A Walking Tour of Boston- Private Guide Included!

by Esther Friedman
Thursday Nov 17, 2005
  • COMMENTS (0)

When I realize I’ve lived in Boston since 1990, and never walked a guided tour
of the freedom trail, or taken a duck boat tour, I wonder if I can really
identify myself as a true Bostonian.

Luckily, has made the guts and glory of Boston’s illustrious history available to all, through a guided audio tour. All a curious explorer needs is a CD or MP3 player and two feet. East Boston resident, Robert Pyles talks you through the streets and the years, starting in 1623, on the Boston Commons (with Boston’s first settler) up to the Big Dig. Pyle is joined by a slew of prominent Bostonian proprietors, journalists, writers and character actors, including Dicky Barrett of the “Mighty, Mighty Bosstones.” They narrate stories and take on the voices of Boston’s famous and infamous, and bring them back to life.

If you don’t mind some bloody descriptions and violent re-enactments, highlighted by clashing swords, breaking glass, and some screams of agony, nd if your children are not squeamish, the tour can be educational and fun for the entire family. It walks the listener through Beacon Hill brownstones and ast the State House. It reveals little known, yet historically significant, cobblestone alleys (such as Bosworth Street) where a set of stairs represents last vestige of the “Province House,” the mansion which housed the Royal Governors of British Massachusetts. Squealing brakes on MBTA buses, Boston Shoppers and rumbling taxi cabs, fade away into images of marching Redcoats’ bayonets pointed at “patriot thugs” on State Street.

The tour is a blast. There are points which seemed intentionally over-dramatized, which actually makes the listen particularly enjoyable, especially in the midst of depicting some childishly violent behavior: An actor channels the dramatic voice of twenty-year old Benjamin Woodbridge, “On these grounds here I spent my last living moments, for he over-powered me.” Apparently on July 4th, 1728, a young man named Henry Philips accused Woodbridgeof cheating in a card game and felt the need to duel.

“He pointed to me and whispered a deadly invitation” Woodbridge intones. Next, swords swipe the air, clashing metal on metal, followed by Woodbridge’s anguished cry, “a burning; A flame in my heart. He ran me through, his blade down my back.” With that Woodbridge fades away into eternity.

But when Boston resident and social activist Judy Richardson, narrated and led me down Holmes Alley, part of the real Underground Railroad, I found myself feeling a bit less cheeky about the entire experience.

Richardson explains how slave catchers prowled the Northeast. “Imagine you are one of those slaves,” she directed me. I was transported back to 1850, a slave being pursued. “I’ll tell you where to go,” Richardson said. I ran down Holmes Alley, a tiny cobblestone path tucked between two Beacon Hill brownstones, right to the African Meeting House where abolitionist Frederick Douglas once orated and pioneered for equal rights.

As the tour continues, we honor literary giants such as Nathanial Hawthorne and Ralph Waldo Emerson at the “Boston Athenaeum.” We learn that in 1911, North Vietnamese leader Ho Chi Minh baked pastries at the Omni Parker Hotel, home of the “Boston Cream Pie,” and civil rights legend Malcom X bussed tables there in the 1940.

As you take in the history, Boston proprietors such as such as Mary Ann Milano Pyles, co-owner of the Union Oyster House, Luigi “Big Lou” DeMarco of Café Graffiti in the North End, and Paddy Grace of Boston’s “The Littlest Bar,” invite the listener, to enjoy a pint, a cappuccino, or to take a seat at the Oyster Bar.

Whether you are a tourist or a resident, I would highly recommend the journey. My only complaint is that the directions get confusing at some points. For example the recording guides the listener to historical landmarks on the Boston Commons but neglects to point out obvious landmarks like “Frog Pond” and a tall Civil War monument which looms above. I discovered that Merchants Row off of State Street doesn’t have a street sign. And finding Scott Alley, across the street from Quincy Market, seemed more complicated than necessary. However, in my experience of Boston residential life, one spends a great deal of time getting lost; it just wouldn’t be Boston without some befuddlement over directions or missing street signs.

So if you are a transplant, like me, who now calls Boston “home,” but haven’t taken the time to explore Boston’s history, the Audissey tour is your opportunity to claim your residency. By the time I stood on Long Wharf where I turned to take in a view of Boston’s Skyline, I finally felt, after fifteen years, like a true Bostonian.

For more information and to purchase the tour, go to

Esther Friedman is a Boston based freelance writer.


Add New Comment

Comments on Facebook