Ellen, good choice of trips! I'm actually planning a similar trip for probably early October, and have done some research also.
I'm sure I'm not telling you anything you don't know, but since The Sterns are from CT, there are quite a few CT eateries featured in the "Restaurants" section of this website.
Also, there was a Hot Dog Tour of CT a few years ago, here is the thread from then, note especially the writeup by John Fox:
http://www.roadfood.com/Forums/topic.asp?TOPIC_ID=5048&SearchTerms=ct+hot+dog+tour FWIW, here's some tenative stops I'm planning, based on various sources of information. I've alreasdy been to many of the apizza & seafood places on trips to Boston over the years, so this time I wanted to concentrate on Hot Dogs and burgers.
Day One:
Fairfield - Rawley's Hot Dogs
Fairfield - Superduper weenie
Stratford - Dannys (Hot Dogs)
Stratford - Windmill (Old bar w/Hot Dogs & Birch Beer)
Monroe - Mr. Mac's Canteen (Hot Dogs)
Hamden - Glenwood Drive In (Hot Dogs, Burgers)
Then several brewpubs, after 7 or 8 hot dogs I should be good for 3 or 4 beers over 3 or 4 hours.
Day Two:
Torrington - Sheik's ( Hot Roast Beef)
New Britain -Capitol Lucnch (Hot Dogs)
Meriden- Ted's (Steamed Cheeseburgers, I've had these before at O'Rourke's, they are a treat even if you usually like them charbroiled)
Cheshire - Blackie's (Hot Dogs)
Newtown - Carminuccio's (Pizza, Buffalo Chicken)
Bethel - Roadside Chili House (Chili and Chili Dogs).
In between, a couple of stops at musuems and parks to walk off the food.
Hope this helps, have fun and report back (as I'm sure you will!)
PS: The Colony does have great pizza, stopped there on the way to Boston last year.