We live in the suburbs of Boston, about 26 miles Southwest of Boston (about where the marathon starts). The stay at home advisory for Massachusetts is extended until May 18 and if you are in an area where social distancing is unlikely then facemasks are mandatory. The Mayor of Boston has ordered facemasks to be worn in the city. Unfortunately, I can't offer anything definitive, but everything we are hearing is that there will continue to be pretty significant restrictions in the city of Boston through the summer. Things like mandatory facemasks, outdoor seating only in restaurants or restaurants at 25% capacity, groups no larger than 10 people, etc. The further you get away from Boston, into the suburbs and more rural areas of Western Massachusetts it may be a bit easier as population density decreases pretty dramatically. We don't hear nearly as much about the restrictions in the other main cities in Massachusetts (Lowell, Fall River/New Bedford, Worcester, and Springfield). Not sure if this helps with any of your decisions, but it does seem as though Boston proper will be under stricter guidelines than other parts of the state, and it sounds as though it will be through most of the summer.