New Year’s Day Ride – Boston, MA 1/1/2022 *CANCELLED*

Snow has pushed us off! We will try again next year.

Registration Link:


Inspired by the challenge and the community spirt in Pittsburgh, I want to have us ride some hills in Boston. One of the best days during the year is often New Year’s Day. This features little traffic. Did you know that Boston has hills? There used to be three hills on a narrow peninusla jutting into the harbor. Those hills aren’t quite there, now. One remains. We will tackle the hill plus travel through the Dorchester Heights & West Roxbury, conquer Breed’s Hill, roll through the North End, and finish in South Boston.

This will be a change of pace and have some epic scenery.
Some of the hills have gradients of 16%, but everything is short. Nothing is like Chris’s Logan Street or Canton Ave(37% with cobbles). We can do this.

We will ride in a neutral easy going pace. Perhaps I should say slower than normal. We want to watch for traffic. Everyone will stick together from hill to hill. When I blow the whistle the front group will charge up the hill. The following group will take their time up the hill. We will regroup at the top of each hill. The elevation profile of this ride is actually not much more gain than riding the Plymouth 50 mile route.

3 Points for the first person on any hill.
2 Points for the second person on any hill.
1 Point for the third person on any hill.
Double your points if you KOM on Strava.

Pope John Paul II Park

We will start on the flat in the parking lot of Pope John Paul II Park. This is free parking and near the rail trail. We will ride the rail trail into the dense sections of the city. After climbing some hills in Dorchester, Roslindale, West Roxbury, and Jamacia Plain, then we will take another rail trail into town. We will climb Beacon Hill. We can stop for coffee on Tremont St and those that do not want to partake on each hill can stop at the coffee shop for a break. Next, we will head for Bunker Hill monunment. Afterwards, we will roll south through the North End, South Boston, and Dorchester to return to Pope John Paul II Park.

A Dozen Hills
Walk Hill
Cummins Highway
Monterey Hill
Bearberry Hill
Bellevue Hill
Bussey Hill
Scarboro Hill
Beacon Hill 3x
Breeds Hill (Bunker Hill)
Telegraph Hill
Savin Hill

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