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Join Our Cast


"We are an exciting and dynamic company, marked by constant growth and change."

Join the ranks of the fun employed! When you travel to new destinations, it’s always best to have someone you can trust that knows the city inside and out. How would you like to be that person for the thousands that visit Boston every year?

Old Town Trolley Tours has been entertaining visitors in cities across the country for over 40 years. Our company is made up of a diverse, highly motivated team of people who are ambassadors for their city, and we are always looking for dependable, enthusiastic people to join our team.
Working with Old Town Trolley Tours is far from your average desk job, the City of Boston will be your office as you showcase this exciting destination to people from all over the world.

The informal, humorous, and informative way we communicate is our trademark and we’ll teach you to become among the very best tour guides in the country. If you think you fit this description and are looking for an exciting career, we would love to hear from you!

We are looking for:

Commercial Driving Conductors

We are currently recruiting Conductors to join our team of informal, humorous, and entertaining drivers who are responsible for delivering our tours to thousands of people each year. An Old Town Trolley Conductor is responsible for driving one of our custom designed sightseeing trolleys on a predetermined route while narrating some of the stories and history of this fascinating city.

If you would like to learn more, please click on the link below, we would be delighted to talk to you about this role, and you could even join one of our tours to hear one of our experienced Conductors in action to see if this is the role for you.



An Old Town Trolley Dispatcher is responsible for keeping our sightseeing service running throughout the day. The Dispatcher makes sure that all trollies are where they are supposed to be and deals with all the challenges and problems that are encountered during a regular service day. This role is not a driving role, but you must have a good working knowledge of the streets of Boston, be able to make decisions, analyze problems and keep accurate records of vehicle locations and times throughout the day.

If you enjoy working in an environment where no two days are the same, where your logical thinking and problem solving skills are valuable assets, then click on the link below and learn more about this exciting and challenging opportunity.


See other Job Opportunities Here,
Or call us:

  • Boston: 844-738-6562
  • Retail All Cities: 866-538-6562



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