There are hundreds of options from an Escape Room to a high end dinner. Narrow it down for yourself or your will get a ton of suggestions that you don't want or won't use. I'll start.

Drive down to Leverett Circle and while there dump a piggy bank out the window of your car. Now, park (illegally of course) and using only ped walk signs, collect all the money you can. Winner is the person with the most money.