Charlestown began as an independent community, founded by English colonists before they established Boston across the harbor on the Shawmut Peninsula. As the Massachusetts Bay Company prepared for its massive migration to New England, it dispatched engineer Thomas Graves from England in 1629 to lay out a town for the newcomers. The area of earliest settlement, at Town Hill (now called City Square), still retains the elliptical street pattern that Thomas Graves laid out.

At the beginning of the Revolutionary War, Charlestown’s population had reached about 2,000. Following the battles of Concord and Lexington on April 19, 1775, the British army head toward Charlestown in retreat, and most townspeople fled when they heard the news. Two months later, on June 17, the Battle of Bunker Hill was fought in Charlestown. The American troops lost the battle, but the strength and determination they showed, together with the great British losses, demonstrated that the Colonials were serious about independence. On their way out of town British troops burned the oldest section of Charlestown to the ground and full-fledged reconstruction would not take place until after the war ended in 1781. No other Boston neighborhood has such a fine group of frame houses from this period.

By 1785, 13 wharves lined Charlestown’s harbor, and soon new bridges increased trade. In 1800, the United States Navy opened the Navy Yard at Moulton’s Point, establishing what would become one of Charlestown’s major employers for more than 150 years. Between 1830 and 1870, Charlestown’s population tripled to more than 28,000. It was annexed to Boston in 1874.

Beginning in 1901, the elevated streetcar line made the neighborhood accessible to more people, stimulating industrial growth, but it also casting a visual blight over Charlestown. During World War II, the Navy Yard employed 47,000 workers, but peacetime brought severe unemployment and decline, heightened by the opening of the Tobin Bridge in the 1950s. More change has come in the last two decades, with the dismantling of the “El” and the closing and redevelopment of the Navy Yard revitalizing the old town.

Our walking tour will begin on the site of that fateful battle...

1. 
Bunker Hill Monument
Monument Square

Massachusetts governor Lt. General Thomas Gage seemed not to be overly concerned when his beaten troops returned from Lexington and Concord. He did nothing, except write letters to London. The Americans at Cambridge were busily sealing off Boston before Gage decided to occupy Dorchester Heights, south of Boston and Breed’s Hill in Charlestown, across the Charles River. The Americans learned of Gage’s scheme on June 13, 1775, and laid plans to fortify Bunker Hill, next to Breed’s Hill. The Americans under Colonel Richard Gridley, engineer of the Provincial Army of New England, began their defenses the night of June 16 mistakenly, however, on Breed’s Hill. This is where the battle would be joined the following morning. A British mapmaker had mislabeled the hill “Bunker Hill” and so the battle would always be called. Colonel William Prescott commanded the Massachusetts militia and positioned his troops behind a stone wall all the way to the Mystic River to his north as well as in the hastily built redoubt. General William Howe was chosen by the British to charge the hill with four infantry regiments and an artillery company. There was little doubt that Howe had been given enough firepower to dispatch a thousand farmers in a crude fort. The main assault began at 3:00 in the afternoon. Word had spread around Boston and most of the city was perched on rooftops to see what would happen. A first charge by the British was unsupported by artillery as they had brought the wrong size ammunition. The ferocity of the defensive fire stunned the redcoats, who fell back and regrouped. a second charge was turned back in similar fashion. The Americans knew the disciplined British troops would come up the hill a third time and they knew there was not enough powder to sustain another defense. Yet they held the hill. The British, supported by full artillery now, finally overran the redoubt and were met by bayonets in desperate hand-to-hand combat. Just before 5:00 p.m. the Americans abandoned Breed’s Hill and Boston to the British. From an army of 2,200 men the British suffered over 1,000 casualties, including 140 dead. Although over 400 American men were dead or wounded, Nathanael Greene was moved to say, “I wish we could sell them another hill at the same price.” The Bunker Hill Monument Association was formed in 1823 to create one of America’s earliest memorials to the Revolution. A proposal by Horatio Greenough for an obelisk, an ancient Egyptian architectural form to honor war heroes and dead, was accepted and the cornerstone laid in 1825. A newly invented derrick, which would soon be in general use in construction, lifted large granite blocks in place. The 221-foot high memorial was completed in 1842; 294 steps lead visitors to the observation deck. There is no elevator. Also on the site is a statue of Colonel Prescott. The visitor center features battle dioramas and exhibits of the Battle of Bunker Hill on Breed’s Hill. 

LEAVE THE MONUMENT TO THE WEST ONTO LAUREL STREET THAT RUNS PERPENDICULAR TO THE SQUARE. 

2. 
Charlestown High School
30 Monument Square

Charlestown’s first high school was constructed on Monument Square in 1847-48. It was replaced by a more commodious building on the same site in 1870. Finally a third and still larger granite high school infused with classical features was built in the same location in 1907. After more than 125 years of educational duty Charlestown High School moved on in the 1970s; the classrooms were then converted into residential units.

WALK TO THE END OF LAUREL STREET AND TURN LEFT ON CEDAR STREET. TURN RIGHT ON HIGH STREET. 

3. 
29-41 High Street

This block is populated with handsome Victorian rowhouses, executed in brick with granite steps.

TURN LEFT ON GREEN STREET.

4. 
Dexter Mansion
14 Green Street

Boston-born and Harvard-educated, Samuel Dexter came to Charlestown to practice law in 1788 when he was 27. He lived in this grand wooden house with a cupola on the roof but did not remain in town long - he was elected to the United States House of Representatives and then the the Senate; it was Dexter who wrote the memorial eulogy to George Washington when the “Father of Our Country” died in 1799. he went on to serve in the Cabinet of President John Adams. While the Dexter Mansion has stood for over 200 years it has been been greatly rearranged in that time.  

TURN LEFT ON MAIN STREET. 

5. 
Five Cent Savings Bank
Main Street at 1 Thompson Street

This was the prince of the Charlestown commercial district when it was raised in 1876. Architects George F. Moffette and George R. Tolman drew up the plans for the exuberant High Victorian Gothic Style with dormers peeking through the decorative mansard roof. The client was the Five Cent Savings Bank, an ancestor of Citizen’s Bank that took its first deposits in 1854. The building also housed Charlestown’s Masonic Lodge on its top three floors.

6.
Round Corner House
121-123 Main Street

The living space on most houses constructed in Charlestown in the early 1800s contained living space upstairs above shop space; this one from 1814 features an eye-catching round corner. It belonged to Captain Joseph Cordis, a shipwright turned merchant who, it was said “was among the first in town to engage in mercantile pursuits on what was then considered a large scale.”

7. 
Timothy Thompson House
119 Main Street

This house was rebuilt in 1794 after it was burned in 1775. Benjamin Thompson, president of the Warren Institute for Savings, state senator and United States congressman, was born here.

8. 
Warren Tavern  
2 Pleasant Street at Main Street

This is the oldest tavern in Massachusetts; the first building erected after the British burned the town in 1775. Named in honor of General Joseph Warren, who died leading patriot troops at Bunker Hill, it was the meeting place of King Solomon’s Lodge, the first Masonic Lodge in Charlestown, organized in 1784 with Paul Revere as its Grand Warden.

9. 
Austin Stone House
92 Main Street

Nathaniel Austin was Middlesex County sheriff and major-general of the Massachusetts Militia. The granite for this 1822 building was dug out of Austin’s quarry on Outer Brewster Island in Boston Harbor. From 1827 to 1871 the tenant occupying the ground floor was the Bunker Hill Aurora and Farmers and Mechanics Journal, Charlestown’s first successful newspaper.

TURN RIGHT ON DEVENS STREET.

10.  
St.Johns Episcopal Church
31 Devens Street

The first Episcopal services in Charlestown took place in a hall on Town Square in 1840 and the cornerstone for this Gothic Revival church designed by Boston architect Richard Bond was laid the following year. Construction of the dark ashlar granite meetinghouse required only six months. Next door the parish house began life as a chapel in the 1870s; the second floor was actually designed first, in the Carpenter Gothic style by William Robert Ware and Henry Van Brunt, two of Boston’s finest Victorian architects. It was hoisted on top of a new brick first floor designed by P.C. Barney in 1901.

RETURN TO MAIN STREET AND TURN RIGHT.

11.
John Hurd House
69-71 Main Street

The core of this house has a foot back in the 18th century when it was raised as a three-story Georgian-style manor house under a hipped roof. The Hurd family reaches back even further in Charlestown - to the 1680s. The building’s commercial days began in the 1870s and a long-time tenant, as the mosaic tiles tattle, was the Donovan and Fallon pharmacy.

12.
John Larkin House
55 Main Square

This 1790s Georgian residence was built for Deacon John Larkin, a patriot best remembered for his role in Paul Revere’s legendary midnight ride. It was Larkin’s horse that carried Revere out to Lexington and Concord to warn the Committee of Safety of the approaching British troops. The horse was never returned. Look up to see the truncated third floor - children’s room s often - and the quoins that wrap the corners of the clapboard house.

TURN RIGHT ON WINTHROP STREET. TURN LEFT ON HARVARD SQUARE.

13.  
Charlestown Free Dispensary
21 Harvard Square

This is one of the rare stone buildings in Charlestown; it was the site of the Charlestown Free dispensary that was organized in 1872 to provide medical and surgical relief of the sick and maimed poor. In its first year there were 1,140 visits resulting in an expenditure of $361.81.

FOLLOW HARVARD SQUARE AROUND TO HARVARD STREET. TURN LEFT.

14.
Edward Everett House
16 Harvard Street

This upscale Federal style townhouse was constructed in 1814 by Matthew Bridge, a wealthy merchant whose energetic efforts contributed greatly to the rebuilding of Charlestown after it was torched by the British. It was the later the home of educator and politician Edward Everett during his congressional and gubernatorial career. Everett was one of the most famous orators in 19th century America but he is best remembered today as the speaker who rambled for two hours immediately before Abraham Lincoln delivered his Gettysburg Address, which took less than two minutes. Later it became the home of William Carleton, a Boston inventor and founder of Carleton College in Minnesota. 

WALK INTO CITY SQUARE PARK.

15.
City Square Park

Charlestown with Market Square at its heart were laid out in 1629. In its almost four centuries the one-acre park has weathered the intrusion of British cannon balls, an elevated train line and bridge ramps. Those days are gone now and City Square, revitalized by the “Big Dig,” soldiers on as an attractive space with lawns, plantings and sculptures.

16.  
City Hall/District Court
1 City Square

This ornate Victorian pile under a domed roof was Charlestown’s City Hall when it was raised in 1868. Boston gobbled up the city only six years later and eventually this civic showpiece was replaced in 1917 by a less showy municipal building. Today it serves as a district court for the city of Boston. 

EXIT CITY SQUARE PARK TO THE NORTH ONTO PARK STREET. 

17.
Roughan Hall
15-18 City Square

Architect Arthur H. Vinal tapped the Italian Renaissance for this multi-use clubhouse frequented by Charlestown fraternal and civic clubs. The oversized windows punctuating the yellow brick facade illuminated a grand two-story hall.

FOLLOW PARK STREET TO FORK AT WINTHROP SQUARE AND TURN RIGHT.

18.
Salem Turnpike Hotel  
16 Common Street at Winthrop Square

Farmers who carted their produce to town to peddle in Market Square found lodging in this clapboard hotel that was completed in 1810.

TURN AROUND AND WALK AROUND THE SOUTHERN EDGE OF THE SQUARE.

19.
Tapley House
14 Common Street at Winthrop Square

John Tapley was a master ironsmith, a craft he learned in the family shipyard on the Charlestown waterfront. Tapley did work on the U.S.S. Constitution after the iconic warship was crippled during the War of 1812. The Federal-style yellow clapboard house was built in 1806 and the Tapley family, nine children strong, lived here into the 1820s when the Tapleys moved out to a small country farm. 

20.      
Training Field School
3 Common Street at Winthrop Square

The red brick grammar school building is the oldest surviving one in Charlestown, although it hasn’t always stood here. The school was constructed in the center of the Training Field in 1828 but was moved across the street to this location in 1847 and picked up a third story in the process. After more than 150 years of classroom use it became a private residence in the 1980s. 

21.      
St. Mary’s Roman Catholic Church Parish Hall
46-50 Winthrop Street at Winthrop Square

This brick building has served as the parish hall for St. Mary’s Church since 1913.

22.      
Winthrop Square

This was the early Colonial training field for the militia and it still sports a martial flavor. The stone gates ushering visitors into the square from the north side memorialize the American militiakilled in the Battle of Bunker Hill. It was dedicated on June 17, 1889 joining a Civil War Soldier’s Monument designed by Martin Milmore that had stood here since 1872. 

TURN LEFT AND WALK DOWN WINTHROP STREET TO WARREN STREET. TURN RIGHT.

23.      
St. Mary’s Roman Catholic Church
55 Warren Street

From his Brooklyn office Irish-born architect Patrick Charles Keely designed over 600 buildings for the Catholic church in the 19th century, including every cathedral in New England for decades. This was one of his last churches, designed in his favored Gothic Revival style in 1887; it was replacing an 1820s model. Fashioned from quarry-faced granite and trimmed in red brick, the church was dedicated in 1892. It is located on the site of the first thatched house in the area that was patched together in 1625.

24.      
Wiley House
59 Warren Street

This eclectic 1871 Victorian town house was created in three acts for local master mason Robert R. Wiley. You can look up and see influences from across the spectrum of 19th century American architecture from the bowfronts of Charles Finch to the oriel window of the Victorian age. 

TURN RIGHT ON PLEASANT STREET.

25.      
23 Pleasant Street

A splash of the vernacular wooden houses of the 1700s remains on Charlestown streets, this one with a gambrel-roof.

CONTINUE ON PLEASANT STREET TO RETURN TO THE TOUR STARTING POINT AT BUNKER HILL MONUMENT.