New England Road Trip – Charlestown, MA and the Boston Navy Yard

This is the first posting of a week-long road trip to New England

Back in September, our youngest left for college and finally, my wife and I had achieved the elusive “empty nest”.  I say elusive because there were times when just as one of our adult children was moving out, another would be moving back home again!

A quick selfie, a large empty car, and 500 miles of road ahead of us, we were off!

As much as I enjoy the TV always being connected to a video game, and the sound of people coming and going at 3:00 am on a weeknight, it was time for them to begin their adult lives.

Then we spent a long cold winter watching Netflix, just the two of us; and by spring, we started to think a little activity around the house would be a refreshing change!  Fortunately it was time to bring the college student home.

We had to drive to Maine to get her. so we decided to make a road trip of it.  I have a lot of family and friends we never get to visit.  This seemed like a nice chance to reconnect and enjoy some spontaneous adventure–and that’s exactly what we did!

The first day would take us all the way to Boston, stopping only for short breaks. This meant Hartford and its beautiful Capitol would be viewed only from the highway.

We would get up early on the Saturday of Memorial Day Weekend and drive 450 miles to Boston in one shot, stopping only for short breaks.  After that we would hop from town to town in New England, never more than 2 hours away.  We had a large empty car with a Thule on top to hold a dorm-room-full of stuff and bring Margaret, our youngest, home.

At 7am we snapped a selfie and were on our way.  We were fortunate to avoid heavy traffic the entire way, through Baltimore, Delaware, the New Jersey Turnpike, the George Washington Bridge, Hartford, it was all smooth and fast.  From what we could see, this was because the rest of the world was heading south!

The Boston skyline as seen from the Navy Yard in Charlestown.

We were staying the first couple nights with my old college friend Denise.  She lives in the beautifully restored Boston Navy Yard.  It’s in Charlestown on Boston’s inner harbor with a spectacular view to your right of the city skyline.  To the far left you can see planes coming out of Logan, and in between there are sail boats, large tankers, and cruise ships.  We pulled in around 4:00 in the afternoon ready for Happy Hour!

From the Boston Navy Yard, a beautiful marina, my friends’ condo buildings, and in the back ground the city skyline.

Denise was visiting family on Cape Cod overnight but had left us keys and a fridge full of beer God love her.  We checked into her guest room opened a couple cold ones and sat on her balcony looking out over Boston Harbor!

A few moments later another old college friend (all my college friends are old) called.  Stephanie lived in the building next door and we made plans for drinks at her place and dinner right there on the pier.  A short time later we were feasting on Wellfleet oysters, straight from nearby Cape Cod, lobster rolls, and local craft brews!  We rehashed old college days, and caught up with the years.  The vacation was off to a fantastic start!

Wellfleet oysters from Cape Cod!
The first–but not the last–lobster roll of the trip!

The next morning I was very excited because Denise had talked up a breakfast place in Charlestown.  I could tell from her description that it was exactly my kind of place.  We walked out of the Navy Yard and under the Tobin Bridge into downtown Charlestown.  Charlestown is a charming New England suburb with tree-lined streets and classic architecture.  Its centerpiece is on Monument St, the Bunker Hill Monument, a 221′ obelisk to commemorate the first battle of the American Revolution. Just up from the corner of Monument St and Bunker Hill St is the Grasshopper Cafe.

The Grasshopper Cafe is on the main drag in Charlestown, MA. On weekends there’s a line out the door for breakfast and it didn’t take long to see why!
A memorable breakfast of Sriracha-ribboned poached eggs on hand-cut corned beef hash!

The first good sign was the line out the door for breakfast!  The waitress called me “hon” and the coffee was perfect.  Next to me at the counter were two guys right out of Central Casting.  It was like I was in a scene from Good Will Hunting.  The guy next to me was on his phone talking in the thickest Boston accent saying, “I don’t want to go to your mothers!  Bring Anthony and Victoria, I’m watching the Sox this afternoon!”

I ordered one of my favorite breakfasts, poached eggs on corned beef hash and the hash was home made and hand-cut!  The eggs had Sriracha sauce and Day 2 of vacation was turning out to be even better than the first!

The charming style of New England
The main drag in Charlestown is Bunker Hill St and if you turn up Monument St you get to the Bunker Hill Monument.

We walked back from breakfast and stopped at the Bunker Hill Monument.  Coming from Washington, DC part of me wants to refer to it as a scale model of the Washington Monument but when you’re right there looking at it the monument is pretty impressive.  It doesn’t cost anything to walk up to the top…and we started to.  It’s a dark claustrophobic circular stairway that offers a little less air every step you go.  About 100 steps in, I turned to my wife and said, “I’ve seen enough”.  It was beautiful out and here I was trapped in this spiral chamber of panic!

At 221′ the Bunker Hill Monument is roughly half the height of the Washington Monument but ascending the dark spiral stairway inside was not for me!

We walked back to the Navy Yard and visited the USS Constitution.  “Old Ironsides” sits in the Navy Yard and had just recently begun a 3 year period of restoration in dry dock.  This dry dock process alone is worth the visit, before you even see the ship!

It’s one thing to read about how dry dock works but to see it actually in practice is pretty impressive!
Even more impressive is to see a ship commissioned in 1797 still on the water! “old Ironsides” got her name because cannonballs in the War of 1812 appeared to bounce right off her 3 layers of oak sides!

Around noon, Denise had returned and I will pick up the next post from there.  Suffice it to say, there are more cocktails, more family, and more fun to come!



  1. Great post, Tone, and not just* because it features Me and My World, but also because it’s so funny. Lots o’ guffaws in this one (“spiral chamber of panic”). Looking forward to Part Deux…


    *Not just, but mainly.

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