I liked the Sam Adams brewery, but it's quite possibly just because I went there on my 21st birthday and it's where I had my first legal drink. It's also my favorite non-cool-kid beer. I have no idea how one drives from Ohio to Boston, but if you cross through lower New York the best alcohol-related tour I've been to was the Tuthilltown Spirits distillery. They have a great story and really cool equipment that still has a lot of their crazy DIY solutions from when they were just starting out mixed in with all these Steampunk-looking machines. Plus they have the FATTEST CAT I have EVER SEEN. Also it's like a mile from where I grew up so you can go hang out with my dad afterward. Edit: Here is a picture of the cat (who is definitely still alive, JUICE), which barely does its fat justice:
There seems to be two routes, one through PA and cutting across lower NY just south of the Poughkeepsie area then cutting through Connecticut. The other is going all the way up along the Lake Erie coastline to Buffalo then across upper NY to Albany and into Mass. Per Google they're both about the same amount of time (approximately 12 hours) so I'm not sure which way I'll be taking yet. What about any of the breweries in Brooklyn? I'm probably going to have to be up there for a few days in the next few months and was thinking about trying to hit up Brooklyn brewing and/or Sixpoint brewing.
In the drive to/from Western PA and Boston we did the first route. Just don't, under any circumstances, drive through New York City. Though that's just general life advice.
If you have to do it, Mass Pike >> 84 >> 80 is the way to go. Then you pick up 480 somewhere in Ohio. It's just the most boring car ride in existence. You can technically take the Mass Pike/90 the whole way, but it adds 2 hours.
Treehouse is great and only about 20 minutes off of 84 just before you get to the Mass Pike. My in laws go camping up in that area and by pure luck I stumbled upon the place when we were driving around last summer. Fantastic beers. As said before, Two Roads is also great. I go there often, since it's only about 20 minutes from my house. Not really anywhere near Boston or your route, though. Would be more of a Boston to DC type stop.
Suddenly all my problems seem inconsequential. Man catches scrotum in a power grinder. "How'd you get the beans above the frank!?" Anyway, I know I am late to the party, but I finally installed Google Chrome's ad blocker. Holy shit, it is like the sky clearing after a hurricane. My computer suddenly runs 50% faster. The sheer amount of bullshit on every page is insane. And NO YOUTUBE ADS? *jizz*
I ate at Waffle House last night. The parking lot was crowded, so I parked in the back near the dumpster and grease trap tank. This morning, when I was driving in to work, something caught my eye in the rearview mirror. I tried to remember if I had left anything like a garbage bag in the back of my truck. I was convinced I had not and thought no more about it. When I walked out to my truck for lunch, I looked in the bed. I am now the proud owner of four used and batter-y Waffle House aprons. WTF? How does that happen? Sadly, they are not "the good ones" with WH embroidered on them. They're just plain brown.