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Adventure East, Biking Trip – Connecticut River Tour

August 13

This 47-mile touring paced, guided tour of the Connecticut River Valley starts in Southampton, MA. We begin riding at the southernmost point of the Manhan Rail Trail segment of the New Haven to Northampton Canal Greenway system. As a ride on a valley floor, the terrain is mostly flat. Soon after the ride starts, we will approach the bustling small city of Northampton, where you will be tempted by the smells of restaurants getting ready for lunch. Passing through the center of Northampton on the rail trail, we will leave the city via the Mass Central Rail Trail on an almost 1600′ rail trail bridge shown in the cover image above. This is the longest crossing of the CT River by a railroad.

Crossing over the CT River on our way into the farm town of Hadley, we will pass by the oldest, continuously operating farm land in the country and we will stay close to the Connecticut River for the remainder of the ride. We will cross West St., which is where the longest town-green in the US is located. At one point we will pass a beautiful 20′ waterfall on our right while the Connecticut River is a stone’s throw away to our left. In Montague, we will pass over a railroad line on a brand new bike and pedestrian bridge on our way to our second rail trail bridge over the Connecticut. Turning south after crossing the river, we will head south on Deerfield’s River Road. The last nine miles of our ride are all but totally flat newly paved roads through quiet farm areas.

This ride is best on a road bike, though we may ride a short section of dirt road. Bring all the food and water you’ll need. In case of a major mechanical complication, or you need to stop because you are nursing an injury, etc., the support van will shadow the ride on the nearest roads.


Duration: Approximately 4 hours riding and 1.5 hours shuttling

Length: 47 miles

Elevation: +1016 -1088 = -72.

Timing: Aside from Meeting Points, all times are approximate

  • 7:30 Meeting Point 1: Adventure East Shuttle. Park at Sunderland Library, 20 School Street, Sunderland
  • 7:45 Meeting Point 2: Hatfield Common, Park Behind Hatfield Town Hall Main Street
  • 8:00 Depart Hatfield Common
  • 8:30 Arrive to start of ride in Southampton to begin ride
  • 1:30 Arrive to Hatfield Common and end of ride
  • 2:00 Shuttle arrives in Sunderland
16 and up
Fitness Level:
Moderate – Must be able to sustain moderate riding pace for several hours.
Skill Level:
Intermediate – Comfortable riding on paved and gravel surfaces and in traffic.
May 15, August 13


August 13


 Adventure East
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