Top Simcoe County Weekend Events to Enjoy This Winter

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Weekend Guide for Jan 23rd to 25th

If you’re looking for Simcoe County weekend events, this winter lineup offers something for every interest. From celebrating community and inclusion on the slopes, to tasting local flavours at participating restaurants, gliding across scenic skating rinks, and enjoying meaningful arts experiences, these events showcase the best of the region. Whether you’re planning a full itinerary or a spontaneous outing, this weekend is packed with ways to connect, explore, and enjoy Simcoe County.

Locallicious 2026 – First Weekend Celebration

Location: Various participating restaurants across Barrie & Simcoe County, Ontario, Canada

When: Friday, January 23 to Sunday, February 8, 2026

Dive into the first weekend of Locallicious, Barrie’s premier culinary festival celebrating the creativity and flavour of local restaurants. Join friends and neighbours as eateries across the region offer special prix-fixe menus (about $35–$45) featuring appetizers, entrées and desserts that showcase unique tastes and community spirit. It’s a delicious way to support local chefs, explore new spots and savour great food with good company. More info here.

Barrie Women’s Show 2026

Location: Bradford Greenhouses Garden Gallery, 4346 Highway 90, Springwater, Ontario, Canada

When: Saturday, January 24 from 10 AM to 5 PM to Sunday, January 25 from 10 AM to 4 PM

Celebrate spring with friends at the Barrie Women’s Show, a vibrant and inclusive weekend event packed with live fashion shows, inspiring guest speakers, wellness and beauty insights, food and decor ideas, and unique finds from local makers. This welcoming community-focused trade show offers fun and inspiration for everyone, with proceeds from ticket sales supporting Roots For Youth. More info here.

The Skate Escape 2026

Location: Friday Harbour Resort, 3999 Friday Drive, Innisfil, Ontario, Canada

When: Open Thurs to Sunday (weather permitting)

Slide into winter magic with The Skate Escape at Friday Harbour Resort! This festive outdoor experience invites everyone to glide across a beautifully lit rink. Visitors can also try snowshoeing, fat biking or cross-country skiing, and enjoy warm treats, seasonal sips and local shopping along the Promenade. With rentals available and free rink access (weather permitting), it’s a cheerful way to spend time with friends and family this season. More info here.

Pride Weekend 2026

Location: Horseshoe Valley Resort, 1101 Horseshoe Valley Rd W, Barrie, Ontario, Canada

When: Friday, January 23 to Sunday, January 25, 2026

Get ready to shine at Horseshoe Valley Resort’s fourth annual Pride Weekend celebration, a welcoming winter event full of colourful community spirit and outdoor fun for everyone! From lively rainbow-skiing and glow tubing to guided snowshoeing under the stars. This inclusive weekend invites guests of all ages to celebrate diversity, connect with others and enjoy scenic snowy slopes in a friendly, joyful atmosphere. More info here.

Artist Talk: “Rising Up and Reaching Out” with Tom Wilson

Location: Midland Cultural Centre, 333 King Street, Midland, Ontario, Canada

When: Saturday, January 24 from 2 PM to 4 PM

Join the Midland Cultural Centre for a heartfelt artist talk with celebrated Canadian musician and visual artist Tom Wilson. In this welcoming community event, Tom shares insights into his exhibition Rising Up and Reaching Out. He will be blending his powerful visual art with stories, readings from his memoir and a stirring a cappella performance. It’s an inspiring afternoon of creativity and connection for art lovers of all ages. More info here.

With so many Simcoe County weekend events happening, it’s the perfect time to get out and experience what’s local. From food and culture to outdoor winter fun, these events bring people together and highlight the vibrant communities across the county. Support local businesses, try something new, and make the most of the season by enjoying everything Simcoe County has to offer this weekend.