Find your fall cozy in South Eastern Ontario with these October Events

As more leaves float to the ground each day, pumpkin spice is in the air, and we’re here for all the fall cozy, SEO has harvest and fall events in the bag. If you’re looking to experience vibrant communities in South Eastern Ontario this fall, here are 24 reasons to get out and explore. Nothing beats fall events in SEO!

1. October 3 to 5: First Peoples’ Performing Arts Festival of the 1000 Islands
The 9th annual celebration of Indigenous culture, creativity and community at the Royal Theatre Thousand Islands! The experience highlights the power of First Nations, Inuit, and Metis artistry - look for a friendship feast, makers market, family activities, storytelling, Indigenous musicians, dancers and actors - and more!

2. Starting October 3: Pumpkinferno Upper Canada Village Morrisburg
Explore the magic of Pumpkinferno, a nighttime walk-through experience where over 9,000 hand-crafted pumpkins come to life in a spectacular display of artistry and creativity along the streets and paths of Upper Canada Village’s historic landscape.

3. October 4: Oktoberfest in Rockland
Grab your lederhosen and your friends and come experience Bavarian! Oktoberfest at Brauwerk Hoffman Rockland and RiverRock Inn & Conference Centre will be a two-day extravaganza, featuring live music, craft wine and cider, food vendor and live music.

4. October 4: Moon Musings Gallery Show and Ceremony
Celebrate the cycles of the moon through ceremony and art! This combination experience of art show and ceremony takes place just before the full harvest moon at Klotzek Gallery in Yarker. Feel the magic of the moonlight!

5. October 4: Wolfe Island Gravel Grinder
Two fun bike rides around the beautiful back roads of Wolfe Island! Live music, great food at the finish line cap off a 40 km and a 75 km ride. Presented by Limestone City Cycling, Wolfe Island Commons and Township of Frontenac Islands, a portion of the proceeds goes to support the Wolfe Islands Commons.

6. October 4: Culture Days - Tin Can Ukulele Lessons at Rossland Gardens
Free lessons on a tin can ukulele?! Um, yes please. Borrow a tin can uke made by artisanal luthier Ross Stuart on Amherst Island and play a lively tune in the music garden outside his workshop while learning basic strumming and a few chords to get your started. What a unique island experience!

7. October 4 and 5: Pumpkin Fest & Corn Maze at Forman Farms
Forman Farms is the place for fall fun Oct. 4 and 5! Bring your family to the farm on Brewer’s Mills Road near Seeley’s Bay for wagon riders, corn maze, pumpkin cannon, face painting, food vendors, kids activities, entertainment and more!

8. October 5: Harvest Brigade and Broken Stone Winery
This immersive experience helps harvest the grapes at Broken Stone! Spend the day learning and picking grapes with helpful instruction, a delicious lunch, ceremonial grape stomp and barrel rolling competition! 

9. Until October 25: Emerging Narratives at the Cline House Gallery
Two artists and friends, paintings, different subject matter: one looking out into the natural world, the other looking inward and painting objects close by indoors.

10. October 5: Helping Harvest at Trail Estate Winery
It has become an annual tradition now - the community helps the folks at Trail Estate harvest grapes. Get expert insights into the first steps for making the wine. Enjoy picking and a harvest feast mid-afternoon. This is a family-friendly event!

11. October 5: PEC Oyster Fest
This 4th annual competition will be tasty! Sand and Pearl Oyster Bar will host a fierce but festive Oyster Shucking Tournament on Oct. 5 with fresh shucked oysters, scotch, complimentary passed oysters and more. Sign up to compete or come cheer them on!

12. Starting October 3: Ontario Festival of Small Halls
Big music in small places! The Ontario Festival of Small Halls is back this fall with unforgettable music in beloved community spaces. With artists like Chantal Kreviazuk, Devin Cuddy Duo, Danny Michel, Tim Baker, Whitehorse, Irish Mythen, Ben Caplan, Hawksley Workman and more in unique places across South Eastern Ontario this is one festival that you don’t want to miss. Discover small towns and revel in top notch Canadian live music!

13. October 10 to 13: Pirates at the Aquatarium in Brockville
A swashbuckling adventure awaits with Pirates at the Aquatarium! From live sea shanties performed by the pirates themselves to an exciting new puppet show, pirate quests and even pony rides, even the high seas are no match for the fun to be had. Plan to attend… argh!

14. October 11: Jane Siberry at Leopard Frog Farm
One of Canada’ most original and influential singer-songwriters, Jan Siberry, is performing at Leopard Frog Farm on Loughborough Lake! Don’t miss out on this amazing concert in the barn. Siberry is being inducted into the Canadian Songwriters Hall of Fame 2025 and her album, The Speckless Sky has been honoured by the Polaris Prize this year!

15. October 11: Oeno After Dark
Picture this: Oeno Gallery’s Sculpture Garden lit up! Three acres of winding paths and more than 150 sculptures typically bathed in darkness at night - now illuminated. The night will feature fire dancers, the Aurora Borealis choir, live music and much more. Get your tickets for this unique experience!

16. October 11: Fallin’ For Maple in Tamworth
Happy fall, y’all! This brand new, autumn-inspired market showcasing more than 40 vendors from across the region is combined with activities for the whole family! Look for live music, photo booths, maple taffy, axe throwing, horse-drawn wagon rides and even maple sausages and burgers!

17. October 14 to 19: Senior Moments at Upper Canada Playhouse
The boys are back! Jimmy and Lucien (Sandy Gillis and Marshall Button) probe the mysteries and wonders of aging. This fabulous comedy duo will have sides aching and tears of laughter rolling!

18. October 17 and 18: Comedy Central: Ali Hassan
Host of CBC’s Laugh Out Loud, Ali Hassan brings Does This Taste Funny? to the Regent Theatre in Picton! It’s a hilarious deconstruction of Ali’s journey from food to comedy.

19. October 18: Christmas in the Saw Mill
Step in the historic sawmill transformed into a magical Christmas market! Find unique jewellery, stunning paintings, handcrafted pottery and textile treasures from more than 30 talented local artists and artisans.

Countylicious is back. 

From Thursday, October 23, to Sunday, November 16, 2025, this celebrated culinary event invites food lovers to enjoy three weeks of dining inspired by the harvest season.

20. October 23 to 25: Matilda at the Brockville Arts Centre
Presented by the Brockville Operatic Society, Matilda is always a hit with children and adults alike. The story of a special little girl with a powerful imagination, the performance is packed with high-energy dance numbers and catchy songs.

Looking for some spooky events in SEO? Check out this blog for a screaming good time.

21. October 24 and 25: Comedy and Queen’s Court at Aultsville Theatre
The weekend is on fire at Aultsville Theatre in late October as Cornwall Comedy Classic is making laughter echo on Oct. 24, while Queen’s Court, a celebration of Freddie Mercury and Queen is performing on Oct. 25. We’re talking non-stop rock anthems, and solid music. Book the next Monday off of work - you’re going to need it to recover from an epic weekend! 

22. October 24 and 25: Laser-guided Tour of the Night Sky
See the night sky as it was 100 years ago – remarkable views await at Ontario’s most southerly point to offer a clear night sky unobstructed from light pollution! The Dark Sky Viewing Area in L& A County opens up a world of wonder. The popular laser-guided stargazing tour on October 24 and 25 is a great way for novice stargazers to get to know the night sky.

23. October 26: Sydenham Fall Trail Run
Lace up and enjoy an 8km run on the Cataraqui Trail along Sydenham Lake! See the fall colours with a water view during the run which takes place on Sunday, October 26. Got young runners? The Little Eagles Kids Run gets in motion as a 2km run for children up to age 12! The run is hosted by MT Adventures, which stages unusual and exciting experiences such as adventure treks, trail rides and runs.

24. October 30: Merrickville Art Walk
Lace up and Experience Main Street West transformed into Art Alley on Thursday, Oct. 30 from 11 a.m. to 4 p.m. Featuring new artists showcasing their work and creating live on site. See the creativity flow!

Whether it’s apples or corn, mazes or trail walks, fall art events or live theatre one thing is for sure: you can find your fall cozy in South Eastern Ontario.