@Pintabone If you drive through NYC, then CT, you could hit NEBCO which has some great beers.
Obviously if you go up 84 and skip RI, you could hit the new treehouse but if you continue to RI instead, see below.
Also my suggestion would be to go to try Proclamation Brewery as TheDudeLebowski had mentioned. Great sours and even better IPA's BUT RI will only let you carry out 72 or 74 ounces of beer per person, so that stinks.
If you follow along 95, you will drive right by Grey Sail brewing which, I've been told, is really good too.
Trillium is good. I think they were better before they got huge but not bad. Haven't been to the tasting room in a while so I'm not sure if it still functions in the same way it used to. They used to allow you to try 4 samples off of a list available and that was it for tasters. If you go in the summer though, downtown Boston has the Trillium beer garden which is really cool with great prices for full size beers. I will warn you, it is small and anywhere between 3-7 pm your fighting for space with the people who work downtown.
Castle Island is right down the road from Trillium and as of lately they have been churning out some great D/IPA's.
North side of Boston (route 1 north or 93 north) in Everett is Night Shift. Great beers, cools space, tons of beer to go. I don't think they do samples though, only full size pours.
Continuing north, when you get to Portsmouth you can hit the Portsmouth Brewery which can be hit or miss. There is also, Stoneface (kind of pricey but pretty good) and Great Rhythm which can be, eh.
Across the bridge in Kittery though, there is a place called Tributary which has some great beer (the old Portsmouth Brewery head Brewer) and is known for its occasional stout "Mott the Lesser" yes this is the old "Kate the Great" from the Portsmouth Brewery. There is an unbelievable seafood place called Roberts Maine Grill in Kittery right off of Route 1 that has great craft beer all the time.
Portland, oh god where do I start? If I could move to any city in the states, it might be this one.
Rising Tide - Cool spot, decent beer, fun time, corn hole, west coast feel to it, lots to go
Lone Pine - not bad place to stop, if you hit a special release, you'll do great, if not, you can find better choices
Bissell Brothers - try and hit the release, they don't make anything bad. Unbelievable beer. Great funky tap room. Definately stop here! its right off of 295 too! no excuses
Allagash - Free samples for everyone! Little bit off the highway
Austin Street - right across the road from Allagash. They are going to be the next big thing in this city. Great beer, super clean taste, finish great. Their DDH versions are so good, and their milk stout
Foundation - in the same building as Austin Street and that's the only reason I'm listing it. If you like English malt beer, maybe it's for you but its not my jam
There are so many more I could list but that should be good for now
Freeport - MBC. Usually a pizza truck or BBQ outside. Small but cool place. Get Lunch IPA to go if they have it. Really good stuff. Try a flight though.