For my birthday in April (24th, same as Barbara Streisand and Shirley MacLaine) I spent the afternoon traipsing between 5 separate establishments eating and drinking in a town about 10 miles north of Boston (Woburn).
I had very good Indian buffet, xian based hand pulled noodles, competent fried chicken, decent pastry, and would have a had a world class mai-tai (and a side of VERY good Sichuan dumplings in a chili vinagrette), had not the word gotten out and the 30 seat bar where this is possible was packed 20 minutes after opening at 5pm ( with two parties of two waiting).
Have, in previous birthday done Northern Chinese, Greek, old school steak house, and homemade donuts, in the same block!(North Cambridge)
The whole thing, with drinks was under 100usd, mostly on foot, took the entire afternoon and was a total hoot.
Full disclosure: I dont mind eating alone, was unable (legally) to be driving for several hours of the afternoon, and was in no hurry.
So, I come to your town where do I go?
Maybe five places, varied ( not BBQ, BBQ, BBQ, BBQ, and banana pudding)
Like I said , 100 for the works, (parking, beers, food,etc,)
Best if mostly on foot or close driving range.
Hook me up.