1989 The first Freedom Rally is held on a parking ramp off of Route 2 in North Adams. MassCann is subsequently founded by seven activists, including Steven Epstein (see: "Uneven Steven") and Reading native Bill Downing; the latter went on to serve as president for nearly 15 years.
1990 The second rally, held in Charlestown to honor the glorious hemp riggings on the USS Constitution, attracts about 900 people, many of whom get high in public.
1991 Despite some rain, the third annual event brings more than 1000 people to the Massachusetts State House steps.
1992–1994 MassCann moves the party to the Parkman Bandstand on Boston Common, and sees its crowd grow to about 10,000 by 1994.
1995 Three firsts: the stage moves to the much bigger Carty Parade Ground; the first official Boston Freedom Rally T-shirts are made; MassCann turns a decent profit for the first time.
1997–1998 Despite hard-fought municipal attempts to extinguish the Freedom Rally, MassCann wins an injunction in Suffolk Superior Court that allows the 1997 show to go on. The city responds by making 150 arrests, suing MassCann for $17,000 in damages, and making another futile attempt to stop the party in 1998.
2003 A reported 45,000 people attend the rally — a record at the time. With the crowd buzzing about attempts to decriminalize (which wouldn't end up happening for another six years), police are relatively lax, arresting only 45 people.
2004 The rally gets rained on, causing MassCann to lose $25,000 on the event, and to subsequently having to borrow funds from members just to stay afloat.
2009 Following the passage of a statewide ballot initiative in November 2008 that decriminalized possession of less than one ounce of marijuana, MassCann hosts the first Freedom Rally where folks can toke without fear of arrest. Nevertheless, 136 civil citations are issued for $100 apiece.
2011 With dreams of legalized weed coming closer to fruition, MassCann expects its largest Freedom Rally crowd of all time.