Uxbridge Holiday Trail

Have a Hallmark Holiday Season in these Charming Historic Downtowns

Another Christmas is upon us. Here in York Durham Headwaters, we’re brimming with holiday activities and experiences that will fulfill everyone’s cherished traditions—and hopefully they’ll make some new ones, too. To kick off the season, we invite you to explore one of our historic downtowns that will be sure to get you into the holiday spirit. All throughout YDH, these charming small towns and villages are gearing up for their signature celebration events. If you’re new to our historic downtowns, then get ready for a host of events that practically bring the Hallmark Channel to life in front of your eyes.


Orangeville Holiday Lights

Settled nearly two hundred years ago, the Town of Orangeville in Headwaters still retains much of its historic charm, with 1800s-era and turn-of-the-century buildings lining the town’s tree-lined main streets. This town was made for strolling, which is perfect for your Christmastime shopping adventures—or to simply take in the lights and spend a day absorbing all the Christmassy vibes. Check out these three beloved Orangeville Christmas events this year. Don’t forget to warm up with a hot chocolate or specialty coffee at the coziest café in town, Mochaberry.

Christmas in the Park This free, month-long event kicks off on December 1st with its opening ceremonies. Located at the Kay Cee Gardens from 5:30 p.m. to 10 p.m. every Saturday until December 31st, this event features music, entertainers, millions of dazzling lights, community displays and hot drinks. Gather with friends and family in this idyllic setting, and make new friends this season with Christmas in the Park.

Joy and Lights Tree Lighting – Friday, November 17th is Joy and Lights, Downtown Orangeville’s official old-fashioned tree lighting celebration. From 5:30 p.m. until 8:30 p.m., you and your loved ones will be delighted by strolling carolers and street performers. Be there as local merchants take part in the first ever Yuletide Window Reveal at 6:00 p.m. Of course, no tree lighting ceremony is complete without a visit from St. Nick himself. The lighting ceremony takes place in Town Circle at 7:00 p.m. While you wait, double your stamps in your Joy Book with some Starlight Shopping.

Orangeville Christmas Market – On November 18th visit the Orangeville Christmas Market for an unparalleled local shopping experience filled with holiday magic and wonderful artisans and vendors. Please bring a donation of non-perishable food items for the Orangeville food bank.

Port Perry

Couple Holiday Shopping

Downtown Port Perry is home to beautiful historic buildings which provide a charming façade for visitors to the downtown. Over the holidays the street lamps are decorated and the stores join in with festive decorated store fronts. The new skating rink beside the lake with be open starting December 2nd for skating. Enjoy happy hour at the PORT Cheese co, for a wine and cheese pairing, or enjoy a glass of locally brewed beer or cider at The Old Flame brewery.  Book a romantic meal at one of the downtown restaurants, Pickles and Olives is right across from the park, or Marwan’s and the Jester’s Court are a short walk up the beautifully lit Queen Street. You can’t make a trip to Port Perry without some holiday shopping at all the charming downtown shops including beautiful jewellery from Dana’s Goldsmithing, something sweet from the Nutty Chocolatier, holiday cookies and gifts from “over the pond” from The Wee Tartan Shop, local artistic treasures from Meta 4 Gallery or Scugog Arts and so much more!

Holiday Horse Drawn Carriage Rides – Horses Molly and Polly absolutely love their job of bringing visitors around their hometown. Have a cozy carriage ride through the streets of Downtown Port Perry, which is a time-honoured tradition here. Details of the event are still being determined, so be sure to watch for updates on www.discoverportperry.ca.

Scugog Arts Christmas Shop– Discover unique, hand-crafted gifts for your loved ones this holiday season at this annual event. From November 20th to December 31st, artists and artisans will be ready and waiting with an amazing variety of lovingly crafted goods, including paintings, fibre, pottery, wood, prints, ornaments and handmade cards. The market will be open on Thursdays and Fridays, from 11 a.m. to 8 p.m.

Once Upon A Christmas – On Friday November 24th at 5pm join the Port Perry Farmers market and Chambers of Commerce in a storybook celebration. Fill downtown Port Perry with the spirit of the holiday season! Enjoy a holiday farmer’s market, candlelit walk & tree lighting, carolling, live music & more surprises!

Town Hall Theatre Holiday Cabaret – ‘Tis the season to join some of SCS Musicals’ most requested singers, musicians, comedic actors and newcomers for some festive fun! On November 25th and 26th ring in the season with song, dance and lots of laughter – an original musical extravaganza of traditional and modern holiday songs, dance and comedic skits to perk up your mood and get you in the holiday spirit!


Stockings in Window
Uxbridge Holiday
Rutledge’s window, and storefront display, curated and created by: Del Clarkson, A Thing of Beauty, Seasonal Designs by Del @ 2022

The Trail Capital of Canada welcomes you to its historic downtown district for a magical holiday season. Uxbridge comes to life for the holidays with several Christmasy experiences. It’s definitely a great romantic “hallmark” destination. Book a ride on a holiday themed train ride with YDHR, cuddle up for a holiday themed movie with a glass of wine at the Roxy theatre, stroll through Centennial Park to catch the presentation of the “Living Nativity” (with Actors and animals), drive, stroll, or catch a trolley ride, on select evenings, through the Fantasy of Lights in Elgin Park. Also be sure to check out these ho ho holiday events.

Optimist Fantasy of Lights – From December 2rd until January 6th, Uxbridge will be transformed by one of the largest lights displays in all of Canada. You and your loved ones are invited to drive through the lighted display in Elgin Park between 6 p.m. and 9:30 p.m. No ticket is required, but donations are appreciated, and will go towards the Optimist Club’s youth programs.

Holiday Trail – If you love the Fantasy of Lights, we’re sure you’re going to want to stay and explore even more. The Uxbridge Holiday Trail invites you to explore the Trail Capital of Canada by continuing through Downtown Uxbridge to see the festive shop windows and catch a wave from Santa and Mrs. Claus. Details have yet to be released, so check in at www.discoveruxbridge.ca for updates.

Uxbridge Farmers Market Christmas Market – A trip to the Uxbridge Farmers’ Market in the makes a lovely excursion any time of the year. However, it’s extra special when it’s transformed into the annual Christmas market during the holiday season. Details have yet to be released, so check in at https://uxbridgefarmersmarket.ca/ for updates.


Santa and Mrs. Claus Kissing

If you’re looking for a picturesque rural community with tons of charm, history, and shopping, you’ve found it in Erin. This quaint village is situated amongst lush rolling countryside and meandering rivers. It’s the perfect place for traditional holiday activities that you look forward to every year. Don’t miss Erins most popular event happening this Christmas.

Window Wonderland – On November 17th, Erin welcomes you to celebrate this cherished tradition, which begins with the Annual Tree Lighting Ceremony. All of Erin comes together on Main Street to unveil all of the beautiful window displays. It’s the perfect way to kick off your own Christmas this season. PLUS shops remain open until 8pm for some evening community shopping cheer!


Main Street Christmas

Established in 1830 and initially known as Brownsville after the first landowners, Schomberg has evolved into a charming community with lots of historic detail preserved for your enjoyment today. The historic downtown offers amazing shops and one of a kind dining opportunities, and is ideal for a slow day taken at your own pace. At Christmastime, Schomberg comes alive with shopping, decorations, lights and its signature event:

A Main Street Christmas – Immerse yourself in the holiday traditions of a bygone era. Stroll up and down Main Street while you enjoy carolers, fire side reading, music, jugglers and entertainers, and favourite Christmas refreshments like roasted chestnuts, cookies and hot cider. Od course we cannot forget Santa who will be joining the celebrations as well. The evening is brought to a spectacular close with the Farmers’ Parade of Lights brought to you by our local farming community with brightly decorated farm equipment driven down Main Street. This event takes place on Saturday, December 2nd between 4 p.m. and 9 p.m., so mark your calendars now. Santa Claus parade at 4pm and Farmers’ Parade of Lights at 7:30pm.


Unionville Christmas

Nestled within the thriving urban city of Markham is the historic town of Unionville. Visiting this adorable town is like stepping into another world. Christmas is a magical time here, where turn-of-the-century (and older!) buildings and homes are decked in their holiday finest. Come to Unionville and enjoy one of their many celebrated restaurants, some even located in these turn of the century homes, to delight in these Christmas traditions, and make them a tradition of your own. May we also recommend stopping into Old Firehall Confectionary for some regular or flavoured hot chocolate made with the finest melted Belgian chocolate and topped with whip cream and marshmallows #Drool.

Christmas Light Displays – Make some holiday memories this season, and be sure to snap a few photos for the memory book, as you stroll down Main Street and take in beautiful light displays. You’ll be amazed at how this town (which, in truth, is picturesque in every season) transforms. You’ll think you were at the North Pole! Be sure to pop into some of the local stores for refreshments and local shopping. This unofficial event is free and lasts into January.

Olde Tyme Christmas – On December 9th join your friends in Unionville for an afternoon of merrymaking. This event features light displays, music, a Christmas train ride, a candlelight parade, and much more. If you want to star in your own Hallmark holiday adventure, then put this celebration at the top of your list.

Breakfast With Santa – Don’t miss out on the most magical and delicious event of the year – Breakfast with Santa on Main Street Unionville! Join Unionville Arms and Jakes on Main for a delightful morning filled with joy, laughter, and of course, Santa Claus himself, on December 16th and 17th.

Hallmark is a registered trademark of Hallmark owned by Hallmark Cards, Inc.

Rutledge’s window, and storefront display, curated and created by: Del Clarkson, A Thing of Beauty, Seasonal Designs by Del @ 2022

York Durham Headwaters Go to Home Page