Crazy 8 – Day 9: Family History, Surprise States & One More Ice Cream Stop

 Day 9 began with another round of loading everything back into the cars. By now we have this down to a science! We pulled out around 9:00 a.m. and headed first in search of breakfast.

Since our hotel was an all-suite hotel with full kitchens, they didn't serve breakfast. The hotel gave a good local recommendation and sent us to Tucker's. It turned out to be a great choice! Everything was made to order, breakfast was very good, and with everyone fed, we were ready to get back on the road.

Back on the road we go after breakfast.  Well, I've Never Seen THAT Before!

It wasn't long before something along the interstate caught my eye. There on a big blue highway sign were the words:

“NH LIQUOR STORE — LOTTERY TICKETS — NEXT RIGHT.”

😂 I don't think I have ever seen lottery tickets advertised on an interstate highway sign before! Apparently in New Hampshire, they really don't want you to miss your chance to become a millionaire. 🤷‍♀️

Just another one of those things you see while traveling that makes you say, “Well, I've never seen THAT before!”

Meanwhile, in the Other Car...

The van peeps had their own “Did you SEE that?” moment. 😂

As they traveled along I-495 near Haverhill, Massachusetts, they spotted a giant dog sculpture alongside the highway. Naturally, our car didn't see it and so no one managed to get a picture of it, but Susan did some investigating afterward and found out what they had seen.

It is called the American Dog, a huge metal sculpture created by artist Dale Rogers. Susan's research says it stands about 26 feet tall — so it's certainly big enough to get your attention from the interstate!

No actual Crazy 8 photograph of the dog exists, so we'll just have to trust the van peeps on this one. 😂 At least they came back with documentation!

A Very Special Stop in Springfield

Our next stop was Merrick Park in Springfield, Massachusetts, and this one was especially meaningful for Mark.

Here stands the impressive statue of Deacon Samuel Chapin, one of the founders of Springfield — and Mark's 8th great-grandfather!

It was pretty special seeing Mark standing beside a monument honoring his ancestor, knowing that nearly four centuries separate the two of them. We took plenty of pictures — Mark with his 8th great-grandfather, and of course Mark and Susan together with a pretty important member of their family tree. ❤️

The statue, commonly known as The Puritan, depicts Deacon Chapin in his Puritan clothing, complete with his hat, cape and Bible. The inscription on the base identifies him as “Deacon Samuel Chapin — One of the Founders of Springfield.”

We've stopped at a lot of historical places during this trip, but this one was different.

This was family history.

“David getting the shot — while Mark got the shot of David getting the shot! 😂”

Another Springfield Surprise

While we were in Springfield, we discovered another famous connection — Dr. Seuss!

Theodor Seuss Geisel was born in Springfield, and the city celebrates its famous hometown author. We passed the Springfield Museums, home of The Amazing World of Dr. Seuss Museum, and Susan caught a colorful mural filled with familiar Dr. Seuss characters.

We didn't have time to visit the museum, but it was another fun discovery.

From Mark's 8th great-grandfather to Dr. Seuss — Springfield gave us quite a range of history! 😂

A few more pictures from our vist in Springfield.

Surprise — We're in Connecticut!

After leaving Springfield, we continued south and suddenly there it was:

WELCOME TO CONNECTICUT.

Wait...we're going through Connecticut? 😂

I honestly hadn't even realized Connecticut was part of today's route until the sign appeared in front of us. Well, okay then — Connecticut it is! 🤷‍♀️

Another state for the Crazy 8!

We stopped at Red Robin for lunch, gave ourselves a little break from the road, and then continued on.

As we traveled through Naugatuck, another interesting sight caught our attention — the tall old clock tower rising above the town. By Day 9, we've gotten pretty good at spotting unusual things from the car. If something interesting appears outside the window, somebody in one of these two cars is probably going to get a picture of it! 😂

Naugatuck clock tower Waterbury, CT

Our Last Night on the Road

Eventually we made our way to Tarrytown, New York, our final overnight stop before heading home.

But before we checked into the hotel, there was one more important piece of Crazy 8 business to take care of.

ICE CREAM! 🍦😂

We stopped at Main Street Sweets, a little local ice cream shop on Main Street where the ice cream is made right there on the premises. After nine days on the road, I think we've firmly established that the Crazy 8 can locate an ice cream shop just about anywhere.

Susan even posed with hers, and while we were there we found a sign that seemed especially appropriate after nine days of traveling together:

“There will be a $5.00 charge for whining.”😂😂😂

At this point in the trip, somebody could have made a small fortune!

With our ice cream finished, we made our way to the hotel and checked into our last hotel of the trip. Tomorrow morning we'll load everything into the cars one final time and begin the last leg home to Virginia.

It's hard to believe we're already here. We've covered a lot of miles, have seen some beautiful places, learned a lot of history, laughed at plenty of things we never expected to see — and eaten what may be a record-breaking amount of ice cream. 😂

I'm actually getting this one posted tonight instead of finishing it tomorrow morning! 😂 Since tomorrow is simply our drive home, I decided I'd better get the pictures sorted and the blog finished tonight. That way, in the morning we can load the cars one last time, get on the road and head for home — without me still hunting for pictures and trying to finish a blog before we leave!

Looking back, it's pretty amazing how much we've packed into these nine days. We've seen beautiful scenery, visited places filled with history, crossed covered bridges, wandered through little towns, admired old cars, found lighthouses, eaten lobster in Maine, discovered things we never knew were there, laughed at plenty of unexpected moments and somehow managed to find an ice cream shop in just about every corner of New England. 😂

And just how much ground did the Crazy 8 cover?

Virginia • Maryland • Pennsylvania • New York • Vermont • New Hampshire • Maine • Massachusetts • Connecticut

Nine states in nine days! 🚙🚙

Tomorrow morning we'll load up one last time and point the cars toward Virginia. No sightseeing agenda, no list of stops and — most importantly — no blog for me to finish before we leave so I won't be  holding anyone up! 😂

Thanks for riding along with the Crazy 8 on our New England adventure. We've certainly made plenty of memories and have the pictures to prove it!

One more sleep...and then HOME! ❤️🏡

Crazy 8 – Day 8: One Last Day in Maine

 Day 8 started with us packing everything back into the cars and saying goodbye to our beautiful house in Trenton. We really enjoyed our stay there, and after three nights it had started to feel a little like home — but it was time for the Crazy 8 to start making our way south.

Wayne and Grace sitting outside waiting to get into the cars to head out.

Before we got very far, we finally stopped at the little bakery right near the house. Of course, we found all kinds of yummy things and immediately wondered why in the world we hadn't thought to run up there one of the previous mornings and bring breakfast back to the house! Oh well — better late than never. 😂

And then there was one more very important stop before we really got going — Dunkin'! 

One last important stop in Trenton — everybody knows Judi has to find her Dunkin'! ☕😂

One More Look at the Penobscot Narrows Bridge

Before we made our way farther south, we stopped again near the Penobscot Narrows Bridge, where David, of course, found a few things the rest of us might have walked right past. 😂

The plaques there commemorate the Waldo-Hancock Bridge, which opened in 1931 and once crossed the Penobscot River at this spot. It was considered an engineering achievement in its day and was even recognized by the American Institute of Steel Construction as the “Most Beautiful Steel Bridge” in its class.

The old bridge is gone now, replaced by the beautiful Penobscot Narrows Bridge that we had crossed earlier in our Maine travels. David got a great picture of the newer bridge from below — and, naturally, pictures of the plaques telling the story of the one that came before it. We love finding these little pieces of history along the way!

Camden

Our first sightseeing stop was Camden, Maine, another beautiful little coastal town. We managed to find a parking place right across from the Camden Public Library, but there was one little catch — it was only 15-minute parking!

Some views - 

So Camden became a rather quick visit. 😂 We walked around a little, took some pictures and even met a beautiful four-legged resident along the way. I would have enjoyed having more time there, but those 15 minutes were ticking!

One of the friendly faces we met during our very quick stop in Camden. 🐾

So Camden became a rather quick visit. 😂 We walked around a little, took some pictures and even met a beautiful four-legged resident along the way. I would have enjoyed having more time there, but those 15 minutes were ticking!

Rockland — Lunch With a Bobby Flay Connection!

From Camden we continued to Rockland, where we had lunch at Archer's on the Pier.

This wasn't just another seafood restaurant. Owner and chef Lynn Archer competed against Bobby Flay on Throwdown with Bobby Flay with her Maine lobster club sandwich — and she beat Bobby Flay! Her winning lobster club is still on the menu as the King of Clubs. Of course, that made our lunch stop even more fun. Archer's current menu actually calls Lynn's lobster club her “Bobby Flay throwdown winner,”!

Mark got the Lobster and Bib today!

Wayne never passes up a Lobster Roll 

We also had quite a view from Rockland. The Seabourn Ovation was anchored nearby, and I had to find out where that beautiful ship was going.

Seabourn's Ovation anchored near Rockland — and this one sent me down a rabbit hole figuring out where she had come from and where she was going! 😂

It turns out there was quite a story behind that beautiful ship. The Seabourn Ovation was in Rockland that day on its way to Montreal. Some passengers had boarded in New York for a 12-night fall foliage cruise, but others had been aboard since August 22, when the ship left Reykjavík, Iceland, on a 34-night journey that will end in Montreal on September 25. Imagine spending 34 nights traveling from Iceland, through Greenland and Canada, down the New England coast and then back into Canada! Now THAT'S a cruise! 🚢

Somewhere along the way, Susan suddenly spotted Big Jim — and when you're talking about a 40-foot-tall fisherman, that's quite a sight to see from the car! 😂

Of course, she wasn't able to get a picture, so I had to look him up later. Big Jim was built in 1959 and originally stood along Route 1 in Kittery, welcoming motorists to Maine. He later spent many years at the Stinson sardine cannery in Prospect Harbor and became something of a Maine landmark.

After more than 60 years of Maine weather, Big Jim was definitely in need of some TLC. In 2026, he was restored and put on display at the Penobscot Marine Museum in Searsport. And that's exactly where Susan happened to see him as we drove by!

Big Jim in his Stinson Canning days — the 40-foot Maine fisherman Susan spotted as we passed through Searsport. Photo courtesy of Penobscot Marine Museum.

Sometimes the things you see completely by accident turn out to have the best stories. 😊

We also passed this Trading Post along the way, another one of those things that catches your eye as you're traveling through Maine.

Portland Head Light

Our next big stop was Portland Head Light at Fort Williams Park in Cape Elizabeth.

Blue skies, beautiful water, rocky coastline, sailboats and that gorgeous lighthouse — we certainly couldn't complain about the weather or the view.

Portland Head Light is the oldest lighthouse in Maine. Construction began in 1787, and the lighthouse was completed after the new federal government took responsibility for the country's lighthouses. It was first lit in 1791. Fort Williams itself later served as a military installation protecting the entrance to Casco Bay and Portland Harbor.

Today it is difficult to imagine this peaceful, beautiful place as a military installation. We were much more interested in taking pictures — and we certainly took plenty of those! With eight people and several cameras and phones, I'm fairly certain we photographed that lighthouse from every possible angle. 😂

And then we spotted a gelato stand whose sign boldly proclaimed:

“Best Gelato West of Italy!”

Well, really. What were we supposed to do with a claim like that?

Obviously, we had to investigate. 😂🍨

Grace had decided not to make the walk down toward the lighthouse, so David got her an affogato — gelato topped with espresso — and headed back to the car to deliver it to her.

A little while later Susan suddenly said, “Did David go to your car?”

“Yes.”

Then she mentioned that she had heard a car alarm going off about that same time.

I said OH NO.

Off I went toward the car while also trying to figure out how to shut the alarm off using the Honda app.

There was just one small problem.

I was going the wrong way. 😂😂

Fortunately, Michael went in the RIGHT direction, had the actual key and managed to get the alarm shut off.

Crisis averted.

Apparently even our CR-V wanted its moment in the Day 8 blog! No pictures though to share. 😉

Kennebunkport

From Portland we continued south toward Kennebunkport, where we drove out toward Walker's Point to see the Bush family compound.

There really wasn't a convenient place for us to park and get the pictures we would have liked, so this was more of a drive-by visit. We still managed to get a few shots across the water, and with the beautiful coastline and sailboats offshore, there was certainly plenty to look at.

Then it was time to continue south.

Eventually we crossed the Piscataqua River Bridge, leaving Maine behind and entering New Hampshire.

That felt a little bittersweet. We had spent several days exploring Maine and had certainly packed a lot into them — lighthouses, lobster, little towns, beautiful scenery, shopping, interesting people, plenty of food and more than a few laughs.

We settled into the Everhome Suites Portsmouth-Newington for the night.

By the time we got everything unloaded and settled, Day 8 was officially in the books.

This morning we'll load those cars yet again and continue making our way toward home. We're definitely heading south now, but knowing the Crazy 8, I have a feeling there are still a few adventures left before we actually get there.

Day 8 is in the books! ❤️🚗