The Durham Region is gearing up for a season of merriment and celebration! Discover a world of holiday enchantment with our comprehensive guide to the top Christmas and Holiday events.
Optimist Fantasy of Lights
From cozy Christmas markets to the dazzling Santa Claus Parades and the grandeur of Santa train rides, here is a list of festive activities that will fill your heart with joy and warmth!
Contents:
- Santa Claus Parades and Christmas/Holiday Light Displays
- Live Concerts & Theatre
- Markets, Train Rides and All Other Holiday Events
Santa Claus Parades and Christmas/Holiday Light Displays
Bright and Merry Market – Tree Lighting & Market
Friday, November 14, 2025 | 5 p.m. – 9 p.m.
Memorial Park, 110 Simcoe St S, Oshawa
Free
Winter Nights, City Lights – Pickering
Enjoy live entertainment, food vendors, new art installations, instagram-worthy photo ops, a market tent, and roaming characters. Bring the whole family out for some holiday fun!Details
November 14 & 15, 2025 | 5:30 pm to 8:30 pm
The Esplanade Park, The Esplanade, Pickering
Free
Journey into Enchantment Drive-thru
November 15 to December 27, 2025
Ajax Downs Racetrack, 50 Alexander’s Crossing, Ajax
$32.95 & up per vehicle
Santa Claus Parade of Lights Oshawa
A spectacular nighttime parade with colourful and brightly lit floats, dancers, and marching bands winding their way through the streets of Oshawa much to the delight of little boys, girls and the young at heart. Details
Saturday, November 15, 2025 | 6:00 PM
King St. W to Simcoe St. S to Bond St. W, Oshawa
Free
Uxbridge Santa Claus Parade
Since 1961, the Uxbridge Santa Claus Parade has been a tradition in celebration of the holiday season. Brock Street is closed to allow the parade to wow the thousands of residents and visitors who come out for the fun. Details
Saturday, November 15, 2025 | 11 AM
Brock St., Uxbridge
Free
Bowmanville Santa Claus Parade
Saturday, November 15, 2025 | 10:30 a.m.-12:30 p.m.
Roenigk Dr. to Memorial Park, Bowmanville
Free
Newcastle Santa Parade
The Newcastle Santa Parade is a wonderful event starting with a fantastic fireworks display at 5:30 pm followed by 70 entries that range from marching bands, to clowns and beautifully light up floats that children of all ages enjoy. Details
Sunday, November 16, 2025 at 5:30 pm
King Ave. West, Village of Newcastle
Free
Newcastle BIA Winter Wonder Lights
Join for the annual Newcastle BIA Community Town Hall Lighting Ceremony. Come out to the Community Hall in downtown Newcastle. We will be lighting up the hall, the tree and the parkette. There will be horse-drawn wagon rides, treats and activities at our local businesses. Details
Sunday, November 16, 2025 | 5:15 pm to 7 pm
Newcastle Community Hall, 20 King Ave. West, Newcastle
Free
Holiday in the Hills
Our six-week festival brings Christmas to life and creates true holiday magic for all ages. Come and enjoy the traditional Christmas Market, all of the fun children’s activities and see the beautiful Christmas lights on display. Details
November 22 to December 22, 2025
Orono Fair Grounds, 2 Princess Street, Orono
$13.44
Whitby Lights the Night Christmas Festival
Join us for Whitby Lights the Night Festival, 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!The Lights will continue throughout the season with over 200,000 magical lights and ground displays in Civic Park, Celebration Square and Grass Park. Details
Lights: November 21, 2025 – January 5, 2026
Holiday Festival: Friday November 21, 2025 | 5:00 p.m. to 8:30 p.m.
Whitby Civic Park, 575 Rossland Rd E, Whitby
Free
Pickering Santa Claus Parade
Join the City of Pickering and the Kinsmen & Kinette Club in celebrating the highly anticipated return of the Santa Claus Parade. This year, the Parade’s theme is Holiday Storytime, where groups are invited to represent pop culture or cultural stories about the holidays in their float design. Details
Saturday, November 22, 2025 | 6:00 PM – 08:00 PM
Vaughn Willard Public School to The Shops at Pickering City Centre, Pickering
Free
Orono Santa Claus Parade
Come and join Orono in welcoming Santa Claus. The town crier, floats, bands and many surprise visitors will escort the jolly man himself. Details
November 22, 2025 | 10:00 AM
Mill St, Orono
Free
Santa’s Spectacle of Lights – Town of Ajax Santa Claus Parade
Saturday, November 22, 2025 | 6 – 7:30 p.m.
Bayly St. and Harwood Ave. S, Ajax
Free
Christmas Tree Lighting and Candle Light Walk
Come and have your first chance to meet Santa and his friends at the candlelight procession Downtown to light trees and enjoy the merriment of various choirs and local musical talents! Details
November 28, 2025 | 5:00 PM – 8:00 PM
Queen Street/ Palmer Park, Port Perry
Free
Beaverton Lions Santa Claus Parade
Beaverton Lions Annual Santa Claus Parade of Lights and visit with Santa at the Beaverton Fire Hall. Details
Saturday, November 29, 2025 | 6PM
Main Street, Beaverton
Free
Cannington Lions Santa Claus Parade
Annual Santa Claus Parade. Theme: “Candy Land Christmas”. Details
Saturday, November 29, 2025 | 11 AM
Around Downtown from/to Cannington Arena
MacLeod Park, 72 Peace St, Cannington
Free
THEE Farmers Parade of Lights
THEE Farmers Parade of Lights
THEE (Tyrone, Haydon, Enniskillen, Enfield) Farmer Parade of Lights is an annual celebration of Christmas in the country with decorated farm equipment. Farmers from the community say thank you to friends and neighbours for sharing the roads year round with slow moving vehicles and farm machinery by lighting up the night with a gorgeous display of Christmas spirit. Details
Wednesday, December 3, 2025
Parade Begins at Old Scugog Rd and Concession 9, North of Enniskillen.
Free
Moonlight Magic Bowmanville
Join us for our annual Christmas Tree-lighting ceremony in Historic Downtown Bowmanville. Usher in the holiday season with this very popular event. Bring the entire family downtown for a carol sing and countdown to the lighting of Bowmanville’s huge Christmas Tree in the town square. You can also have your picture taken with Santa and his elves. Details
Friday, December 5th, 2025 at 5:00pm until 9:00pm
Main Street, Historic Downtown Bowmanville.
free
Scugog/Port Perry Santa Claus Parade
Get ready for some festive fun because the Scugog Santa Claus Parade is back for 2025. Details
Saturday, December 6, 2025 | 5:00 PM – 8:00 PM
Simcoe St, Port Perry
Free
Whitby Santa Claus Parade
Saturday December 6, 2025 | 10 a.m. to 12 p.m.
Brock Street S, Whitby
Free
Uxbridge Optimist Fantasy of Lights
Drive through fantastic light displays – over 75 light displays from community groups, businesses, schools, churches, families etc. from all around the Uxbridge area. Come and share your winter holiday with us in our amazing Christmas light display. Details
December 6th, 2025 – Januray 3rd, 2026 | 06:00 PM to 09:30 PM
Elgin Park, Elgin Park Drive, Uxbridge,
Free
Courtice Santa Claus Parade
Welcome the holiday season with the annual Santa Claus parade. Details
December 7, 2025 | 12 p.m.
Nash Road, Courtice
Free
Sunderland Santa Claus Parade
Santa Claus is coming to town in Sunderland ! Details
Saturday, December 13, 2025 | 7:00 p.m.
Sunderland Brock Memorial Arena, 20 Park St, Sunderland
Free
Live Concerts & Theatre
Shrek The Musical
November 20 to December 13, 2025
Oshawa Little Theatre, 62 Russett Avenue, Oshawa
$30.00 – $40.00
The Debaters Live – Holiday Special
To celebrate all the great laughs and questionable facts from the past two decades we’re crossing the country with a holiday tour for all ye faithful fans and listeners. Joining host Steve Patterson on this hilarious sleigh ride are a couple of his favourite debating elves ready to deliver a delightful evening of stand-up comedy and two joke-filled debates in the format made famous on CBC Radio. Details
Sunday, November 16, 2025 | 7:30 PM
Regent Theatre UOIT, 50 King St E, Oshawa
$58.50 to $68.50
Tartan Terrors Christmas
Welcome to a Tartan Terror Christmas! The Tartan Terrors Christmas show is a mix of Celtic and Classic Christmas, as well as wonderful Hogmanay tunes to round out the evening. The show will be filled with many moments that warm the heart and make you laugh with friends and family. Details
Friday, November 21, 2025 | 8:00 PM
Regent Theatre UOIT, 50 King St E, Oshawa
$45
George Canyon & Aaron Pritchett – Coast to Coast Cowboy Christmas Tour
Wednesday November 26, 2025 | 7:00 PM
BOND|ST Event Centre, 44 Bond St E, Oshawa
$64
A Next Gen Holiday Concert
Join Music4Life String Orchestra for a vibrant afternoon of string music and select seasonal tunes with highlights of the next generation . This family-friendly concert will feature a wide range of seasonal selections performed by our full community string orchestra, showcasing the warmth and joy of string music and the holiday season. Details
Saturday November 29, 2025 | 2:30 PM
Forest Brook Community Church, 60 Kearney Dr, Ajax
$20-$25
‘A Christmas Celebration’ with Durham Chamber Orchestra
Durham Chamber Orchestra welcomes you and the holiday season with selections of best loved traditional music.. Details
Sunday, November 30, 2025 | 2:00 p.m. – 3:00 p.m. @ Port Perry United Church 294 Queen St, Port Perry
Sunday, December 7, 2025 | 2:00 p.m @ Forest Brook Community, Church 60 Kearney Dr, Ajax
$25 to $30
The Arrogant Worms Holiday Show
The Arrogant Worms have spent over three decades making fun of a big dumb world. Their songs have been played on the radio, the internet, and in outer space (on the space shuttle Endeavour). Details
Friday, December 5, 2025 | 8:00 PM
Regent Theatre UOIT, 50 King St E, Oshawa
$35
A Christmas Carol ft. Dufflebag Theatre
The Queen has always been the “fairest in the land” — her Magic Mirror tells her so! But when the Queen hears that Snow White has surpassed her, she’ll do whatever it takes to get rid of her—forever! Fortunately, Snow White escapes into the deep, dark woods, where she comes to a tiny cottage. Little does she know that the seven dwarves living there will help save her! Laugh out loud as Snow White and some audience members encounter hapless huntsmen, bad apples and little men with big hearts and short tempers. Will she find her “happily ever after?” Details
Saturday, December 6, 2025 | 2:00 PM
St. Francis Centre, Pickering Village, Ajax
$22.63
Murder, Mayhem & Mistletoe
The Piano Café invites you to an unforgettable Murder Mystery Ugly Sweater Night — a festive evening filled with laughter, intrigue, and just the right amount of holiday mischief.
Santa’s acting like a Grinch, Mrs. Claus has had enough, and the elves? They’ve gone on strike! When fiery Scottish elf Ginger McSnappy takes matters into her own hands, things take a deadly turn — and it’s up to you to help solve the mystery.
Friday, December 12, 2025 | 7 PM
The Piano Cafe & George Stanley Inn, 217 Queen St, Port Perry
$50
Ontario Philharmonic – Nutcracker – A Holiday Tradition
The magic of Tchaikovsky’s celebrated Nutcracker comes to Ontario Philharmonic. This magisterial and iconic ballet for the Holiday Season is presented in its full orchestral version with engaging multimedia projections, giving you the opportunity to follow the story plot while immersed in the glorious sounds of the orchestra. Details
Saturday, December 13, 2025 | 7:30 PM
Regent Theatre UOIT, 50 King St E, Oshawa
$67.80 to $76.84
Home for the Holidays starring Alex Whorms
Ajax-born and award-winning singer/songwriter, screen composer and recording artist Alex Whorms, returns “home for the holidays” with her band for a special concert presentation, mixing her original music with some holiday favourites. It’s an experience that will warm your heart on a cold December evening. Details
Saturday, December 13, 2025 | 7:00 PM
St. Francis Centre, Ajax
$43.63
Holiday Dreams – A Spectacular Holiday Show
Holiday Dreams – A Spectacular Holiday Show! is a 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—it’s a full-on spectacle designed for today’s audience. Details
Saturday, December 13, 2025 | 7:00 PM
Tribute Communities Centre,
99 Athol Street East, Oshawa
$56 to $81.75
The Barra MacNeils – An East Coast Christmas
With their captivating vocals, distinctive harmonies and extraordinary musicianship, The Barra MacNeils inject new life and energy into the sights and sounds of Christmas, prompting the Halifax Daily News to describe them as “a treasure of the East Coast, rich with tradition and unmatched in ensemble performance”; and the Globe & Mail to name the recording on which this tour is based “one of the best five Christmas albums of all time!” Details
Sunday, December 14, 2025 | 7:30 PM
Regent Theatre UOIT, 50 King St E, Oshawa
$83.75
Next Generation Leahy’s Christmas
Monday, December 15, 2025 | 8:00 PM
Regent Theatre UOIT
50 King St E, Oshawa
$45
Celtic Tenors – A Celtic Christmas Tour
Celebrate the holiday season with the most successful crossover act to emerge from Ireland. These world-class artists will perform holiday classics that will have the audience smiling into the season with uplifting harmonies. Details
Tuesday, December 16, 2025 | 8:00 PM
Regent Theatre UOIT, 50 King St E, Oshawa
$60
The Jersey Nights Before Christmas Show
The Jersey Nights Before Christmas Show! Four superb vocalists, a live band, the legendary music of Frankie Valli and the four seasons, nostalgic hits by artists of the magic area, a special presentation of Christmas classics, and Santa! This is an evening of fun for the whole family.
7:30 PM
Pickering Casino Resort, Pickering
$58.50
Living Nativity
Ontario Philharmonic is thrilled to welcome the celebrated Elmer Iseler Singers with conductor Lydia Adams. This treasured holiday season program, filled with spirited choral works and Christmas carols, will remain ringing in your ears for days on end. Details
Centennial Park, Uxbridge
Free
The Elmer Iseler Singers & Ontario Philharmonic Brass Quintet
Ontario Philharmonic is thrilled to welcome the celebrated Elmer Iseler Singers with conductor Lydia Adams. This treasured holiday season program, filled with spirited choral works and Christmas carols, will remain ringing in your ears for days on end. Details
7:30 PM
Regent Theatre UOIT, 50 King St E, Oshawa
$67.80 to $76.84
Elvis’ Wonderful World of Christmas
Celebrating 25 years of festive magic, Michaels and his ensemble bring the warmth of Graceland to life with beloved holiday favorites like “Blue Christmas,” “Silver Bells,” and “Do You Hear What I Hear,” plus classic Elvis hits.
7:30 PM
Pickering Casino Resort, Pickering
$62.25 & up
Elvis Wonderful World of Christmas Graceland Edition
Inspired by the music of Elvis Presley, this Yuletide spectacular is hosted by none other than the man himself. Steve Michaels sings the Christmas Classics as well as serenading you with the King’s own holiday season favourites. The Wonderful World of Christmas is a Graceland of wonderment, celebrating the most glorious time of the year. Details
Saturday, December 20, 2025 | 7:00 PM
Regent Theatre UOIT, 50 King St E, Oshawa
$59
John McDermott – Family Christmas
Sunday, December 21, 2025 | 3:00 PM
Regent Theatre UOIT, 50 King St E, Oshawa
$49
HOOK: A NEW FAMILY MUSICAL
In the grand British tradition where audiences cheer the hero and boo the villain, Hook shifts the focus of the timeless classic Peter Pan to focus on our anti-hero, the one and only, Captain Hook! This production will feature flashy musical numbers, outrageous costumes, comedy, magic, mayhem, and of course…you’re part of the show! Details
December 27 – 31, 2025
Town Hall 1873 Theatre, 302 Queen St, Port Perry
$26 to $40
Markets, Festivals and All Other Events
Downtown Whitby Christmas Market
Each year, the Christmas Market allows friends and families to come together to celebrate the spirit of Christmas and enjoy a magical outdoor market, fun and festive activities, live performances, delicious local food, and the best holiday shopping in Durham Region. The event is FREE and attendees of all ages are welcome. Details
Friday, November 14: 4:00 p.m. – 9:00 p.m.
Saturday, November 15: 10:00 a.m. – 8:00 p.m.
Celebration Square, 405 Dundas St. W., Whitby
Free
Leaskdale Loop Christmas Market
Follow the Leaskdale Loop where you can find farm market fare, pick your own produce, lavendar & syrup right where they are made. Discover various artisans, historical sites, vintage barns, food stops, and more. Connect with the makers and growers, feel good about the products you take home. Details
November 15 & 16, 2025
Various Locations, Leaskdale
Free
Christmas in the Village
Embrace the magic of small-town traditions with family and friends as we celebrate the holiday season in Downtown Brooklin. From visiting Santa to seasonal crafts and scavenger hunts, there is so much to do! Details
November 22, 2025 | 9:00 am – 2:00 pm
Brooklin Village, Whitby
Free
Durham Potters Guild
November 15-16, 2025
Ajax Community Centre, 75 Centennial Rd, Ajax
Free
Picks & Giggles Holiday Market
Support local retailers and discover unique gifts, artisanal treats, and festive décor while enjoying a magical atmosphere filled with holiday cheer! We’ll also feature exciting entertainment throughout the market. Details
November 22, 23, 29, 30m Dec 6, 7, 13, 14, 2025 | 10 AM to 5 PM
Top floor of the old Sears building, Oshawa Centre, 419 King Street West,
Oshawa
Admission: $5 at the door
Kids under 14: Free!
Winterfest Vendor Market
Start (or finish) your holiday shopping while enjoying some holiday tunes and apple cider in the Parkwood Gift Shop. while supporting Parkwood and a host of local artisans at our Friends & Family Holiday Sale. Details
November 22 & 23, 2025 | 10 AM to 3 PM
Parkwood National Historic Site, 270 Simcoe Street North, Oshawa
$5
Holley Trolley
Hop on, hop off, and experience the twinkling charm of Port Perry’s shops, restaurants, and festive streets — all dressed up for the holidays. Details
Weekends, November 22 to December 7, 2025
Various Locations, Port Perry
Free
Parkwood Christmas Tours
Using historic décor, the main floor of the mansion will be transformed into a Christmas wonderland! Details
November 27, 29, December 10 to 12, 14 to 23, 27 to 30, 2025
Parkwood National Historic Site, 270 Simcoe Street N, Oshawa
$22 + HST
Holiday Swag Workshop
Join our Museum Interpreter and harvest fresh greenery from our museum site. Then create two of your own swags. Add in ribbon and natural accents such as pinecones and other natural bits you collect. Learn some history about the materials and how they were used for holiday decorating in the past.Details
November 29 & 30, 2025
Pickering Museum Village, 3550 Greenwood Road, Pickering
$48.66 per person
Black Queens of Durham Holiday Market
The Black Queens of Durham Holiday Market is a fun event open to the entire community and family.
We’ll have amazing food vendors, lively music, face painting, a photo booth, a dedicated kids’ section, and much more. We’re pulling out all the stops to make this year’s event even bigger and better than ever before. Details
December 6 & 7, 2025
Audley Recreation Centre, 1955 Audley Rd, Ajax
Free
A Storybook Christmas
December 6, 7, 13 & 14, 2025
Pickering Museum Village, 3550 Greenwood Rd., Greenwood
$6.78 to $11.30
Oshawa Holiday Village
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.
December 6, 13 and 20, 2025 | 3 PM – 7 PM
Victoria Lane (between the Regent Theatre and Market at 70 King), Oshawa
Free
ROYAL CHRISTMAS EVENT
Join us for a joyful holiday tradition, filled with a festive breakfast, heartwarming storytelling, creative Christmas crafts, and selfies with Santa. Wander through our sparkling outdoor Christmas walk, discover hidden elf friends, build your own bracelet, and send your letter straight to the North Pole. A Magical Christmas is the perfect way to celebrate the season with the entire family! Details
Sunday, December 7, 2025 | 9 AM & 1 PM
Royal Ashburn Golf Club,
995 Myrtle Rd W, Whitby
$42 + hst
A Country Path Christmas
Visit participating shops and farms in Clarington to find unique gifts and treats. Instead of being one weekend only, we invite you to choose your own day(s) to drive along A Country Path and browse at our numerous shops to see the unique treasures we have in store. Details
until December 23rd
Various Locations, Clarington
Free
Knox Farm Christmas
Visit with Santa to see if you’re on the good list! See Santa’s Elves in their workshop. Reserve your spot on the Santa Express to visit with Santa and the Elves at the North Pole! Stop by the stables to wish Rudolph a good flight…help do the chores while learning about food & farming. Gather around the campfire to celebrate the holidays!
December 6, 7, 13, 14, 20, 21, 2025
Knix Pumpkin Farm, 6325 Enfield Rd, Hampton
$28.72
Pingle’s Red & Green Christmas
This year’s Christmas event starts out by bringing the magic of the season into our Animal Barn! Enjoy a short walk through the farm, then meet the barnyard crew, and capture that perfect Christmas photo with Santa among the twinkling lights and rustic decor. Details
December 6 to 21, 2025
Pingle’s Farm Market, 1805 Taunton Road East, Hampton
$16.55
Bakersville Animated Gingerbread Village
A community display of Gingerbread houses that runs through the holiday season.Details
December 6 to January 4, 2026 | During Library hours
Scugog Memorial Library, 231 Water St, Port Perry
Free
Pickering Winter Wonderland
Join the City of Pickering and Nautical Village businesses for an exciting event in Millennium Square this Winter! Enjoy an opening day live ice carving, select holiday vendors, winter character performers, buskers, s’mores stations, and miniature train rides through Nautical Village. Details
December 6 & 13 | 11:30 am – 3:00 pm
Millennium Square, Pickering
Free
Uxbridge Holiday Trail
Throughout December, get your holiday shopping done at one of a kind boutiques, and dine at local restaurants in Uxbridge! Discover the Holiday Charm of Uxbridge, enjoy the Snow People featured in the shop windows, and Holiday Trail specials at local restaurants while attending festive events! Details
December 5 & 6, 2025
Downtown Uxbridge, Brock St, Uxbridge
Free
Adventures with Santa
Travel along the North Pole trail on a mission to find Santa!
Santa’s helpers will guide you through the trail to complete a series of tasks to get you closer to find the guy in the big, red suit. Along the way, you’ll meet up with Mrs. Claus, elves, & some other special friends of Santa’s.
Weekends, December 6 to 14, 2025
Willowtree Farm, Durham Regional Road 21, Port Perry
$20/person (ages 2-92)
Festive Nights on the Farm
Festive Nights on the farm! TBA Details
TBA
Brooks Farms, 122 Ashworth Road, Mount Albert, Uxbridge
TBA
Christmas in Ontario
View Comments (1)
A Cowboy Christmas George Canyon & Aaron Pritchett
Wed, 26 November in Oshawa