During my most recent visit back to Boston a friend of mine took me on a visit to the most amazing vintage store I've ever come across, Bobby From Boston. The store is owned by Bobby Garnett, who is basically the grandfather of vintage. Bobby actually consults for Ralph Lauren, who is my favorite designer and looking at the selection at Bobby's makes you feel like you're in a Ralph Lauren store, except it's authentically vintage. He has owned shops through-out Massachusetts, including one in P Town during the 70's called "Uptown Strutters Ball." Bobby's flagship location Bobby from Boston in the South End is the ultimate in vintage merchandising. Walking into Bobby from Boston is like taking a step back in time. A time when men dressed well not only to be respectful for those around them, but because it was tied to their own confidence and self respect. This is THE place for men's vintage wear. The menswear selection is based on beat-up workwear, military garb, letterman sweaters from the 40's, 50's and up, and insane amounts of gorgeously broken-in leather goods - jackets, belts, bags that you would not believe. More like a trip to a museum …

One hundred and fifty years ago, fugitive slaves like George Latimer and Ellen and William Craft fled by steamship from Virginia and Georgia plantations to Boston where they were taken in and protected. Thankfully, African Americans traveling to Boston today via the Logan International Airport have a much easier flight.

You will be hard-pressed to find a city in the union today with more indelible markers from its black citizenry than Boston. As one of the original thirteen colonies, its prime location nestled in the nook of the Atlantic, meant just as Puritan settlers were sailing into harbor of this new bay colony, the “perpetual servants” from the West Indies were also soon in sight – as early as the 1600s! As such, African Americans have long been established in the Commonwealth. Second, slavery did not take hold consistently, or for long, in the region. By 1783 at the absolute latest, all black Bostonians were free – a claim that can scarcely be applied to any other place in the US. Finally, and most importantly, the old and new mingle here like no place else.

Once in the city, you’ll find the streets are not in the traditional …

I slipped on my most comfortable shoes and embarked on a tour of my own design, creating a loose itinerary following the trajectory of African American residential life in Boston.

My research taught me that the earliest black neighborhoods were located in the North End, followed by a densely populated period in the north slope of Beacon Hill. At the turn of the century most blacks moved to the West End, the South End, or Roxbury. Next, Boston underwent another reorganization in the late fifties and from there blacks continued to move on, mostly to Mattapan and Dorchester. To streamline my day, I chose to connect Beacon Hill, the South End, and Roxbury.

Exploring Beacon Hill between Charles Street and Joy Street, I came across sites like the African American Meeting House, the Abbie Smith School, and the home of Rebecca Lee Crumpler, the nation’s first African American doctor. I then headed to the South End, alternating walking down both Tremont Street and Columbus Avenue where I spotted landmarks like the Harriet Tubman Home of Boston, Wally’s Café and Jazz Club, and St. Cyprian’s Episcopal Church, one of the oldest West Indian churches …