Brattleboro → Keene
I'm a roadie living in Northampton, MA. I did a century up to Brattleboro, VT last summer where I had been thinking of going to Keene, NH as well. I couldn't find a suitable route to do it, though -- I didn't find NH Hwy 9 to be particularly bike-friendly (narrow shoulder, high-speed limit, trucks), and I am not at all familiar with the area. I'm thinking about doing the century again this summer because it was hella fun, and I was wondering if anybody knew of any secret way to get between the Brattleboro and Keene.
(FWIW, I ended up biking back down Brattleboro Rd on the NH side of the river. I don't recall that being super pleasurable either. Maybe I should just stick to the VT side of the river around there, unless any NH people have some advice.)
Connect to Rt 5 North in Nhampton to Bernardston,cross over river to Rt 10 to Northfield, then North on Rt 10 all the way to Keene.
Northfiekd to brattleboro 10 north to 63 to hinsdale to 119 to brattleboro.
Look into Rubels bike maps for western Mass
i haven't ridden on 10 except for a short stretch near bernardston.
brat-keene - Bernardston, MA
this route would hurt. but it would be pretty nice.
i've ridden this route (both directions) from bernardston to westmoreland.
i've not ridden from westmoreland to hurricane rd.
have not ridden hurricane rd, but had a friend that used to live there and drove it several times.
not sure on the exact route into keene, depends really on where you want to go.
Commuter & cyclotourist
Welcome to the forums! I'm across the river from you in Hadley.
I've only done the stretch of NH Route 9 from Brattleboro to Route 63, but I didn't find it terribly attractive. I was wondering about the route that Bmike posted but have only done the stretch south from 9 on 63 on one of my own century rides.
NH Route 119 south from Brattleboro to Hinsdale didn't seem too bad to me. I've done it both ways, most recently northbound (Route 63 north from Amherst to Hinsdale, then 119 into Brattleboro, lunch at a café there, and then Route 5 south for a ways before cutting over on back roads in Gill).
Are you new to Northampton, or just to southern VT and NH? If you just moved to the area, there are some good ride suggestions on the Northampton Cycling Club's forum, and on the Berkshire Brevets' page (look for the cues & profiles link in the column on the left). The Shelburne Falls 200K is easily adaptable as a century (more or less) from Northampton, and some of the other rides are good too.