June 4, 2025
Freedom Trail & Beyond: Historic Boston Walks Starting at The Liberty Hotel
In a city where every brick has a backstory and every cobblestone corner could double as a history lesson, The Liberty Hotel offers a stay that’s both rooted in the past and boldly connected to the present. Housed in the former Charles Street Jail, The Liberty blends 19th-century architecture with luxury and edge-making it the perfect place to start your journey through Boston’s most iconic historical landmarks.
Whether you’re a first-time visitor or a local looking to rediscover the city, here’s your guide to walkable historic adventures starting right from your room key.
Beacon Hill: Your Historic Backyard
Step outside the lobby and you’re in Beacon Hill, one of Boston’s oldest and most storied neighborhoods. With its gaslit streets, Federal-style row houses, and ivy-draped charm, this area feels like a living postcard. Walk along Charles Street for locally owned boutiques and cafés, or head toward Louisburg Square, once home to writers like Louisa May Alcott and current residents of note.
It’s a neighborhood where history whispers from every window-and you’re staying right in the middle of it.
The Freedom Trail: Your Path to Revolution
Just a few blocks from The Liberty’s front door begins Boston’s Freedom Trail, a 2.5-mile brick-lined route that takes you through 16 nationally significant historic sites. The walkable trail begins at Boston Common-America’s oldest public park-and passes through dramatic chapters of American history:
- Massachusetts State House
- Park Street Church
- Granary Burying Ground
- Old South Meeting House
- Old State House
- And eventually, across the river to Bunker Hill Monument
You can start your walk in the morning and finish before dinner, with plenty of time to detour for coffee or snap a few photos at Paul Revere’s statue along the way.
Charles River Esplanade: Where Nature Meets History
While the Freedom Trail showcases Boston’s revolutionary heart, the Charles River Esplanade offers a different kind of historic perspective-one rooted in leisure, movement, and civic pride. Just steps from The Liberty, this waterfront path stretches along the Charles River, offering skyline views, jogging paths, and docks for watching rowers glide by.
Whether you’re walking, running, or just sitting with a morning coffee, the Esplanade is a peaceful, picturesque break between landmark visits.
Local Landmarks Worth the Turn
Beyond the official trail, you’ll find plenty of hidden gems within walking distance of the hotel. Take a few extra steps to discover:
- The Boston Athenaeum, one of the oldest independent libraries in the U.S.
- The African Meeting House, the oldest Black church building still standing in the country
- King’s Chapel and Burying Ground, dating back to 1686
Each site tells its own story-and at The Liberty, you’re staying at a hotel that’s part of the city’s story too.
A Stay With a Story of Its Own
Before it became a boutique hotel, The Liberty was the Charles Street Jail-home to famous inmates like Malcolm X and Sacco & Vanzetti. Today, its stunning transformation honors that history with preserved architecture, bold design, and a touch of rebellious spirit.
After a day of walking through the past, return to an evening of elevated dining at Clink, cocktails at Alibi, or open-air relaxation in The Yard-all spaces that blend the building’s rich legacy with modern sophistication.