Meet Our Conductors

William “Commander AJ” has worked with OTT since January of 2024. A native of Dorchester MA, AJ has always loved captivating a crowd.

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.

Head Conductor

Marisol “Beanie” has been with Old Town Trolley since 2001. She considers her hometown to be Boston, MA. While many people know she was adopted, what folks do not know is that she was found in a basket, all dressed in blue, on a doorstep, one summer evening back in 1980 in South America, when she was 2 years old.

Becca, “Ginger,” has been a conductor at OTT since 2021 and is from Camden, Maine! After getting a bachelor’s in biology and learning to drive buses during her undergraduate studies, Becca worked in cancer research (she has been published in a cancer research journal!) until deciding to go to nursing school and starting at OTT. She is now working full-time as a nurse in a Boston hospital and is a Tour Conductor part-time because she missed sharing her love of Boston with her guests. In her free time Becca embroiders, solves Rubik’s cubes in less than a minute, lifts weights, rock climbs, enjoys a good nap, and avoids cardio workouts.

“Mr. Chris” returned to his hometown of Boston in 2022 to work for OTT alongside his brother, Leo. Living most of his life in Seattle, WA, Mr. Chris made a name for himself in the radio industry. After a cross-country move, he now has joined us as first as a mechanic, and now as a driver.

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.

Steve “Crafty” has been a conductor with OTT since 2021. A Chelmsford native, Crafty knows Massachusetts like the back of his hand.

Head Conductor

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.

Chris “Gonzo” was hired in 2014. He hails from East Islip, aka “East Cupcake,” NY. He’s written a book (a collection of yuk-yuks) entitled “Turn Up The Heat, I’m Thinking.” While awaiting alien transport he loves to cook, garden, bike, gamble, golf, shoot hoops, play billiards, write, read, draw, hang out with USS Constitution Commanders, and give enthusiastic and sometimes enlightening trolley tours.

Ryan, “Hummer” has been a conductor for Old Town Trolley Boston since 2021. Originally from Quincy, Massachusetts (Home of the Presidents!) Ryan enjoys spending his free time playing Dungeons & Dragons and rooting for the Celtics!

Justin “JD” has been working as a tour conductor for Old Town Trolley Boston since 2011. A native of Methuen, MA, JD enjoys learning about history (the weirder the better), baking, and collecting vintage electronics.

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.

Joshua, “Good Will,” starting at OTT in 2024, was born and raised in Charlestown. Charlestown is in his blood & bones. He has two dogs, a one-eyed cat, and a duck named Quack. Exploring the best places for regional delicacies and browsing the old burial grounds of the city are his specialties. Loves donuts & pizza, coffee & 1st edition books.

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.

“Captain Matty” has been part of the Old Town Trolley Tours of Boston since 2014. Although he hails from Alabama, he has taken to New England like peas and carrots (his words.) A veteran performer of Walt Disney World, and a published author, Matty loves telling a good story, and looks forward to sharing history with all y’all!

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.

Moses started at OTT in 2024 but was welcomed to the United States from Africa six years ago and says that the city of Boston has taken good care of him. He decided that the way he wanted to give back to the city was to welcome visitors and show them the sights as a conductor for Old Town Trolley. Like his namesake parted the Red Sea, he wants to lead guests into the unknown to show them the spirit of such a historic city.

Kayaki, “North,” a Cambridge native, has been working for OTT Boston since February 2023. In that short amount of time, he was awarded Conductor of the Month and earned a safe driver award. He takes pride and joy in what he does and loves entertaining his guests. When he is not in uniform, he enjoys spending time with his family and working out.

Matthew, “Quint” has been with Old Town Trolley since February of 2019, and when he is not playing conductor, dispatcher, ghost driver, or training other drivers, he immensely enjoys soaking up a mai tai, model railroading, and WWII history. He also might have a small fascination with sharks.

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.

David, “Red,” has worked as a conductor at Old Town Trolley since 2022. Red was born and raised in Boston and takes a lot of pride in giving interesting information about his hometown. Prior to OTT, Red worked as a tour guide in Los Angeles, showing homes of the rich and famous. He loves to travel and has been to 49 states and 30 countries. He ran in his first half marathon this year and hopes to run in the Boston Marathon one day.

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.

Casey, “Salem,” has been with OTT since 2023, first starting as a Sales Representative and then making the jump to Conductor in 2024, in hopes of being able to share her love for Boston and its vast history with others. She was born in Plymouth and raised in Hanover. Her family has lived in the same county of Massachusetts since 1620. Her roots in Massachusetts run deep, going from the Mayflower to the Salem Witch Trials. Ask her about it and she will talk your ear off.

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!

Karen, “Sparkle,” a Somerville native, began as a conductor at OTT in 2024. She enjoys shopping, family, singing, and making people smile. She enjoys being the “Nana” of seven grandchildren, including two sets of twins.

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.

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.

In 2002, “Uncle Steve” drove 20 miles from Brockton to apply for a part-time, evening job with OTT Boston, but they snookered him into working full-time. Five years later, he went looking for greener pastures, but the old saw proved true, so “Uncle Steve” returned in 2019. (He was surprised how much older his co-workers looked.) His hobbies are working for OTT, exploring New England, and working for OTT – in that order.