50+ Christmas Markets and Holiday Events In Durham Region This Season
‘Tis the season for some festive fun! If you’re looking to fill your calendar with all things merry and bright, you’ve come to the right place. From festive farm events to tree lighting ceremonies to merry markets and everything in between, there are no shortage of reasons to celebrate the season in Durham Region.
A Country Path Christmas
November to December 31 | Various locations in Clarington
What better way to kick off the festive season than with a day shopping local along A Country Path! Take part in the annual Holiday Scavenger Hunt by stopping at any of the locations along the path to receive a scavenger sheet. Each location offers unique, one-of-a-kind gifts for that special person on your list. Hours vary by location.
Beaverton Christmas Market
November 28 | Simcoe Street, Beaverton
Come on down to the heart of downtown Beaverton on Saturday, November 28 for a fun and festive Beaverton Christmas Market! The local stores will be open and vendors will line the streets from 4 to 9 p.m., with the annual parade at 6 p.m. Enjoy a hot beverage from a local café, dine-in for a delicious bite to eat, and take a stroll around town to enjoy all the magic of the season. Sponsored by the local downtown businesses.
Bright & Merry Market
November 20 | City Hall’s Civic Square and North Parkette, Oshawa
Join the City of Oshawa for their annual Bright and Merry Market! Enjoy an evening filled with twinkling lights, festive entertainment, holiday cheer, and Santa himself. This free event takes place on November 20 from 5 to 9 p.m. with live music, on-street entertainment, and artisan vendors offering handmade gifts, décor, and tasty treats.
Brooklin Merry Market
November 7 | Heydenshore Pavilion, Whitby
Get a head start on your holiday shopping at the Brooklin Merry Market and support local makers, creators and small businesses! This free event takes place from 10:30 a.m. to 3:30 p.m. and features more than 50 local vendors, live music, food trucks and festive treats, plus a visit from Santa! Shop handmade treasures and one-of-a-kind gift ideas.
Candlelit Christmas Concerts
November 28 to December 20 | Across Durham Region
Enjoy an intimate evening surrounded by candlelight as a live string quartet performs Christmas classics at Wilmot Orchards on November 28. The Christmas Classical by Candlelight takes place the following evening on November 29 at the historic Newcastle Community Hall. Plus, don't miss The Biltmore Theatre's Candlelight Christmas Classic on December 20 in Oshawa, featuring a selection of cherished holiday melodies.
Christmas at Parkwood Estate
November 7 to January 3 | Parkwood Estate, Oshawa
Deck the halls at Parkwood Estate this holiday season! Book a guided Christmas tour to see how the mansion transforms into a winter wonderland; shop unique gift ideas at the Winter Fest Vendor Market on November 21 and 22; or, partake in one of their special holiday workshops, like custom Christmas doormats, cookie decorating and wreaths.
Christmas Cheer Mingle & Jingle
November 29 to December 20 | Applewood Farm & Winery, Scugog
Applewood Farm & Winery kicks off the season with their Merry, Magic and Christmas Cheer event on November 29! Enjoy a full day of festive fun, from 11 a.m. to 5 p.m., with delicious treats, live music, and drinks around the campfire. Plus, don't miss their annual Christmas party on December 20. The winery is also open December weekends for fireside flights and holiday tunes.
CPKC Holiday Train
November 29 | Oshawa and Bowmanville
The annual CPKC Holiday Train will be travelling through Durham Region on November 29. Catch a glimpse of the beautifully decorated train and enjoy musical performances. The train will make its first stop in Bowmanville (Scugog Road & Wellington Street) for 2 to 2:30 p.m. before heading west to Oshawa (680 Laval Drive) from 3:15 to 3:45 p.m. Train schedules vary, so we recommend showing up at least 15 minutes early.
Deer Creek's Brunch With Santa
December 13 | Deer Creek Golf Club, Ajax
Join Deer Creek Golf Club for their most beloved annual event—Brunch with Santa! The festive fun includes pictures with Santa, story time with Santa's elves, pony and horse-drawn carriage rides, a hot chocolate bar, crafts and colouring, and of course, brunch! Seatings take place at 11:30 a.m., noon, and 12:30 p.m.
Downtown Whitby Christmas Market
November 13 and 14 | Celebration Square, Whitby
Join the Downtown Whitby BIA for two unforgettable days of festive fun and holiday cheer at the annual Downtown Whitby Christmas Market! This free event features a variety of seasonal attractions, including an outdoor market, live performances, treats, crafts, trolley rides, photos with Santa, and magical characters.
Frozen: The Broadway Musical
November 12 to December 5 | Oshawa Little Theatre, Oshawa
Bring the kids for a day of family fun and enjoy a Broadway musical adaptation of Disney’s beloved animated film, Frozen. The story follows the royal sisters Elsa and Anna, where Elsa’s magical ability to create ice and snow inadvertently plunges their world into eternal winter. Recommended for children ages 5 and up.
Holiday In The Hills
November 21 to December 22 | Orono Fair Grounds, Orono
Holiday in the Hills brings Christmas to life and creates true holiday magic for all ages! Wander through the festive trail of lights, indulge in festive food and drinks, and enjoy endless entertainment for the kiddos. Build your own plushie, send your letters off to Santa, decorate cookies, and meet festive characters like the Grinch and Rudolph. Santa's dance and tree lighting take place every night at 6:30 p.m.
How The Gretsch Stole Christmas
November 29 | The Biltmore Theatre, Oshawa
How The Gretsch Stole Christmas is a festive holiday rock sing-along, taking place from 2 to 5 p.m. at The Biltmore Theatre. Enjoy classic holiday favourites and original songs with Will Gillespie—your host, emcee and lead guitar player—featuring special guests Susan Robinson and NEPO, BABY! Sing-along and indulge in hot chocolate, apple cider and savoury snacks.
Jinglefest Holiday Concert
December 19 | Beaverton Town Hall, Beaverton
Get in the holiday spirit at the First Act Youth Company (FAYC)'s Jinglefest! Members of both the Young Company and FAYCompany will take the stage together in a fully-staged holiday concert. After the show, the festivities continue with holiday mingling, selfies with Santa, hair tinsel, a raffle, and plenty of seasonal treats!
Jingle & Roar Christmas Market
November 28 | Beaverton Fair Grounds, Beaverton
Kick off your holiday shopping at the Jingle & Roar Christmas Market! From 4 to 11 p.m., enjoy live entertainment, food, face painting, Santa visits at the firehall, and partake in the annual Christmas Light decorating contest. Watch as Beaverton flips the switch to turn on the Christmas lights all over town! The annual Beaverton Lions Santa Claus Parade leaves the fairgrounds at 6 p.m.
Journey Into Enchantment
November 20 to December 26 | Ajax Downs Casino, Ajax
Experience the magic of the holiday season at Journey into Enchantment! With more than two million lights illuminating a two-kilometre route, you can enjoy a dazzling drive-thru tunnel, 2D and 3D displays, musical lights, holiday characters, and more at this captivating drive-thru Christmas event at Ajax Downs! Time slots are ticketed per vehicle.
Knox Farm Christmas
December 5 to 20 | Knox Pumpkin Farm, Hampton
Join Santa and the Elves for a Knox Farm Christmas—a holiday event your children and loved ones will remember forever. Enjoy a visit with Santa, wish Rudolph a good flight, learning about food and farming, pick-your-own pre-cut Christmas tree, and gather around the campfire to celebrate the holidays! The event runs for three weekends only. Tickets must be purchased in advance.
Ladies Christmas Crawl
November 6 | Simcoe Street, Beaverton
Kick off the festive season with an evening of shopping in downtown Beaverton! The Ladies Christmas Crawl offers a night of shopping and sipping throughout the local businesses of this charming small town. From 5 to 8 p.m., explore one-of-a-kind gifts and delicious treats along Simcoe Street.
Market at 70 King's Holiday Cheer Market
November 21 | Market at 70 King, Oshawa
Enjoy a festive afternoon and evening of local shopping, unique finds and holiday fun at the Holiday Cheer Market. The market is free to attend and takes place from 3 to 8 p.m. during the Oshawa Santa Claus Parade of Lights! Explore local vendors, makers and artisans, and shop handmade gifts and unique holiday finds. Plus, enjoy festive photo opportunities, seasonal drinks and treats, and family-friendly fun.
Markets Ontario Holiday Pop-Ups
December 4 to 20 | Markets Ontario, Bowmanville
Join Markets Ontario for their Holiday Pop-Ups every Friday, Saturday and Sunday in December leading up to Christmas! Explore local artisans, shop from a wide range of vendors and a variety of products, and get all of your holiday shopping done in one place. These festive pop-ups are the perfect chance to shop local this holiday season!
Mary Street Winter Market
November 14 | Unique Town Boutique, Whitby
Shop local businesses and artisans at the annual Mary Street Winter Market! The event is free to attend and takes place from 10 a.m. to 5 p.m. with festive fun for the whole family. Shop a curated mix of local makers, artisans, food vendors and small businesses, and enjoy festive photo-ops, photos with Santa, raffles, and a scavenger hunt.
Moonlight Magic & Christmas Market
December 4 | King Street and Temperance Street, Bowmanville
Discover the magic of Historic Downtown Bowmanville at the annual Moonlight Magic & Christmas Market! This free event takes place from 5 to 9 p.m., with a special tree-lighting ceremony on Temperance Street at 6:30 p.m. Enjoy complimentary horse-drawn wagon rides, a visit from Santa, carolers, food and drinks, and children's activities. The downtown small businesses are offering extended shopping hours until 9 p.m.
Old Scugog Road Christmas Lights
December 1 to 31 | Old Scugog Road, Bowmanville
Travel along Old Scugog Road, starting near Andelwood Court, in Bowmanville for a light display that is snow joke! Each year, the residents of Old Scugog Road deck the halls (or in this case, streets) with beautiful lights and extravagant decorations—more than just your traditional twinkle lights. This is a residential road and not a ticketed event, please kindly respect the area during your visit.
Ontario Philharmonic
December 12 and 18 | Regent Theatre, Oshawa
Immerse yourself in the glorious sounds of a full orchestra when you join Ontario Philharmonic for not one, but two special holiday performances! Experience the sounds of The Nutcracker live on December 12, or attend the Holiday Jamboree with RESOUND Choir on December 18. Other upcoming performances at Regent Theatre include O Christmas Tea: A British Comedy or Elvis: A Christmas Special.
Oshawa Holiday Festiverse
November to December | Various locations, Oshawa
Unwrap Oshawa's holiday magic with countless ways to celebrate the festive season! The Oshawa Holiday Festiverse is your one-stop for all things merry and bright across the city. Discover dazzling family-friendly events and activities offered by local businesses, and mark your calendar for the Santa Claus Parade of Lights on November 21 for twinkling floats, enchanting decorations and magical dancing and music.
Picks & Giggles Classic Holiday Market
December 13 | Kingsway College, Oshawa
Picks and Giggles’ annual Classic Holiday Market takes place at Kingsway College, featuring freshly brewed hot beverages from local coffee shops, sweets from local bakers, meet and greets from special guest appearances, live music, and more! Admission is $5 at the door per event. Kids ages 14 and under are free. The market is open from 10 a.m. to 5 p.m.
Port Perry Lakefront Farmers’ Market
November 20 | The Latcham Centre, Port Perry
Gather your family and friends for an evening of holiday shopping at the Port Perry Lakefront Farmers’ Market! The holiday pop-up takes place from 5 to 8 p.m., held in conjunction with Port Perry’s annual tree lighting. Enjoy a traditional candlelit walk, caroling, gingerbread decorating, festive food and drinks, and shopping. It’s the perfect excuse to shop local and spread a little holiday magic.
Royal Ashburn Christmas Event
December 13 | Royal Ashburn Golf Club, Whitby
Gather the family for A Royal Christmas Event at Royal Ashburn Golf Club! Enjoy a festive breakfast, Christmas sing-a-longs, holiday crafts, and photos with Santa. Wander through the magical outdoor Christmas walk to meet Santa's elves, build your own bracelet, and mail your letter straight to the North Pole. Seatings take place between 9 and 11 a.m.
Santa Claus Parades
November 15 to December 12 | Various events across Durham Region
Mark your calendar, because Santa Claus Parades are coming to town! Bundle up and enjoy the magic of the season at one of Santa’s many visits across Durham Region. This beloved tradition features a festive street procession and is the perfect way to kick off the holiday season.
Santa's Cottage
November 1 to December 23 | 4405 Ritson Road North, Oshawa
Meet Santa himself at Santa's Cottage this season! The Christmas Barn Market is free to visit (no ticket required), Fridays to Sundays until December 23. For a more personalized experience, grab tickets for a Jingle Mingle visit—available Tuesdays and Thursdays throughout November and December. Be sure to bring your camera or phone!
Snow White Panto
December 27 to 31 | Town Hall 1873 Theatre, Port Perry
This holiday season, DreamCo Theatre is bringing you along for a magical adventure! Join them for Snow White Panto, and enjoy a performance bursting with laughter, toe-tapping songs, dazzling costumes, audience participation, and plenty of fairy-tale fun. Other upcoming shows at Town Hall 1873 Theatre include the John Denver and Glen Campbell Christmas Tribute on December 3, and An Elvis Christmas on December 19.
Stars on Ice: Holiday Tour
December 10 | Tribute Communities Centre, Oshawa
Celebrate the holidays with Stars on Ice—Canada’s premier figure skating show! This exclusive holiday tour brings Olympic, World and National champions together for a dazzling celebration on ice. Enjoy show-stopping performances, spectacular ensembles, and plenty of holiday cheer for one night only in Oshawa.
Sugar & Snow Holiday Market
November 28 and 29 | Chestnut Hill Developments Complex, Pickering
From 10 a.m. to 4 p.m., explore local vendors and artisans at the Sugar & Snow Holiday Marketplace in Pickering! This festive two-day market will be the perfect place for holiday shoppers to discover unique gifts, tasty treats, handmade creations, and so much more. It's the perfect time to shop local and grab some delicious goodies for the holidays.
The Merry Little Market
December 12 | Little Beasts Brewing Co., Whitby
Get into the holiday spirit and shop local vendors at The Merry Little Market. The event takes place from 1 to 6 p.m., is free to attend, and will feature local brews and local shopping all under one roof! Explore unique gifts, and enjoy photo-ops, raffles and more festive fun.
Tindall Farm Christmas Markets
November 21 to 22 and December 5 to 6 | Tindall Farm & Market, Uxbridge
Get a jump start on your shopping at the Tindall Farm Christmas Markets. Explore a variety of artisan vendors and shop the farm store to bring home a one-of-a-kind gift. While you’re in the area, check out the other stops along the Leaskdale Loop. This self-guided driving tour is made up of a variety of small businesses and historical sites.
Uxbridge Farmers' Market's Holiday Edition
November 1 to December 13 | Uxbridge Arena, Uxbridge
Get ready for the holiday season at the Uxbridge Farmers’ Market! The markets are held on Sundays from 10 a.m. to 3 p.m. until December 13 (excluding November 29). Each market features a unique variety of local farmers, makers, and bakers. The first three markets include both indoor and outdoor vendors, while the final three markets are indoor-only.
Uxbridge Holiday Trail
December 4 and 5 | Brock Street, Main Street and Toronto Street, Uxbridge
Get into the holiday spirit at the annual Uxbridge Holiday Trail. From 5 to 8 p.m., enjoy dazzling light displays, vintage decorations, live music, festive markets, and special guest appearances. Discover the holiday charm of Uxbridge with these cherished community events that offer the ultimate holiday experience for all ages. Shop, eat, drink, and play!
Uxbridge Music Hall: Holiday Edition
November 12 to December 20 | Uxbridge Music Hall, Oshawa
Enjoy a musical or theatre performance in the gorgeous setting of the Uxbridge Music Hall. Upcoming shows include Irving Berlin's White Christmas from November 12 to 21, Elf: The Musical from December 3 to 6, and The Nutcracker from December 16 to 20.
Uxbridge Optimist Fantasy of Lights
December 5 to January 2 | Elgin Park, Uxbridge
The Uxbridge Optimist Fantasy of Lights famous drive-thru event is back! This free event exhibits more than 100 light displays, and guests are welcome to drive or take the foot path to view these stunning festive lights. Open seven days a week from 6 to 9:30 p.m., including Christmas Eve and Christmas Day.
Vintage Holiday Weekend in Port Perry
December 11 to 13 | Queen Street, Port Perry
Take a step back in time this holiday season at the Vintage Holiday Weekend! Join the Port Perry BIA for three days of festive charm with live music, carolers, shopping, photo-ops, and festive treats. On December 11, enjoy extended shopping hours and explore the downtown businesses to find the perfect gifts.
Whitby Lights The Night Festival
November 27 to January 4 | Civic Park, Celebration Square and Grass Park, Whitby
Kick off the festive season at Whitby Lights the Night! On November 27, enjoy a magical evening of live entertainment, a Christmas Farmers' Market, and a dazzling lighting ceremony. The light display will continue throughout the season, from dusk to 10 p.m. until January 4, with more than 200,000 magical lights and displays. Get ready to be dazzled by twinkling lights, festive activities, and all the holiday magic that makes Whitby so special!
Willowtree Farm's Adventures with Santa
December 5 to 20 | Willowtree Farms, Scugog
On weekends throughout December, travel along the North Pole trail on a mission to find Santa at Willowtree Farm's Adventures with Santa experience! Meet Mrs. Claus and the elves, who will help you complete a series of tasks to find Santa himself. Little ones can also enjoy craft stations, outdoor games, hot chocolate, and roasted marshmallows by the fire.
Winter Nights, City Lights
November 13 and 14 | Esplanade Park, Pickering
Watch as festive lights and fireworks light up the nights sky at the City of Pickering's annual Winter Nights, City Lights celebration! Bring the family to enjoy live entertainment, food vendors, a vendor market, insta-worthy photo ops, and magical characters from 5:30 to 8:30 p.m. The annual tree lighting and fireworks take place each night at 6 p.m.
Winter Wonderland
December 5 and 12 | Millennium Square (Liverpool Road), Pickering
Join the City of Pickering and Nautical Village businesses for a magical Winter Wonderland event in Millennium Square this winter! Enjoy an opening day live ice carving, select holiday vendors, buskers, s’mores stations, and miniature train rides through the village. The event takes place from 11:30 a.m. to 3 p.m. and is free to attend.
Make It A Holiday With Heart
This season, head to Durham Region and discover the simple joys that make this time of year memorable. From the sparkle of lights to that first sip of hot chocolate, the holidays are all about the moments that make your heart feel full.
Tag @DurhamTourism on social media in all your magical moments. Whether you're starting a new tradition or revisiting an old one, we'd love to know what you tried and loved most!