Live Music Nightly

Get into the holiday spirit in beautiful downtown Westport, Ontario with Christmas Markets, Gingerbread Competitions, Lion’s Santa Claus Parade while shopping our unique stores! Join us in Westport for a Gingerbread-themed weekend on Friday November 21st and Saturday November 22nd, 2025. Our annual Westport Holiday Shop ‘N Hop is back featuring outdoor markets, tree lighting, carollers, gingerbread competitions, in-store events, ugly sweater competitions and much more! Christmas begins in Westport!

Businesses compete in an ugly sweater competition

Live Music with Chris Murphy (Member of David Francey/Turpin’s, Acoustic Folk, Perth Road Village) @ The Cove Inn 5-9pm

Shops are open late until 8pm with events at participating businesses.

Gingerbread house competitions at Rosie Yumski’s Fine Foods

Westport Lions Club Santa Claus Parade at 2pm

Live Music with the Annual Santa Claus Parade Country Hoedown – Henry Norwood + Shawn McCullough 5-9pm

Events at participating businesses

PJ Day

Events at participating businesses

Peoples’ Choice Award for best decorated business and village home

• The Cove Inn: Friday – Chris Murphy plays live 5-9pm.
  Saturday – Annual Santa Claus Parade post party with Henry Norwood and Shawn McCullough live from 5-9pm
• Creative Gardens Floral Design: Workshops with Laura Moses (Workshop event listings and purchase tickets from Laura’s online store)
• Heritage China & Crystal (Black Dog Inn): Easy Entertaining Platter Design
• Lake Effects: Ornament Gift with purchase
• Life is Good Westport: Loot Bags and Gift Cards with purchase
• Lyons Holiday House: In-store specials all weekend
• Missy’s of Westport:
• Pinecone: In-store specials all weekend
• Rosie Yumski’s Fine Foods: In-store specials all weekend
• Tangled Garden Cafe: Lunch and Dinner specials
• Tasty Goodness Bakery:
• Trevor Connell Photography: Polaroids with Santa
• Upper Rideau Bed and Breakfast: Friday – Outdoor bonfire with s’mores 4-8pm (Cross the street to the Gristmill for mulled cider and treats)
  Saturday – After the Santa Claus Parade 3-6pm open house with Hot beverage and treats
• Seasons of Westport: Gift with each purchase and in-store specials
• Village Green: In-store specials all weekend
• Wags, Whiskers & Wings: In-store specials all weekend as well as fundraiser for PAWS. Sunday – Pet photos with Santa 12-4pm
• Watercolour Westport: Saturday – Watercolour Kitchen Party with Chef Francois from Scheuermann Winery. Two sessions: 3:30pm – 5:30pm and 6-8pm, “Christmas Appetizers Made Easy.” $25/person with only 20 spots available per session. Click here for the invite and here to purchase tickets.
• Westport Dreamin’:
• Westport Brewing Company: Live music and beer swag gift bundles; Also special gingerbread beer CASK tasting
• Westport Home Hardware: Are your Christmas Lighting Specialists
• Westport Village Pharmacy:
• The Wood Fired Cafe: Friday night outdoor smoked meat special menu