Looking for a free Santa Claus parade, an evening of Christmas lights or a holiday show the whole family can enjoy? Durham Region has events spread across Oshawa, Whitby, Ajax, Pickering, Clarington, Uxbridge, Scugog and Brock Township.
Some celebrations last only one evening, while others run for several weekends. There are outdoor markets, illuminated drives, children’s activities, theatre performances and Christmas concerts. Admission is free at many community events, but certain attractions, concerts and workshops require tickets.
Optimist Fantasy of Lights
Use the city summaries and activity suggestions below to choose an outing, then jump to the full listings for dates, venues, prices and event links. Times, fees and availability can change, so check the linked event details before travelling.
Find Events Quickly
- Holiday Fun by city and community (few suggestions)
- Christmas activities for families and children
- Holiday outings for couples and friends
- Free Christmas events
- Santa parades and Christmas light displays: all listings
- Holiday concerts and theatre: all listings
- Christmas markets, festivals and other events: All listings
Where Can You Celebrate Christmas in Durham Region?
The best place to start depends on where you live and the kind of outing you have in mind. These city-by-city highlights point to some of the events already included in the full calendar below.
Oshawa
Spend an evening in downtown Oshawa as the streets come alive with Christmas lights, music and holiday festivities. Start with the Bright and Merry Market on November 20, where you can browse handmade gifts, enjoy seasonal treats, ride the holiday trolley and watch the festive lights illuminate City Hall’s North Parkette at 8:30 p.m. The Santa Claus Parade of Lights follows on November 21.
Make an evening of it with dinner at Avanti Trattoria for Italian favourites or Berry Hill Food Co. for a relaxed meal. For more holiday entertainment, catch Frozen the Broadway Musical or Stars on Ice. Plus there’s plenty of concerts at Regent Theatre. Pingle’s Farm also offers free admission Christmas market and Santa photo for $5. If you prefer a quieter festive outing, explore the beautifully decorated interiors of Parkwood Estate during its Christmas Tours.
Whitby
Spend a festive afternoon exploring downtown Whitby’s shops, cafés and Christmas markets. Start with the Downtown Whitby Christmas Market on November 13 and 14, or browse local handmade gifts at the Annual Winter Market on November 14. For a small-town Christmas atmosphere, visit Brooklin’s Christmas in the Village on November 21 for Santa visits, crafts and holiday shopping.
As evening falls, head to Whitby Lights the Night on November 27 for live entertainment, a Christmas farmers’ market and the lighting of more than 200,000 festive lights. The displays continue nightly through January 4, giving you plenty of opportunities for an evening stroll. The Whitby Santa Claus Parade follows on December 5. For holiday music, catch the Durham Chamber Orchestra’s A Baroque Christmas at St. Mark’s United Church on December 13.
Make a day or evening of it with a meal at KB Food for seasonal Canadian cuisine, The Vault Gastropub for casual dining in a former bank building, or explore downtown Whitby’s restaurants and cafés. With holiday lights, local shopping and live performances, it’s easy to put together a relaxed Christmas outing without leaving Whitby.
Ajax
Take the family for an evening drive through thousands of festive lights at Journey into Enchantment, running from November 20 to December 26. For a traditional community celebration, head downtown on November 28 for Santa’s Spectacle of Lights, featuring illuminated floats followed by a Christmas tree lighting and festivities at Town Hall.
There’s plenty to enjoy indoors, too. Browse handcrafted pottery at the Durham Potters Guild show on November 14 and 15, or take the kids to A Very Merry Magic Show on December 5. Holiday music fans can catch the Music4life String Orchestra on December 5 or Bublé Christmas Starring Jay Davis on December 12. The Black Queens of Durham Holiday Market also brings more than 100 vendors together on December 6.
Make it a family evening with dinner at Magwyers Pub for comfort food or Portly Piper for a casual meal before heading to the parade, Christmas lights or a performance.
Pickering
Start your Christmas celebrations at Winter Nights, City Lights on November 13 and 14, when Esplanade Park fills with festive entertainment, food vendors, illuminated installations and musical fireworks. The Pickering Santa Claus Parade follows on November 28, taking a temporary route along Whites Road this year.
For another family outing, visit Pickering Winter Wonderland on December 5 and 12 at Millennium Square. Enjoy ice carving, holiday performers, s’mores stations and miniature train rides around the Nautical Village. If you enjoy making your own Christmas decorations, the Holiday Swag Workshop at Pickering Museum Village on December 12 and 13 offers a hands-on seasonal activity.
For a musical evening, catch ABBA Revisited Christmas Special on December 5 or The Wonderful World of Christmas on December 19 at Pickering Casino Resort. You could also combine a visit to Winter Wonderland with a waterfront meal at PORT or WATR Taverna & Ristorante overlooking Frenchman’s Bay.
Clarington
If you enjoy traditional small-town celebrations, Clarington has several ways to spend a festive afternoon or evening. Newcastle begins with Winter Wonder Lights and the Newcastle Santa Parade on November 15, complete with illuminated floats and fireworks. Bowmanville’s Santa Claus Parade takes place November 21, while downtown’s Moonlight Magic on December 4 brings Christmas carols, Santa visits, wagon rides and a tree lighting. After exploring historic downtown Bowmanville, settle in for dinner at Chanterelle Bistro, or browse the downtown business directory for cafés and casual dining options.
In Orono, explore the Christmas lights, market and children’s activities at Holiday in the Hills, or gather along Mill Street for the Santa Claus Parade on November 28. Courtice hosts its Santa Claus Parade on December 6. For holiday shopping at your own pace, explore participating farms and shops along A Country Path Christmas.
There are quieter festive experiences, too. Enjoy a Candlelit Christmas Concert at Wilmot Orchards in Newcastle on November 28.
Uxbridge
Uxbridge offers a lovely mix of Christmas traditions and countryside outings. Start with the Uxbridge Santa Claus Parade on November 21, then return after dark for the Optimist Fantasy of Lights at Elgin Park. Running nightly from December 5 to January 2, the free attraction features more than 100 illuminated displays, with both drive-through and walking options.
For a festive afternoon, explore the Leaskdale Loop Christmas Market on November 21 and 22 or December 5 and 6, stopping at participating farms, artisan shops and local businesses. Downtown Uxbridge also celebrates the season with the Uxbridge Holiday Trail on December 4 and 5, featuring seasonal shopping and decorated storefronts.
Prefer a warm theatre seat? Uxbridge Music Hall presents Irving Berlin’s White Christmas in November and Elf: The Musical Jr. from December 3 to 6. Make a day of it by browsing Brock Street’s independent shops before a meal at 9 by TIN for Italian-style dishes or The Corner House Pub & Grill for a relaxed family dinner.
Scugog
Spend a little time wandering historic downtown Port Perry, where independent shops, decorated storefronts and seasonal events make for a relaxed Christmas outing. The Christmas Tree Lighting and Candlelight Walk is associated with the November 20 holiday celebrations, while the Port Perry Santa Claus Parade takes place December 5. You can also explore the Bakersville Animated Gingerbread Village at Scugog Memorial Library throughout December. Enjoy a meal at Marwan’s Global Bistro or Jester’s Court Pub & Eatery before exploring the holiday lights.
Families with young children can book Adventures with Santa at Willowtree Farm on weekends from December 5 to 20, where Santa’s helpers guide visitors along a themed trail. Downtown Port Perry’s Vintage Holiday Weekend from December 11 to 13 offers another opportunity for seasonal shopping. Holiday theatre fans can catch Snow White the Panto at Town Hall 1873 Theatre from December 27 to 31.
For an adult outing, visit Applewood Farm Winery in Seagrave for Deck the Halls Day on November 21, Christmas Market and Mingle on November 29, or Fireside Flights and Holiday Tunes during December weekends. The winery’s Annual Christmas Party follows on December 20.
What Are Good Christmas Activities for Families and Kids?
For an outing built around Santa, consider Adventures with Santa at Willowtree Farm, where children follow a themed trail, or Pingle’s Christmas in Oshawa for seasonal farm activities or choose from any of the the Santa Parades in the region. Christmas in the Village in Brooklin also includes family crafts and a Santa visit.
Children who enjoy lights may prefer Journey into Enchantment in Ajax or the free Uxbridge Optimist Fantasy of Lights in Elgin Park. For an indoor option, A Very Merry Magic Show has two one-hour performances on December 5, while Elf: The Musical Jr. runs December 3 to 6.
Where Can Couples and Friends Enjoy a Holiday Outing?
For a relaxed evening together, browse Whitby’s Christmas Market or take in Whitby’s illuminated displays. If you would rather spend the evening indoors, the listings include Candlelight: Christmas Classics, Stars on Ice and several Christmas tribute concerts.
Applewood Farm Winery has Christmas Market and Mingle on November 29 and an annual Christmas party on December 20. Adults looking for a late-night music event can consider The Emo Nightmare Before Christmas in Oshawa on December 12; that event is restricted to ages 19 and older.
Which Christmas Events in Durham Region Are Free?
Free outdoor options include Oshawa’s Bright and Merry Market, Pickering’s Winter Nights, City Lights, Whitby Lights the Night and the Uxbridge Optimist Fantasy of Lights. Community Santa parades in Oshawa, Ajax, Whitby, Bowmanville, Newcastle, Port Perry and other Durham communities also have free admission.
Free entry does not necessarily mean a no-cost visit. Food, vendor purchases, photo packages or optional activities may cost extra.
Santa Claus Parades and Christmas/Holiday Light Displays
Winter Nights, City Lights – Pickering
Pickering lights up Esplanade Park with live performances, food vendors, art installations and a market. Tree lighting and musical fireworks begin at 6 p.m. each evening. Details
Friday and Saturday, November 13 and 14, 2026 | 5:30 p.m. to 8:30 p.m.
Esplanade Park and Chestnut Hill Developments Recreation Complex, 1867 Valley Farm Rd., Pickering
Free
Journey into Enchantment Drive-thru
This Ajax light show includes a roughly two-kilometre drive-through route and a walk-through section with illuminated displays and character visits. From Santa and his reindeer soaring through the skies to joyful elves spreading holiday cheer, each scene will fill your heart with delight and wonder.
November 20 to December 26, 2026 | Select evenings from 5:15 p.m.; closing times vary by date
462 Kingston Rd E, Ajax
$39.09 per vehicle & up
Bright and Merry Market – Tree Lighting & Market
The free downtown market includes local crafts, seasonal entertainment, Santa visits, a festive trolley and an 8:30 p.m. illumination at City Hall North Parkette. Details
Friday, November 20, 2026 | 5 p.m. to 9 p.m. (lighting at 8:30 p.m.)
City Hall Civic Square to Memorial Park, 50 Centre St. S.
Free
Santa Claus Parade of Lights Oshawa
Oshawa’s evening parade features illuminated floats and performers travelling along King Street West. Details
Saturday, November 21, 2026 | 6:30 p.m.
King Street West, Oshawa (Gibbons Street to Division Street)
Free
Uxbridge Santa Claus Parade
The long-running Uxbridge parade follows Brock Street through downtown, with community floats and Santa. Details
Saturday, November 21, 2026 | 11 a.m.
Brock Street, Uxbridge (from near the arena toward Uxbridge Secondary School)
Free
Bowmanville Santa Claus Parade
Bowmanville’s community Santa parade follows King Street, with decorated floats and festive performances. Details
Saturday, November 21, 2026 | 10:30 a.m.
King Street West, Bowmanville (Scugog Street to Simpson Avenue)
Free
Newcastle Santa Parade
The Newcastle Santa Parade combines fireworks with illuminated floats and music. Fireworks start before the procession. Details
Sunday, November 15, 2026 | Fireworks at 5:30 p.m., followed by parade
King Avenue, Newcastle (west to east through the village)
Free
Newcastle BIA Winter Wonder Lights
The annual lighting of Newcastle Community Hall, the Christmas tree and nearby parkette takes place ahead of the Santa parade. Details
Sunday, November 15, 2026 | Hall lighting at approximately 5 p.m.
Newcastle Community Hall, 20 King Ave. W., Newcastle
Free
Holiday in the Hills
Holiday in the Hills opens its seasonal festival at the Orono Fairgrounds with a holiday market, lights and children’s activities. The organizer has confirmed opening day but not a complete closing date on the page reviewed. Details
November 21 to December 22, 2026
Orono Fairgrounds, 2 Princess St., Orono
Ticketed; see official site for current admission prices
Whitby Lights the Night Christmas Festival
The Whitby holiday celebration includes a farmers’ Christmas market, entertainment, Santa and a tree lighting. More than 200,000 lights remain on display after the festival evening. Details
Festival: Friday, November 27, 2026 | 5 p.m. to 9 p.m.; lighting at 5:30 p.m. Lights: November 27, 2026 to January 4, 2027, dusk to 10 p.m.
Civic Park, 555–575 Rossland Rd. E., Whitby
Free
Pickering Santa Claus Parade
Pickering’s parade has a temporary 2026 route on Whites Road because of City Centre construction. Details
Saturday, November 28, 2026 | 10 a.m.
Whites Road, Pickering (Dunbarton High School to St. Mary Catholic Secondary School)
Free
Orono Santa Claus Parade
The village parade features festive floats, bands and Santa, travelling south along Mill Street. Details
Saturday, November 28, 2026 | 10:30 a.m.
Mill Street, Orono (from Mill Lane toward Orono Fairgrounds)
Free
Santa’s Spectacle of Lights – Town of Ajax Santa Claus Parade
Santa’s Spectacle of Lights proceeds through downtown Ajax, followed by a tree lighting and gathering at Town Hall and the Main Library. Details
Saturday, November 28, 2026 | 6 p.m. to 7:30 p.m.
Bayly Street from Mackenzie Avenue, then north along Harwood Avenue South to Ajax Town Hall
Free
Christmas Tree Lighting and Candlelight Walk
Downtown Port Perry’s candlelit walk and tree lighting feature carolling, seasonal activities and a holiday market. The farmers’ market confirms a November 20 holiday pop-up, but a separate official start time for the tree-lighting procession was not verified. Details
Friday, November 20, 2026 | Holiday market 5 p.m. to 8 p.m.; candlelit walk and tree-lighting time to be confirmed
Downtown Port Perry and Latcham Centre, 121 Queen St., Port Perry
Free community activities; verify details with organizer
Beaverton Lions Santa Claus Parade
Beaverton’s holiday celebrations include a nighttime parade, festive entertainment and a visit with Santa at the Fire Hall. Details
Saturday, November 28, 2026 | Parade at 6 p.m.; related activities begin earlier
Downtown Beaverton; parade from the fairgrounds via Main, Simcoe, Osborne and Bay streets
Free
Cannington Lions Santa Claus Parade
The Cannington Lions parade celebrates a Candy Land Christmas with its route beginning and ending near the arena. Details
Saturday, November 28, 2026 | 11 a.m.
Cannington Arena, MacLeod Park, 72 Peace St., Cannington
Free
THEE Farmers Parade of Lights
Local farmers decorate tractors and other farm equipment with Christmas lights for this rural evening procession. Details
THEE Farmers Parade of Lights
Wednesday, December 2, 2026 | Approximately 5:30 p.m.
Old Scugog Road at Concession 9, north of Enniskillen
Free
Moonlight Magic Bowmanville
Historic downtown Bowmanville hosts Christmas carols, Santa, children’s entertainment, free wagon rides and a tree-lighting ceremony. Details
Friday, December 4, 2026 | 5 p.m. to 9 p.m.; ceremony at 6:30 p.m.
Temperance Street and downtown Bowmanville
Free
Scugog/Port Perry Santa Claus Parade
Port Perry’s annual Santa Claus parade begins at the fairgrounds and features seasonal floats and community participants. Details
Saturday, December 5, 2026 | 5 p.m.
Scugog Fairgrounds, 15835 Old Simcoe Rd., Port Perry (parade starting point)
Free
Whitby Santa Claus Parade
The annual morning parade travels along Brock Street in Whitby with floats, community organizations and Santa. Details
Saturday, December 5, 2026 | 10 a.m. to noon
Brock Street, Whitby (Manning Road to Trent Street)
Free
Uxbridge Optimist Fantasy of Lights
See more than 100 illuminated displays by vehicle or along the returning Fantasy Trail walking path. No reservations are needed. Details
December 5, 2026 to January 2, 2027 | Nightly, 6 p.m. to 9:30 p.m.
Elgin Park, Elgin Park Drive, Uxbridge
Free; donations welcomed
Courtice Santa Claus Parade
Courtice’s community Santa parade takes place along Nash Road. Details
Sunday, December 6, 2026 | Noon
Nash Road, Courtice (Townline Road to George Reynolds Drive)
Free
Sunderland Santa Claus Parade
Sunderland welcomes Santa with an evening parade through the village beginning near the arena. Details
Saturday, December 12, 2026 | 7 p.m.
Sunderland Brock Memorial Arena, 20 Park St., Sunderland
Free
Live Concerts & Theatre
Frozen the Broadway Musical
November 12 to December 5, 2026
Oshawa Little Theatre, 62 Russett Avenue, Oshawa
$39.25 – $44.00 including fees
Irving Berlin’s White Christmas
Enjoy a holiday musical filled with romance, comedy and Irving Berlin’s classic songs, including White Christmas. The story follows two former soldiers turned entertainers who team up with a singing sister act to stage a Christmas show at a Vermont inn. When they discover the inn belongs to their former commanding officer and is struggling financially, they set out to help save it. Details
November 12 to 15 and 19 to 21, 2026 | Thursdays and Fridays at 7:30 PM; Saturdays at 2:00 PM and 7:30 PM; Sunday, November 15 at 2:00 PM
Uxbridge Music Hall, Uxbridge
$30 Adults; $25 Students and Seniors (including taxes and fees)
Candlelit Christmas Concert at the Orchard
Wilmot Orchards invites you to experience a Candlelit Christmas Concert! This November 28, step into the holiday spirit with an intimate candlelit evening featuring Christmas melodies performed by a string quartet, paired with cozy refreshments. Everyone is welcome to join Wilmot Orchards for this festive holiday experience!
Saturday November 28, 2026 | 4:30 PM to 7 PM
Wilmot Orchards, 3337 Concession Rd 3, Newcastle
$50
O CHRISTMAS TEA: A BRITISH COMEDY 2026
Combining British propriety with an unabashed love for the unexpected, London’s 3-time Impresario Award-winning duo steep an outrageously funny and brilliantly inventive show reminiscent of classic British pantos. Rich in wordplay, comic physicality, and cleverly crafted interactive elements, O Christmas Tea is uproarious fun, yet it is the duo’s boundless imagination and endearing chemistry that provide the real magic and heart of this play.
Sunday, November 29, 2026 | 3:00PM & 7:30PM
Monday, November 30, 2026 | 7 PM
Regent Theatre UOIT, 50 King St E, Oshawa
$39.00 – $69.00
A Baroque Christmas with Durham Chamber Orchestra
Durham Chamber Orchestra, your community orchestra, welcomes you and the holiday season with holiday selections from the wonderful Baroque era. Details
Sunday, November 29, 2026 | 2:30 p.m @ Port Perry United Church 294 Queen St, Port Perry
Sunday, December 13, 2026 | 2:30 p.m @ St Mark’s United Church, 201 Centre St S., Whitby
$10 to $30
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
Saturday, November 28, 2026 | 7:00 PM
Regent Theatre UOIT, 50 King St E, Oshawa
$45
How The GRETSCH Stole Christmas
Spend an afternoon singing along to classic Christmas songs and original holiday music with Will Gillespie, Susan Robinson and friends. Presented live on The Mezz at Biltmore Theatre, the concert features projected lyrics and illustrated holiday backdrops so the audience can join in. Special guests Nepo, Baby! will also perform. Hot chocolate, apple cider and other beverages will be available. Details
Sunday, November 29, 2026 | 2:00 PM
The Biltmore Theatre, 39 King Street East, Oshawa
$20 advance; $25 at the door, plus fees. All ages.
Elf: The Musical Jr.
Vocally Inspired Performers presents Elf: The Musical Jr., a family-friendly Christmas musical based on the popular holiday film. The story follows Buddy, a human raised by elves at the North Pole, as he travels to New York City to find his father and discover where he belongs. Featuring music by Matthew Sklar and Chad Beguelin, the approximately 75-minute production includes lively choreography, colourful costumes and holiday songs. Suitable for ages 3 and older. Details
December 3 to 6, 2026 | December 3 and 4 at 7:00 PM; December 5 at 2:00 PM and 7:00 PM; December 6 at 2:00 PM
Uxbridge Music Hall, Uxbridge
$29 Adults; $23 Students (including taxes and fees)
Music4life String Orchestra presents Greatest Moments
We’ll mark a decade of making music together with Greatest Moments — a celebration filled with memorable favourites, festive selections, and music inspired by some of the moments we’ve loved most over the past ten years. We are thrilled to welcome the extraordinary, award-winning Celtic fiddling family The Fitzgeralds as our featured guests!
Saturday December 5, 2026 | 2 PM
Forest Brook Community Church, 60 Kearney Dr, Ajax
$25
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
Saturday, December 5, 2026 | 7:30 PM
Regent Theatre UOIT, 50 King St E, Oshawa
$84.75
A Very Merry Magic Show
Magicians BenTastic and Magic Mel join forces for an interactive Christmas magic show featuring comedy, storytelling and illusions. Designed for children and adults, the performance includes audience participation and plenty of playful surprises. Two one-hour performances are scheduled, giving families a choice of morning or afternoon showtimes. Details
Saturday, December 5, 2026 | 11:00 AM to 12:00 PM and 2:00 PM to 3:00 PM
Ajax Centre for the Arts, 78 Church St. S., Ajax
$20
ABBA Revisited Christmas Special
ABBA Revisited combines the Swedish pop group’s familiar hits with seasonal music in a special Christmas concert. The tribute performance features costumes, vocal harmonies and live renditions of ABBA favourites, with holiday songs woven into the setlist. Details
Saturday, December 5, 2026 | 8:00 PM
The Arena at Pickering Casino Resort, 888 Durham Live Avenue, Pickering
$48 & up
John McDermott – Family Christmas
Treasured by audiences young and old, this long-standing tradition weaves together heartfelt performances of seasonal classics, McDermott’s unmistakable storytelling, and the warmth that has defined his career for over thirty years. Accompanied by his gifted ensemble of merry musicians and inspired by his enduring love for Christmas, McDermott creates an unforgettable evening of music, nostalgia, and holiday cheer. Details
Sunday, December 6, 2026 | 3:00 PM
Regent Theatre UOIT, 50 King St E, Oshawa
$59
Stars on Ice 2026 Holiday Tour
Olympic, World and National figure skating champions take to the ice for a holiday-themed performance featuring elaborate choreography, costumes and group routines. Headlined by Olympic bronze medallists Piper Gilles and Paul Poirier, the cast includes Kaetlyn Osmond, Keegan Messing, Roman Sadovsky, Ekaterina Gordeeva, Satoko Miyahara, Gracie Gold and Jeremy Abbott. Details
Thursday, December 10, 2026 | 7:00 PM
Tribute Communities Centre, 99 Athol St. East, Oshawa
$50.50 to $154;
The Emo Nightmare Before Christmas
Celebrate the holiday season with a late-night party featuring your favourite classic emo anthems. Dance and sing along to familiar tracks throughout the evening at this Christmas-themed emo music event. 19+. Details
Saturday, December 12, 2026 | Doors at 10:00 PM
The Biltmore Theatre, 39 King Street East, Oshawa
$14.10
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
Sunday, December 13, 2026 | 2:00 PM
Regent Theatre UOIT, 50 King St E, Oshawa
$59
Bublé Christmas Starring Jay Davis
Canadian musical theatre performer Jay Davis brings the music of Michael Bublé to the stage in a Christmas tribute concert. Accompanied by the Feeling Bublé Band, Davis performs a selection of Bublé’s popular hits and holiday favourites, combining live music with the singer’s familiar style and stage presence. Details
Saturday, December 12, 2026 | 7:00 PM to 8:30 PM
Ajax Centre for the Arts, 78 Church St. S., Ajax
$40
Sharon, Lois & Bram’s Candles, Snow & Mistletoe with Sharon Hampson
Enjoy a special screening of the 1993 CBC holiday musical Candles, Snow & Mistletoe, featuring Sharon, Lois & Bram on an unusual train journey home for Christmas. The one-hour film screening is followed by behind-the-scenes stories with Sharon Hampson, a live singalong with Sharon, Randi and Ethan, an audience Q&A and a meet-and-greet. Books and music will also be available for purchase. Details
Saturday, December 12, 2026 | Show at 2:00 PM; Doors at 1:00 PM
The Biltmore Theatre, 39 King Street East, Oshawa
$34.95 to $39.95
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
Wednesday, December 16, 2026 | 8:00 PM
Regent Theatre UOIT, 50 King St E, Oshawa
$60
Next Generation Leahy’s Christmas
Get ready for a festive and energetic performance with Leahy, the Next Generation Christmas show! This Canadian powerhouse family band’s live performance is filled with the high-energy, infectious Celtic-based music people associate with the Leahy heritage. Fiddle, accordion, singing, piano, and French-Canadian step-dancing all find a voice on stage. Details
Sunday, December 20, 2026 | 7:00 PM
Regent Theatre UOIT, 50 King St E, Oshawa
$45
Candlelight: Christmas Classics
Enjoy an evening of Christmas music performed by the Listeso String Quartet in the warm glow of candlelight. The 60-minute concert features traditional carols and seasonal favourites, including Carol of the Bells, O Holy Night, Jingle Bells, Last Christmas, All I Want for Christmas Is You and music from The Nutcracker and The Holiday. The concert is suitable for ages 8 and older, with children under 16 required to attend with an adult. Details
Sunday, December 20, 2026 | 4:15 PM, 6:30 PM and 8:45 PM
The Biltmore Theatre, 39 King Street East, Oshawa
From $35.10; booking fees may apply
The Wonderful World of Christmas: Legacy Tour
Elvis tribute artist Steve Michaels celebrates the Christmas music of Elvis Presley in a live concert featuring a backing ensemble and vocalists. The performance brings together seasonal favourites such as Blue Christmas and Santa Bring My Baby Back, along with gospel-inspired selections reflecting Elvis’s musical legacy. Details
Saturday, December 19, 2026 | 7:30 PM (Doors open at 6:30 PM)
The Arena at Pickering Casino Resort, 888 Durham Live Avenue, Pickering
$58.50 & up
Living Nativity
Experience the joy of that First Christmas at this outdoor re-creation of the Christmas Story, complete with narration, authentic costumes, and live animals. Details
Centennial Park, Uxbridge
Free
SNOW WHITE THE PANTO
Join DreamCo Theatre this holiday season for a magical adventure as we bring the timeless tale of Snow White to life in true British pantomime style! Bursting with laughter, toe-tapping songs, dazzling costumes, audience participation, and plenty of fairy-tale fun, Snow White the Panto is an unforgettable theatrical experience for the whole family. Details
December 27 – 31, 2026
Town Hall 1873 Theatre, 302 Queen St, Port Perry
Adults: $40; Seniors: $32; Children (12 and Under): $26
Markets, Festivals and All Other Events
Downtown Whitby Christmas Market
Friday, November 13: 4:00 p.m. – 9:00 p.m.
Saturday, November 14: 10:00 a.m. – 8:00 p.m.
Celebration Square, 405 Dundas St. W., Whitby
Free
Annual Winter Market – Downtown Whitby
Explore Downtown Whitby’s Annual Winter Market, hosted by Unique Town Boutique and DBS Experiences. Shop from local artisans, makers, food vendors and small businesses while enjoying seasonal treats, holiday entertainment and family-friendly activities. Highlights include the Mary Street Discovery Passport scavenger hunt, raffle prizes, giveaways, festive photo opportunities and photos with Santa. Details
Saturday, November 14, 2026 | 10:00 AM to 5:00 PM
103 Mary Street, Downtown Whitby
Free admission
Pingle’s Christmas
Find thoughtful gifts, make magical memories with Santa, pick the perfect Christmas tree, indulge in festive treats, and enjoy cozy moments around the fire — all in one merry place. Details
November 21st until December 24, 2026
Pingle’s Farm Market, 1805 Taunton Road East, Hampton
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 21 & 22 & December 5 & 6, 2026
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 21, 2026 | 9:00 am – 2:00 pm
Brooklin Village, Whitby
Free
Durham Potters Guild
November 14 & 15, 2026
Ajax Community Centre, 75 Centennial Rd, Ajax
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 21 & 22, 2026 | 10 AM to 3 PM
Parkwood National Historic Site, 270 Simcoe Street North, Oshawa
$5
Deck the Halls Day
Kick off the Christmas season at Applewood Farm Winery with festive decorations, Christmas music and a special holiday drink. Spend a relaxed afternoon on the farm’s outdoor patio while enjoying the seasonal atmosphere. Details
Saturday, November 21, 2026 | 12 PM to 5 PM
Applewood Farm Winery, 2055 Saintfield Road, Seagrave
Free winery admission; food and drinks extra
Parkwood Christmas Tours
Using historic décor, the main floor of the mansion will be transformed into a Christmas wonderland! Details
November 26, 28, 29, December 2, 10 to 30, 2026
Parkwood National Historic Site, 270 Simcoe Street N, Oshawa
$26.18
Christmas Market and Mingle
Spend an afternoon browsing a small Christmas market at Applewood Farm Winery, featuring local vendors, live music, freshly prepared pizza and drinks. The outdoor farm setting offers a relaxed place to do some holiday shopping and enjoy seasonal refreshments. Details
Sunday, November 29, 2026 | 11 AM to 4 PM
Applewood Farm Winery, 2055 Saintfield Road, Seagrave
Admission not specified; purchases extra
Bakersville Animated Gingerbread Village
A community display of Gingerbread houses that runs through the holiday season.Details
December 5 to January 3, 2027| 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 5 & 12 | 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 4 & 5, 2026
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 5 to 20, 2026
Willowtree Farm, Durham Regional Road 21, Port Perry
$20/person (ages 2-92)
Black Queens of Durham Holiday Market
Get your holiday shopping done all in one place at our Holiday Pop-Up Market! With over 100 local vendors, this is your chance to find unique gifts, seasonal must-haves, and one-of-a-kind items you won’t find anywhere else. Whether you’re checking off your gift list or just getting started, this market makes holiday shopping easy and enjoyable! Details
Sunday, December 6, 2026 | 12 – 7PM
Durham Convention Centre, 630 Beck Crescent, Ajax
Free
Fireside Flights and Holiday Tunes
Spend a December weekend by the fire at Applewood Farm Winery, enjoying holiday music and seasonal drinks. Warm up with moonshine-spiked hot apple cider or mulled wine while taking in the winter scenery from the farm’s outdoor patio. Dress warmly for the weather. Details
Weekends in December 2026 | Friday to Sunday, 12 PM to 5 PM,
Applewood Farm Winery, 2055 Saintfield Road, Seagrave
Free winery admission; beverages extra
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
December 13th 2026 | 10 AM to 5 PM
Kingsway College, Oshawa
Free
Vintage Holiday Weekend
There is something special about the holidays in a small town historic downtown. Surrounded by twinkling lights, festive music, charming storefronts and the pleasure of finding something wonderfully unique in a local shop. Details
December 11 to 13, 2026
Port Perry, 192 Queen Street, Port Perry
Free
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
December 12 & 13, 2026 | 10:00 AM – 12:00 PM
Pickering Museum Village, 3550 Greenwood Road, Pickering
$50.12
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 13, 2026 | Various Times
Royal Ashburn Golf Club,
995 Myrtle Rd W, Whitby
$47 + 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
Applewood Farm Winery Annual Christmas Party
Celebrate the holiday season at Applewood Farm Winery’s annual Christmas party, featuring live music by Mike Burns from noon to 4 p.m. Enjoy freshly prepared pizza, festive drinks and a relaxed afternoon at the farm before its seasonal closing. Details
Sunday, December 20, 2026 | 12 PM to 5 PM; live music 12 PM to 4 PM
Applewood Farm Winery, 2055 Saintfield Road, Seagrave
Free winery admission; food and drinks extra
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 5 to 20, 2026
Knox Pumpkin Farm, 6325 Enfield Rd, Hampton
Christmas in Ontario
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A Cowboy Christmas George Canyon & Aaron Pritchett
Wed, 26 November in Oshawa