Weekend Guide for May 16th to 19th
Looking for the best Victoria Day weekend events in Simcoe County? Whether you’re into live music, local food, vintage shopping, or just soaking up the sunshine, there’s something exciting happening in every corner of the region. From Barrie to Blue Mountain, this guide has you covered with the best local events from May 16 to May 19, 2025.
Expect a mix of outdoor festivals, family-friendly markets, cultural celebrations, and evening entertainment—including fireworks and street parties! Keep scrolling to explore what’s going on near you and make the most of your long weekend in Simcoe County.
Victoria Day Weekend at Friday Harbour
Location: Friday Harbour Resort, Innisfil, ON
When: Friday, May 16 to Monday, May 19, 2025
Celebrate Victoria Day weekend at Friday Harbour with live music, shopping along the Promenade, recreation rentals, and a vibrant outdoor market. Highlights include a spectacular fireworks display over the harbour on Saturday at 10 PM and the Beach Club After Dark party from 11 PM to 2 AM. Enjoy DJ sets and live performances at CIBC Pier throughout the weekend. Click here for more info.
Portarama Family Festival
Location: Various venues in Port McNicoll, ON
When: Friday, May 16 to Sunday, May 18, 2025
Celebrate the 40th anniversary of the Portarama Family Festival over the Victoria Day weekend! Enjoy free live entertainment, a vibrant parade, family-friendly activities, delicious food, local vendors, and more. Highlights include a town-wide garage sale, car show, and fireworks. Events take place at Patterson Park, Talbot Park, the Library, and other community spaces. Click here for more info.
May Long Weekend at Blue Mountain
Location: Blue Mountain Village, 156 Jozo Weider Blvd, The Blue Mountains, ON
When: Saturday, May 17 to Monday, May 19, 2025
Kick off summer at Blue Mountain Village with a vibrant street party featuring live music, groove dancing, giant games, scavenger hunts, and campfire sing-alongs. Enjoy performances by artists like Genevieve Cyr, Mik Perlus, and Dean James, plus DJ sets and family-friendly activities all weekend long. Click here for more info.
Bikes, Brews & BBQs – May Long Weekend Bash
Location: Horseshoe Valley Resort, 1101 Horseshoe Valley Road West, Barrie, ON
When: Friday, May 16 to Monday, May 19, 2025
Kick off bike season at Horseshoe Resort with a weekend of trail riding, live music, craft brews, and BBQ on Ontario’s largest outdoor patio. Enjoy the Lap-A-Palooza challenge, vendor village, and performances on the Coors Outdoor Stage. The Bike Park opens daily from 11 AM to 6 PM, with beer tents and live music on Saturday and Sunday.
Ukrainian Vyshyvanka Day Festival
Location: Meridian Place, 30 Simcoe Street, Barrie
When: Sunday, May 18, 2025, from 11:00 AM to 5:00 PM
Celebrate Ukrainian heritage at the 3rd Annual Vyshyvanka Day Festival in downtown Barrie. Enjoy traditional music and dance performances, authentic foods, arts and crafts, and activities for all ages. Vyshyvanka Day highlights the significance of the embroidered shirt as a symbol of national pride and unity, making this a meaningful and fun event for the whole community. Click here for more info.
Sunshine City Vintage Bazaar Market
Location: 22 Matchedash St N, Orillia, ON
When: Saturday, May 17, 2025, from 10:00 AM to 4:00 PM
Hosted by My Moon Collective, The Lone Wolf Cafe, and Pocket Skate & Vintage, this outdoor market features a curated selection of vintage clothing, home goods, handmade creations, and more. Set in the parking lot next to The Lone Wolf Cafe, it’s a perfect spot to browse unique finds and support local vendors. Click here for more info.
No matter how you choose to spend it, there are many Victoria Day events in Simcoe County. These are shaping up to be packed with good vibes, local flavour, and unforgettable moments. Whether you’re dancing in the streets, treasure hunting at vintage markets, or catching a lakeside fireworks show, there’s no shortage of ways to make the most of the long weekend. Be sure to plan ahead, support local businesses, and soak up all the fun this region has to offer!