There’s nothing quite like the holiday season in Simcoe County. From glowing light displays and festive markets to the smell of fresh pine and the sound of laughter downtown, the whole region comes alive with cheer.
At The Walker Team, we love celebrating everything that makes our communities special — and this time of year is no exception. Whether you’re shopping local, enjoying a visit with Santa, or taking in the magic of a tree lighting, there’s something for everyone to experience this season. Here’s our guide to the most festive events happening across Simcoe County — perfect for a joyful day out with family and friends!
Orillia Christmas Farmers’ Market
November 14, 21, & 28
Orillia Public Library | Free Admission
The beloved Orillia Farmers’ Market gets a festive twist throughout November. Explore local vendors offering holiday baking, handmade gifts, and seasonal produce. It’s the perfect way to support Simcoe County farmers and artisans while embracing the small-town Christmas charm.
More Info: Orillia Christmas Farmers’ Market
Santa Claus Parade & Tree Lighting Celebration
November 15
Downtown Barrie | Free Admission
Downtown Barrie | Free Admission
Downtown Barrie comes alive with holiday cheer during this magical evening celebration. The Santa Claus Parade winds through the streets with beautifully lit floats, marching bands, and plenty of festive spirit — all leading up to the breathtaking Noella Tree Lighting at Meridian Place. Families can enjoy live entertainment, hot cocoa, and the joy of watching Barrie’s waterfront glow with Christmas lights as Santa officially kicks off the holiday season.
More Info: Barrie - Santa Claus Parade & Tree Lighting
Alliston Santa Claus Parade
November 15
Alliston | Free Admission
The Alliston Santa Claus Parade brings festive excitement to the heart of town with colourful floats, cheerful music, and glowing holiday lights. Organized by the Rotary Club of Alliston, this beloved evening parade features community groups, local businesses, and, of course, Santa himself waving to the crowd. It’s a joyful kickoff to the Christmas season that families look forward to every year.
More Info: Alliston - Santa Claus Parade
Christmas Market at The Coldwater Mill
November 15
Coldwater | Free Admission
Step back in time at this charming Christmas market held inside the historic Coldwater Mill. Browse a variety of artisan vendors, discover local crafts, and treat yourself to warm drinks and baked goods while holiday music fills the air. It’s a cozy event that beautifully captures the small-town spirit of the season.
More Info: Coldwater Mill - Annual Christmas Market
Sugar Plum Fair Craft Show
November 15–16
Nottawasaga Inn Resort, Alliston | Adults $7.50, kids under 12 free
Get your holiday shopping started at one of Ontario’s most popular craft fairs. The Sugar Plum Fair features more than 100 local artisans showcasing handmade gifts, décor, and festive treats. From intricate jewellery to gourmet goodies, there’s something for everyone on your list — plus plenty of inspiration for your own holiday décor.
More Info: Nottawasaga Resort - Sugar Plum Fair Craft Show
Outdoor Christmas Market at Quayle’s Brewery
November 15-16 & 22–23
Coldwater | Free Admission
Quayle’s Brewery brings together local makers, live music, and festive food for this annual outdoor Christmas Market. Sip on craft beer or hot cider as you browse dozens of vendors in the crisp country air. The twinkling lights, rustic setting, and family-friendly atmosphere make it a must-do event this season.
More Info: Quayle’s Brewery - Outdoor Christmas Market
Magic of Lights
November 21 – January 3
Springwater Provincial Park, Midhurst | Approx. $30 per car
Pack up the car, cue your favourite Christmas playlist, and take a drive through this dazzling light display at Springwater Park. Magic of Lights features over a million LED lights and giant holiday scenes that sparkle from every angle. It’s a holiday classic for families, couples, and anyone who loves a little extra sparkle.
More Info: Barrie - Magic of Lights
Friday Harbour Holiday Market
Select Dates November 21 to December 28
Friday Harbour Resort, Innisfil | Free Admission
Stroll through a festive lakeside village lined with holiday huts, twinkling lights, and the scent of roasted chestnuts. The Friday Harbour Holiday Market features local artisans, live entertainment, and plenty of family activities — all set against a stunning waterfront backdrop. Don’t miss the magical tree-lighting ceremony that kicks off the season!
More Info: Friday Harbour - Holiday Market
Orillia’s 21st Annual Tree Lighting Ceremony
November 21
Orillia Opera House | Free Admission
Gather in downtown Orillia as the city’s tree comes to life in a dazzling evening celebration. Families can enjoy live music, entertainment, and plenty of festive spirit as the Opera House courtyard fills with twinkling lights. A beautiful way to start your holiday season in Orillia.
More Info: Orillia’s 21st Annual - Tree Lighting Ceremony
Cookstown Light Up Night
November 22
Downtown Cookstown | Free Admission
Downtown Cookstown transforms into a winter wonderland for this annual Light Up Night celebration. The streets sparkle with lights and music as families gather for the tree lighting, wagon rides, visits with Santa, and hot chocolate from local shops. It's a small-town holiday charm at its very best.
More Info: Cookstown - Light Up Night
Midland Santa Holiday Parade
November 22
Midland | Free Admission
Downtown Midland comes alive with the sights and sounds of the season as the annual Santa Claus Parade makes its way through the heart of town. Featuring colourful floats, live music, local groups, and of course, Santa himself, this long-standing community tradition captures the joy and togetherness that make the holidays so special. Families can enjoy hot chocolate, shop local downtown, and soak in the festive waterfront atmosphere.
More Info: Midland - Santa Holiday Parade
Wasaga Beach Santa Claus Parade
November 22
Wasaga Beach | Free Admission
Kick off the holidays with a beachside twist at the Wasaga Beach Santa Claus Parade! The streets come alive with twinkling floats, festive music, and community spirit as families gather to welcome Santa to town. After the parade, enjoy hot chocolate, local food vendors, and the lighting of the Christmas tree near Nancy Island. It’s a heartwarming celebration of holiday joy in one of Simcoe County’s most vibrant communities.
More Info: Wasaga Beach - Santa Claus Parade
Orillia Santa Claus Parade
November 22
Downtown Orillia | Free Admission
Downtown Orillia is bursting with holiday cheer as the Christmas Kickoff and Santa Claus Parade return for another festive year. The streets fill with twinkling lights, decorated floats, live music, and community spirit as Santa makes his grand entrance to officially launch the season. With family-friendly activities, downtown shopping, and plenty of photo ops, it’s a joyful celebration that brings everyone together for a true small-town Christmas experience.
More Info: Orillia - Santa Claus Parade
Angus Santa Claus Parade
November 22
Angus | Free Admission
This daytime parade fills downtown Angus with floats, festive costumes, and local cheer. It’s a wonderful event for families — kids can wave to Santa, collect candy, and enjoy the excitement as the community comes together to celebrate.
More Info: Angus - Santa Claus Parade
Merry Makers Market
November 22
Shanty Bay | Free Admission
This popular local market brings together talented artisans and small businesses offering everything from home décor and knitwear to candles, cookies, and handmade ornaments. With holiday music playing and the smell of baking in the air, it’s an easy and enjoyable way to shop local while supporting your community.
More Info: Shanty Bay - Merry Makers Market
Enchanted Holiday Forest of Lights
November 28 – 29 & December 5 – 6
Drysdales Tree Farm, Egbert | Tickets available online
For two magical weekends, Drysdale’s Tree Farm transforms into an illuminated wonderland filled with glowing art, live music, and festive fun. Stroll through the Enchanted Holiday Forest of Lights, enjoy a night market inside the holiday greenhouse, and warm up by the fire with marshmallows and mulled drinks. With live entertainment, local vendors, and a cozy, candlelit atmosphere, this is one of Simcoe County’s most enchanting new holiday traditions.
More Info: Enchanted Holiday Forest of Lights
Gilford Christmas Market
November 29
Gilford Local Eatery | Free Admission
This charming market celebrates all things handmade and heartfelt. Discover beautiful gifts, baked goods, and local crafts while kids enjoy holiday activities and a visit from Santa. It’s a warm, family-friendly community event where neighbours gather to celebrate the season.
More Info: Gilford - Christmas Market
The Handmade Holiday Market
November 29-30
Creemore Legion | Free Admission
A holiday shopping tradition for many, The Handmade Holiday Market showcases local artisans. You’ll find everything from pottery and artisan chocolates to cozy knitwear and custom wood décor. With a cheerful atmosphere, great food, and creative makers, it’s a must-visit weekend for holiday shoppers.
More Info: Creemore - The Handmade Holiday Market
CPKC Holiday Train
November 30, 2025
Springwater | Free Admission (Donations Encouraged for Local Food Banks)
The CPKC Holiday Train rolls into Simcoe County with dazzling lights, festive music, and live performances from country stars Jade Eagleson and Teigen Gayse. Families are invited to bring non-perishable food donations and enjoy the show as the iconic train makes its way across Canada in support of community food banks. It’s a magical and meaningful way to celebrate the season.
More Info: CPKC Holiday Train - Simcoe County
Spice Holiday Market
December 5-6
Southshore Community Centre, Barrie | By Donation
This indoor artisan market has become a go-to for those who love supporting local makers. Featuring small-batch goods, handmade crafts, and festive treats, it’s a lively weekend of shopping and community connection. Stop in for gifts, stay for the cheerful atmosphere, and meet the creative minds behind each product.
More Info: Spice Holiday Market
Coldwater Lions Santa Claus Parade
December 6
Coldwater Road | Free Admission
Bundle up and head to downtown Coldwater for one of the most heartwarming holiday parades in Simcoe County. Presented by the Coldwater Lions Club, this evening parade lights up the streets with festive floats, cheerful music, and plenty of community spirit. The glowing lights against the historic village backdrop make it a magical experience for families — and Santa’s arrival at the end is sure to delight kids of all ages.
More Info: Coldwater - Santa Claus Parade
Angus’ Christmas Tree Lighting
December 5
Mill Street, Angus | Free Admission
Join friends and neighbours for this classic Angus tradition as the town’s Christmas tree is lit for the season. Enjoy live entertainment, carollers, and sweet treats while Santa greets families downtown. It’s a heartwarming way to usher in the holidays with your community.
More Info: Angus - Tree Lighting
From small-town parades to twinkling light displays, Simcoe County knows how to celebrate the season. Each of these events captures the warmth, creativity, and community that make our region so special. We hope you and your family enjoy exploring them all — and create some new holiday memories along the way.
From all of us at The Walker Team, wishing you a joyful, safe, and fun holiday season!
