Why you’ll love breathtaking seaside Gloucester Massachusetts!

In 2008 when we were just in the new dating phase of life, we went on a 2-week trip to Bill’s extended family in Gloucester, Massachusetts. So, we started out on our road trip adventure to get to Massachusetts in 26 hours. Which included driving day and night with Bill’s Dad also along for the journey.  

Starting in Nebraska we trekked across I-80 and I-90 east through Iowa, Illinois, Indiana, Ohio, Pennsylvania, New York, and into Massachusetts.  

We stayed at Bill’s Aunt and Uncles house. They had a boat at the dock to hang out on. It was summer vibes walking through the town and, and the New England coast to explore. While flying would have made getting there quicker, having access to a vehicle made for fun drives through the small towns. At this time Ubers weren’t a thing in these areas. However, the train system was easy for access to Boston and multiple towns with stops along the way! We did it! 

Boat rides around the harbor were so pretty. Imagine July sun with cool breeze from the water and smell of fresh sea air. When the captain of the boat says I’ll drive around on the boat, you go with the flow. And the views were not disappointing.  

Some history for the movie and book buffs, The Perfect Storm story is about a boat crew from Gloucester, MA that went out in 1991 and were trapped in a Hurricane. Thirteen lives were lost during that storm, including the entire 6-man crew of the Andrea Gail. Gorton’s Fisherman is located in Gloucester and Tuna and Lobster fishing is a major source of income from this harbor. 

Move west to North I-95 through New Hampshire and into Maine. Kittery was a quick 1-day trip to the Kittery Outfitters. No joke I think all of the cute cabin style decorations you could ever want are all in this store! So much to see. Grab a bite to eat at Bob’s Clam Hut and headed back to Gloucester Massachusetts.

July was not the orange, red, yellows that you think of New England fall foliage, but I loved the gree tree cover anyways. Driving through the small town feel like you never really leave one town but flow down the road twisting through tree covered areas to the next town.  Really old homes are turned into Antique shops. They were so much fun to walk through. If only we had enough space in the truck to bring the 200-year-old furniture pieces we found home, but we didn’t, and they were left for others to buy.  

Golfing with Bill’s Dad in Reading at the Hillview Golf Course was great. Bill’s Dad worked at this course when younger. Watch out for the geese, they have a few that call the course home. Then it rained! So, it was a short golf session. 

Salem, MA was a must since we were in the area. Yes, Hocus Pocus plays all October long in our house! So, a quick day trip to Salem was worth it! In July you don’t get the crazy of October Halloween crowd, but it still has the feeling of magic and spirits.  

The Salem Witch Museum is similar to a wax museum feeling. The Witch House and museum is a very historic house pointedly painted black. It makes you feel like you have traveled back in time to an old kitchen and bedrooms of the 1600s. It is a really small building and only takes a few minutes to go through and is actually a home of the Judge and of the actual convicted witches.  

Walking the streets of this old historic town was wonderful. There are lots of tours to do, but just going to individual shops down the main strip of town was an entire day. We walked to the Salem Maritime National Historic Site. This was our first time getting a National Parks Passport stamp! And now I’m addicted to it! Both of us love history and National Parks.  

We stopped at the Maritime Museum and found our first NPS Passport book in the Gift shop and added our first 2 cancellation stamps! After that we walked to the waterfront and saw The Friendship of Salem docked in Salem Harbor.  

America’s National Parks Online Store

A quick day trip to Boston was another must and so we used the train that leaves Gloucester and arrives at Boston North Station. It too just over an hours time and then we did the tour group Hop On Hop Off. This bus system is easy to get on and off at designated tourist spots in the city. We went to Boston Commons, The Cheers bar and had lunch, drove by cemeteries where famous Americans were laid to rest, as well as the USS Constitution and Cassin Young Destroyer. 

Our favorite part was the Harbor Cruise included in the tour. It was a little over an hour and was so much fun! 

We went under the plane route for the airport, the Harbor port, city skyline, Coast guard station, and the USS Constitution and USS Charles Young.  

The USS Constitution is the oldest commissioned ship in the Navy and is still maned with its own crew. We didn’t get to hear the cannons go off, but they do it at sunrise and sunset every day. We then took the bus to the Navy Yard to tour the USS Constitution and the USS Cassin Young Destroyer.

Just make sure to watch your time of the night. You don’t want to be stuck with a taxi ride all the way back because you missed the last train of the night. It was a very easy way to travel without a vehicle.

Getting up at 3am and going on the boat in the dark isn’t a normal vacation thing to do. Captain “Uncle B” was taking us to a secret fishing location off the coast of Gloucester Massachusetts. While we didn’t catch any fish, we did catch some awesome views of the whales. We were on a fishing boat and not a large whale watching tour boat and had to be careful of them. These whales were not afraid of us at all! 

26 hours straight back to Nebraska and we knew we had to take the chance to stop at Niagara Falls State Park in New York. We walked to the Falls, looked at the crazy people who get on the boats to go into the mist. We didn’t go into Canada, but one day in future we will! 

• Mile Marker One                Lobster Rolls 
• Blue Marlin Grille               Mussels  
• JT Farnham’s                     Fried Clams 
• Nichol’s Candies                Maple Candies 

• Whale Watching Cruises 
• Walk the Harbor and see the Fisherman’s Memorial with the Drawbridge 
• Rocky Neck Art Colony shops and Restaurant 
• Cape Pond Ice Company Tour 
• Hammond Castle Museum 
• Just go for a drive 

Want to see more of our 2008 Massachusetts Trip? Visit the Gallery