30+ Christmas Markets and Holiday Events In Durham Region This Season
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Bright & Merry Market
November 14 | Downtown Oshawa (City Hall to Memorial Park and Centre Street to John Street)
Join the City of Oshawa and kick off the holiday season at the Bright and Merry Market in downtown Oshawa! Experience a holiday market, seasonal displays, live entertainment, buskers, and a holiday trolley. Finish your visit by snapping a photo with Santa, along with the tree lighting at 8 p.m. The event is free to attend. Guests are encouraged to bring a non-perishable food donation to support Feed the Need in Durham. Donation bins will be located at City Hall, The Robert McLaughlin Gallery, and Oshawa Public Libraries - McLaughlin Branch, for the duration of the event.
Downtown Whitby Christmas Market
November 14 and 15 | Celebration Square, Whitby
Join the Downtown Whitby BIA for two unforgettable days of festive fun and holiday cheer at the seventh annual Downtown Whitby Christmas Market! Enjoy an outdoor market featuring unique gifts, crafts, and holiday essentials from Downtown Whitby shops and local vendors. Grab a bite to eat from one of the food trucks, enjoy live performances, and climb aboard the trolley for a fun ride around the event, perfect for both kids and adults! The event will also feature carolers, free children’s activities, photos with Santa, magical characters and more. This event is free to attend, and a perfect excuse for friends and families to come together and celebrate the holiday spirit.
Santa Claus Parades
November 15 to December 13 | Locations across Durham Region
Santa Claus is coming to town! Bundle up and enjoy the magic of the season at one of Santa’s many visits across Durham Region. There's a full lineup of parades set to spread festive cheer, and visits by parade goers can also mean a thriving holiday season for local merchants with stops at shops and restaurants along the parade route. This beloved tradition features a festive street procession and is the perfect way to kick off the holiday season.
Leaskdale Loop Christmas Crawl
November 15 and 16 | Leaskdale Loop, Uxbridge
Get in the mood for Christmas with a free self-guided driving tour along the Leaskdale Loop Christmas Crawl! Made up of a variety of small businesses and historical sites, each destination is within 10 minutes of each other. Art, woodworking, pottery, handcrafts, baked goods, maple syrup, cider, vintage goods and much more await you along the loop. Between 10 a.m. and 5 p.m. (varies by location), get a jump on your Christmas shopping from the local artisans or visit our historical sites! In case you can't make it, Tindall Farm Market will also continue a second weekend of Christmas Markets on December 6 and 7.
Beaver River Christmas Market Days
November 15 and December 6 | Beaverton Thorah Eldon Historical Society, Beaverton
Share your holiday spirit and shop local goodies at the Beaver River Christmas Market Days! The craft show will be held from 9:30 a.m. to 3 p.m. on November 15 and December 6 at the Beaverton Thorah Eldon Historical Society's Meeting Place and Log Cabin (284 Simcoe Street, Beaverton). Explore a line up of vendors to find knitting, crocheting, pottery, children's toys, jewellery, and so much more. On December 6, the Log Cabin will feature a bake sale with all proceeds going to the historical society, and the Meeting Place will host craft tables. Both events are a part of the fundraising efforts for the Beaverton Thorah Eldon Historical Society. It's a great place to do some Christmas shopping!
1840 Vineyard's Winter Market, Santa & Grinchmas
November 16 and 29, and December 6 | 1840 Vineyard, Orono
Join 1840 Vineyard for a whole lot of festive fun! On November 16, the fourth annual Winter Market returns from noon to 5 p.m. for a festive day of supporting local with food vendors, makers and artisans, and enjoying all the vineyard has to offer! On November 29 from 11 a.m. to 4 p.m., celebrate the season at Cookies and Cocoa with Santa! Visit Santa and his sleigh and enjoy cookies, a hot cocoa bar, plenty of festive fun. On December 6 from 11 a.m. to 3 p.m., head to the vineyard for Grinchmas! Meet the Grinch himself for photos, and enjoy green cocoa and cookies. The original Grinch animated movie will be playing in a cozy viewing area. Each ticket is for a one hour visit inside with Santa or the Grinch, and unlimited time exploring the outdoor space, stopping for photos and warming by the fire. Tickets are time slotted.
Whitby Lights The Night Festival
November 21 to January 5 | Whitby Civic Park, Whitby
Kick off the festive season at Whitby Lights the Night! On November 21, enjoy a magical evening of live entertainment, Christmas Farmers' Market, and a dazzling lighting ceremony. Celebrate the spirit of the season with family-friendly activities, festive treats, and a joyful community atmosphere! Plus, don't miss the special Whitby Farmers' Market at Night from 4 to 8 p.m. If you can't make it to opening night, don't worry! The light display will continue throughout the season—from dusk to 10 p.m.—with over 200,000 magical lights and ground displays in Civic Park, Celebration Square and Grass Park. Get ready to be dazzled by twinkling lights, festive activities, and all the holiday magic that makes Whitby so special!
Applewood Farm's Christmas Cheer Mingle & Jingle
November 22 | Applewood Farm & Winery, Scugog
Applewood Farm & Winery is changing things up this year with their Christmas Cheer Mingle & Jingle on November 22! 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. The winery will also be debuting their brand new Christmas Cheer Moonshine. It's a great time to kick off the holiday season and celebrate local cheer. Admission is free, and canned food donations are encouraged. Guests can also visit the winery on weekends throughout December for fireside flights.
Holiday In The Hills
November 22 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, send off your letters at Santa’s Mail Room, become a certified elf at the Elf School, practice your toy building in the Toy Shop and build your own holiday plushie at the Bear Factory. Decorate gingerbread cookies at the Gingerbread House, stuff and donate a stocking at the Giving Tree, meet the Grinch, Rudolph and friends, win in an epic snowball fight, play the night away at the reindeer stables, and indulge in festive food and drinks by the fire. Plus, don’t miss Santa’s Dance and Tree Lighting Ceremony every night at 6:30 p.m.
Picks & Giggles Classic Holiday Market
November 22 to December 14 (weekends only) | Oshawa Centre, Oshawa
Picks and Giggles is bringing small businesses to the busiest mall in Durham Region! This year’s annual Classic Holiday Market is taking place at the Oshawa Centre—located in the upper level of the old Sears building—and will feature freshly brewed hot beverages from local coffee shops, sweets from local bakers, meet and greets from special guest appearances, live music daily, and more! Admission is $5 at the door per event, or $10 for access to all eight market days. Kids ages 14 and under are free. The market is open from 10 a.m. to 5 p.m.
Parkwood Estate Christmas Tours
November 24 to December 27 | Parkwood Estate, Oshawa
Deck the halls at Parkwood Estate National Historic Site in Oshawa with a guided Christmas tour to view their stunning décor and get into the holiday spirit! Using historic décor, the main floor of the mansion will be transformed into a Christmas wonderland. Guests also have the opportunity to visit on November 24 for an exclusive sneak peek before Christmas tours become available to the public. The estate also hosts a variety of workshops throughout the season, including Custom Christmas Doormats, Holiday Cookie Decorating, Holiday Wreaths, and more.
Jingle & Roar Christmas Market
November 28 | Beaverton Fair Grounds, Beaverton
Journey Into Enchantment
November 28 to December 27 | Ajax Downs, 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! Tickets are required per vehicle. Time slots are ticketed per vehicle and run from approximately 5 to 10:30 p.m.
Holly Trolley Ride & Shop
November 28 to January 4 (weekends only) | Downtown Port Perry, Scugog
On weekends from noon to 4 p.m., hop aboard the free Holly Trolley for a magical ride through town. Sign carols, visit with Santa, and stop at charming boutiques and artisan markets along the way. Step into the storybook setting with historic storefronts and locally-owned shops dressed in holiday finery when you visit downtown Port Perry this season! Plus, don't miss the Bakersville Animated Gingerbread Village at the Scugog Memorial Library throughout December. Enjoy a picturesque day of gift hunting and memory making!
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. In it's 27th year of spreading holiday cheer, the train also raises money, food and awareness for those struggling with food insecurity. Train schedules vary, so we recommend showing up at least 15 minutes early.
Christmas In The Village
November 29 | Old Kingston Road, Ajax (Pickering Village)
Join the Town of Ajax in Pickering Village on November 29 from 2 to 6 p.m. and experience a fun-filled day of activities at Christmas in the Village! Enjoy Santa photo opportunities, a trackless train ride, horse and wagon rides, s’more's and hot chocolate, face painting, a vendor marketplace, live entertainment, and more along Old Kingston Road! The event is free to attend and bound to bring you lots of holiday cheer.
Town Trolley Santa Pub Crawl
November 29 | Town Hall, Port Perry
Travel on the Town Trolley as it heads to visit five pubs and breweries throughout Port Perry. Enjoy sing-a-longs, and come dressed as Mr. or Mrs. Claus for the Town Trolley Santa Pub Crawl! A buffet dinner and snacks are included, drinks are additional. A portion of proceeds are donated to North House on behalf of all ticket sales. Please enjoy responsibly.
Jinglefest Holiday Concert
November 29 | Beaverton Town Hall, Beaverton
Get in the holiday spirit at the First Act Youth Company (FAYC)'s Jinglefest! For the first time, members of both their 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! The annual holiday fundraiser is more than just a celebration, it helps FAYC to continue providing high-quality performing arts education. The funds raised go directly toward hiring guest teaching artists, building sets and costumes, upgrading tech and studio spaces, supporting student sponsorships, and so much more.
A Country Path Christmas
November to December 31 | Various locations in Clarington
What better way to kick it off than by spending the day shopping along A Country Path! As you drive through the winding roads, take in the scenic beauty of the season—the crisp air, the twinkling lights, and the cozy charm of Clarington's rural stores. To make your shopping even more fun, take part in the annual Holiday Scavenger Hunt! Stop 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 and many will be hosting special festive events throughout the season.
Plus, mark your calendars to meet Mr. and Mrs. Claus on November 15 and December 14 from 2 to 4 p.m. at Tyrone Mills! Pets are welcome and guests are invited to bring non-perishable food items for the Bowmanville Salvation Army.
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.
Beaverton Stroll & Shop
December 5 | Simcoe Street, Beaverton
Enjoy a winter wonderland as you Stroll & Shop in the heart of downtown Beaverton! Wander along Simcoe Street from 6 to 9 p.m., grab a hot beverage from The Shortiss Café, and shop the downtown stores to find the perfect Christmas gift and holiday décor. Explore stores like The Cozy Swan for one-of-a-kind gifts, Whimsy Beaverton for wedding and home décor, and Wild Child for new and used children's clothing and sports equipment. Plus, there will be chances to win prizes! The downtown stores are planning an amazing Stroll & Shop for you.
Moonlight Magic & Christmas Market
December 5 | Downtown Bowmanville, Clarington
Discover the magic of Historic Downtown Bowmanville at the annual Moonlight Magic & Christmas Market! The event takes place from 5 to 9 p.m., with a special tree-lighting ceremony on Temperance Street at 6:30 p.m. Enjoy children's entertainment, complimentary horse-drawn wagon rides and a visit from Santa ; explore handmade items at the Christmas Market; grab a hot beverage or bite to eat from the vendor tents or nearby restaurants and cafes; listen to the sounds of the local choir; snap a photo with a surprise guest; and be sure to visit the downtown small businesses offering extended shopping hours until 9 p.m. (for one-night only)! Admission and parking are free, and food and toy drive donations are encouraged.
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Home For Christmas With Irwin Smith
December 5 | Town Hall 1873 Theatre, Port Perry
Get ready to kick off the holiday season with an unforgettable evening of music and memories! On December 5 at 8 p.m., beloved Port Perry performer Irwin Smith returns with "Home for Christmas" at Town Hall 1873 Theatre. Guests will enjoy an intimate holiday show filled with warmth, laughter, and toe-tapping tunes. Known for his smooth vocals, masterful piano playing, and charming storytelling, Irwin brings the spirit of the season to life with a mix of traditional favourites and modern holiday classics. Whether you're coming with family, friends, or flying solo, Irwin invites you to share in the joy, nostalgia, and musical magic that make this time of year truly special!
Uxbridge Holiday Trail
December 5 and 6 | 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. on December 5 and 6! This year's theme is Sound of the Season—a fun and festive time to shop, eat, drink, play, and enjoy live music. Take a free ride on the town trolley to the festival of lights, take photos with Mr. and Mrs. Claus, and celebrate in the nostalgia of this year's theme, vintage holidays! The highly anticipated return of the Uxbridge Holiday Trail and Cindy Wood Christmas Crawl will feature dazzling Christmas lights, 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.
Markets’ Holiday Pop-Ups
December 5 to 28 (weekends only) | Markets Ontario, Bowmanville
Join Markets Ontario for their busiest season of the year at their Holiday Pop-Ups every Friday, Saturday and Sunday in December! Explore local artisans and shop from a variety of different products during the month of December in Historic Downtown Bowmanville. The market will have 20+ vendors popping up each day, and is the perfect chance to shop local this holiday season.
Pingle’s Festive Farm Fun
December 5 to 28 (weekends only) | Pingle’s Farm Market, Hampton
Join Pingle’s Farm for not one, but two festive fun events this holiday season! Bring the family and enjoy a day of festive fun at the Red & Green Christmas Whobilation to enjoy a bite to eat and a Grinch experience like no other! Capture your picture-perfect moment with Santa at the brand new animal barn and celebrate the season in the decked-out greenhouse. If a date night is more your speed, check out Pingle’s Ugly Christmas Sweater Party on Fridays and Saturdays throughout December! Enjoy a festive, adult-only night of ugly Christmas sweaters, an all-you-can-eat merry menu, live holiday music, cozy campfires, and insta-worthy Christmas cocktails! This event is 19+ only. Both events are ticketed.
Pickering's Winter Wonderland
December 6 and 13 | 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, miniature train rides through the village. The event takes place from 11:30 a.m. to 3 p.m. and is free to attend.
Willowtree Farm's Adventures with Santa
December 6 to 14 (weekends only) | Willowtree Farms, Scugog
Mark your calendar for Adventures with Santa at Willowtree Farm! On weekends throughout December, from between 10 a.m. and 4 p.m., kids can enjoy an adventure with Santa’s helpers through a variety of stations to lead you to the big guy. Little ones can enjoy craft stations, outdoor games, and hot chocolate and roasted marshmallows by the bonfire. Don’t miss the North Pole set-up in the greenhouse, a story-time stroll with Mrs. Claus, or the Candy Cane Scavenger Hunt! Plus, you can give the on-call “reindeer” (a.k.a. the goats) a special treat!
Santa's Cabin at Knox's Pumpkin Farm
December 6 to 21 (weekends only) | Knox Pumpkin Farm, Hampton
Join Santa and the Elves for Christmas at Knox’s Pumpkin Farm—a holiday event your children and loved ones will remember forever! Enjoy a visit with Santa to see if you’ve made the good list and meet Santa’s Elves in their workshop. Stop by the stables to wish Rudolph a good flight, help with chores while learning about food and farming, pick-your-own pre-cut Christmas tree, and gather around the campfire to celebrate the holidays! The event is open from 10 a.m. to 3:30 p.m. on Saturdays and Sundays throughout December. Tickets must be pre-purchased in advance.
Oshawa Holiday Village
December 6, 13 and 20 | Victoria Lane (between Regent Theatre and Market at 70 King), Oshawa
For the very first time in 2025, Oshawa shines bright with its very own Christmas market! Step into a sparkling winter wonderland on Victoria Lane where holiday magic fills the air. Discover amazing local artisans, charming vendor huts, and joyful live music. Delight in delicious seasonal treats, enjoy fun interactive activities, and be sure to visit Santa Roger for a special holiday photo. Oshawa Holiday Village is so much more than a market. It’s a heartwarming celebration of community spirit, holiday joy, and festive traditions. Join us this December to create unforgettable memories and become part of Oshawa’s dazzling new holiday tradition! Use the Oshawa Holiday Experience as your go-to guide for all the festive activities happening in Oshawa this holiday season.
Uxbridge Optimist Fantasy of Lights
December 6 to January 3 | Elgin Park, Uxbridge
The Uxbridge Optimist Fantasy of Lights famous drive-through event is back at Elgin Park in Uxbridge from December 6 to January 3! The trail exhibits more than 100 light displays and guests can also enjoy a beautiful stroll through the Fantasy Trail foot path! Drive through the path of light displays, open seven days a week from 6 to 9:30 p.m., even on Christmas Eve and Christmas Day. The event is free to attend, however donations are kindly encouraged and go towards supporting local youth initiatives.
A Royal Ashburn Christmas
December 7 | Royal Ashburn Golf Club, Whitby
Gather the family for the annual Royal Christmas Event at Royal Ashburn on December 7! Enjoy a joyful holiday tradition filled with a festive breakfast, heartwarming storytelling, creative Christmas crafts, and selfies with Santa. Wander through the sparkling outdoor Christmas walk, discover hidden elf friends, build your own bracelet, and send your letter straight to the North Pole. This magical Christmas event is the perfect way to celebrate the season with the entire family! Seatings take place between 9 a.m. and 12:30 p.m.
Holiday Dreams: A Spectacular Holiday Show
December 13 | Tribute Communities Centre, Oshawa
Holiday Dreams: A Spectacular Holiday Show is a memory-making holiday experience that will leave audiences of all ages cheering for more! Don't miss this high-energy, modern holiday production that blends advanced technology with world-class entertainment. Featuring jaw-dropping holograms, immersive projection mapping, and dazzling lasers, this isn’t your typical holiday show. The stage comes alive with some of the most amazing, award-winning acts seen on America’s Got Talent and other international television programs. From acrobats and contortionists to aerialists, daredevils, and more, Holiday Dreams delivers nonstop thrills, wonder, and excitement.
Deer Creek's Brunch With Santa
December 14 | Deer Creek Golf Club, Ajax
Join Deer Creek Golf Club for their most beloved annual event—Brunch with Santa on December 14! Enjoy a delicious brunch, meet Santa himself, and make memories to last a lifetime. 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! Celebrate this magical time of year with loved ones at Deer Creek. Brunch seatings take place at 11:30 a.m., noon, and 12:30 p.m.
Sugar & Snow Holiday Marketplace
December 13 and 14 | 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. Enjoy a magical weekend filled with festive cheer, handmade gifts, delicious treats, unique finds, and holiday vibes! It's the perfect time to shop local and grab some delicious goodies perfect for right before the holidays.
Scugog Lakefront Skate & Market
mid-December to March (weather depending) | Palmer Park, Port Perry
Glide across the outdoor Scugog Lakefront Skate and Market under twinkle lights, and warm up with rich hot chocolate and seasonal treats. The holiday market is open weekends from 10 a.m. to 2 p.m., and skating is open daily (weather permitting). Located in the Joe Fowler north ball diamond, the outdoor rink and vendor village provides a unique and extended pleasure skating experience with food and artisan market right in the heart of downtown.
As if this list wasn’t full of enough holiday cheer, check out our list of Christmas Tree Farms Near Toronto for more festive fun. While you’re planning a fun day out with the kids or the perfect ‘holidate’ with your significant other, we’d love to share in the fun! Tag @DurhamTourism on social media in all your adventures.
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