Oh Dam! The Upper Charles River

Chasing the current to reveal the past.

The Charles River flows over 80 miles eastward from Hopkinton to Boston. As it winds through the communities of Weston, Waltham, Newton & Watertown, discover what lies along the banks of this historical and hard-working section of the river. See how it aided industry & prosperity of the region. Join this leisurely scenic ride – mostly along the Charles River Greenway – with bridges & boardwalks, towers & tombstones, factories & mills, and two roaring dams! We begin our journey “down” to the river with a spin through Beaver Brook Reservation. Ride past historical buildings along the river that date back to the Industrial Revolution and have been reimagined and repurposed for modern use. Pedal the properties of two grande estates. Measure how many times we cross the Charles River. Be on the lookout for abundant wildlife frolicking in the wind & wetlands along the banks of the waterway. Conclude our ride through the “watch city” of Waltham, and head back “up” to where we began.


Tour Essence

  • Ride through the expansive grounds and witness the grand mansions of Gore Place & Lyman Estate.
  • Follow nearly 11 miles of the tranquil and tree-lined Charles River Greenway’s paved and unpaved paths along both banks of the river.
  • Hear the roar of water flowing through the Watertown & Moody Street Dams, which control the level of the Charles River and create calm flat waters for canoeing & kayaking.
  • Traverse the Blue Heron Bridge, an impressive and architecturally beautiful elevated river crossing.
  • Ride behind the historic Waltham Watch Company factory, a restored building dating back to 1854 with an impressive location. The company’s existence led to Waltham being nicknamed the “Watch City.”
  • Dismount and climb the spiral steps of the impressive Norumbega Tower, an often overlooked Weston landmark erected in 1889.
  • Post-ride visit to Mighty Squirrel Brewing Co. in Waltham. “Celebrate mighty moments” with this local craft brewery and kick back with one of their creative craft brews.

What to Expect:

Price: $85 per person or $300 for a group of four.  
Level:  Easy
Start/End Location:  Waltham, MA. Park against the stone wall opposite Mighty Squirrel Brewing Co.
Mileage:  18 miles
Start/End Date: Private tours available.  Contact us at 800-866-7314


Joy Spadafora, an exuberant cyclist with an adventurous spirit.

Lauren Hefferon, Director and Founder of Ciclismo Classico.


BOOK your day trip! Call Ciclismo Classico at 800-866-7314 today!


Contact Us for More Information