Weekend Guide for Dec 19 to 21
Looking for something special to enjoy this season? Our guide featuring Simcoe winter outings highlights the best festive events and winter activities happening across the region. From creative workshops and holiday markets to magical family attractions and snow-filled adventures, this curated list brings together the season’s most heartwarming experiences. Whether you’re planning a day with friends or creating memories with family, you’ll find plenty of ways to celebrate the joy of winter right here in Simcoe County.
Handmade Holidays at Five Points
Location: Five Points Theatre, 1 Dunlop Street West, Barrie
When: Friday, December 19, 2025 from 6:00 PM to 9:00 PM
Celebrate the season with friends at this cozy, creative evening designed for grown-ups to unwind with festive cheer! At Handmade Holidays, you’ll rotate through hands-on craft stations to make four thoughtful holiday gifts. From stovetop potpourri and giftable hot chocolate mixes to unique ornaments and greenery arrangements. All materials are included, and the bar and concessions will be open for even more seasonal fun. More info here.
Winter Break Activities at Simcoe County Museum
Location: Simcoe County Museum, 1151 Highway 26, Minesing, ON
When: Saturday, December 20, 2025 to Sunday, January 4, 2026, from museum opening times (typically morning to afternoon)
Enjoy carefree winter fun with the whole family at the Simcoe County Museum’s Winter Break Activities! From December 20 to January 4, drop in for hands-on crafts, outdoor explorations, seasonal games, tasty treats and themed daily activities that spark curiosity and connection. It’s a cheerful way to embrace the holidays together, explore heritage exhibits, and make joyful memories in a welcoming community setting. More info here.
SZN5 Snow Show
Location: Orillia Opera House, 20 Mississaga St W, Orillia, ON
When: Friday, December 19, 2025 from 6:00 PM to 9:00 PM
Come together for a heartwarming celebration of the season at the SZN5 Snow Show, a festive annual holiday performance by Titanium Arts Lab at the historic Orillia Opera House. This joyful event brings dance, music and community spirit together in an entertaining showcase featuring talented performers from the Academy and Company programs. It’s a perfect way to welcome the holidays with friends and family in a warm, welcoming atmosphere. More info here.
Drysdale’s Christmas & Holiday Village
Location: Drysdale’s Tree Farm, 6635 Simcoe County Rd 56, Egbert, ON
When: Saturdays & Sundays from November 15 to December 21, 2025, 10:00 AM – 4:00 PM
Step into a weekend winter wonderland at Drysdale’s Christmas & Holiday Village, where family-friendly festive vibes fill the crisp air. Wander through snowy trails and enjoy live carolling, horse-drawn wagon rides, cozy bonfires with marshmallow roasting, holiday music, magicians, visits with Santa & Mrs. Claus, and delicious refreshments. Browse fresh and pre-cut trees or explore unique gifts in the Evergreen Store while making warm holiday memories together. More info here.
Winter’s Gift Holiday Market
Location: Blue Mountain Foundation for the Arts, 65 Simcoe Street, Collingwood, ON
When: Saturday, December 20, 2025 from 11:00 AM to 3:00 PM (also running Wednesdays–Saturdays weekly through January 3)
Get into the holiday spirit with this warm and welcoming Winter’s Gift Holiday Market. Where over 30 local artists and craftspeople share their unique creations. From paintings and pottery to jewellery, textiles and festive decorations. It’s the perfect place to meet makers, shop thoughtful gifts and support local arts. Enjoy browsing one-of-a-kind treasures while celebrating community creativity this season. More info here.
Winter Activities at Horseshoe Resort
Location: Horseshoe Resort, 1101 Horseshoe Valley Rd W, Barrie, ON
At Horseshoe Resort, winter is packed with excitement for every age and interest. Guests can enjoy skiing, snowboarding, snow tubing, snowshoeing, fat biking, and cozy après-ski experiences, all set against the stunning snowy landscape of Horseshoe Valley. With family-friendly fun, scenic trails, and activities running all winter long, it’s an inviting spot to embrace the season, stay active, and make unforgettable memories in a welcoming resort atmosphere. More info here.
With so many festive activities to explore, Simcoe winter outings offer endless opportunities to enjoy the magic of the season. Whether you’re shopping local, getting creative, meeting Santa, or embracing the snow, every event adds a little extra warmth to the winter months. We hope this guide helps you discover new favourites and inspires you to get out and celebrate everything our community has to offer this holiday season.