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Having lived in and around Boston my entire life, I get the greatest joy from sharing my city with others. There is truly something for everyone here and I like sharing the hidden gems. I have been in the industry for 9 years, giving tours of Boston, Lexington, Concord, Salem, and the North Shore.
I have 4 children and 3 grandchildren. I grew up in Roxbury; via Dorchester, now in Mattapan. Past jobs: Human Resources Generalist for a local Clinical Laboratory, Human Resources/Business Manager with a small business. Consultant, local Community Health Centers for DCHC and MCHC. Salvation Army seasonal worker (Thanksgiving and Christmas); Lyft/Uber Driver, Hospital Shuttle Driver. I enjoy volunteering, reading, singing, mac & cheese, and traveling.
How long have you lived in Boston?
I was born at University Hospital and have spent my entire life inside Route 128
What is Boston’s best-kept secret?
The view of the city from Piers Park in East Boston
What is the one thing that you always carry with you?
A pocketknife. “Be Prepared”, you might have heard once or twice.
What is your favorite picnic area in Boston?
Not in the city. But it has a view of Boston. Buck’s Hill in the Blue Hills Reservation. Also, Boston Rock at Prospect Hill in Waltham.
Which author would write your life story?
I would have to go with Michael Crichton. The way my life story has played out, it can only be science fiction.
What was the best thing that happened to you at work?
Discovering that I actually have a talent for a job that I tried on a whim. Giving up a desk job to drive a trolley has been life-changing.
What’s your favorite movie about Boston/filmed in Boston?
I will go with the two that I am actually in. Field of Dreams (I was at Fenway) and Amazing Grace and Chuck (I was at the old Boston Garden)
What’s your secret talent that no one knows about?
I can write a Haiku on demand about virtually any subject. So quickly, that some of my friends have accused me of having a secret, online, “Haiku Generator.”
Hello! I’m Eber, trolley driver in the beautiful city of Boston! Love my job and I really enjoy interacting with people from all corners of the world showing the revolutionary city! I also love photography and to travel!
Gene is originally from Charlestown and has lived his entire life in Massachusetts. He attended Northeastern University and played college football. Gene taught physical education for eight years. He was the regional sales manager for a commercial furniture company and was also an office furniture representative for Office Max and Cort Furniture. Gene enjoys gardening, fishing, and canning products. He’s made wine, rumtopf and specialty liquors. Most of all, he enjoys spending time with friends and family.
Jennifer is originally from Brockton, home to Rocky Marciano. She loves attending Red Sox games as much as she does Comic Con or going to a brewery. Her heart stays in Boston, but she works to travel.
John was born and bred in Boston, the home of the bean and the cod, where the Lowells speak only to the Feeleys and the Feeleys only to God. A true Renaissance man, addicted to lifelong learning.
John was born in Worcester, Massachusetts and was semi-educated at Trinity College Hartford and the University of Southern California in Los Angeles. He has been driving at Old Town Trolley Tours of Boston for 15 years. Among his many hobbies, Rockabilly Guitar is easily his favorite and driving for Ghosts & Gravestones is the highlight of his work week.
I was born right here in Boston just after Ben Franklin. I escaped the city as an infant and grew up in Duxbury, now living in Plymouth. Father of five, husband of one. My first job in 5th grade was selling Christmas cards door-to-door. Fifteen years later I moved up to vacuum cleaners. Then it was super balls, drain cleaning with Roto-Rooter for ten years, then Data Centers. I love hiking and skiing in New England, history, and pizza. In 2021 my wife and I spent six months traveling across the country in a 28’ travel trailer. What an awesome country we live in.
Hi there! My name is JD. I was born and raised in Methuen, MA, about 30 miles North of Boston. My father is a history teacher, so I grew up with a deep love of history and earned my BA in History in 2008. I was hired by OTT in 2011 and have had a blast sharing my love of history with our guests from all over the world. I married my high school sweetheart in 2012. As of 2022, we’ve been married for 10 years, but we’ve been together for 20! We’ve got two cats, Calvin and Hobbes. Hobbes has been “helping” me write this, so it’s his fault if there are typos and spelling errors. Anyway, I feel like I’m rambling. Come take my tour if you want to hear some bizarre stories of Boston. Hope to see you soon!
Laurent was born, raised, educated, and has lived all his life in Massachusetts. His favorite mode of recreational transportation is skis. He learned 3 decades ago, was immediately captivated, and almost just as immediately began teaching others the wonders of the sport and the mountain environment. In college philosophy class, he became enamored by the phrase Cogito Ergo Sum (I think therefore I am); however after he graduated college & began to ski, he realized his own personal motto might really be “I Ski Therefore I Am.” Laurent is now a Professional Ski Instructor Association (PSIA) Level 2 Certified Alpine Instructor at Blue Hills Boston where he has taught over 2,000 lesson hours to over 1,000 students, over the past 3 seasons.
My name is Marisol, but everyone calls me “Beanie.” I started with Old Town Trolley back in 2001! I have been part-time, full-time and year-round since then, and in San Diego as well! OTT has been my second family. From a single lady, to a married mom of 2. I am a proud Coast Guard wife (15 years and counting). Giving tours of Boston is truly where my heart belongs. I love being a Tour Guide and always have. This is Me!
Capt. Matty here. I’m just a good ol’ farm boy from the deep South of Mobile, AL. That’s right. I’m the only conductor who can pronounce the letter “R.” After 10 years working at Walt Disney World, I came with my family to Boston to better pursue my passion for history and film making! When I’m not on tour, I’m either writing, or hanging out with my three amigos: Jackson, Jacob and Jameson! Ready for a good time? Come on my tour! It’ll make you happier than a tornado in a trailer park!
Hello Team! My name is Matthew. I am a Massachusetts native, born in Maynard and currently live in Leominster with my wife, Holly. Looking to make a bit of a leap from working 12 years of retail, 8 years in convenience stores. I have a few hobbies, but typically on my days off I can be found running my model B&M engines on my small layout. Big fan of classic films; Jaws may be high among my favorites.
Michael “Bear” was born in Boston and grew up in Sudbury, Massachusetts. He has a BS in Communication from UMass Amherst and a MATS from Recent College in Vancouver, British Columbia, Canada. Michael is a veteran of the 101st Airborne, spent two years commercial fishing in the Pacific Northwest, and is currently writing his first book. He was a conductor at Old Town Trolley Tours of Boston from 2006-2016 and returned in 2018.
Hello, my name is Rocky Waters. I am originally from Grand Rapids, MI. I have always loved history so I have worked several jobs in tourism, including as far away as Alaska, before settling here in Boston early 2020. I really love to read and always need to carry a book with me wherever I go.
Russ is a native Bostonian and has loved giving tours of his hometown since 2005. Yes, he “paahks” his “caah.” Russ is a sports fan who loves the Red Sox, Bruins, and Celtics equally.
My name is the Skipper. I grew up in Worcester, MA but have lived in Marblehead for over fifty years. I had a thirty-year career in the CAD/CAM industry, but since that devolved, I have had to reinvent myself; first as a salesman, then a professional ski instructor, a sail boat captain, a duck boat captain and now a trolley driver. I guess that is progress? I used to play squash and run, but my ortho guy won’t let me anymore. I guess it’s not bad being allowed to be lazy as I get older!
Born and raised in South Boston. I enjoy watching and playing basketball. I am an avid history buff, more specifically The Revolutionary War. Being a Conductor has allowed me to share my love for my city and its rich history. Random fact: I have the uncanny ability to tell the difference between wicker and rattan instantly.
Howdy – I am Steve “Crafty”. I’m a single dad with 2 kids. Lifelong Massachusetts resident, (currently living in Waltham). I enjoy hockey (playing and watching), music (especially live), stand-up comedy, history, and debating politics and social issues.
Quote: “Some people see things that are and ask, why? Some people dream of things that never were and ask, why not? Some people have to go to work and don’t have time for all that.” – G. Carlin
Something most people don’t know about me: I once sold meat door to door. Well, I asked people if they wanted to buy it… not sure if I actually ever “sold” any.
I was born just south of Boston. I have relocated twice over the years – once to Oregon for 10 years and then to Maine for 9 years. I spent more than 25 years as a construction worker and then another 20 years in the school bus industry. I’m so happy to be doing a job and sharing the city that I truly love! You know what they say: Boston: “you’re my home!” I am very friendly and love meeting new people! Hope to see you on my trolley!
I am a Boston native, born and raised in the house I live in now. I love BBQ so much, Redbones (a BBQ joint from Somerville) catered my wedding. I saw many concerts in the old Boston Garden – Styxx, Queen, the Cars, Crosby Stills Nash and Young, The Police, Billy Joel, Van Halen, Tori Amos, Todd Rundgren, and The GoGos. I was 45 years old when I started playing and loving hockey. My three children attend Boston Latin School and my wife graduated from Harvard University, BA ’88.
Uncle Steve was born in Central New York. He graduated from Syracuse and married a gal whose family came over on the Mayflower – so they moved to Massachusetts, raised a family – and 50 years flew by. He closed his business in 2001, applied to Old Town Trolley Tours for a part-time conductor position and the rest is history!