Rush is a substitute honors history teacher at Manchester Middle School who regularly wears colonial-era clothing, including a tricornered hat and knickers, to class. He possesses a time-traveling horse and uses his smartphone to broadcast live historical events as "movies" for his students. He views history not as a collection of dry facts, but as an exciting, moral adventure that he desperately wants his students to experience firsthand.

Liberty is a talking, time-traveling horse with a spotty memory stretching back to the Revolutionary War era. He has supernatural abilities to create time portals, turn invisible, and briefly stop time. Despite his magical nature and extensive historical knowledge, he maintains a playful personality and is constantly distracted by his appetite for food.

Tommy is the skeptical class clown and an athlete at Manchester Middle School. He initially views history as boring, but his sharp intellect surfaces when he attempts to scientifically explain Liberty's time-travel abilities. His perspective on education shifts rapidly as he begins experiencing historical events firsthand.

William is a deeply religious and pragmatic leader of the Pilgrim colony. He acts as a primary source of information regarding the colonists' motivations and challenges as they seek to establish a new society. He views their journey as a divinely guided mission and bears the heavy responsibility of ensuring the group's survival in a harsh environment.

Freedom is a perceptive, empathetic student who possesses an intuitive ability to communicate non-verbally with animals. Though initially quiet, she quickly becomes an essential participant in the time-traveling group. She is deeply compassionate and pays close attention to the emotional sacrifices made by the historical figures they encounter.

Captain Myles Standish is the military officer hired to protect the Plymouth colony. He is a stern, disciplined man of action who focuses strictly on defense and maintaining order among the passengers. He takes a practical approach to colonial life and shows a willingness to pass his combat skills on to Tommy.

Elizabeth is the middle school principal's daughter and a minor antagonist in the modern-day classroom. She acts with entitlement and frequently attempts to bully the more reserved Freedom. She is determined to expose Rush Revere's unconventional methods and prove the existence of his hidden horse to her father.

Squanto is a member of the Patuxet tribe who acts as an indispensable ally and translator for the Pilgrims. Having previously spent time in Europe after being kidnapped, he bridges the cultural gap between the settlers and the local Indigenous population. He generously teaches the colonists essential survival and farming techniques in the New World.

Principal Sherman is the traditional, formal administrator of Manchester Middle School. He maintains strict expectations for classroom behavior and is highly skeptical of Rush Revere's unconventional teaching methods. He often serves as a roadblock when his daughter Elizabeth attempts to prove the existence of Liberty the horse.

Francis Billington and his unnamed brother are mischievous young passengers on the Mayflower voyage. They exhibit reckless behavior, constantly finding ways to cause trouble both on the ship and once the colony is established. Despite their troublemaking, their wild exploration sometimes yields useful geographical discoveries for the settlement.

Samoset is a Native American leader from the north who initiates first contact with the Pilgrims. Having learned broken English from European fishermen, he opens diplomatic channels between the colonists and the local tribes. He is hospitable and helps lay the groundwork for future peaceful interactions with regional leaders.

Massasoit is the powerful sachem of the Pokanoket people who watches the colony from afar before formally introducing himself. He holds significant regional authority and establishes a crucial peace treaty with the Pilgrim leadership, ensuring mutual security during the early years of the settlement.

Dorothy is William Bradford's wife, a devout Puritan who embarks on the long journey to America. She makes the incredibly difficult sacrifice of leaving her young son behind in Europe for his safety while she faces the perilous transatlantic voyage with her husband.

Captain Christopher Jones is the master of the Mayflower, responsible for navigating the difficult and dangerous transatlantic crossing. He utilizes navigational tools like the cross-staff and makes critical executive decisions for the safety of his ship, including determining when coastal waters are too dangerous to proceed.

Elder William Brewster is the primary religious leader of the Pilgrim group aboard the Mayflower. He provides spiritual guidance to the passengers and interprets significant survival events as signs of divine intervention and favor for the colony.

Stephen Hopkins is a prominent spokesperson for the "Strangers," the non-Separatist passengers on the Mayflower. He challenges the authority of the Pilgrim leaders when the ship fails to reach the Hudson River, prompting a major debate over who holds the power to command the colonists.

John Howland is a passenger on the Mayflower whose life is miraculously saved during a massive storm when he manages to grab a trailing rope. His dramatic rescue becomes a major point of discussion among the passengers, who view his survival as a deeply meaningful event.