May Means Bay State & Berkshire Bike Month

By Berkshires Macaroni Kid May 1, 2024

Part of the larger Baystate Bike Month in Massachusetts, Berkshire Bike Month runs from May 1 to May 31! Locals are invited to join cycling events of all kinds taking place around the county. 

Berkshire Bike Month is a joint initiative between the Berkshire Bike Path Council, Berkshire Regional Planning Commission, MassBike, and the Pittsfield Community Design Center (PCDC). 

Kick off Bay State Bike Month in the Berkshires with a celebratory event in downtown Pittsfield. This is the time to come out on your bike and be seen as we celebrate cycling all through the month of May. All ages and abilities are welcome, we want to see all kinds of bikes and riders on the street! All ages are welcome; riders under 16 should arrive with a parent or guardian. Riders are responsible for their own safety and must follow the rules of the road and the instructions of the ride leader.

Parking is available on-street or in municipal lots for free after 4:00pm. Rain will postpone the event to the following day.

  • 5:30pm: Meet at Park Square for kickoff and remarks
  • 5:45pm: Social ride around downtown Pittsfield begins
  • 6:30pm: Social hour at Hot Plate Brewing Co., 1 School Street

Berkshire Bike Month 2024 Calendar

NORTH ADAMS | Downtown Bike Around

May 03, 2024 6:00 PM

Every first Friday at 6:00pm, meet on Eagle Street for this family-friendly downtown bike ride.

SHEFFIELD | Historic Town Ride [15 rider limit]

May 09, 2024 10:00 AM

This is an on-road ride through the town of Sheffield to learn more about historic locations around the area. Riders will embark from Sheffield Town Hall at 10:00am. Experience with road cycling is recommended for this ride.

PITTSFIELD | Downtown Mural Bike Tour

May 11, 2024 10:00 AM

View Pittsfield's public art up close and on two wheels on this exclusive tour. This casual-pace ride will take place in and around downtown Pittsfield via public streets. All ages are welcome.

PITTSFIELD | Mother's Day Community Bike Ride

May 12, 2024 10:00 AM

An all-ages ride on the Ashuwillticook Rail Trail in Pittsfield. Enjoy a relaxed pace Sunday morning ride hosted by the City of Pittsfield Parks and Recreation Department.

BERKSHIRES | Bike to Work Day 2024

May 17, 2024 7:00 AM

Promote bicycling as a healthy and safe alternative for commuting to work! Join this national day of cycling and get out on a ride to work.

PITTSFIELD | Melville Street Bike Rodeo Block Party

May 18, 2024 10:00 AM

Join MA Safe Routes to Schools for a downtown Pittsfield block party and bike rodeo on Melville Street.

GT BARRINGTON | DuBois Black History Bike Ride (under development)

May 19, 2024 10:00 AM

Explore some of Berkshire County's most signficant sites in our long story of Black History.

PITTSFIELD | Blessing of the Bikes

May 19, 2024 11:30 AM

Have your bike blessed for protection in the coming season.

SHEFFIELD | Social Ride and Dinner

May 26, 2024 4:00 PM

Come out for a ride around Sheffield's back roads, ending with a stop for dinner at Depot Square.

For more information and event details, visit