30 Christmas Markets and Holiday Events In Durham Region This Season
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Holiday in the Hills
Location: Rowe Street, Orono | Date: November to December 22
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 and Giggles Classic Holiday Market
Location: Oshawa Centre, Oshawa | Date: November 23 to December 13 (weekends only)
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 and a free swag bag(while quantities last). Kids ages 14 and under are free. The market is open from 10 a.m. to 8 p.m. on Saturdays and 10 a.m. to 7 p.m. on Sundays.
Markets’ Holiday Pop-Ups
Location: Markets Ontario, Bowmanville | Date: November to December 22 (weekends only)
Join Markets Ontario for their busiest season of the year at their Holiday Pop-Ups every Friday, Saturday and Sunday from 10 a.m. to 3 p.m.! Explore local artisans and shop from a variety of different products during the month of December in Historic Downtown Bowmanville. If visiting before December 11, you can also bring your non-perishable food items, new unwrapped toys, or gift cards to local grocery stores—all items collected will be donated to the Bethesda House, a non-profit organization offering emergency services to women and children.
Christmas at Parkwood Estate
Location: Parkwood Estate, Oshawa | Date: November to December 27
There’s plenty of holiday cheer to be had at Parkwood Estate National Historic Site in Oshawa! Throughout December, join Parkwood for a guided Christmas tour to view their stunning Christmas décor and get into the holiday spirit! The estate will also be hosting a variety of workshops throughout the season, including a Custom Christmas Doormat Workshop, Holiday Ornament Painting, Gingerbread House Making, and more.
CPKC Holiday Train
Location: Oshawa and Bowmanville | Date: November 29
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 by Tyler Shaw and Shawnee Kish. 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 always recommend showing up at least 15 minutes early. In its 26th year of spreading holiday cheer, the train also raises money, food and awareness for those struggling with food insecurity.
Brooks Farms Festive Nights
Location: Brooks Farms, Uxbridge | Date: November 29 to December 23 (Fridays and Saturdays)
Enjoy a whole lot of festive fun at the Brooks Farms Festive Nights! This season, take part in a magical evening of lights and live music surrounded by holiday cheer. Enjoy a magically lit Christmas forest, holiday displays and plenty of photo opportunities, live music by local musicians, bonfires and marshmallow roasting, holiday characters like Elsa and the Grinch, a story time wagon ride, a craft market with local artisans, festive treats at the Hungry Hut, and—of course—a special visit with the real Santa! Tickets are $24.99 + HST and include a whole lot of festive fun.
Christmas in the Village
Location: Pickering Village, Ajax | Date: November 30
Join the Town of Ajax in Pickering Village (Old Kingston Road) on November 30 from 3 to 7 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, and more! The event is free to attend and bound to bring you lots of holiday cheer.
Applewood Farm Holiday Makers Market & Mingle
Location: Applewood Farm & Winery, Scugog | Date: November 30 and December 22
Don’t miss the annual Holiday Makers Market and Mingle on November 30 at Applewood Farm & Winery. From 10 a.m. to 4 p.m., explore amazing vendors, delicious food, live music, and drinks around the campfire. It's a great way to kick off the holiday season and support local makers this Christmas. Bring a friend, bring a gang, or come alone and make new friends here. Admission is free, and canned food donations are encouraged. The farm will also be hosting a Holiday Sip and Sing on December 22 to enjoy fireside drinks and live music with Mike Burns.
A Country Path Christmas
Location: Various locations in Clarington | Date: November to December 31
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. The draw will take place December 21 to win a$300 holiday basket. 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.
Mark your calendars for Archibald’s Christmas Market on December 1 to shop from more than 20 local vendors and enjoy a complimentary hot apple cider and wine tasting, visit Makers on Enfield’s Christmas in the Workshop on December 7, or stop by Tyrone Mills to meet Mr. and Mrs. Claus on December 14.
Journey into Enchantment
Location: Ajax Downs, Ajax | Date: November to January 1
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, and run from approximately 5 to 10:30 p.m.
A Holly Trolley Holiday In Scugog
Location: Downtown Port Perry, Scugog | Date: November to January 5 (various dates)
On November 29 until 8:30 p.m., enjoy an evening of late-night shopping and holiday cheer at the Holly Trolley and Shop Event! Stores will stay open late and you can enjoy a complimentary Trolley ride through the beautifully lit town between 4:30 and 8:30 p.m. As of December 5, Santa will be returning to downtown Port Perry—shop the stores and visit Santa at his hut from Thursdays to Sundays. Plus, don’t miss the Bakersville Animated Gingerbread Village from December 7 to January 5 at the Scugog Memorial Library, and ride the Holly Trolley on weekends throughout December, courtesy of the Port Perry BIA. There’s nothing like the holidays in downtown Port Perry!
Whitby Lights The Night Festival
Location: Whitby Civic Park, Whitby | Date: November to January 5
Kick off the festive season at Whitby Lights the Night! The light display illuminates Whitby Civic Park with more than 200,000 magical lights. The lights will continue throughout the season—from dusk to 10 p.m.—with ground displays in Civic Park, Celebration Square and Grass Park. Snowflakes also line Downtown Whitby and seasonal décor in Downtown Brooklin welcomes both residents and visitors throughout the community. Get ready to be dazzled by twinkling lights, festive activities, and all the holiday magic that makes Whitby so special!
Old Scugog Road Christmas Lights
Location: Old Scugog Road, Bowmanville | Date: December 1 to 31
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.
Christmas Concerts, Plays and Art Shows
Location: Across Durham Region | Date: December 1 to 31
There’s no better way to ring in the season than with a Christmas concert, play, or art show across Durham Region. Check out Durham Chamber Orchestra’s Colours of Christmas on December 1, DuffleBag Theatre’s A Christmas Carol on December 7, the Port Perry Artists Association Comfort and Joy Winter Art Show on December 7, Theatre on the Ridge's The Christmas Tree at Two Blokes Cider from December 6 to 14, Concert to Feed the Need in Durham on December 8, A Bluesy Christmas on December 14, Professors of Funk Christmas Special on December 18 and 19, or Dream Co. Theatre’s Another Christmas Carol from December 27 to 31.
Bratmas Charli XCX Christmas Party
Location: Biltmore Theatre, Oshawa | Date: December 6
Merry bratmas! Dance the night away at the Biltmore Theatre’s Charli XCX Christmas Dance Party on December 6, from 10 a.m. to 2 a.m., featuring music from Charli XCX, Billie Eilish, Slayyyter, Troye Sivan, Kim Petras, Shygirl and more! This is a DJ event and Charli XCX will not be in attendance. Tickets are $19.50 and guests must be 19 or older.
Moonlight Magic & Christmas Market
Location: Downtown Bowmanville, Clarington | Date: December 6
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 6:30p.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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Beaverton Downtown Christmas Open House
Location: Downtown Beaverton, Brock | Date: December 6
Enjoy an evening of shopping, goodies and festive fun at the Beaverton Downtown Christmas Open House! Many local businesses and a few from the outer areas will be here to have some fun. From 6 to 9 p.m., enjoy a fun Christmas evening exploring shops, cafes, and restaurants. Run into the Grinch himself while exploring local gems like Shirley’s Country Clutter, The Shortiss Cafe and Bar, Underground Bakeshop, and more.
Uxbridge Holiday Trail
Location: Brock Street West and Toronto Street, Uxbridge | Date: December 6 and 7
Get into the holiday spirit at the annual Uxbridge Holiday Trail! Shop, eat, drink, play, and enjoy live music at the fun and festive event on the evenings of December 6 and 7 from 5 to 8 p.m.! 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.
Pingle’s Festive Farm Fun
Location: Pingle’s Farm Market, Hampton | Date: Weekends from December6 to 22
Join Pingle’s Farm for not one, but two festive fun events this holiday season! On Saturdays and Sundays from December 7 to 22, 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 from December 6 to 21!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.
Leaskdale Loop Artisan Christmas Crawl
Location: Leaskdale Loop, Uxbridge | Date: December 7 and 8
Get in the mood for Christmas with a free self-guided driving tour along the Leaskdale Loop Artisan 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 4 p.m. (varies by location), get a jump on your Christmas shopping from the local artisans or visit our historical sites! Don’t miss Chef Alex Page for a free cooking demonstration and sampling at Banjo Cider—hosted in partnership with Durham Tourism and Durham Farm Fresh —from 1 to 3 p.m.
Pickering's Winter Wonderland
Location: Millennium Square (Liverpool Road), Pickering | Date: December 7 and 14
Join the City of Pickering and Nautical Village businesses for a magical 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 Nautical Village, and the Public Art installation “Same Material / Different Time” by Studio Jordan Shaw. The event takes place from 11:30 a.m. to 3 p.m. and is free to attend.
Knox Farm Winter Wonderland
Location: Knox Pumpkin Farm, Hampton | Date: December 7 to 22 (select dates only)
Join Santa and the Elves at Knox’s Winter Wonderland—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 select dates only. Tickets must be pre-purchased in advance—reserve your spot on the Santa Express to visit Santa and the Elves at the North Pole!
Willowtree Farms Adventures with Santa
Location: Willowtree Farms, Scugog | Date: December 7 to 22 (Fridays and Saturdays only)
Mark your calendar for Adventures with Santa at Willowtree Farm! 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! Tickets are $20 + HST and available online for visits between 10 a.m. and 4 p.m.
Uxbridge Optimist Fantasy of Lights
Location: Elgin Park, Uxbridge | Date: December 7 to January 4
Located at Elgin Park in Uxbridge, from December 7 to January 4, the Uxbridge Optimist Fantasy of Lights famous drive-through event exhibits more than 100 light displays. Back this year, guests can also enjoy a beautiful stroll through the Fantasy Trail foot path! This is free to attend, however donations are kindly encouraged and go towards supporting local youth initiatives.
Children's Winter Fest
Location: Scugog Shores Museum, Scugog | Date: December 8
Scugog Shores Museum is bringing back their annual Children’s Winter Fest, with a few new parts! How much do you know about Christmases of the past? What about other winter festivities and activities? The museum is bringing together all things winter fun at this festive event from 11 a.m. to 3 p.m. on December 8!Create your own winter craft, taste the warming refreshments, visit Santa Claus at the village, and more. Admission is ‘pay what you can’ to support your local museum.
1840 Vineyard Ugly Sweater Party
Location: 1840 Vineyard, Orono | Date: December 12
Join 1840 Vineyard for their annual Ugly Sweater Party! On December 12 from 6 to 9 p.m., grab your friends, co-workers, family and loved ones and enjoy an amazing tapas menu from Chef Niall of Tapas & Tales. Enjoy a welcome glass of mulled wine and live music around the fire, while showing off your ugliest attire! The bar will be open with seasonal cocktails, wine by the glass or bottle, and wine specials for all of your holiday celebrations. Tickets are $50 + HST.
The Brooklin Christmas Cottage
Location: Old Brooklin Community Centre, Whitby | Date: December 14 and 15
Enjoy a family-friendly event at The Brooklin Christmas Cottage—where the kids will get to build a Christmas decoration, play games, snack on cookies and hot chocolate, and chat with Santa himself! Events take place from 10 a.m. to 5 p.m. on Saturday and 1 to 6:30 p.m. on Sunday. Non-perishable food items are being collected for donation and a part of the proceeds will be going to Feed the Need Durham. Tickets are $12 to $14 and are time slotted.
Jingle N' Mingle Holiday Market
Location: BOND|ST Event Centre, Downtown Oshawa | Date: December 14
Jingle all the way to BOND|ST Event Centre’s Holiday Market in downtown Oshawa! Taking place from 10 a.m. to 5 p.m., the Jingle N' Mingle Holiday Market will feature a curated selection of local small businesses to shop, plus live music and fun holiday vibes. Entry is donation-based, pay as you wish, and all ages are welcome to join in on the fun!
Oshawa Holiday Shop Local Event
Location: Downtown Oshawa | Date: December 14
Get into the holiday spirit at the Oshawa Holiday Shop Local event on December 14! From 11 a.m. to 4 p.m., shop at small businesses in downtown Oshawa while enjoying a family-friendly and festive atmosphere, and warm up with free hot chocolate and Christmas cookies as you explore the event. Meet and take pictures with Santa, the Grinch, the Abominable Snowman, and Mickey and Minnie Mouse; enjoy live holiday music at the North Pole stage; and take advantage of gift-wrapping services at Market at 70 King, with proceeds supporting Lakeridge Health Community Support Services. Local downtown retailers will be offering special promotions and sales on unique holiday gift ideas, so you can feel good that you are supporting local businesses while finding one-of-a-kind gifts.
Use the Oshawa Holiday Experience as your go-to guide for all the festive activities happening in Oshawa this holiday season.
Scugog Lakefront Skate and Market
Location: Palmer Park, Port Perry | Date: December to March
Skate the day away at the outdoor Scugog Lakefront Skate and Market! Weather permitting, you can enjoy a whole day of fun by the lake—grab a hot chocolate and shop local artisans from the market, before lacing up your skates and heading on the ice. 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. Skating will be available seven days a week from 10 a.m. to 10 p.m. with vendor kiosks anticipated to be open most weekends.
As if this list wasn’t enough, check out our list of Santa Claus Parades in Durham Region for a full lineup of parades set to spread holiday cheer. 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 tree farm adventures.
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