In early May we need to drive from DC to a family event in Waltham, MA, near Boston, and are open to suggestions for an interesting roundtrip route that avoids cities. We like beautiful scenery, cute towns and unique historic sites and experiences. We anticipate spending one night on the road to and from Waltham, so feel free to suggest where those nights could be.

Many thanks!

I have made this trip many, many times in both directions when my kids were in college in NC.

I won't give you details, but basically, there are two routes that avoid I-95, which you ought to avoid!

For route 1, try heading west from DC to I 81 up through PA, then connecting somewhere (there are lots of alternatives) to I-84 across CT and then the Masspike into Boston.

The other route for you is across Maryland to Lewes, Delaware, where you take the Cape May ferry. You can spend the night in Cape May, walking around to see the Victorian architecture, then leave early the next morning and still be in Waltham late the second afternoon.

Most of the mapping sites will route you across the Bronx on I-95 because it is the shortest route. For this particular trip, I like the Tappan Zee bridge to I-684 to Brewster,NY, where you can connect with I-84 to Hartford and on to Boston.

I almost forgot. If you are going to the Boston area in early May, you should book your hotel rooms NOW. It is graduation time and rooms are very scarce. We needed a place to stay after returning from Paris the first weekend in May last year. The cheapest city hotel I could get even on Priceline was $175 plus tax, and most were long since sold out.

The area around Lancaster PA has some very pretty countryside. Going up through East Stroudsburg PA will take you through the Delaware Water Gap park, which is really beautiful.

Further on, in New York, you can either cross the Hudson on the Tappan Zee and take I84 to the Mass Pike (fastest). Or take the Tappan Zee to the Merrit Parkway/ Wilbur Cross parkway for a more pleasant drive.

Or, for beautiful scenery and views, head up the west side of the Hudson on the Palisades Parkway, the NYS Thruway, and then take the Mass Pike east to Boston. This is a more out of your way but will take you through the river valley and the south Berkeshires. The Mass Pike itself is a pretty scenic drive most of the way.

Ackislander is right about avoiding I95, but I'm not sure there is much scenic about that route. I will say, I think the prettiest route across Connecticut is to pick up the Merritt Parkway, and take it to 91 then to I84.

But if you want to take more time, stay inland as capxx suggests. I like taking the GW Bridge, then take the Henry Hudson up to the Taconic. The Taconic parkway is VERY pretty and much less crowded than any of the shorter, more eastern highways.

2 options for a stopover....you could stop someplace in the Hudson River valley, like Tarrytown. You might find someplace with a view of the river. Or you can stop in the Berkshires.

There is probably a scenic coastal route, though I'm not sure what it is. You could stop for a night someplace along the coast in Connecticut, like Mystic.

PS Brandeis commencement is May 18th. Brandeis is in Waltham, so if that is your weekend, beware.

And if anyone is going to that Brandeis graduation, look for me, I'll be wearing a big grin.

Unfortunately there is not great lodging in the PA stretch of I81.My best recommmendation for a quick stop is a visit to Harpers Ferry, WV and then return back to I81 via Gettysburg. Pretty country that allows amateurs to get a decent feel of their history.