"Each walk is designed to incorporate the new and old, the natural and man-made. View Boston as you never have before on foot."
—Jessica Chmara, Boston Forward
Boston is a walker’s town. It’s as clear as the brick red path marking the Freedom Trail, the bright blue signs of the Harborwalk, and the green of the Emerald Necklace series of parks. Boston’s nearly 400-year history has led to the development of hidden neighborhoods, historic sites, and iconic parks that tempt both Bostonians and visitors out… See more details below
Boston is a walker’s town. It’s as clear as the brick red path marking the Freedom Trail, the bright blue signs of the Harborwalk, and the green of the Emerald Necklace series of parks. Boston’s nearly 400-year history has led to the development of hidden neighborhoods, historic sites, and iconic parks that tempt both Bostonians and visitors out onto the sidewalks, paths, and trails lacing this close-knit city. In addition, the Big Dig project, which helped revive downtown and the waterfront by moving Interstate 93 underground, has created an energy and excitement that has driven projects like the Harborwalk and the Rose Fitzgerald Kennedy Greenway. Walking Boston offers the best of Boston’s new and old rambles. This portable guide features detailed maps, original photos, and public transportation information for every trip. Route summaries make each walk easy to follow, and a “Points of Interest” section summarizes each walk’s highlights.
Beacon Hill: Cobblestones and Gaslights
Boundaries: Charles St., Beacon St., Joy St., Cambridge St.
Distance: Approx. 2 miles
Parking: Charles St. Parking Garage at 144 Charles St.; Boston Common Parking Garage on Charles St.
Public Transit: Charles St./MGH T Station on the Red Line; busses 43 and 55
San Francisco has Nob Hill, Manhattan has Park Avenue, and London has Belgravianeighborhoods where heritage, architecture, and money are inextricably linked. For Boston, it’s Beacon Hill, a maze of cobblestone streets and well-kept row houses arranged along Beacon Hill between Storrow Drive and the State House. The neighborhood is a National Historic District, an elite enclave of privilege, and a vibrant communityall in one. It’s the type of place where you can live just down the street from both the Museum of African American History and John Kerry.
Beacon Hill comes alive in early spring when window boxes and flowering pear trees explode into color. And if a passing thundershower forces you to duck into one of the many good cafes or shops along Charles St., so much the better. If you take this walk at dusk, you’ll appreciate the gas lamps throughout Beacon Hill that still burn 24 hours a day. The lamps are just one of the many details, like brass door knockers and ornate ironwork, which give Beacon Hill its considerable charm.
Begin at the Charles St./MGH T Station and head south on Charles St., toward the Boston Common. Charles St. is Beacon Hill’s town square. Pass through here on any evening and enjoy the jostling camaraderie of residents picking up dinner or dry cleaning. The mix of stores is wonderfully eclectic, with trendy clothing boutiques and hardware shops standing cheek by jowl with important historical sites.
One of those sites was on the right, at 148 Charles St., the former site of the James T. Fields House, home to renowned 19th-century publisher and literary icon,which was torn down and replaced with a parking garage in the early 20th century. It’s a shame to think that cars are now parked on the site where Fields, gathered many of America’s most famous writers, including Nathaniel Hawthorne, Ralph Waldo Emerson, and Henry Wadsworth Longfellow for dinner parties.
A short bit down Charles St. is the Charles Street Meeting House on the right, at 70 Charles St. (the corner of Charles and Mt. Vernon St.). Built in 1804, this former white Baptist church became the African Methodist Episcopal Church in 1876 and echoed with the voices of important abolitionists like William Lloyd Garrison, Harriet Tubman, and Frederick Douglass. In 1920, the church was saved from the wrecking ball by being relocated 10 feet toward the river to make room for an expanded Charles St. Note the cupola that is in place of the traditional steeple often used for New England churches; it seemed to foreshadow its current, more secular use as a cafe and stores.
Continue on Charles St. If you’re in the mood to stop, try one of the sandwiches on freshly baked baguettes or a great salad from Cafe Bella Vita, on the right at 30 Charles St. Alternatively, you can a grab a few groceries and a good bottle of wine for a picnic from DeLuca’s Market, on the left at 11 Charles St. These cafes and markets, along with their quaint store signs and the cobblestone street, give Charles St. a European feel. Walking past DeLuca’s brings you to the corner of Charles and Beacon streets (there’s a Starbucks here). From here, you can see the Boston Common stretching out to the left and up the hill, and the Public Garden on the right side of Charles St.
Turn left at the corner with the Starbucks and head up the hill on Beacon St. Facing the Common are the former homes of judges, ministers, and public figures.
Turn left on Joy St. and walk to 5 Joy St., home of the Appalachian Mountain Club (open weekdays only). Located in a little brick house, this recreation and advocacy group for the Northeast offers a variety of programs and suggestions for those looking to leave the city behind. Its bookstore is stocked with great guides and maps for the New England area. You do not need to be a member of the club to use the resources.
Turn left on Mt. Vernon St. and just down the hill is 55 Mt. Vernon, the Nichols House Museum. This was once the home of activist and philanthropist Rose Standish Nichols, who stipulated in her will that her 1804 Charles Bulfinch-designed house and eclectic collection of Victorian and Colonial furniture be open to the public in perpetuity. Take the $5 tour to see the Bulfinch architectural details and dark Victorian furnishings, but more importantly to learn about this fascinating and bold woman. She was a suffragette, author, and landscape designer in an age when women were supposed to keep house and gardens, not design them.
Continue downhill, and, as you walk, note the carefully preserved elm trees that lend the street so much of its leafy serenity. Other notable details include the wide variety of brass door knockers, boot scrapers, and ironwork.
Turn left on Walnut St.
Make a quick right on Chestnut St. to continue down the hill. The houses at 13, 15, and 17 Chestnut are perhaps the nicest wedding presents one can give. Wealthy Boston merchant James Swan and his wife, Hepzibah, gave one to each daughter in the early 19th century on the occasion of their nuptials. Designed by Charles Bulfinch, the houses have marble columns and recessed arches.
Continue down the street to 29A Chestnut and note the windows of the house of actor Edwin Booth (brother of John Wilkes Booth, who assassinated President Abraham Lincoln). Their purple tint is the result of a manufacturing defect that caused the glass to turn purple when exposed to air. Although it happened accidentally, these windows were viewed as prettier than normal windows and quickly became a must-have fashion in Victorian Boston. Keep your eye out for them throughout Beacon Hill.
Turn right on W. Cedar St. and follow it one block to Acorn St.
Turn right on Acorn. This narrow alley has been called the most photographed street in the world. While that may be an exaggeration, the steep street, with its gaslights, grass growing between the cobblestones, and classic Victorian houses is certainly worth setting up your tripod.
Turn left on Willow St. and follow it to Louisburg Square.
Veer left across Mt. Vernon St. and then veer right to take the west (downhill side) of Louisburg Square. Louisa May Alcott, whose 19th-century novel Little Women is an American classic, lived her last days in the fine house at 10 Louisburg Square. Although her childhood included other residences on Beacon Hill (at 20, 43, and 81 Pinckney St.), the runaway success of Little Women allowed her to move into the more fashionable Louisburg Square toward the end of her life.
Turn right on Pinckney St. for additional examples of Beacon Hill’s literary pedigree. But first, a bit of its current history: At the northeast corner of Pinckney and Louisburg Square is one of the homes of former presidential candidate and U.S. Senator John Kerry. But don’t linger too long in front of the palatial pied-a-terre; the Secret Service will take note.
Climb the hill toward Joy St. American novelist Nathaniel Hawthorne, who wrote The Scarlet Letter and Mosses from an Old Manse, lived at 54 Pinckney, and a young Henry David Thoreau lived at 4 Pinckney well before his sojourn at Walden Pond.
At the top of the hill, turn left on Joy St. After you crest the hill and descend toward Cambridge St., you come to the Museum of African American History, at 46 Joy St. The museum, which consists of the African Meeting House and the Abiel Smith School, honors and celebrates Boston’s, and especially Beacon Hill’s, role in advocating for the rights of slaves. The meeting house, built in 1806 primarily with black labor and funds from both the white and black communities, served as the focal point for the New England abolition movement. It was here that the white abolitionist William Lloyd Garrison founded the New England Anti-Slavery Society, which helped drive the campaign to abolish slavery as well as assist escaped slaves in finding freedom. It was also here that escaped slave and leader Frederick Douglass gave a speech after being run out of Tremont Temple. This is the oldest black church still standing in the United States and offers a wide variety of exhibits and programs exploring African-American history.
Next door, Abiel Smith School offers a sense of what life was like for African-American elementary students in the 1800s. Operating as a school from 1835 to 1855, this was the first building in the nation constructed as a public school for black children. The interior has been renovated and reconstructed with displays featuring examples of mid-19th-century education.
Turn left to head down Smith Ct. (right next door to the museum). The houses are typical of the ones owned by free blacks in the 19th century, before many of them migrated to South Boston.
At the end of Smith Ct., turn left on tiny, winding Holmes Alley, where escaped slaves could flee from bounty hunters by either blending into the crowds of free blacks who gathered there or slipping behind doors in the alley. Slip down the alley yourself to access South Russell St.
Turn left on S. Russell St.
Turn right on Myrtle St. and go one block to Irving St.
Turn right on Irving.
Turn left on Phillips St. Just past Garden St., on the right, is Vilna Shul, the oldest synagogue in Boston and home to the Boston Center for Jewish Heritage. Stop in to gaze at the stained glass Star of David and the sanctuary flooded with natural light from three skylights.
Continue three blocks to the Lewis and Harriet Hayden House, at 66 Phillips St. Although the house is now private and you’ll have to admire it from the outside, the front porch is actually the most interesting part. According to local legend, kegs of gunpowder were stored underneath the front porch so that when slave hunters came to this stop on the Underground Railroad, the Haydens (Lewis himself was an escaped slave) could greet the white men with lit candles and threaten to drop them on the gunpowder below the porch if they tried to come inside.
After the Hayden House, turn right on W. Cedar St., which runs out to Cambridge St.
Turn left on Cambridge St.
Turn right on Charles St. to return to your starting point.
POINTS OF INTEREST
Charles Street Meeting House 70 Charles St., Boston, MA 02114
Cafe Bella Vita 30 Charles St., Boston, MA 02114, 617-720-4505
DeLuca’s Market 11 Charles St., Boston, MA 02114, 617-227-2117
Appalachian Mountain Club 5 Joy St., Boston, MA 02114, 617-523-0636
Nichols House Museum 55 Mt. Vernon St., Boston, MA 02114, 617-227-6993
Museum of African American History 46 Joy St., Boston, MA 02114, 617-725-0022
Vilna Shul/Boston Center for Jewish Heritage 18 Phillips St., Boston, MA 02114, 617-523-2324
1. Begin at the Charles St./MGH T Station and head south on Charles St.
2. Turn left on Beacon St.
3. Turn left on Joy St.
4. Turn left on Mt. Vernon St.
5. Turn left on Walnut St.
6. Turn right on Chestnut St.
7. Turn right on W. Cedar St.
8. Turn right on Acorn St.
9. Turn left on Willow St.
10. Veer left to cross Mt. Vernon St., and then veer right to take the west (downhill) side of Louisburg Square.
11. Turn right on Pinckney St.
12. Turn left on Joy St.
13. Turn left on Smith Ct.
14. Bear left on Holmes Alley.
15. Turn left on S. Russell St.
16. Turn right on Myrtle St.
17. Turn right on Irving St.
18. Turn left on Phillips St.
19. Turn right on W. Cedar St.
20. Turn left on Cambridge St.
21. Turn right on Charles St. to return to your starting point.
Back Story: Charles Bulfinch
Born in Boston in 1763, Charles Bulfinch attended Harvard before settling into his career as America’s first native-born professional architect. He established his practice by designing many of the houses on Beacon Hill before being tapped to design the Massachusetts State House, which was begun on July 4, 1797.
After that, he went on to enlarge Faneuil Hall, design numerous churches, like St. Stephen’s Catholic Church in the North End, and design private homes, including three for Harrison Gray Otis, a prominent Boston politician and developer of Beacon Hill. Known for his intelligent use of brick and granite and for the stately elegance of his public buildings, Bulfinch is credited with transforming much of Boston from a wooden port town to an impressive 19th-century metropolis. However, Bulfinch was better at design than financial management, and in 1811, his debts sent him to jailironically in a prison of his own design.
In 1818, President James Monroe offered Bulfinch $2,500 a year for 12 years to help design the U.S. Capitol. Although some of his details have been replaced, much of the Bulfinch-designed Capitol Building remains.
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