This is it, folks! The darkest month of the year is bringing some serious light in South Eastern Ontario. Your lead up to the holidays is sure to be festive with cooking classes, live music, food tours, light shows and much more to amp up the holiday cheer in the region. Read on for 28 heart-warming December events in South Eastern Ontario!

Bay of Quinte


1. Fantasy of Lights Quinte West
Quinte West’s annual Fantasy of Lights event shines a spotlight on local holiday cheer! It returns in both Fraser Park and Frankford Tourist Park, with the displays remaining lit throughout the month of December.

2. Wagon Rides in Downtown Trenton
Go dashing through the snow this month in a free horse-drawn wagon ride! The Trenton Downtown Business Improvement Area will have free rides throughout the downtown each day from December 10 to 23 from 6 p.m. to 9 p.m. Hop aboard for the ultimate local must-do this holiday season. Oh what fun it is to ride!

Prince Edward County


3. Holiday Open House Three Dog Winery
Mulled wine by the fire. Live music. Unique vendors in a heated tent and warm fare to indulge in. Even raffles, games and prizes with proceeds going to the local food bank. Three Dog Winery’s Holiday Open House is back! It may be chilly outside, but this event on Saturday, December 2 will warm your heart. Mark it on the calendar and stop by 1920 Fish Lake Road near Picton to enjoy community, local shopping and, of course, fabulous wine. Cozy up to the holidays at Three Dog Winery!

4. Wassail in the County
Tour the festive wineries of Prince Edward County and toast the vintage with world-class wines. The ever-popular Wassail event is back, and with more than 20 participating wineries over multiple weekends, it’s sure to be memorable. Saturday, December 2, and Sunday, December 3 are the final dates of Wassail for this year. Enjoy warm bevvies, crackling bonfires and fun food. We hear that at many wineries, there is a small gift for those who come carolling and singing songs from the Wassail songbook! Download a songbook and arrive singing.

5. Holiday photos in the barn by ANDARA Gallery
Celebrate the festive season with a portrait session! Until Sunday, Dec. 17, from noon to 4 p.m. on weekends, the stunning century barn located at 54 Wilson Road near Bloomfield will be decorated to the nines and ready to capture your special festive moment. Be sure to call ahead for reservations – photos will be taken by appointment only and with your own device. ANDARA Gallery’s owners will compose and take your festive photo using your phone camera in exchange for a donation to the PEC Memorial Hospital Foundation’s “Back The Build” campaign. Look for the giant 16-foot Christmas tree from Skootamatta Christmas Tree Farm!

6. Ugly Sweater Party at Karlo Estates
A fun annual event! Join in at the Speakeasy at Karlo Estates for the party to kick off the holidays on Saturday, December 16, 2023, from 6 p.m. to 9 p.m. Upon arrival, you’ll receive a complimentary tasting with a small food pairing – but if you show up in an ugly holiday sweater, you’ll get two free tastings! There will be prizes for the three ugliest sweaters. Celebrate with a fun and friendly competition.

7. Susan Aglukark’s ᐅᐱᓐᓇᖅ – Upinnaq Christmas at Base 31
Be transported to the heart of Inuit culture, as the Sergeants Mess Hall at Base 31 comes to life with Aglukark’s trailblazing singer-songwriting, drawing on her remarkable career spanning almost three decades. Taking place on Saturday, December 16, 2023 this is a show not to be missed! As a multi-award-winning artist and an Officer of the Order of Canada, Susan Aglukark invites you to experience the magic of her holiday event – and be a part of this unforgettable cultural experience in Prince Edward County.

8. Shakura S’Aida’s New Year’s Eve Bash
Ring in the new year in style at Base 31, as Shakura S’Aida takes revellers on a musical journey to get toes tapping and hands clapping. Don’t miss this incredible New Year’s Eve experience on Sunday, December 31, filled with music, dancing and the spirit of PEC’s vibrant history. S’Aida and her band will play hits by Diana Ross and The Supremes, Elvis, The Beatles, and more over three sets, with a pause at midnight to celebrate 2024 with a complimentary glass of bubbly.

Lennox & Addington County


9. Greater Napanee Parade of Lights
The jolly ol’ elf himself will be in Napanee on Saturday, December 2, 2023 for the Parade of Lights! Beginning at 5:30 p.m., the parade departs from Enviro Park Lane and Napanee District Secondary School. Look for lights, smiles and lots of holiday spirit!

10. A Winter’s Eve Light
Free admission to a performance at the Museum of Lennox and Addington! See the Spin Starlets, Rhythm Works and more as A Winter’s Light returns on Tuesday, December 12, 2023 from 6 p.m. to 9 p.m. Toronto’s hottest hoop troupe will be lighting up the night, and performances by Rhythm Works will be shaking things up with energetic bucket drumming!

11. Light Up the Park
NorthFire Circus will be lighting up the Park on Friday, December 8, 2023 from 5 p.m. to 7 p.m. with festive street walkers, a fire performance at 6 p.m. near the pavilion at Conservation Park, and more! Enjoy a night of festive lights in Greater Napanee!



12. Kingston Trolley Tours Christmas Light Tour
Cozy up in the Red Trolley and watch the city shine! Kingston Trolley Tours Christmas Light Tour is 75 minutes of fun for the family – carol along to Christmas classics while viewing the lights around Kingston. Tours are running from Thursday to Sunday until December 24, then daily from December 25 to 31. Light up  your season in Kingston!

13. Kingston Food Tours
Discover this historic city one bite at a time! Kingston Food Tours are running its classic tour and tapas tour every Friday, Saturday and Sunday throughout December! See the city through a local’s perspective into Kingston’s culture, its delicious food, history and unique architecture. Savour exclusive tastings at the best local restaurants in downtown Kingston, while uniquely Kingston stories of people and events are woven through the tour. A tour is the perfect for an experience gift, for introducing visiting relatives to the city and for savouring the holiday season!

14. Celebrate the Holidays with Miss Emily
Enjoy Miss Emily’s remarkable artistry and holiday tunes on Saturday, Dec. 9 at 7:30 p.m. at the Isabel Bader Centre for the Performing Arts. Her foot stomping, heart-wrenching adventures in rhythm, blues, jazz, and rock and roll has earned her two Maple Blues Awards and a JUNO nomination! Get into the rhythm of the holidays at this feel-good show.

15. Good Lovelies Holiday Tour
Want nostalgic holiday sounds this holiday season? The Good Lovelies deliver! With their trademark combination of folk-roots, old-time swing, soul and bluegrass this is a holiday show stopper. Get ready for this trio of songwriters, multi-instrumentalists and expert harmonizers to bring some magic to your season on Saturday, December 16 at the Jennifer Velva Bernstein Performance Hall at the Isabel.

16. Holiday Spice Drag Show and Party
This will be fabulous! Billed as a festive holiday birthday drag fundraising extravaganza, The Grad Club will be full of festivities with the birthday girl, Rowena Whey, co-hosting with Tyffanie Morgan, on Saturday, December 2, 2023. This is also a fundraiser for Rainbow Railroad, a global not-for-profit organization that helps at-risk LGBTQI+ people get to safety.

17. Festival of Lights and Candy Cane Lane
The town will be a glow! Starting on Friday, December 1, 2023, Gananoque will be enchanting starting in Town Park with trees full of lights, holiday cut out displays, mirrors to take your pictures, a walkway of lights to wander, as well as the big tree out front of Town Hall strung with lights. Join in the grand illumination of the park and opening of Candy Cane Lane at 6:30 p.m. on December 1! Revel in live music, photo ops, hot chocolate and apple cider Make your holidays sparkle in Gananoque this season.

1000 Islands Rideau Canal Waterways


18. Nature Journaling in North Grenville

A unique monthly walking workshop! Perfect for adults and families, Nature Journaling is held at various trails around North Grenville with the hope that participants foster a deeper connection and interest in the local green spaces through art. With a mix of outdoor art instruction and discussion of trail ecology, the walks build creativity and curiosity. The next one is taking place on Saturday, December 16 at the Kemptville Campus. Advance registration is required but admission is free!

19. Turpin’s Trail Christmas in Westport
Join in the fun with live music at The Cove on Saturday, Dec. 2 with Turpin’s Trail to celebrate the Christmas season! Enjoy a holiday buffet at 7 p.m. and the show from 8:30 p.m. to 11 p.m. This Celtic/Folk quintet of Chris Murphy, Jon McLurg, Jessica Wedden and Noal St.Amand is known for their tight harmonies and acoustic instrumentals on guitar, mandolin, banjo, Irish Bouzouki, ukulele, and Bodhran. Revel in the energy and talents of this favourite group!

20. Christmas Wreath of Carols – Kemptville Men’s Choir
Share the joy of the season with this uplifting musical event. The Kemptville Male Choir presents Christmas Wreath of Carols on Saturday, Dec. 16 from 2 p.m. to 4 p.m. at St. John’s United Church in Kemptville. Join in for a heartwarming celebration of timeless carols and festive melodies!

21. The Last Blue Christmas – North Grenville Concert Choir
This lovely collection of traditional and new Christmas songs are sure to boost your holiday spirit! Three performances by the North Grenville Concert Choir will encourage community to attend. On December 8 at 7 p.m. and again December 10 at 3 p.m., the concert will take place at St. John’s United Church, Kemptville. On Saturday, Dec. 9, the show will run at 3 p.m. at St. Clare’s Anglican Church in Winchester. Find your magic through song!




22. River of Lights
This enchanting holiday light display on Blockhouse Island in Brockville features thousands of twinkle lights set to music. The free show is about 40 minutes long and on a repeating loop – drive down and enjoy the show from your car while tuning your radio to the show frequency, or walk about in the crisp winter air to see and hear the full show! Watch the trees dance with lights while contemporary and classic holiday tunes entertain you. Running now until January 2, 2024. 

23. Clow’s Christmas Trail on Hallecks
Be transported back to your childhood with magic memories of Christmas! This 1.5 km walking trail through the woods is decorated by the Clow Family each year to bring cheer to families. Running Friday-Sunday throughout December from 6 p.m. to 8:30 p.m., with special hours around Christmas. Spend time together in this outdoor wonderland visiting the Christmas displays including the Elves Lodge, the Candy Shop, the North Pole office, winter sports land and more. We hear that you might even spy some special visitors walking the trails! Tickets can be purchased online. 

24. Christmas at the Brockville Arts Centre
Take in some festive programming during December at the Brockville Arts Centre! The fun kicks off December 6 with Newfoundland’s JUNO-award winning, The Ennis Sisters. With a mix of original, holiday classics and a little Irish step-dancing this event is sure to ignite your festive spirit! Next, on December 9, the arts centre welcomes the holiday favourite, The Nutcracker. An enchanting performance by the State Ballet Theater of Ukraine whisks you off to a winter wonderland filled with toy soldiers and colourful characters. Finally, The Fitzgerald’s provide a cheerful and energetic soundtrack to your holidays! On Wednesday, December 13, The Fitzgerald’s: A Canadian Christmas blazes onto the Brockville Arts Centre stage featuring triple fiddle arrangements of holiday favourites, songs and tunes complemented by the group’s high-energy Ottawa Valley step dancing! Christmas entertainment begins at the Brockville Arts Centre.

SDG Counties


25. Alight at Night – Upper Canada Village
Stroll through one of Ontario’s largest outdoor light festivals! More than a million lights sparkle in the postcard-perfect setting at Upper Canada Village near Morrisburg. Alight at Night transforms the historic village into a captivating winter wonderland, providing a fun, festive and family-friendly experience for all ages.  Running from December 1, 2023 until January 6, 2024, guests can celebrate with the return of old-fashioned carol singing, a sound and light show, a visit with the Village’s Victorian St. Nick (until December 23), dining, and more.

26. Home for the Holidays at Upper Canada Playhouse
Feel the warmth of the season at this new holiday family concert from Leisa way and the Wayward Wind Band – created just for the Upper Canada Playhouse audience! This show features a host of traditional, new and fun Yuletide music to put you in the Christmas spirit and is on stage from December 6 to 17, 2023. Get ready for some interactive moments and sing-a-longs with the band!



27. Twelve Days of Holiday Cheer
Holiday spirit will be at an all-time high in Cornwall! On Friday nights (4 p.m. to 9 p.m.) and Saturdays (12 p.m. to 6 p.m.) running until December 23, visitors to Downtown Cornwall will find plenty to see and do with 12 Days of Holiday Cheer. Music will be at the corner of First and Pitt Streets, watch for a wandering Santa greeting residents, photo cutouts for family selfies and special demos such as egg nog tasting, hot chocolate, cookie making lessons, and more. Look for the full schedule and plan to attend!

Prescott & Russell


28. Welcoming the Holidays at Broken Stick Brewing
Broken Stick Brewing has festive cheer all wrapped up in a bow! Starting with Breakfast with Santa on Saturday, December 2 from 9 a.m. to noon, guests can enjoy pancakes and syrup with Santa himself! The following day on Sunday, Dec. 3, Drag Bingo Holiday Queens rolls out the red carpet for an evening of winter-wonderland themed drag bingo starting at 6 p.m. Finally, on Sunday, Dec. 10, hop on a sleigh ride with Santa to enjoy a trip through the woods from 2 p.m. to 5 p.m.

Christmas cheer starts in South Eastern Ontario with enchanting December events! Which one will you put on the calendar?