Who needs a vacation?

There’s so much to do here!

Downtown Orillia, located in the core of the city, is host to over 20+ events annually. Pack your bags, fill up your tank, grab the family and head to Downtown Orillia to enjoy one (or many) of our amazing events happening all year long.

Check out what’s happening next in Downtown Orillia!

Downtown Orillia 2019 Events Postcard Front
Downtown Orillia 2019 Events Postcard Back

Upcoming Events

Jul 22

Streets Alive! Pedal Powered

June 15th-October 20th, 2019 in Downtown Orillia

Orillia’s very own living art program, Streets Alive!, kicks off for another great season of dazzling art pieces. This year’s theme is pedal power, featuring decorated bikes of all kind.

Jul 22

Annie 2019 (Local Young People’s Theatre)

July 9th-August 20th, 2019 in Downtown Orillia

Duck Soup Production is pleased to present this popular comic strip.

July 9, 16, 23 & 30

August 6, 13 & 20

Jul 26

Downtown Orillia Night Market

6:00 - 9:00 pm

Downtown Orillia’s Night Market

Come join us at this fun Night Market in Downtown Orillia! The Night Market is a great way to kick off the Downtown Summer Block Party beginning the next day on Saturday, July 27!

Enjoy the ambiance, watch the sunset and listen to the sound of great music on the street. Grab a treat from your favourite vendor or artisan, get your produce for the weekend, meet up with friends and enjoy the atmosphere.

Meet us on the street in the Orillia Library and Opera House block between West and Andrew Street from 6 pm – 9 pm on Friday, July 26! 

If you are an artist, artisan, antique collector, farmer or food vendor, we would love to have you at our Night Market. Complete and return the Night Market Vendor Form 2019 along with the $35 fee and we will reserve your spot on the street.

For more information please contact the office at info@downtownorillia.ca or by phone at 705-325-3261.

Jul 27

Summer Block Party

9:00 am – 5:00 pm / Downtown Orillia

Downtown Orillia Summer Block Party

A downtown summer street festival like no other! Showcasing a fusion of art, fun interactive activities, live music, delicious food, kid zones, and sizzling sidewalk sales!!!

Entertainment by

  • Isabella Hoops
  • Kobbler Jay
  • Northland Rail Service
  • Neema Children’s Choir
  • Live DJ Gord Kirby and many, many more.


Stay tuned for more features and entertainment to be announced in the coming month.

If you are a downtown merchant and would like us to advertise your participation in this event and your festival deals, please complete and return the Merchant Participation Form .











Call For Vendors!!


Downtown Orillia is looking for vendors for our upcoming Downtown Summer Block Party on July 27th! If you an artisan, artist, community group, food or concession vendor and would you like an opportunity to sell your products at the this event, get in touch!

If this sounds like something you’d like to be a part of give us a call at 705-325-3261, email us at info@downtownorillia.ca or simply download and complete the appropriate vendor forms and drop it off at our office or send it in via email or mail. Don’t delay, spaces are filling up fast!

Artisan Vendor

Outside Vendor (you do not make what you sell)

Food Vendor

Confection Vendor

Community Group

Jul 27

Strings for Students

8:00 pm - 1:00 am

Geneva Event Centre

16 West St. S. Orillia


Raising money to be able to donate 15 Fender CD-60 Acoustic Guitars with case to Patrick Fogarty Secondary School.

The hope is to donate to every high school in Orillia over the next couple years. And if it goes well, move onto donating to other schools in the Muskoka and Simcoe areas.

With the help of local business owner Jeff Gilbert of Gilbert Guitars, we will be able to donate these 15 guitars if we reach our goal of $4,000 before the end of August.

These guitars will be donated to the school before the start of the new school year in September and will then be the property of Patrick Fogarty. The students will use these guitars for the duration of the class right up until their exam and then pass it onto another student during the next semester that the program is offered.

For more information visit https://www.facebook.com/events/2342515466019844/

Aug 17

21st Annual Downtown Orillia Classic Car Show

9:00 am – 5:00 pm / Downtown Orillia

A jaw-dropping collection of over 400 classic cars line the Downtown streets! Enjoy live entertainment, great dining, shopping and the largest car show in the region!

Pre- Registration is now open!

It is our privilege to invite you to bring your vehicle to our 21st Annual Downtown Orillia Classic Car Show being held this year on Saturday August 17th, 7am-5pmWe know that you will enjoy the live music and activities taking place throughout the day.  Your registration includes a 2019 dash plate, special offers and coupons to many downtown businesses and chances to win great door prizes!

PLUS Pre-registered vehicles receive two ballots for a chance to Win a Classic Longblock Engine Rebuild by Parry Automotive Orillia*!

Fill in the attached registration form and return it with your $15 pre-registration fee ($13.27 + HST) now!

2019 Car Show Pre Reg Form

Aug 24

Surfin Safari-The Ultimate Beach Party Show

August 24th, 2019 in Downtown Orillia

Surfin Safari-The Ultimate Beach Party Show

Bill Culp Productions is pleased to bring you this musical tribute with an outstanding live band as you hear the music of Jimmy Buffet, Frankie Avalon, Jan & Dean, The Ventures, and of course The Beach Boys!

Aug 24

Starry Night Art & Gallery Tour

August 24th, 2019 in Downtown Orillia

Experience Downtown Orillia’s vibrant arts community and meet local artists in their studios and at host galleries, all under the starry sky!

Aug 31

Port of Orillia Pirate Party

August 31st-September 1st, 2019 in Downtown Orillia

Get your best pirate costume on and join the Port of Orillia’s second annual Port of Orillia Pirate Party! Live entertainment, a treasure hunt through Downtown Orillia, and “Walk the Plank” at Couchiching Beach Park presented by the Orillia District Chamber of Commerce.


Sep 14

Downtown Orillia’s Farm to Table Dinner

Downtown Orillia

Join us on the main street in Downtown Orillia and enjoy a magical evening of local fare prepared for you by seven downtown restaurateurs and chefs! Enjoy the ambiance, listen to the sound of music, watch the sunset & enjoy a delicious dinner on the main street.

Treat yourself to a delectable outdoor dinner with locally sourced, organic food, prepared by downtown restaurateurs Rustica Pizza VinoShine Juice Bar & CafeTre SorelleBrewery Bay Food Co., Eclectic Cafe, Bakes by the Lake and Mariposa Market. A special six-course prix fixe menu inspired by farm fresh ingredients, complete with wine & beer pairing, will be created especially for 125 dinner guests. Signature event gifts, provided by downtown businesses, will be presented to each guest at the end of the evening.

The evening promises to be a magical dinner experience full of relaxation, delicious fare and great company. Tickets sales will begin at the beginning of August but stay tuned to this page and the Downtown Orillia Facebook & Instagram pages for announcements on features, courses and how to purchase tickets.


Servers Needed! 

If you are interested in helping out at this unique evening event in Downtown Orillia, get in touch! We are looking for 13-15 qualified servers for the event. If you are interested in helping out check out the job opportunity below and email us at office@downtownorillia.ca or give us a call at 705-325-3261 today!

Downtown Farm to Table Server posting


Sep 17

Banff Centre Mountain Film Festival World Tour

September 17th, 2019 in Downtown Orillia

Sojourn Outdoor & Travel Store along with partners Rab, Banff & Lake Louise Tourism is pleased to present the radical outdoor films that were not shown last January.

Sep 18

Murray McLauchlan- Artist Life Stories

September 18th, 2019 in Downtown Orillia

An up close and personal evening. A speaker night with a difference. Cameron Smillie interviews Murray about his years in music including stories about his many awards.  And Murray will play some tunes!

Sep 19

Snowbird Lifestyle Presentation

Orillia Opera House at 7:00 pm

A Concert and Information session for retirees and pre-retirees who spend their winters in warmer climates

Free event, but it is reserved seating so tickets must be arranged in advance.


Sep 28

Doors Open & How-To Festival

September 28th, 2019 in Downtown Orillia

Explore the variety of hubs offering different cultural activities at this year’s Doors Open & learn a new skill at the Orillia Public Library during its How-To Festival in Downtown Orillia! Discover your creative side and try your hand at painting, sculpting, dancing and so more.

Oct 4

Green River Revival

October 4th, 2019 in Downtown Orillia

Calling all fans of Creedence Clearwater Revival.  Green River Revival presents the music of CCR with a historical storyline that also incorporates several costume changes.

Oct 9

Pavlo- Artist Life Stories

October 9th, 2019 in Downtown Orillia

An up close and personal evening. A speaker night with a difference.  Cameron Smillie interviews Pavlo about his years in music including stories about his many awards. And Pavlo will play some tunes!

Oct 17

Orillia Jazz Festival

October 17-20th, 2019, in Downtown Orillia

Now in its 28th year, the Orillia Jazz Festival occurs in various host locations in the downtown and all over Orillia! Come discover a new-found love or reignite a passion for all things jazz!

Oct 18

Cure For The Common Comedy

October 18th, 2019 in Downtown Orillia

The Second City presents The Cure For The Common Comedy!  See the stars of tomorrow performing fresh new material and laugh your way out of whatever you got yourself into.

Oct 23

The Haunting

October 23rd, 2019 in Downtown Orillia

Come experience all things that go bump in the night in Downtown Orillia. Haunted tours begin at The Opera House & Orillia Museum of Art & History and continue throughout frightful spaces downtown!


Oct 26

Kids Halloween Costume Parade

October 26th, 2019 in Downtown Orillia

Bring the family, dress in costume and join us for this FREE fun costume parade & contest! Trick OR treat at participating downtown merchants’ businesses & enjoy kid’s activities & more.

Nov 15

Children’s Candlelight Parade

November 15th, 2019 in Downtown Orillia

Bring the Christmas spirit to life as we light up the downtown! Join the countdown to light the Opera House tree, enjoy free hot chocolate & treats plus meet SANTA!

Nov 17

Orillia Santa Claus Parade

November 17th, 2019 in Downtown Orillia

The largest Christmas parade north of Toronto! Help welcome Santa as over 100 floats and bands lead the way for him through Downtown Orillia.

Nov 29

Black Friday

9:00 am – 5:00 pm / Downtown Orillia

Take advantage of outrageous specials throughout the Downtown + half off Downtown Dollars (while quantities last). Stores are open late but we won’t tell if you book the day off work to SHOP!

Nov 30

Ballet Jorgen’s 2019 The Nutcracker

November 30th, 2019 in Downtown Orillia

Imagine Tchaikovsky’s Christmas tale uniquely re-imagined, Canadian Style. The Nutcracker, A Canadian Tradition adds Canada’s own twist to this much-loved Classic. Make this magical production a part of your family’s holiday traditions.

Saturday, November 30 at 2:00 and 7:30 pm.

Dec 6

Wizard of Oz – Panto in Ruby Red Slippers

December 6th, 2019 in Downtown Orillia

A new magical pantomime from the producers who brought you Cinderella the Panto in 2018.

A brand new spin on the timeless tale of a young girl who finds herself transported to a strange new world full of magic, side-splitting jokes, music that everyone knows and a spectacle of a musical adventure.  Remember to Boo and Cheer!

Dec 7

Horse & Wagon Rides

December 7, 14, & 21st, 2019

Downtown Orillia

Hop aboard a free horse drawn wagon rides at the Pizza Pizza intersection between 1- 3 pm. Explore the Downtown and take a trip back in time as you get into the Christmas spirit!

Rides occur on December 7, 14 & 21 @ 1:00 – 3:00 pm.