Quick Trips: Boston’s Liberty Hotel Turns Christmas Upside Down

There may be no other hotel in Boston that captures the Christmas spirit than The Liberty, nestled in the heart of the city’s vibrant Beacon Hill neighborhood — which in and of itself, is Charles Dickens-level charming. The

hotel was recently named the best hotel in Boston and the 19th best hotel in the world in the 2023 Condé Nast Traveler Reader’s Choice Awards. So it’s unanimous: it’s a pretty sweet spot. 

Just ninety minutes door-to-door from Newport, you’ll be struck the moment you see The Liberty’s all-stone façade. Originally built in 1851, the building was one of the best examples of the “Boston Granite Style” of the mid-19th century — only this building had a singular infamous purpose at the time: it was the Charles Street Jail.  After nearly a century and a half of housing some of Boston’s most notorious criminals, the jail closed in 1990. 

Today, the luxury Liberty Hotel capitalizes on the building’s historic past, boasting 298 imaginatively re-invented rooms and suites with sweeping views of the city skyline and Charles River. Soaring 90 feet into the sky, the jail’s central atrium was beautifully preserved and features the building’s trademark arched windows and historic catwalks. The preserved jail cells within the hotel restaurant and wrought-iron work on the windows are just two examples of preservation, and the former inmate exercise yard (“The Yard”) is now a private, inspiring urban courtyard. 

YULETIDE FINERY  

So, here are three reasons why you’ll want to make a Liberty Hotel getaway part of your holiday break plans:

1. Aerial Christmas trees. The pièce de résistance of The Liberty Hotel’s holiday finery are the upside down Christmas trees suspended from the soaring lobby’s chandeliers. The trees glow with 1500 holiday lights, 730 ornaments, and 60 yards of bronze sheer ribbon. From personal experience, they are best enjoyed with perched in a lobby wingback white sipping prosecco or an espresso martini.

2.  Curling in the Courtyard. Bundle up and brave chilly temps (although, frankly is hasn’t been uncomfortably cold just yet – yay!) for an unforgettable winter curling experience at The Yard. Guests are assigned a “curling concierge” who will explain the game and how to use the equipment, serve food and beverages, and can assist with any other needs/questions. A curling package includes a sweets menu with cinnamon dusted petite churros with Nutella, handmade apple pop tarts, double chocolate kettle corn, and chocolate chip cookies, or select the savory menu, featuring crispy pork and ginger dumpling with sweet chili sauce, Togarashi chicken sliders with Napa cabbage and spicy kewpie, and sriracha kettle corn — throw it back with a carafe of ancho hot chocolate with Don Julio Blanco Tequila and Ancho Chili Liqueur. (Ho, ho, holy moly — these sneak up on you!) Here’s more info.

3. Feeding body and spirit. The Liberty is home to Scampo, a culinary powerhouse created by legendary Boston-based Chef Lydia Shire; Clink, I savored an unbelievable brunch; Alibi, set in the jail’s old “drunk tank” (a rather apropos to get a nightcap, like the Shawshank Refreshment with Hendricks Gin, melon liquor, kiwi and lime); and of course The Liberty Bar in the lobby which never seems to slow down. We also adored the Catwalk, a guests-only experience on the jail’s actual former catwalks encircling the rotunda with the most up-close view of the Christmas trees and high-traffic atrium.  

Loving Lockup

There are 298 rooms at The Liberty, each with a playful nod to the hotel’s infamous past, from framed skeleton keys and safes as décor and storage, and door-hangers that trade the banal “don not disturb” message for simply said, “Solitary.” Each room offers panoramic views of the iconic Boston skyline and The Charles River framed by floor to ceiling windows. And when it comes time to rest your head, you’ll do so in a lux bed with appointed with imported bed linens. Frankly, being in solitary here is a damn delight.

Insider’s Tips:

Definitely dine at Scampo, and if you can, claim seats at the back bar instead of a table as this perch will give you a front row seat to all the kitchen activity. James Beard award-winning chef Lydia Shire, a Boston culinary legend, has masterminded a menu anchored by Italian-inspired cuisine but drawing on flavors from the Mediterranean and Middle East. We started with the highly-recommended fresh fig, chanterelle, and sottocenere truffle cheese pizza (heaven on plate). Our entrees included swordfish with spicy shrimp harissa meatballs and cool Persian cucumber salad as well as chestnut flour lobster ravioli with candied chestnuts. Perfection. 

When you go to Alibi, the old “drunk tank”of the original jail, check out mug shot of famous musicians (David Bowie, Mick Jagger, Johnny Cash and … Justin Bieber) and movie stars (Hugh Grant, Kiefer Sutherland and … Lindsey Lohan). If it’s a mild night, take advantage of Alibi’s patio. 

Grab a complimentary coffee in the morning before embarking on a brisk walk along the Esplanade to see the Charles glisten in the morning light. Be sure to make your way to the small arched footbridge that looks straight out of a fairytale — it’s not far from the Hatch Shell amphitheater.

 

After some nature-inspo, work your through the legendary and charming gas-lamp lined streets of Beacon Hill, making it a point to see Acorn Street, one of the most photographed streets in the Northeast (and yes, even in the early morning hours, there were two influencers there when I sent). This narrow cobblestone street (more like a wide alley) is flanked by buildings dating back to the 1800s and is almost always dotted with an American flag or two. If you’ve worked up an appetite, The Paramount just down the hill on Charles Street is a stalwart — it’s been there since 1937, the food comes out fast, and it’s diner vibes leaves any pretense behind. 

I also love to walk from The Liberty to the Public Garden. This time year, you have to seek out the bronze ducks in their Christmas finery, and take a spin on the iconic Frog Pond ice rink on Boston Common — it’ll give all the Hallmark Christmas move feels. A bit further off is the Boston Tea Party Ships & Museum, which my family loved when we visited last month. This Saturday, in fact, will be the commemoration of the 250th Anniversary of the Boston Tea Party on December 16, 2023. It’s been a year in the making and a re-enactment and more is planned – here’s the scoop!

Whether visiting for Christmas, a winter getaway or a Boston escape, The Liberty Hotel will make you feel like a local!