After Hours Drag Show

Time & Location Sep 19, 2026, 8:00 p.m. – 11:00 p.m. Higher Ground (Brewery Bay 2nd Floor), 162 Mississaga St E, Orillia, ON L3V 1V9, Canada About the event ORILLIA, ARE YOU READY TO GET LOUD?! Come party with us at your new MONTHLY drag show 💅✨   Featuring performances from the talented Justin Cider […]

Sunshine City Vintage Bazaar

The Sunshine City Vintage Bazaar Summer Series is back! Join us May 16th, Aug 8 and September 19th from 10am–4pm as we bring Downtown Orillia a curated collection of vintage and vintage-inspired clothing, home goods, and handmade creations. Find us a 22 Matchedash Street South, aka the parking lot beside the @lonewolf_cafe Hosted by @mymoon.collective + @pocketskateandvintage + @lonewolf_cafe

Art Lessons with Kerry Walford at Cloud Gallery

Create Art at Cloud Gallery! Spend your Saturday with one of Cloud Gallery’s top artists – Kerry Walford. Create a beautiful piece you’ll be to hang at home. Create at 12 x 12 oil painting on canvas All materials provided No experience required Small class size, personalized instruction Ages 16+

Live Audience Psychic & Mediumship Readings

Join Psychic Medium Barbara Quinton for an elevated and interactive evening of live audience psychic and mediumship readings, September 18th from 7:30-9:00PM at Brewery Bay. Upon entry guests can add their name to a draw for an opportunity to sit with Barbara during the event for a dedicated mini psychic reading, bringing with them 1 […]

Big Beautiful Queens

Get ready to be dazzled by a cast of FIERCE local queens who are bringing all the glam and laughs in one unforgettable drag show! Get ready for an unforgettable night at Brewery Bay Food Co! Join us on September 12 for the BIG BEAUTIFUL QUEENS drag show. It’s going to be a fabulous evening […]

Don’t Sweat the Fall Stuff

The Old Dance Hall Players have been delighting audiences in Orillia for 10 years with its special brand of improv comedy — zany, irreverent, captivating, and loads of fun! All seats: $30.00 | General admission seating Recommended for ages 14 and up Estimated run time: 90 minutes | There will be one 20-minute intermission

Downtown Orillia Pirate Party

Set sail for family-friendly adventure at the Orillia Pirate Party in Downtown Orillia! Dress in your best buccaneer attire and join the community for a full day of high-seas excitement across the downtown core. The Ship Stage features non-stop entertainment, including children’s entertainment with Dr. Bonkers, a Pet Costume Contest l, clown performances and juggling […]

Jakob Pearce & Dave Hewitt at Brewery Bay

Time & Location Aug 29, 2026, 7:00 p.m. – 10:00 p.m. Higher Ground (Brewery Bay 2nd Floor), 162 Mississaga St E, Orillia, ON L3V 1V9, Canada About the event Join Jakob and Dave for a free night of music in Higher Ground to say goodbye to summer vacation! Cover: No cover; No reservations. Date: Saturday, […]

Summer Music Showcase at Brewery Bay

Live music on the patio? Sign us up! We have Anna Lewis and Madison Mueller coming in, each performing a two-hour set on the last Friday night of summer vacation! Cover: No cover; No reservations. Date: August 28th First Set: 3:00PM – 5:00PM Second Set: 7:00PM – 9:00PM

The Pirates are Coming to Orillia!

The Pirates Are Coming to Downtown Orillia! On Saturday September 5th from 10am – 4pm head Downtown Orillia for a day packed with pirate-themed fun! The Downtown Orillia Pirate Party is a free, family-friendly street festival where Mississaga Street will transform into a lively celebration of all things pirate. Mississaga Street will be closed to […]