends. Check the schedule to see what’s playing this Labour Day weekend.
More info: orillialakecountry.ca/event
Pack a blanket, bring some popcorn, and enjoy an outdoor movie under the stars. Movies in the Park is a community favourite, offering a fun, free evening for families and friends. Check the schedule to see what’s playing this Labour Day weekend.
More info: orillialakecountry.ca/event
7. Barrie Labour Day Picnic – Free
Centennial Park, Barrie | September 1, 2025
A family tradition in Simcoe County, the Barrie Labour Day Picnic brings the community together for a full afternoon of activities. Enjoy live entertainment, kids’ games, vendors, food, and a chance to connect with neighbours as summer winds down. It’s a free, family-friendly way to celebrate the holiday by the waterfront.
A family tradition in Simcoe County, the Barrie Labour Day Picnic brings the community together for a full afternoon of activities. Enjoy live entertainment, kids’ games, vendors, food, and a chance to connect with neighbours as summer winds down. It’s a free, family-friendly way to celebrate the holiday by the waterfront.
8. Memories of Summer: Queen Flash Tribute – FREE
Stonebridge Town Centre, Wasaga Beach | August 30, 2025
Close out summer with an unforgettable concert experience in Wasaga Beach. “Queen Flash” brings the legendary music of Queen to life with high-energy performances and plenty of crowd favourites. It’s a perfect night of music, nostalgia, and celebration.
Tottenham, New Tecumseth | August 31, 2025
Step back in time aboard the South Simcoe Railway’s scenic train tour. This heritage ride takes you through the countryside in restored vintage coaches, offering a unique glimpse into Ontario’s past. A great choice for families and history buffs alike.
10. Back to School Bash at Tanger Outlets Cookstown – Free
Tanger Outlets, Cookstown | August 30, 2025
Why not make back-to-school shopping fun? Tanger Outlets Cookstown is hosting a special event with live entertainment, family activities, and exclusive deals throughout the Labour Day weekend. It’s the perfect mix of savings and celebration, helping you check off those last-minute school lists while enjoying a lively atmosphere.
Why not make back-to-school shopping fun? Tanger Outlets Cookstown is hosting a special event with live entertainment, family activities, and exclusive deals throughout the Labour Day weekend. It’s the perfect mix of savings and celebration, helping you check off those last-minute school lists while enjoying a lively atmosphere.
More Info: tanger.com/cookstown/events
No matter how you like to spend your Labour Day weekend—whether it’s relaxing by the lake, enjoying live music, or joining community celebrations—Simcoe County has something for everyone.
From all of us at The Walker Team, we wish you a safe, fun-filled holiday weekend!
