“Cheers to the Season!” — Your Guide to Holiday Happenings in Boston (2025)
“Cheers to the Season!” — Your Guide to Holiday Happenings in Boston (2025)
The holiday season is upon us, and Boston shines brightest this time of year. From twinkling lights and festive markets to outdoor winter cheer and cozy pubs perfect for a post-stroll pint, there’s no shortage of magic around town. Whether you’re exploring with friends, family, or coworkers, we’ve rounded up the best ways to celebrate the season — all within easy reach of Beacon Hill.
Classic Boston Holiday Lights & Tree Lightings
Boston kicks off the season with several beloved lighting celebrations that make great daylight or evening outings before retreating to a warm bar or pub:
Boston Common Tree Lighting — One of the city’s most iconic seasonal traditions, where the massive Nova Scotia tree is illuminated amid music and festivity.
Copley Square Tree Lighting — A charming affair with Santa, live music, and treats — ideal for a stroll afterward.
Commonwealth Avenue Mall Lighting — Just after the Common lights up, the lights along the Mall glow to life, perfect for an evening walk before warming up indoors.
Holiday Lights at Christopher Columbus Park & Martin’s Park — Smaller neighborhood lights that add sparkle to your walk through the North End and waterfront.
Festive Markets & Seasonal Strolls
Beacon Hill Stroll — Enjoy Victorian carolers, storytelling, holiday treats, and charming stalls right on Charles Street. It’s a perfect low-key holiday outing before heading to one of our nearby bars for a celebratory drink.
Holiday Kingdom in Downtown Boston — Giant illuminated nutcrackers, holiday lights, and pop-up markets make this a great daytime adventure (or pre-dinner walk).
Snowport & Seaport Holiday Tree Lighting — A bustling holiday hub with lights, markets, and music.
New & Unique Seasonal Highlights
Boston Frostival — A brand-new winter initiative featuring synchronized LED drone shows over Boston Common on Saturday nights through Dec. 20. It’s a magical twist on traditional light shows.
Shows, Music & Cultural Cheer
The Nutcracker by Boston Ballet — A holiday classic running through most of December at the Citizens Bank Opera House.
Holiday Pops at Symphony Hall — Traditional festive music that’s perfect for a date night or group outing.
Hanukkah Celebrations & Menorah Lightings — Public menorah lighting ceremonies around town throughout December.
Ice Sculpture Strolls & First Night Events — Especially fun if you’re planning a New Year’s Eve visit.
Warm Up After the Walk — Beacon Hill & Nearby Bars to Visit
After a day of holiday sights, stop by Cheers to grab a drink, continue the celebration, or simply warm up with friends. We've got a long list of festive cocktails to warm your spirit.
Tips for Making the Most of the Season
Bundle up! Many light displays and markets are outdoors — a warm coat, hat, and gloves make all the difference.
Plan early for shows & Nutcracker performances — They sell out fast.
Holiday crowds are happiest earlier in the evening — pre-dinner strolls lead to great cocktail hours.
From historic traditions and new holiday spectacles to cozy pubs perfect for lingering over a craft cocktail, Boston’s winter season has something for everyone. So grab your mittens, rally your crew, and make this festive season one to remember — and don’t forget to stop by for a warm, cheerful libation!
Cheers! 🍻