As the air cools and the city’s brownstones take on golden hues, Boston reveals a whole new kind of magic. From lantern-lit nights and walkable tours to festive holiday markets and historic celebrations, the colder months in Boston are anything but quiet. Whether you’re here to sip cider by the harbor or toast the new year under twinkling lights, staying at The Boxer Boston places you in the heart of it all, just steps from TD Garden, the North End, and a flurry of fall and winter festivities. Discover what magic awaits you this fall and winter season.
October Highlights: Lights, Action & Halloween Thrills
The Lantern Festival at Franklin Park Zoo | October 1–November 3, 2025
Prepare to be amazed as dusk falls upon Franklin Park Zoo, transforming it into a glowing dreamscape. The annual Boston Lights: A Lantern Experience features over 60 dazzling displays, from giant dragons to glowing underwater scenes, all stretching across the 72-acre park. Walk beneath illuminated archways and explore immersive worlds. The lantern experience is a family-friendly tradition that dazzles visitors of all ages.
Head of the Charles Regatta | October 17–19, 2025
Ultimate sports lovers won’t want to miss the world’s largest rowing competition: the Head of the Charles Regatta. Over 11,000 athletes from around the globe battle it out across the Charles River in Cambridge, drawing more than 300,000 spectators. As the crews race along with the crisp fall foliage as a backdrop, the vibe is both competitive and celebratory. Don’t miss the Riverbank Vendor Village, boat races punctuated by cheers, and the festive atmosphere along Memorial Drive.
Beacon Hill with a BOO! | October 31, 2025
Take part in one of Boston’s most beloved Halloween traditions for over 30 years. Explore the shadowy side of one of Boston’s most historic neighborhoods on a spirited 90-minute walking tour through Beacon Hill. Led by expert guides, Beacon Hill with a BOO! blends true tales of murder, mystery, and mischief with Halloween flair, all along gas-lit streets and cobblestone alleys. It’s a fun and eerie way to experience the city’s haunted history just minutes away.
November Delights: Festive Markets & Month-Long Celebrations
Holiday Market at Snowport | November 7–December 28, 2025
Snowport in the Seaport District kicks off the holiday season with over 100 vendors offering handmade gifts, seasonal treats, and mulled wine to-go. Wander among wooden chalets, sip hot cocoa by the fire pits, and don’t miss the curling lanes for a little festive competition. It’s New England charm meets European holiday flair.
SoWa Winter Festival | November 28–December 28, 2025
Take a short trip to Boston’s South End to kick off the holiday season at the SoWa Winter Festival, returning to the iconic Power Station. This indoor winter market showcases over 100 local artisans and food vendors offering handmade gifts, gourmet treats, specialty cocktails, and festive entertainment. With creative maker workshops, a food-truck bazaar, live music, and a cozy atmosphere for just $10 at the door, it’s a joyful celebration of New England crafts and community charm. Open most weekends and evenings through December, it’s an ideal stop for early holiday shopping and seasonal eats.
December Magic: Lights, Music & Traditions
Boston Common Tree Lighting | December 4, 2025
A beloved tradition since 1941, the Boston Common Tree Lighting marks the official start of the city’s holiday season. With live music, ice skating, and the lighting of a giant spruce gifted from Nova Scotia, this heartwarming event is pure holiday spirit and free for families to enjoy from 6-8 pm. Bundle up, grab a cider, and watch Boston shine.
The Nutcracker at Boston Ballet | November 29–December 28, 2025
Clara’s magical journey comes to life at the Citizens Bank Opera House, where the Boston Ballet stages one of the country’s most acclaimed productions of The Nutcracker. Lavish costumes, Tchaikovsky’s timeless score, and exquisite choreography make this a holiday essential—even if it’s your first time seeing it.
First Night Boston | December 31, 2025
Ring in the New Year at First Night Boston, the city’s biggest New Year’s Eve celebration since 1976. Expect an unforgettable evening of live performances, ice sculptures, fireworks, and a midnight countdown on Boston Common. It’s a spirited, inclusive festival that captures the essence of winter in Boston: resilient, joyful, and brimming with life.
Your Winter Retreat in the Heart of Boston
After a day spent soaking in the culture, history, and festive energy of the city, return to The Boxer for a stay with rich historical charm. Book direct and save, and experience the city’s most inspiring season, from our front door to the final encore.