It may be a long while before the time machine is finally invented. Until then, a comfortable pair of shoes is all you need to explore Roxbury’s nearly 400 years of recorded history.
Start at John Eliot Square, at the intersections of Centre, Roxbury, Dudley and Highland streets. English settlers founded the Town of Roxbury here in 1630. Although the town hall no longer exists, two other historic structures remind us of our colonial roots. At 183 Roxbury St, the Dillaway-Thomas House, is the second oldest house in Roxbury and a true survivor of the kinds of change that happen in urban neighborhoods. This house was built in 1750 as the parsonage for the First Church in Roxbury and later became the headquarters for John Thomas, a major in the American army during the Siege of Boston. While in private ownership, it suffered a few accidental cooking fires in the 1800s and some intentional ones in the 1970s. The building even survived demolition plans for the neighboring middle school. Today it is part of Roxbury Heritage State Park/DCR, a quiet oasis in the heart of Boston, with a great view of downtown. If the gates are open, walk in and enjoy the grounds and the view.
Walk across the street to admire the First Church in Roxbury, which first gathered in 1631. Originally founded by Puritans, it became a Unitarian Church in 1810. This building, however, is not the original church, it is the fifth! In fact, a total of five church buildings have existed on this site, with some torn down to make room for larger buildings and at least one lost to a fire. The current building was completed in 1804 and is the oldest wooden church building in Boston.
Before heading uphill, walk to Zero Centre Street and take a close look at the large stone standing upright outside the building. If you walked along Roxbury Street, you just walked in the footsteps of William Dawes (Paul Revere’s counterpart) to the Parting Stone. Paul Dudley (1675-1751), Chief Justice of the Massachusetts colony, set up a series of parting stones to guide travelers through the rural areas outside Boston to other parts of Massachusetts. This stone marked the split between the southern road to Dedham and the northern route to Cambridge, which Dawes used when he warned the Americans of the British invasion on April 18, 1775. Look carefully on the sides to see which way was which. Can you guess which way he went?
You, however, will not take either road. Instead, walk up Highland Street. Once the British were gone, Roxbury began rebuilding. Farms eventually were purchased by wealthy Bostonians looking to escape the crowded city. They replaced farms with estates and mansions, two of which still remain along the Highland Street corridor. The cream-colored Edward Everett Hale House (built 1841) is on the right at 12 Morley St. It’s named after the prominent Unitarian minister at the First Church, who was known as a liberal reformer with a deep interest in abolition and education. Further up the street is the white Alvah Kittredge Mansion (built 1836) at 12 Linwood St., which was built by developer and merchant Alvah Kittredge. Both houses were built in Greek revival style, a popular choice at the time as Americans sought a visual connection between our young democracy and the historic Greek democracy. Both also once fronted Highland Street, but were moved and turned on to their current streets in the 1880s-1890s during the development boom that covered the hill with row houses and multi-family housing. The Hale House is still owned by a sole owner while the Kittredge Mansion will be redeveloped into multi-family housing.
As you continue along Highland Street and cross Cedar Street, you will soon be enveloped by the tall canopy of mature trees. As squirrels chant around you and hawks fly above, keep an eye out for the small but historic, William Lloyd Garrison House on the rocks above you to the right. This house was built in the 1840s during Roxbury’s early period of suburban growth. Garrison, an abolitionist leader and the most prominent owner of the house, retired to this house after emancipation and lived here until his death in 1879. The house was nicknamed Rockledge due to the large outcroppings of Roxbury Puddingstone on the property.
Keep following Highland Street and then turn right up Fort Avenue to reach one of the highest points in Boston, Highland Park. Highland Park was the location of the Roxbury High Fort, which was constructed to guard the land route out of Boston against the British. The fort fell into disrepair in the 19th century and was destroyed by the City of Boston to accommodate the Cochituate Stand Pipe (a water tower) after Roxbury’s annexation in 1868. The water system was abandoned ten years later after construction of a reservoir nearby. The park, however, is still used by area residents and provides another quiet oasis in the heart of Boston.
As you descend the hill, we will briefly recall when the area was German. Continue down Fort Avenue away from Highland Street. At the traffic light, merge with Centre St and follow to 45 and 47 Centre St. In the 1800s, Germans lived in large numbers in Roxbury. They were skilled entrepreneurs and built dozens of breweries along the Stony Brook, which once flowed above ground where Columbus Avenue now exists. John Roessle, owner of the former Roessle Brewery, lived at 47 Centre St. His brewery once existed at 1250 Columbus Ave, where Roxbury Community College currently exists. Louis Prang, another German emigree, lived at 45 Centre St. Prang founded the Louis Prang Art Publishing House in 1856, where he eventually printed the first Christmas card. His factory still exists as converted office space just below on Roxbury St.
Turn off Centre St and head down Gardner St. Directly in front of you amid the grove of trees is Father and Son, a large sculpture designed by local artist John Wilson depicting a father lovingly reading to his son. Take a picture with the family before going inside the Resnikoff Gallery, another opportunity to view local and international works of art. Finish your walk at the relatively new Islamic Society of Boston Cultural Center at 100 Malcolm X Boulevard. The ISBCC is open to all to worship or to learn about Islam.
Don’t leave the area hungry, though. Return to the corner of Gardner and Roxbury streets for a full meal at Ashur restaurant or cross Columbus Ave for tea and pastries at Butterfly Café. Both are Somali owned and offer a taste of the Old World in one of Roxbury’s newly-developed areas.