Waldo planned a walking trip to North Hampton, MA, to visit several Ripley step-relatives along the way. He was twenty. A pocket journal dated August 1823 records this journey.
Leaving his mother’s home in Roxbury on Friday, he walked 60 miles. On Saturday he stayed at an inn in Leicester. There he met a traveler going by stage (coach) to Stafford Springs, CT, known for its healing spring waters. The two travelers briefly discussed a building across the street. Waldo discovered it was a school for girls, closed until they could hire a woman teacher. He noted in his journal that if this notion about women teachers reached the city, he and his brother, William, would be out of work.
On Monday, Waldo arrived in Belchertown, MA. The landlord, Mr. Rice, also owned the hat store, blacksmith shop and two stage lines. Waldo recorded that people in this area do not walk much. Rather, they ride in conveyances. He was offered many rides. Tuesday through Thursday he spent at Amherst, 90 miles from home. He found it interesting that Amherst College, then worth $85,000 dollars, was built by donations.
On Saturday and Sunday he visited with his Ripley relations. In North Hampton he toured a lead mine. Teaching young ladies in Boston must have seemed preferable to living and working in that dark tunnel. On Sunday Waldo attended three church services with Reverend Lincoln Ripley, his step-great uncle.
Monday, Waldo crossed the Connecticut River and stayed at the New Salem Inn. Tuesday, he walked to Princeton to catch a stage back to Waltham, MA. At this last stop, he stayed at the home of Reverend Samuel Ripley. This step-uncle had always been generous to Waldo.
 RWE JV1 pp 268-84