Holiday Magic in Charlestown 2025: Top Events You Won’t Want to Miss

Welcome to the season

As the leaves finish turning and the first chill hits the air, the holiday spirit begins to glow in charming Charlestown, MA. Whether you’re looking for classic tree‐lightings, strolling through twinkling lights, or immersive winter fun, there’s something here for families, couples and neighbors alike. Here are three standout events to mark on your calendar for late 2025.

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1. Light Up Charlestown — Friday, November 28, 2025 at 5 pm

Kick off the holiday season in Charlestown with a festive gathering at Greenway Park. At 5 pm the day begins with holiday music, local food trucks and warm vibes. At 6 pm the big moment: flipping the switch on the tree and lights that will glow throughout the season.  
Why go: Free to attend, great for families, and a wonderful way to get into the holiday mood in your neighborhood.
Tip: Show up a little early to grab a good spot for the lighting and perhaps enjoy a hot chocolate from the concession stand.

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2. Boston’s Winter Fest — December 6-7, 12-14 & 19-30, 2025 (closed Dec 24-25)

Get ready for a large-scale festive experience at Hood Park, 100 Hood Park Dr. in Charlestown. This magical winter carnival and light festival features dazzling holiday lights, a life-size ice castle, a carousel, artisan village and rides for all ages.  
Highlights:
    •    $5 admission (for 2025) to enter.  
    •    Free 3-hour parking in the Hood Park garage.  
    •    Kid-friendly and family‐focused with warm food & drinks, local vendors, and festive attractions.
Tip: Purchase tickets ahead online to avoid lines, go earlier in the evening (5-6pm) for lower crowds, and dress warmly for outdoor winter fun.

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3. Live Reindeer & Holiday Market Night — Monday, December 22, 2025, 6-10 pm

Wrap up the season at Greenway Park with an evening including live reindeer, holiday market vendors, train rides, and visits with Santa & The Grinch. All part of the season’s concluding celebration.  
Why it stands out: It’s free to attend, offers unique photo ops, and combines nature (reindeer!) with holiday shopping and community spirit.
Tip: Bring a camera for the reindeer and Santa moments, and perhaps some extra cash for local vendor gifts and sweet treats.

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Final Thoughts

This holiday season in Charlestown is about community, warmth and festive magic — perfectly balanced between big-event fun and local charm. Whether you’re making memories with family, grabbing a photo opportunity, or exploring holiday shopping with a glow in your heart, you’ll find it here.