Posted : November 20, 2025
Our blog is chock full of great ideas for fun things to see and do in York Durham and Headwaters. We are always adding new content and updating old posts, but sometimes you might stumble upon something from our vault. If this article has inspired you to hit the road, be sure to double-check that the featured stops in this post are still welcoming visitors.
With the festive season upon us, the countdown is on to embrace as much yuletide cheer as we possibly can. Whether you love Christmas markets or the tradition of harvesting your own tree, there is no shortage of holiday adventures to be had in York Durham Headwaters!
However, if you’re looking for a holiday adventure that’s guaranteed to sleigh, look no further than the town of Orangeville. Here are all the festive things to do for a tree-mendous day in YDH!
Enjoy a Cup of Good Cheer at a Local Cafe
Start your day off right with one of the delicious festive flavours you’ll find in Orangeville’s coffee shops. For latte lovers, head to Greystones Café for one of their gingerbread lattes with their housemade gingerbread syrup that’s full of sugar, spice and everything nice. If coffee isn’t your forte, their peppermint hot chocolate topped with crushed candy cane is sure to be a hit. Another great spot is Mochaberry where they always have some delicious holiday flavours. Enjoy their candy cane, gingerbread or spiced eggnog coffees – all of which can be bought by the bag, making it a great gift for the coffee connoisseur on your list!
Support Local & Shop for Meaningful Gifts
Chances are you have a list that you’re checking twice, so cross some folks off your list at the incredible local shops you’ll find in downtown Orangeville. Pear Home is a must for quirky gifts and stunning home decor. Find one of a kind items from local crafters at Dragonfly Arts on Broadway. If you’re looking to treat yourself, More Than Just Baskets do a little of everything, including charcuterie as well as Suzanne Gardner Flowers for ephemeral decor that will impress even the biggest family critics! Don’t forget to stop by the Orangeville Farmers Market if you find yourself visiting on a Saturday for even more local eats, treats and artisanal items.
Spruce Up Your Festive Season at a Christmas Tree Farm
Soak up the magic at the Hockley Valley Tree Farm as you explore 90 acres of pristine forest along the picturesque Nottawasaga River. Sip on a cup of hot coco as you admire their collection of marvellous Balsam, Concolor and Fraser Firs, Scots Pines and Blue and White Spruce. Pop into their holiday market for a menagerie of local goodies and if you purchase a tree, be sure to enjoy the complimentary wagon ride! It’s a great way to spend a few hours on your Christmas getaway in Orangeville.
Revel in the Magic of Snow Globe Dining
There’s no better spot for a magical dinner this festive season than at Adamo Estate Winery. Uncorked is an enchanting experience where you and up to five of your friends and loved ones can partake in a cicchetti-style dinner (think Italian tapas) in your private snowglobe. Surrounded by twinkling lights, bring your cozy clothes as you sip and savour the culinary delights prepared by Executive Chef Iniyan Vijay. You’ll be full to the brim with good wine, good food, good company and plenty of holiday cheer. While you’re there, sample the award-winning repertoire of wines and pick up a few of your favourites for any upcoming holiday gatherings. They have a number of great gift ideas as well!
Wander Through the Whimsy of Christmas in the Park
For three decades and counting, the Optimist Club of Orangeville has been spreading the Christmas cheer with their brilliant light displays. Head to Kay Cee Gardens during the month of December for the town’s best collection of lights! Make sure you come with a full phone battery so you can capture the magic until your heart’s content. Visitors can enjoy eats and treats on select days as well as a variety of live performances all month long. You may even catch a glimpse of Santa, too! Full details can be found here.
Catch A Show from Theatre Orangeville
Lighting up the downtown core since 1994 with their incredible talent, Theatre Orangeville has yet another incredible production to delight attendees of all ages. Every year they have a unique show around the holidays and you won’t want to miss this year’s performance: Rapunzel: A Braid New World. November 27- December 21st, treat yourself, your family and friends to this delightful (and fractured!) romp through one of your most beloved classic fairy tales, all brought to you by the zany stylists who created Cinderella… If the Shoe Fits and Sleeping Beauty… A Fairy’s Tale.
Continue the Fun & Stay Overnight!
With so much tree-mendous holiday fun to be had in not just Orangeville but in York Durham Headwaters, why not stay overnight? This way you can branch out and embrace all the holiday season has to offer with these charming Hallmark-esque downtowns or become the star of your own Hallmark movie.
There are two brand new options in Orangeville to turn your day trip into an overnight getaway. The Hampton Inn and Suites by Hilton is located just 10 minutes from the downtown core and features a free hot breakfast buffet as well as a heated indoor pool and fitness centre. For a more boutique experience, The Nest Suites are located above the Blue Bird Café featuring cozy amenities such as complimentary coffee and tea, bath robes and adorable seating areas. You might get so comfy that you’ll find it a struggle to leave!
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