Port Perry Horse

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 two beloved Orangeville Christmas events this year.

Christmas in the Park This free, month-long event kicks off on December 2nd 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 18th 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.

Port Perry

Port Perry Winter

On the shores of Lake Scugog in Durham Region, the thriving community of Port Perry is like a world of its own. Quaint and charming throughout the year, at Christmas time, the historic downtown district transforms into a winter wonderland. If you’re in the area (read: you’re definitely going to want to be in the area), then you won’t want to miss these two holiday events.

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 Indoor Christmas Market – 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.


Uxbridge Christmas Preparations

The Trail Capital of Canada welcomes you to its historic downtown district for a magical holiday season. Situated in the scenic Oak Ridges Moraine, this area is perfectly suited to an old-fashioned Christmas. Be sure to check out these events happening this season.

Optimist Fantasy of Lights – From December 3rd until January 1st, 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.

Santa Claus Parade – Since 1961, the Uxbridge Santa Claus Parade has been a beloved tradition, where Brock Street in the downtown core is closed and visitors flock to see the displays, floats, and the Big Man in Red himself. This year, the parade is taking place on November 19th at 11 a.m. Dress warm and prepare to get your holly jollies on with this favourite Christmastime event.


Erin Window Wonderland

If you’re looking for a picturesque rural community with tons of charm and history, 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 these two events happening this Christmas.

Window Wonderland – This event is the official kickoff to the Erin Winter Fest. On November 18th, from 6 p.m. to 9 p.m., 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. Don’t forget to check out more great events happening at Erin’s annual Winter Fest this year.


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 shops and 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, music, jugglers and entertainers, and favourite Christmas refreshments like roasted chestnuts, cookies and hot cider. This event takes place on Saturday, December 3rd between 4 p.m. and 9 p.m., so mark your calendars now. Santa Claus parade at 4pm and Farmers’ Parade of Lights at 8pm.


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 to enjoy these Christmas traditions, and make them a tradition of your own.

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 3rd from 2 p.m. to 6 p.m., 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.

Orangeville Holiday Lights

Share to...