Tonya, if you want something a bit less ambitious, why not leave the northern New England states for another trip? Marcy (NY) is either a very long dayhike or a nice overnighter. Katahdin is a fairly long but quite strenuous (in altitude gain) dayhike.
Greylock (MA) and High Point (NJ) are driveups, along with Jerimoth (RI), and Frissell (CT) is a short hike. If you headed out to western MA after Jerimoth, you could bag MA, cross over into NY and bag CT on the way south to bag NJ, and be pointed the right direction to head home.
I thought about doing two trips for New England (went to college in Cambridge, so I know the area) but with this year's long 4th of July weekend, figured on bagging all 8 that we need up there and check the region off the list. We'll fly to Boston on 7/4, spend 7/5 around Sturbridge Village and then start the highpointing on 7/6 with RI, continuing to NJ, CT, MA, NY, VT, NH and ME in that order, or maybe ME then NH on the way back to Boston...haven't worked out that detail yet.