Mount Pleasant Sip & Shop: Two Nights of Holiday Cheer on Main Street

The holiday season is here, and there’s no better way to get into the festive spirit than by supporting local businesses in Mount Pleasant! This year, the Mount Pleasant BIA is bringing back Sip & Shop – a cozy, community-driven holiday shopping experience, with two special nights so you can explore everything our neighbourhood has to offer.

When & Where

  • Main Street (8th-16th Ave, including parts of Broadway and Kingsway)
    Thursday, December 4 · 4-8 PM

  • Riley Park-Little Mountain (16th-28th Ave)
    Thursday, December 11 · 4-8 PM

Each night will feature a lively mix of shopping, sipping, and seasonal cheer, giving you the perfect opportunity to find unique gifts, enjoy festive treats, and discover new local favourites.

Live Music & Entertainment

The holiday magic doesn’t stop at shopping – we’ve lined up some incredible live music for both evenings:

  • Brass trio performances with Andrew from Moar Music

    • Dec 4 at the Triangle Block (4-6 PM)

    • Dec 11 at the 21st & Main Plaza (4-6 PM)

  • Carolers will be spreading cheer along Main Street from 6-8 PM each night, so don’t be surprised if you catch yourself humming along as you browse!

What to Expect

Sip & Shop is all about community. Participating businesses will offer:

  • Special in-store promotions and holiday discounts

  • Complimentary drinks to keep you cozy as you stroll the streets

  • A warm, welcoming atmosphere perfect for friends, family, or solo holiday browsing

Whether you’re finishing your holiday shopping, looking for something special, or just want a festive evening out, these Sip & Shops are the perfect way to celebrate the season while supporting local, independent businesses.

To make the most of your evening, check out our full map of participating businesses for Dec 4 and Dec 11.