Private Walking Tour: Footsteps of Dylan and Springsteen

As a former resident of Greenwich Village, I was surprised by all of the hidden rock 'n roll history dotted on the busy streets. Ann brought stories from venues that have long since closed along with plenty of pictures showing the stacked billings for performances by Springsteen, Dylan, and many of their now famous peers in places that held a hundred people on a busy night. This is an amazing glimpse into the origins of so much of our popular music today.

This tour was a birthday present for my husband, who loves Bruce Springsteen and is also very into music. Ann gave us the inside scoop on the music scene where Springsteen and Dylan began. We learned so much and had a great time! Ann is a fantastic guide - I'm not as into the topic as my husband, but we both loved the tour.

We had a fantastic experience on the Footsteps of Dylan & Springsteen Walking Tour with Ann. Ann was professional, engaging, and exceptionally knowledgeable. Her passion for the music, the history, and the stories behind both Dylan and Springsteen really brought the tour to life. Whether you’re a lifelong fan or simply have a casual interest in either artist, this tour is absolutely worth doing. Ann struck the perfect balance between historical detail, local insight, and entertaining stories, making the experience both informative and enjoyable throughout. As an unexpected bonus, we were incredibly fortunate to meet Steven Van Zandt during the tour — a memory that will stay with us for a lifetime and made an already outstanding experience even more special. We would highly recommend this tour to anyone remotely interested in Dylan or Springsteen. Thanks, Ann, for a memorable and thoroughly enjoyable day in New York! Sent from my iPhone

Such a great Tour. Ann does so much reading and research and extracts the most interesting information and presents it in such a fascinating way. We are tremendous Dylan fans and we had gone just to get a visual of the exact spots he came up in, but walked away with so much more. We are thrilled to learn she now does other popular tours including a Gilded Age one which we can’t wait to go on next. Thanks Ann:)

Prior to the tour, this was not a topic I was knowledgeable about. I love taking walking tours and I wanted to understand more about the history that shaped the Village. Ann was very enthusiastic and truly seemed to know every detail on the topic- a true passion of hers! She also sprinkled in interesting historical facts about the neighborhood throughout. The tour ended at Jones St where she’ll snap a photo of you recreating the Freewheelin Bob Dylan album cover (the super fans in the group were very excited about this!). I felt like I really had a good grasp of the topic by the end, despite starting with zero knowledge. Would definitely recommend!

Ann was extremely knowledgeable about Bob Dylan, Bruce Springsteen, and the West Village's musical history in general. Very friendly and answered all questions. Walking pace was great and it was an overall excellent experience. Definitely reccomend!!

Great informative tour by Ann. Great to see all the places where Dylan, Springsteen and other people played and other locations in their story. Ann was great. I was the only one on the tour that day. I had a great time. Definitely recommend.

A great time. Ann met us on a bitterly cold day when we were the only 2 on the tour. Her knowledge of the music history of the Village was extensive and backed up by a binder of historic photos, news clippings and concert adverts. We left with not only a great feel for the music geography of the neighborhood but tips on where to have lunch and where to see live music later that day. Her passion for the live music scene in the 60's and 70's made us anxious to dig out our vinyl when we get home!

My husband is a true Rocker & I’m a novice but we both thoroughly enjoyed our private walking tour with Ann this weekend. She is very personable & knowledgeable. The pace was steady with a constant stream of information. It was a beautiful stroll through some iconic Rock N Roll sites— past & present. Would highly recommended this tour to anyone with interest in Bob Dylan & Bruce Springsteen!

For my birthday, my college-age daughter signed us up for this walking tour. It was a terrific experience. Ann McDermott is a brilliant guide through Dylan and Springsteen's back pages. She is knowledgeable, informative and well-spoken. We were impressed with the work she had clearly put into researching her subjects—and although she has clearly given this tour many times, she delivered information in a fresh and engaging way. Rambling around the Washington Square Park area, we saw where some seminal parts of the early Dylan and Springsteen stories unfolded. I particularly enjoyed seeing the spot, in front of a long-dead club, where John Hammond told a young Bruce he was going to be a Columbia recording artist and his life was about to change forever. Highly recommended. One note: though there was a good amount of Springsteen content, Dylan is the main focus of this tour; not a surprise given his tighter association with Greenwich Village and the fact that he lived there for so many years.