Weekend Guide for February 27th to March 1st
Looking for exciting ways to spend your weekend across Simcoe County? Our Simcoe Winter Weekend Guide brings together community-focused events happening from February 27th to March 1st. Whether you’re cheering on young athletes, enjoying live local music, supporting meaningful causes, or experiencing inspiring theatre, there’s something happening close to home. Bundle up, gather your friends and family, and make the most of this vibrant winter weekend across Barrie, Orillia, and beyond.
Coldest Night of the Year 2026
Location: Various communities across Canada, including locations in Simcoe County
When: Saturday from 4:00 PM to 7:00 PM
Join neighbours for a meaningful winter walk supporting local charities helping people facing hunger, homelessness, and hardship. Choose a 2 km or 5 km route and enjoy a welcoming, family-friendly atmosphere filled with community spirit. It’s a chance to connect with others while making a real impact close to home. Bundle up, bring your team, and walk together for a powerful cause. More info here.
Infinity Performing Arts Studio presents Lost Heroes of Oro
Location: Georgian Theatre, 1 Georgian Drive, Barrie
When: Friday from 7:00 PM to 9:00 PM; Saturday from 2:00 PM to 4:00 PM and 7:00 PM to 9:00 PM
Experience an inspiring theatrical journey celebrating the courage and resilience of Black hero Richard Pierpoint. Through powerful storytelling, music, and dance, this community production honours an important chapter of Canadian history. It’s a moving performance designed to connect generations and spark meaningful conversation. Bring family and friends for an evening that is both entertaining and educational. More info here.
Ontario Winter Games – Week 2
Location: Multiple venues across Orillia and surrounding areas
When: Friday through Sunday from 9:00 AM to 6:00 PM
The second weekend of the Ontario Winter Games fills Orillia with energy as young athletes compete across a variety of winter sports. Venues throughout the city come alive with competition, teamwork, and hometown pride. It’s a wonderful opportunity to support Ontario’s rising talent while enjoying a lively community atmosphere. Cheer from the stands and celebrate the excitement of winter sport. More info here.
Live Music at Couchiching Craft Brewing Co.
Location: 162 Mississaga Street East, Orillia
When: Saturday from 7:30 PM to 10:30 PM
Spend your Saturday evening enjoying live local music in a warm and welcoming downtown setting. With handcrafted brews and great company, this cozy brewery offers the perfect spot to unwind after a busy week. The lively atmosphere and talented performers create a relaxed night out with friends or neighbours. Settle in, raise a glass, and enjoy the sounds of the community. More info here.
From uplifting performances and energetic competitions to cozy brewery nights and meaningful fundraisers, this weekend truly showcases the spirit of our region. No matter what you choose, you’ll find ways to connect and celebrate locally. Keep this Simcoe Winter Weekend Guide handy and make the most of everything happening close to home.
