Things to Do in Newmarket This October: 9 Local Events to Add to Your Calendar
Looking for things to do in Newmarket this October? From local art and live comedy to giant bounce houses, folk music and some seriously spooky nights, there is plenty happening around town.
Summer may be over, but Newmarket’s event calendar is still packed. Whether you’re planning a family outing, meeting friends downtown or looking for something a little more daring, here are nine October events worth adding to your calendar.
Oktoberfest Newmarket: Prost on Main Street
Main Street is getting a Bavarian-inspired makeover for an afternoon of beer, bites, music and local stops.
Join the pub-crawl on Main St, with an after-party at The George. It’s a fun afternoon for adults who want to dust off their lederhosen to enjoy downtown Newmarket’s restaurants, patios and pubs.
WHEN: Sat, Oct 3, 2026, from 3 to 6 p.m.
WHERE: Main Street, Newmarket
WHO: Adults, 19+ event
AFTER-PARTY: The George patio
The Royal Duck Bounce Park
If your kids have energy to spare, this may be the event for them. As the world’s largest and tallest bounce house, The Royal Duck, is a travelling pop-up bounce park featuring oversized inflatable castles, music, themed photo opportunities and plenty of room to jump. Please check admission options, available sessions and waiver requirements before visiting.
WHEN: Oct 3 to Nov 1, 2026 (weather permitting)
WHERE: Upper Canada Mall, 17600 Yonge St
HOURS: Weekdays from 3 to 7 pm; weekends and holidays from 10 am to 7 pm
Fall N’ Love on Main
Fall in love with Newmarket from Oct 2 - 4th, 2026 during a weekend filled with author talks, workshops, local shopping promotions, speed dating and romantic activities throughout the downtown.
Don’t miss Picture This: A Romantic Fall Photo Shoot for a complimentary professional photo with Newmarket photographer Amy Braithwaite.
Photo shoot details:
WHEN: Sat, Oct 3, 2026, from 10 am to 12 pm
WHERE: Riverwalk Commons, 200 Doug Duncan Drive
WHO: Adults, First come, first served
18th Annual Newmarket ArtWalk
Spend the weekend exploring paintings, photography, jewellery, textiles, ceramics and other original work from local and visiting artists.
The self-guided ArtWalk takes place across multiple walkable venues, including the Newmarket Public Library. It’s an easy way to explore the downtown while discovering artists and businesses along the way.
WHEN: Sat, Oct 3 from 10 a.m. to 5 p.m. and Sun, Oct 4 from 11 a.m. to 5 p.m.
WHERE: Participating venues in and around historic downtown Newmarket
COST: Free
Paranormal Cirque Nightmare
Step under the striped big top for a dark mix of circus, theatre and cabaret. Expect acrobatics, illusions, mysterious creatures and plenty of creepy surprises.
No one under 13 will be admitted. Guests ages 13–17 must attend with an adult.
WHEN: October 9 to 12, 2026 (check website for times)
WHERE: Upper Canada Mall, 17600 Yonge Street
TICKETS: $30 to $85
AGE RESTRICTION: Ages 13 and older only
Haunted Halloween Trail
Take a one-kilometre walk through a forest transformed by creepy decorations, lighting, sound effects and costumed actors. The trail is meant to scare you, so consider yourself warned!
Advance tickets are required and will not be sold at the event. Children 12 and younger must attend with a parent or guardian.
WHEN: Oct 22, 23 & 24, 2026, from 7 to 10 pm
WHERE: Dave Kerwin Trail, Environmental Park, 325 Woodspring Ave
TICKETS: $5 per person
RECOMMENDED AGE: 10+
Newmarket Comedy Festival
Back by popular demand….Two nights. Two different comedy lineups. Get ready to laugh - Friday brings a traditional UK-style stand-up showcase, while Saturday is a mash up of musical comedy and rapid-fire one-liners.
Both nights are hosted by Newmarket-born comedian Jesse Ralph and contain mature themes.
WHEN: Friday, October 23 and Saturday, October 24, 2026
TIME: 8 p.m.; doors open at 7 p.m.
WHERE: Newmarket Old Town Hall, 460 Botsford Street
TICKETS: $35 plus taxes and fees
Happiness & Harmony - A night of Musical Mashups
Enjoy an uplifting evening of live entertainment, delicious food and community connection! This inspiring fundraiser supports Our Happy Place Supportive Services and its inclusive programs for neurodiverse adults.
WHEN: Sat Oct 24 | Doors open at 6 p.m.
WHERE: NewRoads Performing Arts Centre, Newmarket
TICKETS: $45
Tanglefoot: One More Night Reunion Tour
Canadian folk group Tanglefoot returns for a special reunion performance featuring powerful harmonies, storytelling and songs inspired by Canadian history.
An evening of celebration of “the songs, the stories and the spirit of Canada” that shouldn’t be missed.
WHEN: Friday, October 30, 2026
TIME: 8 pm; doors open at 7:15 pm
WHERE: Newmarket Legion, 707 Srigley St
TICKETS: $35
October Plans? Consider Your Calendar Full.
One of the things we love most about living in Newmarket is the incredible sense of community. From free concerts and festivals to local markets and family-friendly activities, there's always something happening close to home.
So bookmark this page or share it with someone who is always asking what there is to do around town. And remember to confirm availability before heading out, several of these events require advance tickets and may sell out.
If you're thinking about making Newmarket your next home, or simply want to stay connected with everything happening around town, be sure to check back each month for our local event roundup or subscribe to our Newsletter.
See you around town!
Kerri & Shaun
Kastle Realty Team