Bar Harbor Maine across route 2 to NH. Stop at the Town and Country resort in Gorham, NH for a night. See Mt. Washington and then cut south to 302 or go back to 2 and continue across to VT. Take a side trip to Lyndonville, Me just off of 91 in VT. Stop at the Miss Lyndonville diner and have some pie.
Continue on 2 to 89 and pickup route 100 south. Follow 100 south to Wilmington and stop there for at least one night. Eat at Dot’s for breakfast. It’s an old time New England diner in a quaint mountain town with lots of touristy things to do.
From Wilmington, turn east and follow route 9 to New Hampshire. In Keene, NH, pickup route 101 East through the Monadnock region and over Temple mountain toward Manchester.
If you stay on 101 it goes all the way to Portsmouth, NH. Without question, the Olde Ferry Landing is the place to stop for the giant scallops or lobster and dine on the river by the tugboats.
Personally, I recommend Portland, Maine Old Port for a stop if you like rustic old cities. For oldsters, DiMillos on the Water restaurant (floating) is excellent. Street and Company have the best upscale Italian seafood in the northeast. Rosies Restaurant and Pub is a must visit for burgers, beer and locals. Gritty McDuffs brews their own beer.
If you are a biker, stop at Bentley’s on Route 1 in Arundel. If not, continue to Portland.
Depending upon the dates, the best leaves will be on route 2 in northern New Hampshire, route 100 in Vermont and in the Monadnock region, specifically around Dublin and Peterborough, NH. Later in the month, the Berkshires in Mass are good.
Downtown Portsmouth, NH and the Old Port area of Portland, Maine are the best small cities to visit. If you head farther west, Burlington, Vermont is interesting.
I lived in various areas of New Hampshire for 55 years and they all have their good points. I’m in far SW Florida now because I hate shoveling snow and I like to ride my convertible and motorcycles year round.
Have fun.
While visiting my son and family in 09/2019 (near Peterborough-home to the “quaint” Jack Daniels Motor Inn), hiked Mount Monadnock. Was a beautiful day and the 360-view at the top—spectacular!
Thank you for the suggestions. Adding to our list.
I prefer the Alagash White