Welcome to Sup Charlottetown! This newsletter will share the best events happening in Charlottetown every week. A new version will be published every Tuesday morning.

That said, here are the top 5+ events you do not want to miss this week.

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⭐ Your Top 5 This Week

This section lists the top 5 must-see events in Charlottetown this week.

1. Street Feast

Friday, May 16th and Saturday, May 17th. All day long. Kent Street.

Kent Street transforms into a two-day block party this May Long Weekend with carnival eats, live music, street games, art, and entertainment. Plus, local favourites serve up food and drink. Admission is free. Click here to view the full schedule of activities.

2. Pinch Penny Fair

Saturday, May 17th. Starts at 10:00 AM. Confederation Centre.

The Pinch Penny Fair returns! Browse a giant indoor yard sale packed with books, toys, plants, tools, and more. Enjoy a silent auction, kids’ zone, and baked goods. Admission $2. Proceeds support arts education and scholarships. Learn more here.

3. Sue Foley at Trailside

Thursday, May 15th. Show starts at 8:00 PM. Trailside Music Hall.

2025 Grammy nominee Sue Foley brings her electrifying Texas blues to the stage with a powerhouse band and her signature guitar style. Fresh off multiple award wins and a Grammy nod, Foley delivers a dynamic show blending deep grooves and fiery solos. Tickets are $50 plus tax here.

4. Jake Vaadeland w/ Shane Pendergast

Sunday, May 18th. Show starts at 8:00 PM. Trailside Music Hall.

2025 Juno Award winner Jake Vaadeland bring his foot stomping blend of roots and bluegrass to the stage. Fresh from a global tour, experience one of Canada’s fastest rising stars live. Tickets are $28 plus tax here.

5. Island Boys Live Comedy

Wednesday, May 14th. Show starts at 8:00 PM. Trailside Music Hall.

Experience island comedy at its best with Shawn Hogan (PEI) and Dan Duvall (Vancouver Island). With Just For Laughs credits and performances alongside Gerry Dee and Shaun Majumder, expect sharp wit and unforgettable storytelling. Tickets are $31 plus tax here.

🎉 Bonus Activities

This section lists several other great events happening this week.

Catch Popalopalots Live Improv Comedy on Saturday, May 17th at 8:00 PM at The Guild. Enjoy an unpredictable night of laughter. Tickets are $20 at the door. Learn more here.

Sterns Youth Downtown Dash is Friday, May 16th at 5:00 PM at Red Shores. Distances range from 500m to 2km for multiple age divisions, ages 13 and under. Learn more here.

Announced today: Come From Away will headline the 2026 Charlottetown Festival. The Tony-nominated Broadway favourite makes its PEI debut next summer. Learn more here.

Voice your opinion on Charlottetown’s Zoning & Development Bylaws at the Public House. Join the discussion on May 14th and 15th. Get full details here.

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See you next Tuesday,