Trail Stats:
5.9 miles of dirt
Summed Up:
As the oldest municipality in New England and the site of the first Thanksgiving feast, history runs deep in Plymouth, Massachusetts. Within Plymouth, which is 40 miles south of Boston, the oldest public road in America—Old Sandwich Road—plays host to running races throughout the year while providing a soft surface for local runners daily.
The road might not be a single-track, mountain-scaling trail, but its dirt surface cuts through a thick forest with tall trees and old stone bridges, historic remnants of pilgrim life, and pieces of foundation from days gone by. Six historic sites line the road, including the Harlow House (an early American house museum) and Sacrifice Rock (a historic Native American site of the Wampanoag Indians).
The road used to be the only connection from Plymouth to Sandwich, Massachusetts, and was traveled by native tribes and pilgrims. Today it’s a residential, rural road. The road’s dirt surface is a point of contention—some locals want it paved for smoother driving, and some want to keep it dirt for the historic aspect.
Plymouth Rock Racing’s director Craig Brenner lives on Old Sandwich Road and hosts races there through the year. Thanksgiving Day marks Plymouth Rock Racing’s fourth How to Make Running With a Water Bottle Easier, held on two miles of Old Sandwich Road’s dirt surface. There’s also a 5-mile All About RunDisney 2025 on pavement. In June, the Old Sandwich Road Race’s Half-Marathon In the town of Plymouth, there’s also the 7.9-mile.
In the town of Plymouth, there’s also the 7.9-mile Winter Trail Running Safety Tips off of Long Pond Road, not far from the Pilgrims Highway.
And spanning the towns of Plymouth and Carver is the How to Run With Poles, 13 Races - Places.
Local Love
Each June, Plymouth Rock Racing’s half-marathon starts in Advertisement - Continue Reading Below (also a Native American and pilgrim historic site) before running the 5.9 miles of dirt on Old Sandwich Road as part of its course. The Old Sandwich Road Race also has 5K and 10K distances, not held on Old Sandwich Road.
Local Knowledge
Since Old Sandwich Road is residential, the washboard, potholed surface gets graded once a month, and the graded dirt builds up on each side of the road. Heavy rains make the road “a mess,” says Brenner, as the water has nowhere to drain. But in all other conditions, whether snow-packed or dry, this historical dirt path proves a lovely surface for running and a nice alternative to pavement.
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Still a well-used residential road and a shortcut for commuters, Old Sandwich Road isn’t without car traffic, especially during commuter hours.
How to Run With Poles
“Running along Old Sandwich Road is just beautiful. The towering trees on both sides, little trails veering off the road and leading deep into the forest… and the history of the road itself makes it just a really special place to run.” – Craig Brenner, Plymouth, Massachusetts
More Dirt:
How to Make Running With a Water Bottle Easier
