In 1614 Gorges sent two ships commanded by Captain John Smith to prepare to start a plantation in New England and to trade with the Native Americans who were natives of the region. Squantum went along as an interpreter. Smith commanded one ship and Captain Thomas Hunt was in charge of the other. It was agreed Squantum would help Smith for a short time, and then he would be permitted to return to his village.

The two ships separated when they reached America. Squantum traveled with Smith, interpreting when Native Americans were encountered. Finally, when Captain Smith was ready to return home, he gave Squantum permission to travel back to his village.