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I have family in Boston so, I've ridden between the 2 a few times. For me its a 3 day trip. I take expressway out of Chicago to get that over with quickly.
Day 1 - Getting across Indiana & western Ohio:
Near LaPorte IN, get on US 20 east -- small towns and not much traffic. If you leave Chicago late in the morning you can eat lunch at Miller's Home Cafe in New Carlisle, IN (its about 20 miles W of South Bend.) US 6 is another option, more truck traffic, but it's mostly 2 lane through open farm country. You can continue on US 20 or US 6 across Ohio, though I usually hop back on the Ohio Turnpike so I can get to dinner with family in Oberlin OH at a reasonable hour.
Day 2 - across Pennsylvania:
Southeastern OH and Southwestern PA are nice, but that's going out of the way so I hot-foot it to PA on I-80. The goal is to go up through the Allegheny National Forest, so I continue on I-80 29 miles to exit 29/PA 8 north (a bad stretch) to Oil City PA and US 62 north (really nice) along the Allegheny River and edge of the Allegheny National Forest. Stop to eat at the Soda Cap in Tionesta PA about 17 miles NE of Oil City (Oil City is so depressed there are no resturants left, just 1 McD, so I'm told) You might try PA 666 if you're not superstitious. I've never had the time, it looks interesting. I take US 62 North to US 6 (sound familiar) near Warren Pa. US 6 is great all the way across PA, though from Warren I usually take a shortcut on PA 59 to rejoin US 6 at Smethport. From Smethport you can continue east on US 6, or go north on PA 446 to NY 417. I've never ridden it but my brothers say NY 417 across NY to Corning is great. I've taken US 6 across PA to Wellsboro. I stayed at the Penn-Wells in Wellsboro, a nice old hotel, on a night when the city was full of bikes and every hotel was full. I don't think you'll have a problem in September.
Day 3 etc, on to Boston
One alternative is to take PA 549 and PA 328 to NY 328 up to Elmira (that whole stretch is great) and then continue east across NY -- this is the more relaxed route. From Elmira I've taken I-88 to Schnectady to make time and I-90 and I-87 around Albany to Troy. I don't think there is a good local road through Albany. From Troy NY take NY 2 to MA 2. MA 2 is a great road all the way across Mass, even as I gets busy near Boston it's still pretty.
The other alternative is to continue on US 6 to Scranton then take I-84 (eat at the Apple Vallet Resturant in Millford PA on US 6 just south I-84 exit 46) to Port Jervis NY, Danbury CT, Waterbury CT, Hartford CT, and on up to the Mass Pike. This is fast road and heavy traffic. Once you cross into NY the traffic (and driving) gets worse the farther east you go. It's as much fun as I-294 and the Dan Ryan. You don't want to go through Hartford at rush hour if you can avoid it.
There are probably scenic alternatives, but I never have the time. If I have extra time to ride with my brothers we want to go north through VT and NH.
I've done the Canadian route, crossing at Port Huron, by car, but never by bike. I think PA and NY are more interesting, but there is the disadvantage of the less interesting parts of IN and OH, plus the traffic in NY east of Port Jervis. Early September usually brings good weather in the Boston area.
If you are riding in ME, NH and VT you can't go wrong.
Have fun --Fred
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