How to See Five States in One Day: Road Trip Through New England

I am a native to the coast of California and still live there. Yes, we can drive the width of California from the ocean to the mountains or to the desert in one day, but we will most likely still be in California as darkness descends. This day we actually were in FIVE states (Connecticut, Massachusetts, Vermont, New Hampshire and Maine) and a full day ahead of our schedule. It baffled me that although I read the mileage distances, the places were closer than I could imagine. We stayed at the speed limit, stopped for lunch and a break in the afternoon and still slept in Maine that night!

Start with Massachusetts:

We began our Memorial Day New England odyssey by renting a car in Boston. It was amazingly simple to get to the freeway from our downtown location. Our first stop was about 90 minutes later in Newport, Rhode Island to see a couple of the “vacation cottages” of the Vanderbilt’s and their 19th century crowd. Unbelievably huge mansions, these residences were only used for the summer season. We saw “The Breakers” and “The Elms”. We drove along and were in Connecticut before we knew it.

Then to Connecticut:

Let me say that my ‘Bucket List’ includes seeing all fifty states. Before this trip, I was at thirty-five. Although I had been to Boston, Rhode Island and New York numerous times in forty years, I had not set foot in Connecticut for some unknown reason. Our destination for the night was New London, CT. We figured we didn’t need hotel reservations except in busy Boston so we were unpleasantly surprised to find that Memorial Day week/weekend is an extremely popular time for graduation ceremonies, so a lot of the hotels were filled. We considered ourselves lucky to get a room at a Red Roof Inn until we got inside of it. Extremely basic, there was a clothes rack in lieu of a closet and bedspreads I was too germ phobic to even consider lying upon. From the momentary grandiose lifestyle of Newport to a motel we would never have considered.

New Hampshire, Vermont, Maine…In One Day!

We set off about 10 a.m. from New London, swung northwest on 9 and then 95 to 91 north back into Massachusetts. Our goal was to go as far north as Lebanon, NH, to spend the night. When we got there, it was only 3:30 p.m. so there was lots of daylight to continue our drive. By then I was tired of seeing New England’s incredible freeways. They are beautiful, all densely tree-lined. I imagine that the fall colors would be incredible, but this was May and therefore all green. Miles and miles of trees with no billboards or commercial signs, just green trees and the occasional exit/entrance ramp. We decided to go on to Concord, NH, a whole fifty-seven miles. Once there, we decided again to push on to Portsmouth, another forty-six miles, or about 45 minutes. We met up with 95 going north and came to the Maine border, crossed over and drove through Portland to worship at the shrine of L.L. Bean in Freeport. Another surprise was the total absence of motorhomes and trailers. I began to look for them early in the trip and for a 600 mile roundtrip to Boston, saw absolutely none for some reason.

Up Next:

On this trip, I added four more states to my list, now at 39. I went to Alaska and Hawaii more than three decades ago, so I had gotten the “tough ones” out of the way already. I still need to see some of the Southern states, and that will be on our next road trip.

Greg Zompolis Written by:

Greg Zompolis is the author of three books, Operation Pet Rescue, Images of America: San Mateo, and the upcoming novel, ‘Boomeraria’. He holds degrees in both Marketing and Graphic Design. He most recently studied Creative Writing at Stanford University. He is a fifth-generation Californian who has wandered through thirty two countries and thirty five states. He has lived in places as varied as Houston, Hollywood and San Francisco. Greg currently resides in San Francisco.