Needham resident Mike Miles spent four days in mid-July paddling and dragging a kayak along the Charles River, from its source in Hopkinton to Boston Harbor.

The river flows 80 miles from Hopkinton to Boston Harbor, according to the U.S. Environmental Protection Agency, passing through 23 cities and towns, including Needham and Dedham, according to CBS Boston. Miles tackled it solo, filming the entire trip for a four-part YouTube series.

He told Hometown Weekly he started planning in November 2025, building a custom Google Maps route that marked every dam and road crossing. He used Street View to estimate daily distances and created a flowchart and spreadsheet with backup plans.

The planning paid off.

But the upper Charles did not cooperate. On Day 1, Miles spent much of his time out of the kayak, hauling it through shallow water, over rocks and around downed trees. At one point, dense river weeds growing six feet above him stopped his boat cold. He could not see the bank and did not know how deep or muddy the water was beneath him.

"Out of the whole trip, that was the scariest part, just worried that if I was stuck here in the middle of all these weeds, no one would see me," Miles told Hometown Weekly.

He also encountered a giant snapping turtle near a beaver dam and chose to walk along nearby train tracks rather than risk stepping past it.

Miles started the trip with a GoPro, a 360 camera and an older camera but pared down to one after advice from British YouTuber Ed Pratt, who traveled the 210-mile River Thames source to sea over 19 days. Miles used AI to build a daily story plan for what footage to capture and conducted a self-interview at the start and end of each day to shape his videos.

The final stretch felt familiar. Miles said he had paddled the lower Charles past the Watertown dams and near the Esplanade many times. Reaching Boston Harbor brought a different kind of challenge: believing he had actually finished.

Miles said one reason he filmed the journey was to show his kids that hard things with unexpected challenges can be overcome. He mentioned a 91-mile trail around Boston as a possible next adventure but said he is waiting for the right spark.