I like your first option but all of them are scenic at certain points

Thanks, tchoiniere!

Anything in particular that commends option 1 over the others?

I would do the first unless I hadn't been to Old Deerfield, in which case I would detour to see it. I think they have closed or are about to close for the season, though.

All these routes are slow and scenic. Do not expect much in the way of gas or food along the way, though I haven't been that way for about two years.

Ackislander, I was thinking the same thing about detouring to Deerfield for Old Deerfield (check to see if its still open), Yankee Candle (their flagship store) then a ride up Mt Sugarloaf.

If you want to do this, just stay on 116 and it will bring you to Deerfield. Yankee Candle and Mt Sugarloaf will be on 116 on your way to Northhampton via Amherst. You could even veer slightly off of 116 after this and drive around the UMass-Amherst campus and go into Main Street Amherst.

The first option is prettiest, imo.

Do not miss going to the top of Mt Greylock for the most extensive views around and a nice homemade lunch at Bascomb Lodge at the summit.

Thanks for the advice, everyone! I'll let you know how it turns out.

Rt 9 is less scenic than 116. I would do N. Admas to Ashfield then take 116 through Conway to Deerfield. There is a back way from Conway to Northampton (through Whately) which is very scenic (lucky me it's my way to work every day) but it's local roads, not state highways. If you thought you wanted to go that way I'll give you directions. But if you have time I would go down to Deerfield and detour up to Historic Deerfield.

From Deerfield to Northampton you can take 91 or Rt 5 which is marginally slower but a little more scenic. You would not go through Amherst unless you were detouring, and it will add at least half an hour (without stopping), Amherst is a lovely college town but it's not 'on the way'.

Do you need breakfast recs in Northampton? If so try Green Bean or Jakes, both downtown and both good.

According to their website, Historic Deerfield this year is open from April 14 to December 30, 2012 (closed Thanksgiving Day, and December 24–25). Seems to me it closed at the end of November last year.

The Memorial Hall Museum next door usually closes sometime in October.

All are well worth a visit.

The Yankee Candle Flagship Store down the street is okay.