Strava-holes won't run afoul of Massachusetts racing laws. They can only be scorned here. The racing laws only apply to motor vehicles. (Massachusetts law defines vehicles to include bicycles, but there are many places in our law which specifically calls out "motor vehicles".) Presumably the lawmakers were able to discern that motor vehicle racing warranted severe penalties, but horse, horse-carriage, and bicycle "races" don't even merit a mention.

Oh, except, organized bicycle races on public ways need to be permitted in Massachusetts.

Also in New Hampshire, organized bicycle (and moped**********) races also need to be permitted:

"Section 265:146 265:146 Permits. – The mayor of a city, or selectmen of a town, may, in their discretion, upon any special occasion, grant permits to any persons to ride bicycles or mopeds, at any rate of speed, for a time not exceeding one day upon specified portions of the public ways of such city or town, and may annex such other reasonable conditions to such permits as they may deem proper."

-mr. bill