There are hotels. And then there’s The Envoy Hotel, Autograph Collection. Located in the heart of the Seaport District, where pioneering spirit brushes up against the creative energy of the Seaport, The Envoy doesn’t just offer you a room; it delivers a pulse. A statement. A basecamp for the bold.

And if there were ever a season to see the city shine, fall and winter are it. Picture cobblestone streets lit by lanterns, crisp coastal air swirling with the scent of cider, and iconic landmarks wrapped in twinkling lights. From festive holiday markets to champagne-fueled countdowns, Boston is bursting with reasons to wander, and The Envoy places you front row to all of it. Discover a lineup of local events destined to make your Boston fall or winter getaway unforgettable. 

October: Lantern Glow & River Row

Boston Lights at Franklin Park Zoo | October 1 – November 3, 2025

The city’s glow hits a whole new level at Boston Lights: A Lantern Experience. Every fall, Franklin Park Zoo becomes an electric dreamscape of towering dragons, glowing jellyfish, and whimsical light tunnels. Sprawling across 72 acres, this is not just your average walk in the park. It’s an immersive wonderland that’ll have your phone out at every turn. Come for the art, stay for the awe.

Head of the Charles Regatta | October 17 – 19, 2025

Over 11,000 elite athletes descend on the Charles River for the Head of the Charles Regatta, one of the largest races in the world. Grab a latte, post up along Memorial Drive, and join more than 300,000 spectators soaking up the competitive spirit and peak fall foliage. With pop-up vendors and tailgate-style energy, it’s Boston doing sport, culture, and community all at once.

Beacon Hill with a BOO! | October 31, 2025

A haunted history tour through one of Boston’s most photogenic neighborhoods? Yes, please. Beacon Hill with a BOO! leads guests on a 90-minute candlelit walk through gas-lit alleys, dishing out tales of old crimes and mysterious happenings with theatrical flair. It’s spooky-season sophistication with a dash of cobblestone charm.

November: Market Magic & Holiday Spark

Holiday Market at Snowport | November 7 – December 28, 2025

Steps from The Envoy, the Holiday Market at Snowport Winter Village transforms Boston’s Seaport into a European-inspired winter village. Wooden chalets. Mulled wine. Artisanal gifts. It’s a curated blend of New England cheer and international flair, with fire pits and curling lanes to warm things up. Pro tip: Hit up the market at golden hour and watch the skyline turn festive.

SoWa Winter Festival | November 28 – December 28, 2025

In the South End’s iconic Power Station, SoWa kicks off its annual Winter Festival, with indie artisans, gourmet treats, and seriously good energy. Think small-batch candles, funky jewelry, locally made spirits, and street food you’ll dream about later. For just $10, you’re in. Plus, it runs through December, so there’s no rush to soak it all in.

December: Traditions with a Twist

Boston Common Tree Lighting | December 4, 2025

This one’s a classic. Every December, a giant spruce (gifted annually by Nova Scotia) takes center stage on Boston Common. The Boston Common Tree Lighting features live performances, hot drinks, and a buzz of seasonal spirit. It’s heartfelt, free, and entirely worth bundling up for.

The Nutcracker at Boston Ballet | November 29 – December 28, 2025

This isn’t just ballet—it’s Boston Ballet. Their rendition of The Nutcracker at the historic Citizens Bank Opera House is rich, grand, and utterly mesmerizing. With lavish sets, masterful choreography, and Tchaikovsky’s iconic score, it’s the kind of tradition that never gets old.

First Night Boston | December 31, 2025

Cue the countdown! First Night Boston is the city’s long-standing New Year’s Eve bash, filled with fireworks, ice sculptures, live music, and good vibes across Boston Common and Copley Square. Whether you’re toasting midnight from a rooftop (might we suggest Lookout, our very own rooftop bar with panoramic harbor views?) or joining the crowds below, this is Boston’s night to sparkle.

Where It All Comes Together

After a day of lantern-lit walks, riverside regattas, or mulled wine in the market, retreat to The Envoy with our advanced purchase rate, so that you save more when you plan ahead. Our hotel rooms overlook the waterfront, and our rooftop is known as one of Boston’s best spots for views.