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Massachusetts Calendar of Events

Welcome to the Massachusetts Calendar of Events! Below you will find a list of events that take place in the Bay State, home of Cool Bike Rides. Be sure to stop by often as rides and events are submitted to us throughout the year. If you'd like to explore another state, be sure to check out the other states on the Events page. As always, if you know of a ride or are hosting one yourself, be sure to e-mail us. Ride safe!

May 5, 2019 - Quabog Riders Motorcycle Hill Climbs begin - 180 West St. (Rt. 32) Ware, MA. Signups close at 9:30 and the events begins at 11:00 AM. Full schedule available on their Facebook page. 

May 9, 2019 - Destination Bike Night 6:00 PM - 9:00 PM - Crestview Country Club Agawam, MA - LA's BackStage Pass will be performing. 

May 16, 2019 - Destination Bike Night 6:00 - 9:00 PM - American Legion Post 275 - 41 Robbins Rd. Chicopee, MA - Bad Magick will be performing.

May 18, 2019 - The Gin Mill's 26th Annual Poker Run Rain or Shine - Swift River Sportsman Club (start and end here)
350 Cold Spring Road Belchertown, Ma 01007. For more info click here. Registration starts at 10:00 AM. 

May 19, 2019 - Boston's 9th Annual Wounded Vet Run - more information and tickets are available at

May 19, 2019 - Holyoke Soldiers' Home Motorcycle Run. Registration at 9:30 - 11:00 AM kickstands up at 11:30. Starts at the Holyoke Soldiers' Home at 110 Cherry Street, Holyoke, MA. You can find more information on their website.  

May 23, 2019 - Destination Bike Night 6:00 - 9:00 PM - Agawam Polish Club 139 Southwick St, Feeding Hills, MA - Equinoxx will be performing.​

May 30, 2019 - Destination Bike Night 6:00 - 9:00 PM - Southampton Harley 17 College Hwy, Southampton, MA - Shovelhead will be performing.

TBA usually early June - Steph's Wild Ride is an organization created in memory of Stephanie Micka. The founders of Steph’s Wild ride are committed to developing an annual day long event that marries Stephanie’s passion for life and raising the much-needed funds to help support individuals and families stricken with cancer. Visit their website for more details:

Jun 6, 2019 - Destination Bike Night 6:00 - 9:00 PM -  AmVET Post 12 754 Montgomery St, Chicopee, MA - Diamondback w/Jimi Bell will be performing.

Jun 13, 2019 - Destination Bike Night 6:00 - 9:00 PM - Ludlow Elks Lodge 69 Chapin St, Ludlow, MA - Shocker will be performing. 

Jun 20, 2019 - Destination Bike Night 6:00 - 9:00 PM - Am Legion Post 275 41 Robbins Rd. Chicopee, MA - Aquanett w/Vague Rendition will be performing.

July 21, 2019 - Big Nick's Ride for the Fallen out on the Cape - visit for more information.

July 28, 2019 - 5th Annual Indian Day at the Springfield Museums, 21 Edwards St., Springfield, MA.

August 25, 2019 - New England Ride for Kids - Framingham, MA Visit their website for more infornation today.

September 5-8, 2019 - Fall Roundup an MMA statewide event - For more information visit the MMA's event group on Facebook

September 8, 2019 - Rice-O-Rama Vintage and Custom Japanese Motorcycle Show and Swap Meet. Hundreds of classic and custom Japanese bikes of all kinds. Everything from old Honda Dreams and 50s to the latest stretched and slammed custom sportbikes. Cafe Racers, Choppers, 2-Strokes, Scooters, Scramblers, Racing bikes, name it, it's there. Singles, Twins, Triples, Fours, Sixes, Turbos, even Wankels. Great food and drink,. Big motorcycle show with trophies in 20 classes. Huge vendors row with tons of hard to find parts and accessories for vintage and modern bikes. .Motorcycles for sale- from “barn fresh” project and parts bikes to beautiful restored and original classics. All riders welcome. If you love old motorcycles, don’t miss this great motorcycle show and swapmeet. Only $5 donation, kids always free. 10 to 5 RAIN OR SHINE. For show and vendor info call 508-439-2473 or visit us at

September 11-15, 2019 - Catskill Mountain Thunder - Though this is a New York event, I understand it's a wonderful time and may make a nice weekend trip for us here in MA. Visit

September 15, 2019 - The Camouflage Ride - Starts at SOK's Runway in Westfield, MA (at the airport). For more information visit their Facebook page

TBA - Brightside Toy Run. Starts at Walmart in Chicopee. Kickstands up at 11:00 AM. More details will be available at

October 13, 2019 - Wicked in Pink Motorcycle Run - For more information on this and other great events, visit 

Cool Bike Rides