If you're searching for the best things to do in Meaford in winter, you might be surprised by just how much is happening around Georgian Bay once the snow starts falling.
Winter transforms Meaford, Grey County and South Georgian Bay into a completely different kind of destination. Downtown streets glow with holiday lights, ski hills come alive, outdoor skating trails open, Christmas markets take over town squares and cozy local events give you plenty of reasons to bundle up and explore.
From Meaford winter events in 2026 to skiing near Blue Mountain, Christmas markets, light displays, skating, snowshoeing and live entertainment, there are winter activities for just about every kind of getaway.
And when you're ready to warm up, Skipping Rock Cottages makes a cozy home base for your Georgian Bay winter getaway, complete with a hot tub, sauna, fireplace and plenty of room to gather with your favourite people.
Here are some of the best winter events and activities in Meaford, Grey County and Grey Bruce to add to your 2026/27 itinerary.
1. Christmas on the Bay in Meaford
December 3–6, 2026 | Downtown Meaford
When it comes to Christmas events in Grey County, we have to start right in our own backyard.
Christmas on the Bay returns to Meaford from December 3–6, transforming Market Square into a charming outdoor European-style Christmas market—with a distinctly local twist.
Wooden vendor kiosks, twinkling lights, seasonal food, handcrafted goods and local artisans create the kind of atmosphere that makes you want to throw on your warmest scarf and spend the afternoon wandering.
Grey County has included Christmas on the Bay among its signature events for 2026.
It's one of our favourite Meaford winter events and an especially fun weekend to stay at Skipping Rock. Spend the day Christmas shopping and exploring downtown before heading back to the cottage for dinner, a sauna and an evening by the fire.
Explore Christmas on the Bay and 2026 Grey County events
2. Experience Christmas in Downtown Meaford
There's something extra special about Meaford during the holidays.
Fun fact: Meaford was a filming location for Disney's One Magic Christmas, and the town has embraced that piece of local history through holiday celebrations and festive experiences.
Pair your Christmas on the Bay visit with a walk through downtown Meaford to visit local businesses, stop somewhere for a warm drink and enjoy the small-town Christmas atmosphere.
If you're planning a Christmas getaway in Ontario and want something quieter than a major city, Meaford gives you that nostalgic holiday feeling while still putting you close to many of the biggest Grey County winter activities.
Explore the Meaford Community Calendar
3. See The Ennis Sisters at Meaford Hall
December 7, 2026 | 7:30 p.m.
Extend your Christmas on the Bay getaway by one more night and catch Christmas with The Ennis Sisters at historic Meaford Hall.
The December 7 concert brings the group's Celtic and Newfoundland roots to the stage through music, step-dancing, humour and holiday favourites.
Meaford Hall itself is worth visiting during a winter stay, and a live performance is an easy way to add something special to a winter getaway in Meaford, Ontario.
Christmas with The Ennis Sisters at Meaford Hall
4. Experience the Festival of Northern Lights in Owen Sound
Launching November 21, 2026 — date currently listed as TBC
If you're exploring Grey Bruce winter events, put Owen Sound's Festival of Northern Lights on your list.
Grey County's 2026 event guide says the festival will feature more than 400 displays and approximately 25 kilometres of lights illuminating the Sydenham riverbanks, River District and Harrison Park.
Bundle up the kids, pack some warm drinks and make an evening of exploring the displays before heading back to Skipping Rock.
It's an easy way to turn your cottage weekend into a mini Grey Bruce winter road trip.
5. Step Back in Time at Moreston by Candlelight
November 28 & December 5, 2026 | Georgian Bluffs
Looking for family-friendly winter activities in Grey County that feel straight out of an old-fashioned Christmas movie?
Add Moreston by Candlelight to your itinerary.
This holiday tradition takes place throughout a 10-acre heritage village and features horse-drawn wagon rides, live music, hot apple cider, holiday cookies and historic buildings decorated for Christmas.
It's nostalgic, family-friendly and a wonderful addition to a family winter getaway in Ontario.
6. Celebrate 50 Years of Olde Fashioned Christmas in Thornbury
December 12, 2026 | Downtown Thornbury
2026 marks the 50th anniversary of Olde Fashioned Christmas in Thornbury.
Downtown Thornbury will celebrate with festive lights, live entertainment, family activities, horse-drawn wagon rides, roaming performers, Santa, holiday treats and late-night shopping.
Thornbury is close enough to Skipping Rock to make this an easy addition to your stay.
Spend the afternoon exploring, shop locally, grab something delicious and stick around as the Christmas lights come on.
7. See Holstein's Non-Motorized Santa Claus Parade
December 12, 2026 | Holstein
Yes, you read that correctly.
Holstein's long-running Non-Motorized Santa Claus Parade returns December 12.
Instead of the usual trucks and motorized floats, the parade celebrates the season without motorized vehicles, creating a wonderfully old-fashioned small-town Christmas experience.
It's one of those wonderfully unique Grey County winter events you aren't likely to experience on a typical city Christmas itinerary.
8. Spend a Winter Evening at Meaford Hall
One of the advantages of choosing a winter cottage rental in Meaford is being close enough to downtown to turn your cottage weekend into a night at the theatre.
December 2026 already has several festive performances scheduled at Meaford Hall.
December 11: Matt Dusk – A Very Sinatra Christmas
December 13: The Nutcracker!
December 20: John McDermott's A Family Christmas
Dinner downtown, a show at Meaford Hall and then back to Skipping Rock for the night makes for a pretty great winter date night—or an evening out with the whole family.
See Upcoming Shows at Meaford Hall
More Things to Do in Meaford & Grey County in Winter
You don't need a festival on the calendar to have an incredible winter weekend.
Some of the best Meaford winter activities and South Georgian Bay winter activities happen all season long.
9. Hit the Slopes at Blue Mountain
If you're searching for things to do near Blue Mountain in winter, skiing and snowboarding are probably already at the top of your list.
Blue Mountain is an easy day trip from Skipping Rock and is preparing for its 85th winter season in 2026/27.
Spend the day on the slopes and then leave the busy resort behind for your own private cottage experience back in Meaford.
That's one of the reasons Skipping Rock works so well as a ski cottage near Blue Mountain: you can enjoy the action during the day and have plenty of private space to spread out when everyone gets home.
Plan Your Blue Mountain Ski Day
10. Try Night Skiing at Blue Mountain
Why end your ski day when the sun goes down?
Blue Mountain offers night skiing during the winter season, conditions permitting.
Spend the morning exploring Meaford, enjoy a slow lunch, hit the slopes later in the day and return to Skipping Rock for a late-night soak in the hot tub.
For groups planning a winter weekend getaway in Ontario, it means you can pack even more into your stay without having to wake everyone up at sunrise.
11. Skate Through a Winter Wonderland
Looking for things to do near Blue Mountain besides skiing?
Trade your skis for skates.
Blue Mountain's winter attractions include the Woodview Mountaintop Skating Trail, where weather and conditions permitting, you can skate outdoors surrounded by the Niagara Escarpment.
It's one of those quintessential South Georgian Bay winter activities that belongs on the bucket list.
12. Go Snowshoeing Through Grey County
Sometimes winter is best experienced at a slower pace.
Snowshoeing is one of our favourite Grey County winter activities because it allows you to experience forests, trails and the Niagara Escarpment after fresh snowfall.
Blue Mountain offers snowshoe trails and rentals as part of its winter outdoor experiences, or you can stay closer to Meaford and make your own winter adventure.
Then it's back to Skipping Rock to warm up.
13. Try Cross-Country Skiing
Downhill isn't the only way to ski around here.
Head to Highlands Nordic in Duntroon for a cross-country skiing adventure through the Niagara Escarpment.
Cross-country skiing can be a great addition to a longer Georgian Bay winter getaway, particularly for groups that want to mix up their activities over several days.
14. Make Après-Ski an Activity of Its Own
The skis eventually have to come off.
Luckily, the fun doesn't have to stop.
Spend an afternoon exploring downtown Meaford, grab a great meal, pick up something delicious to bring back to the cottage or create your own après-ski spread at Skipping Rock.
You can also venture into Thornbury or Blue Mountain Village for dinner, shopping and that unmistakable winter-resort atmosphere.
Then head home for the best part.
Sweatpants.
Fireplace.
Hot tub.
No further plans required.
15. Take a Winter Hike
Grey County's trails aren't just for summer.
A crisp winter walk can be one of the most peaceful ways to experience the region, especially after fresh snowfall.
Explore sections of the Bruce Trail, discover local conservation areas or simply enjoy a snowy walk near Georgian Bay.
Winter hiking is also a great option when you're searching for things to do in Meaford in winter that don't require buying a lift ticket or committing to an entire day.
Always check current trail and weather conditions before heading out and wear appropriate winter footwear.
16. Spend a Slow Day Exploring Downtown Meaford
Don't make the mistake of spending your entire winter getaway driving somewhere else.
Leave time for Meaford itself.
Browse downtown shops, visit local cafés, find somewhere cozy for lunch, explore the waterfront and see what's happening at Meaford Hall.
Winter is quieter than summer—and that's part of its charm.
It's also why a Meaford winter getaway can offer the best of both worlds: you're close to major South Georgian Bay attractions without having to stay in the middle of the crowds.
Build Your Perfect Meaford Winter Getaway
One of the best things about planning a family winter getaway in Ontario is that everyone's ideal weekend can look completely different.
The adventure crew can ski, snowboard, snowshoe and explore.
The Christmas lovers can visit markets, see the lights, shop locally and catch a holiday show.
Families can fill their itinerary with skating, Santa events, outdoor adventures and cottage game nights.
And the slow-weekend crowd?
Sleep in. Make a big breakfast. Explore Meaford. Take a winter walk. Come home and spend the afternoon by the fire.
If your group wants a little bit of everything, there's an easy solution:
Stay an extra night.
Make Skipping Rock Your Winter Home Base
When you're looking for a winter cottage rental in Meaford or a ski cottage near Blue Mountain, location matters—but so does what happens after the day's adventures are over.
At Skipping Rock, coming home is part of the getaway.
Warm up in the sauna, head outside for a soak in the hot tub, make dinner together in one of our two kitchens, start a game night or settle in by the fireplace.
With seven bedrooms, three bathrooms and space for up to 16 guests across the Log Cabin and Garage Loft, there's plenty of room for families and groups to spend a winter weekend together.
From Meaford winter events and Christmas festivals to skiing, skating, snowshoeing, winter hiking and exploring South Georgian Bay, there's more than enough happening to turn one weekend into a new winter tradition.
Whether you're planning a December Christmas getaway, family holiday, ski weekend or simply looking for an excuse to escape the city once the snow starts falling, make Skipping Rock Cottages your home base for winter in Meaford and Grey County.
Ready to start planning?
Book Your Winter Stay at Skipping Rock Cottages
Come for the snow. Stay for everything that happens in between.
Event dates, operating dates and programming may change due to weather or organizer schedules. Always confirm current dates, tickets, operating conditions and availability directly with the event or attraction before your stay.