2026 Portland Holiday Events: Bazaars, Shopping, Christmas Lights, Local Markets

Portland’s 2026 Holiday shopping and event season is here! Throughout November and December, we have a great resource for holiday sales, specials, events, Christmas light displays, parties, local crafts and goods, and GIVEAWAYS.

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2026 Portland Holiday Events:

• November 10: Stimson Lumber Tree Arrival at Pioneer Courthouse Square | 11AM-12:30PM, Free, Say hello to Santa, enjoy free hot chocolate and join in the fun of this annual tradition (more info)
• November 26-29: Portland Thanksgiving Events: Black Friday, Holiday Tree Lighting & More
• November 27: Tree Lighting Ceremony at Pioneer Courthouse Square | 5:30-6:45PM, Free, A joyful community sing-along led Thomas Lauderdale of Pink Martini w/ many of Portland’s finest musical artists and chorale singers (more info)
• December 5-6: Holiday Tea @ Victorian Belle | 2PM & 3:30PM, Artisan Teas, Pastries, Savories
• December 12-13: Holiday Tea @ Victorian Belle | 2PM & 3:30PM, Artisan Teas, Pastries, Savories
• December 18: Great Figgy Pudding Caroling Competition at Pioneer Courthouse Square | 6-8PM, Free, fun, festive, and joyful event bringing hundreds of carolers to a ten-block radius (more info)
• December 19: 35th Annual Tuba Christmas Concert at Pioneer Courthouse Square | 1:30-3PM, Free, 300 tubas play in harmony while the crowd is invited to sing along (more info)
• December 19-23: Holiday Tea @ Victorian Belle | 2PM & 3:30PM, Artisan Teas, Pastries, Savories
• December 25: Portland Spirit Christmas Day Cruises | 11AM & 4PM, Two Hour Cruise, Special Holiday Buffet, Waterfront Views (more info)
• December 26-27: Holiday Tea @ Victorian Belle | 2PM & 3:30PM, Artisan Teas, Pastries, Savories
• December 31: Portland New Years Events, Parties, Champagne Toasts, & More
• January 2-3: Holiday Tea @ Victorian Belle | 2PM & 3:30PM, Artisan Teas, Pastries, Savories

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Related Events and Info:

• Events Calendar: Our Portland Events Calendar & Ticket Giveaways
• Thanksgiving: Portland Thanksgiving Events: Black Friday, Holiday Tree Lighting & More
• New Years: Portland New Years Events, Parties, Champagne Toasts, & More