A Roadtrip through New England

In early July, we flew from Sacramento to NYC on a red-eye. We have taken red-eye’s a number of times, but I guess when you are only flying across the country and not the world, it hits you a little harder. Anyway, when we landed in Newark, we felt like we had been through the ringer. Either way, we rented a car, and drove the short distance to Newark Penn Station, to park and take the train to Penn Station in New York City. I’m not sure how we wound up in Manhattan as this was one of the more complicated trains systems we have had to navigate, but we did. (Why do they both call themselves Penn Station?!?) One thing I will mention though is that the NYC Metro workers were all very helpful and kind!

Manhattan, NYC

We aren’t city people, but when you are close to New York City, you gotta go check it out, if only for a few hours. Besides, we needed to stretch our legs. We took a stroll past the Empire State Building (it would have cost our family over $250 to go up so no thank you!), to Times Square. In Times Square, I was able to relive the coldest and most miserable New Years Eve of my life from when I was in college. Next we hoofed it over to Central Park to see where “Kevin” from Home Alone 2 met the pigeon lady. “Kevin” and “Garfield” (the comic strip cat) are basically Greg’s heroes.

Cheshire, Connecticut

Cheshire, Connecticut is where I lived from age ten to age nineteen, a.k.a. my formative years. We stopped by Copper Valley where I spent all my summers in the pool and on the tennis courts. The swimming pool has long since been filled in and several houses built on top of it. For some reason the tennis courts are still there, but they were pretty quiet! From there we drove by my old house where the people who live there are the ones who purchased it from my parents which was kinda fun. The kids got to see my old Elementary School and High School, as well as the brand new indoor swimming pool that didn’t exist when I lived there! Doug fell in love with this small New England town. I enjoyed my time there as well, except during the winter. One can’t beat California winters!

That night we made it to The Niantic Inn in Niantic, Connecticut. Our room was in the basement, which allowed us to sleep through the thunderstorm that night as we didn’t see the flashes of lightening! The hotel was located a stone’s throw from the beach very walkable. We had a delicious dinner at Spice Club, a Thai restaurant nearby.

Newport, Rhode Island

In the morning we drove to Newport, Rhode Island. Doug had a work call, so the boys and I explored the downtown. We started with the International Tennis Hall of Fame. With more than 2,000 unique objects on display — from racquets, to attire, to trophies, as well as a number of interactive exhibits, this was a perfect stop for a tennis loving family. The boys got to take a stab at being an announcer, take a photo with a holograph version of their hero, Roger Federer, and check out the grass courts. The Hall of Fame is a circle, but Roy still managed to get lost, so there was that.

Since Doug was still on a work call, we moved onto the Audrain Auto Museum. Tickets were $18/adult and $8/child. Founded in 2014, the historic Audrain Building was transformed into a captivating exhibition containing a selection of cars and motorcycles. These vehicles range from brass era Veteran cars to the Supercars of today. I, personally, could have skipped this, but the boys insisted.

After collecting Doug from the local supermarket, we set our sights on the 3.5 mile Cliff Walk. We parked on Narragansett Ave, near the Salve Regina University. Starting at Ochre Court on this map, we made it all the way to The Waves. Normally the kids are not super cooperative on a hike, but this particular one was so unique that it kept their attention the entire time. The mansions that we passed by on the walk were pretty spectacular and had us wondering who lived there. The Cliff Walk should not be missed, it was the highlight of our stop in Newport.

Cape Cod and Martha’s Vineyard

Originally I had booked us an “Adventure Tent” at Autocamp Cape Cod (in Falmouth), but I quickly switched us to an Airstream as the family was not interested in roughing it that night. The Airstream was a tight squeeze (at least we didn’t have the dog to contend with) but we can now check that box and not do it again. In the morning, we took the ferry to Martha’s Vineyard. More on that trip can be found here: Twenty-Four Hours in Martha’s Vineyard.

Plymouth and Salem, Massachusetts

Our next stop was in Plymouth, Massachusetts to see the Mayflower, technically Mayflower II, and Plymouth Rock. Mayflower II was a gift from the U.K. to the U.S. in 1957 for their friendship during the Second World War. The boat is a full-scale reproduction of the real Mayflower that sailed the Atlantic Ocean for 66 days. If we had arrived in town just an hour or so earlier, we could have toured the ship, but thankfully we didn’t so just had to view it from the outside.

As for Plymouth Rock, it is said to be the site of the Pilgrims’ landing in 1620. Although no historical evidence exists to confirm Plymouth Rock as the Pilgrims’ actual steppingstone to the New World, the boulder was identified as the spot in 1741, 121 years after the arrival of the Mayflower. Apparently this rock receives over one-million visitors a year, most of them unfortunately leaving their chewing gum and/or cigarette butts on said rock.

Salem, a city on the north coast of Massachusetts is famous for its 1692 witch trials, during which several locals were executed for allegedly practicing witchcraft. Salem is also home to the secret staircase in New England’s oldest surviving 17th century wooden mansion, The House of the Seven Gables. We briefly visited both locations, but the boys were eager to get moving because Salem had kinda a creepy vibe.

Kennebunkport, Freeport, and Boothbay Harbor, Maine

Kennebunkport is a coastal town in southern Maine that is somehow known for its beaches, which we did not choose to visit. (It was cloudy and 70 degrees) Kennebunkport is also home to the George W Bush compound. George just happened to be in town (the Texas flag was flying) and we are pretty sure that his entourage passed right in front of us while we were walking downtown.

We then headed to Freeport for the night. Freeport is home of the legendary outdoor outfitter, L.L.Bean. It was pouring rain, but we made it to L.L.Bean just before it closed. The kids had a blast riding the strider bike through the aisles and causing general havoc that I tried to control while Doug did some shopping.

On our way to Bar Harbor, we passed by a large inflatable lobster at the Taste of Maine restaurant that caught our attention. Apparently there was a power outage with the storm and so it had just finished inflating again. We got to meet the owners and check out their car. Next we stopped in Boothbay Harbor to stretch our legs before we made it to Bar Harbor.

We then spent a couple of nights in Bar Harbor, Maine, Hiking Around Acadia National Park in the Summer.

Mount Washington, New Hampshire

We left Bar Harbor super early in the morning to make it to Mount Washington. Mount Washington is an ultra-prominent mountain in the state of New Hampshire and the highest peak in the Northeastern United States. While it is known for having the worst weather in the world, on the day that we visited (in July) it was a perfectly clear day with temperatures, at the peak, in the 60s. Apparently 48-hours earlier it was a mess on the mountain.

We chose to take the Cog Railrood to the peak. You need to purchase your tickets earlier because it will sell out. The Cog is the first mountain-climbing cog railway in the world. With an average grade of 25% (some sections approach nearly 38%), it is also the second steepest! After a 45-minute journey we reached the top where we got to hang around for an hour before taking the Cog back down. On that day we could see three different states because the weather was so clear. We also met on older guy who had just run up the entire thing!

Waterbury, Vermont

Our next stop was Waterbury, Vermont to embark on the Ben & Jerry’s Factory Tour. I was employed at a Ben & Jerry’s “scoop shop” in college so I was very interested in checking out the “mother ship”.

The thirty-minute guided tour began with a MOO-vie to learn about our company culture followed by a short walk to the glassed-in mezzanine overlooking the production room floor where our tour guide explained how they make their pints. The factory was in operation at the time, so this was pretty cool to see. We then got a sample of “Churray for Churro’s” (not a fan) at the end of the tour. While I may not be a big fan of their ice cream, I am in awe of their creative marketing team, pure genius.

Before we left for the day, we paid our respects to the “dearly de-pinted” in the Flavor Graveyard.

Stowe, Vermont

Stowe is a town in northern Vermont that is known for its trails and ski slopes. We had booked ourselves one night at the Green Mountain Inn but quickly fell in love with it and the location so vowed to return again in July of 2025. (We currently have one week booked over the 4th of July.) The Inn has welcomed guests since 1833 and has a number of amenities from the outdoor pool, to the game room (with ping pong), fire pits, and the boys favorite – a chess board. The bed was the most comfortable bed we had slept in

Stowe has the cutest downtown full of quaint little shops. Doug found that the local library was having a book sale and wound up purchasing a plethora of old books that he had shipped back to California. We also walked the trails to a legendary bagel shop (it was closed) and an outdoors shop. We barely scratched the surface at Stowe so are eager to return to see all that it has to offer. Stay tuned!

Before heading to Baltimore to visit with family for the 4th of July, we stopped off at a few locations that are known for their maple syrup. One place, Baird Farm, was fascinating to us because there was no one working the farm shop, no cameras, and it was all based on the honor system. There was a cash box to make your own change, and an option, if you didn’t have cash on you, to list your email and they would send you an invoice! This would never work in California!