Someone posted a request for info on upcoming food festivals in the Boston area for a visit here September 12-15. They wanted a "taste of Boston" IIRC. About the time I was composing my response, Chowhound had a massive crash and as you may have noticed, this board was gone for a while. Looks like that post may not have survived the crash (along with one other response, maybe about a Clam Festival in Essex?) But since I saved my post when I realized things were going kerblooie, here it is in all of it's glory.
And if anyone else posted anything here after about 5 pm yesterday, it wasn't deleted by moderators, it just got lost, so try again!
Heck, why settle for a taste of Boston when you can have a taste of New England? The Big E, out in Springfield (about 2 hours from Boston) is an orgiastic feast of food. The midway has your conventional (and not so conventional) midway fare, ranging from the familiar (sausages, french fries) to the less familiar (deep fried Oreos and fried cheese curds.)
Each state gets its own pavilion and they showcase their state's specialties. Some foods on which I've gorged myself in the past include blueberry sundaes in the Maine pavilion, maple milk (like chocolate milk but with maple syrup) and maple fudge in the New Hampshire pavilion, Del's frozen lemonade and clam cakes in the Rhode Island pavilion and the glorious loaded baked potatoes from the Maine pavilion, which IMHO are worth the wait, which at peak times can stretch up to an hour.
This year their website is touting "The Big E Creampuff", which looks pretty good online. Well, see for yourself below.
I feel like Templeton the rat when I roll myself out of The Big E at the end of the day. It starts September 15 and runs every day through September 29. Brace yourself for a wait for parking unless you get there pretty early (and a hint: parking is cheaper the further you go from the gates.) Bring plenty of money, although they do have ATMs there (if you don't mind paying the "we've got you trapped" fee). And DON'T EAT before you go.