Charlestown, one of Boston’s oldest neighborhoods, is home to Bunker Hill, the USS Constitution, and scenic waterfront views. With history, harbor walks, and plenty of local spots to explore, it’s a charming stop along the Freedom Trail.
Where is Charlestown?
Charlestown is a neighborhood of Boston, situated on a peninsula on the northern edge of the city. It’s bordered by the Charles River to the west and the Boston Harbor to the east.
It is located just across the Charles River from downtown Boston’s North End, making it easily accessible by the Charlestown Bridge or the Charlestown pedestrian bridge if you’re walking.
Charlestown is known for its beautiful historic homes, its pathway along the waterfront, but mainly for two of Boston's most famous landmarks — the Bunker Hill Monument and the USS Constitution Ship along the Freedom Trail.
Key Historical Sites
Charlestown is known for its remarkable historical landmarks, many of which have shaped the identity of Boston itself. Here are some of the key historical attractions that make Charlestown a must-visit for history enthusiasts:
1. Bunker Hill Monument
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Arguably the most famous landmark in Charlestown, the Bunker Hill Monument is a 221-foot obelisk commemorating the Battle of Bunker Hill.
The monument stands on Breed’s Hill (now named Bunker Hill), the actual site of the battle.
Visitors can climb the 294 steps to the top for a stunning panoramic view of Charlestown, the water surrounding it, and downtown Boston.
The Bunker Hill Monument is part of the Boston National Historical Park, run by the National Park Service, which includes several other sites in the city related to the Revolutionary War.
2. USS Constitution
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The USS Constitution, also known as "Old Ironsides," is the world’s oldest commissioned warship still afloat.
Located at the Charlestown Navy Yard and run by the US Navy, this iconic ship was launched in 1797 and served during the War of 1812, earning its nickname after British cannonballs seemingly bounced off its thick wooden hull.
Today, you can climb aboard and tour the ship. You can also learn about its storied past at the USS Constitution Museum, which is located in the Navy Yard.
3. Charlestown Navy Yard
The Charlestown Navy Yard itself played a key role in American naval history, especially during the 19th and 20th centuries.
Today, the Navy Yard is a part of the Boston National Historical Park (with certain sites run by the NPS) and offers a glimpse into the past with historic buildings as well as the preserved USS Cassin Young, a World War II-era destroyer ship that you can board.
4. The Warren Tavern
The Warren Tavern, established in 1780, bills itself as the oldest bar in Massachusetts.
Located near the Freedom Trail, this historic tavern was a popular meeting place for notable figures like George Washington and Paul Revere during the American Revolution.
Today, it serves as a restaurant, giving you the chance to step back in time while enjoying a meal and perhaps a pint.
5. The Charlestown Preservation Society
For a deeper dive into the history of Charlestown, the Charlestown Preservation Society offers events that explore the neighborhood's historical homes and landmarks.
The society plays an active role in preserving the character of the area, which includes its iconic 19th-century brick row houses and cobblestone streets.
Modern Charlestown: A Blend of Old and New
In addition to its rich historical heritage, Charlestown has grown into a lively neighborhood that blends old and new. Historic landmarks sit beside modern shops, restaurants, and homes, while a strong sense of community thrives among families, young professionals, and longtime residents.
Things to Do and See in Charlestown
Whether you’re interested in history or simply enjoying the atmosphere of a historic neighborhood, Charlestown offers a variety of things to do. If the weather’s nice, you may find yourself wanting to spend quite a few hours meandering the neighborhood. And there are plenty of things to occupy your time:
1. Walk the Freedom Trail
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The Freedom Trail, a 2.5-mile path that passes through 16 of Boston’s most historic sites, ends with two key landmarks in Charlestown.
I’d highly recommend a walking tour app that you can download to conquer the Freedom Trail at your own pace while learning all about the history and stories that shaped America — with Shaka Guide’s Boston Freedom Trail Parts One and Two.
Part One takes you to the first 14 sites in the heart of the city of Boston, and Part Two takes you to Charlestown and walks you through the history that includes the Battle of Bunker Hill and the details about the ships docked at the Charlestown Navy Yard.
Both parts one and two of Shaka Guide’s Freedom Trail Tour provide you with detailed directions and stories to keep you entertained along the way.
The Shaka Guide tour offers an educational and immersive way to understand the history of the American Revolution.
2. Relax at the Charlestown Waterfront
Walk along the Boston Harborwalk, a hidden gem of a public walkway that follows the edge of the shoreline around Boston Harbor.
Also, walk down to Paul Revere Park under the iconic Zakim Bridge and snap some photos looking up at that incredible span! And after you visit the Navy Yard, head to the beautiful pier beyond the yard for a view of the Boston skyline.
You can even hop on a public ferry back to the city center if you don’t have enough energy to walk all the way back, but that ferry has seasonal hours, so you’ll want to check the schedule if that’s your plan.
3. Dining and Pubs in Charlestown
Charlestown’s food scene has options ranging from casual eateries to lively taverns and upscale dining. A few favorite spots include:
| Restaurant | Description |
|---|---|
| The Warren Tavern | Located on a historic street below the Bunker Hill Monument, go there to dine for the history alone, as it’s perhaps the oldest tavern in Massachusetts. Raise a glass to the Founding Fathers who frequented this place before you, including Paul Revere, Ben Franklin, and George Washington! |
| Pier 6 | A waterfront restaurant with a panoramic view of the city skyline and harbor, serving classic New England dishes with a focus on fresh seafood. Walk past the Navy Yard and down the pier to get there. |
| Blackmoor Bar and Kitchen | Casual dining at the foot of the Charlestown bridge. There are tons of seating inside, as well as outdoor seating on the river in the summertime. |
| Prima | A beautiful Italian steakhouse with a gorgeous hidden bar and velvety booths in the back called “The Rose Room.” This incredible restaurant is located directly on the Freedom Trail, just across the street from City Square Park. |
| The Anchor | An outdoor bar with multi-level seating, all overlooking the harbor. Grab a glass of wine and look out over the water for a picture-perfect view of the Boston skyline. You can also catch a public ferry at the dock just past the bar that’ll float you back to the city if you’re too tired to walk! |
4. Explore the Community
Charlestown is known for its strong community spirit, with frequent events like street festivals, farmer's markets, and parades. The local neighborhood associations often host events that are great for visitors wanting to experience the area's lively culture.
Where is the best place to stay in Charlestown?
The best hotel in Charlestown for Freedom Trail access is the Residence Inn Boston Harbor on Tudor Wharf. This waterfront hotel sits directly on the trail, giving you easy access to the final two stops — Bunker Hill and the USS Constitution. It’s also steps from the Charlestown Bridge, which leads straight into Boston’s North End.
Public Transportation to Charlestown
Walking Across the Charlestown Bridge
The Charlestown bridge (officially named the Bill Russell Bridge) that leads from the North End of Boston into Charlestown makes for an easy walk.
If you’re staying in Boston and want to get as close as you can to that bridge, just take the T subway to North Station, then walk a block to the bridge.
There’s also an Orange Line T station, but it leads to another neighborhood of Charlestown near Bunker Hill Community College, which is further from Boston and closer to Cambridge.
Taking the Ferry
There’s also a public ferry that’s part of the T that can take you across the harbor from the pier in Charlestown on the far side of the Navy Yard to Boston’s Long Wharf near the aquarium and seaport.
This ferry has seasonal hours of operation that vary, does not require reservations, and costs the same as riding the T trains.
So if you walk the whole Freedom Trail, end up at the Navy Yard, and realize you’re too tired to walk all the way back into Boston, you might want to consider taking the ferry when it’s operating — if it’ll get you closer to whatever hotel you’re staying at in downtown Boston.
Parking in Charlestown
If you drive to Charlestown, expect limited parking—it’s still the city. Try an app like SpotHero, watch street signs, and be ready for parallel parking on a hill. The Navy Yard lot is also an option, if spots are open.
To avoid the hassle of driving over the bridge, consider parking on the Boston side. Public lots near North Station (by TD Garden) usually have more availability, and from there it’s just a short walk across the bridge into Charlestown.
Explore the Boston Freedom Trail with Shaka Guide
So, now that you know more about Charlestown, go see it for yourself! With Shaka Guide’s Boston Freedom Trail Tour, you’ll journey through this historic neighborhood at your own pace—walking the Freedom Trail finale at Bunker Hill, strolling cobblestoned streets, and exploring the lively waterfront.
Take the Boston Freedom Trail Audio Tour with Shaka Guide and explore at your own pace with stories, directions, and must-see stops along the way.
Still planning? Check out our Boston Freedom Trail Itinerary and Know Before You Go guide to prep for an epic day.
Need help? Email us anytime at aloha@shakaguide.com!
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