Clothing/Shoes/Weather Gear: Bring good waterproof boots in the winter. The streets can be slushy and snowy! Everyone wears boots in the winter. It's not even uncommon to see women wearing a full business suit with skirt and all and a pair of big klunky boots!
Make sure you have fairly comfortable shoes, because you will probably be doing a lot of walking.
Photo Equipment: Camera is a must because of all the nice arcitecture around.
Miscellaneous: One thing that is a riot is the percentage% of people you will see wearing black. don't worry about it.
Wear shoes that you can walk comfortably in...I noticed also that people did dress casual, but they looked nice...leave the tattered t-shirts at home and wear a belt boys.
Photo Equipment: Definitely pack a camera with you--you never know when a prime photo opportunity will arrive.
Miscellaneous: Bring a light jacket in summer and warmer stuff for winter. Even in summer it still gets a bit nippy at nite.
Bring good walking shoes! If wearing sandals gives you blisters, bring your sneakers/running shoes. Wear any shoes that are comfortable because Boston's a walking city. I brought my sturdy combat boots so I was fine. It's simple planning, however a lot of people forget about how much walking they're about to do.
Photo: My group of friends walking along the Freedom Trail in Charlestown... we had done at least 2 miles of walking by then. Photo by me!
Pack your camera and a pair of good walking shoes!
Miscellaneous: And then ... Meet some great people!
Here's a group from the Boston VT Meeting 2002.
Clothing/Shoes/Weather Gear: Good walking shoes - Boston is a walker's city. Take some kind of rain gear. It was cool and rainy when we were there in June. The nights can be cool anytime.