Ugh, it's New England and it's autumn. Why would anyone traipse around Boston and Cambridge? You want to see autumn colors and beautiful landscapes. Get on a train going North to beautiful Cape Ann, the far, far suburbs. You can head for Gloucester – Italian cafes, a harbor, maybe dinner if you see something you like walking around the town.
Portsmouth is the oldest colonial town in new Hampshire and settled only three years after Plymouth colony in 1623. Much of the colonial history and architecture is maintained in an area known as Strawberry Bank. Some of the best restaurants and shopping in New England can also be found in Portsmouth.
Early October is the height of Leaf Season in Vermont. Just two hours from Boston, four from New York City, can find you driving the byways of rural New England, surrounded by the riotous colours of Autumn. I recommend driving up Vermont Route #100 from Wilmington to just north of Mount Snow, then crossing over the spine of the Green Mountains on the West Wardsboro to East Arlington Road (dirt), stopping off for a picnic lunch at Grout Pond, (and perhaps an hour's walk around the pond), then continue on to Bourne Pond and down to Vermont Route #7 in East Arlington. Obtain a map of Vermont (available at any Vermont Information booth) and get off the main highways, onto secondary, or even dirt, roads. Don't keep to a schedule. Stop at places that pique your interest. The first two weeks of October are the best time, when the leaves are most colourful.
The I 90 is the main turnpike road through Mass. At this time of year the leaves are turning, the sky is blue and the rivers and lakes you will drive by on this easy road are glorious. A long straight major road, easier to find than the traditional "leaf peeper" routes up into NH or Maine.
I 90 W out of Boston.
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