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.

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.

“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.

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

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.

Quack is a native New Englander with a love for all things in Boston. After a 40-year IT business career, he is finally doing something fun with Old Town Trolley of Boston. He joined Old Town Trolley as a Conductor in 2025 and has never been happier. Quack loves history, but he can talk about the art, architecture, culture, and sports of Boston. He loves to interact with and to entertain visitors from all over the world. When not behind the wheel of an Old Town Trolley, he can be found on Cape Cod or in Southern Italy.

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.

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.

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.

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.

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.

I started in 2018, after a previous career in the CAD/CAM industry, and I am formerly a Duck Boat captain and yacht delivery captain. I was born in Worcester, but have lived in Marblehead for over 50 years. I have loved sailing and skiing most of my life, but now I spend more time with my beautiful wife, Dale, and our various kids and grandkids.

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.