Boston is calling Canadians to embrace winter the New England way: with charm, culture, and plenty of cozy celebration. This season, classic winter traditions meet new energy across the city. Boston’s exciting winter season features the launch of their new Frostival program, alongside the city’s iconic holiday lights, festive markets, and engaging cultural experiences. As well, there are plenty of other dynamic winter offerings, from live sports and cozy culinary spots to immersive outdoor art and seasonal activations like the spectacular drone shows on Boston Common.

Boston’s annual Christmas tree, a heartfelt gift from Nova Scotia, symbolizes over a century of friendship and gratitude. Each year, a magnificent white spruce, carefully selected from Nova Scotia’s forests, is sent to Boston to thank the city for its vital emergency aid after the 1917 Halifax Explosion. The 54th tree will be honoured on December 4th on the Boston Common with special ceremonies and strong community engagement on both sides, highlighting the enduring spirit of generosity and friendship. 

Beloved favourites like First Night Boston ring in the New Year, while Snowport in the Seaport and the SoWa Winter Festival showcase the city’s creative spirit. Visitors can explore immersive arts during WINTERACTIVE and honour Black contributions during Black History Month. 

Boston is set to launch its first annual Frostival, a new signature seasonal experience that will feature drone shows over Boston Common, new light installations, culinary events, and winter activations across downtown, the Kennedy Greenway, and Back Bay. Full details will be revealed in the coming weeks—stay tuned for an unforgettable new celebration of food, art, and local spirit. 

Winter in Boston also means sports and spectacle. Cheer on the Bruins, Celtics, or Patriots. This mix of rivalry and camaraderie captures what local fans call Boston’s warm‑hearted winter energy. And of course, 2026 marks the Winter Olympics with many Boston natives heading to Milan to showcase how the city embraces winter sports at the highest level. 

Romantics will find plenty of reasons to linger. Stay in elegant hotels like The Langham, XV Beacon, or The Liberty, many offering igloo dining, fireside bars, and special winter packages. Cozy dinners await at Mistral in the South End and Bistro du Midi in the North End—paired with skyline cocktails at Igloo Bar at the Envoy or the après‑ski ambiance of The Lodge at Publico. And be sure to reserve at one of the restaurants that will be named on the highly anticipated Michelin Guide in Boston

About the Author

Bryen Dunn is a freelance journalist based in Toronto with a focus on tourism, lifestyle, entertainment and community issues. He has written several travel articles and has an extensive portfolio of celebrity interviews with musicians, actors and other public personalities. He’s willing to take on any assignments of interest, attend parties with free booze, listen to rants, and travel the world in search of the great unknown. He’s eager to discover the new, remember the past, and look into the future.