Some ideas: - There is a food truck festival in Somerville - http://foodtruckfestivalsofne.com/ - The public library is holding a big book sale - http://www.thebostoncalendar.com/events/citywide-friends-of-the-boston-public-library-june-book-sale - The River Festival is going on in Central Square (lots of good restaurants in that area too) - http://www.cambridgema.gov/arts/Programs/riverfestival/Visit.aspx - The Greenway Open Market is running by the harbor, we could also explore the North End or Faneuil Hall if we ventured over there. - http://newenglandopenmarkets.com/greenway/ I think we should give some consideration to transit so we're not bouncing all over the city. Maybe something like Sam Adams, then take the Orange Line up to the North End/Faneuil Hall area. From there we could take the Orange further up to check out Somerville, or take the Red up to Central for their Festival, or go west along Newbury/public library getting closer to Brookline.