A Few Days in Boston and Maine


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North America » United States » Massachusetts » Boston
September 1st 2018
Published: September 1st 2018
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On our New England road trip, after we visited Mystic Pizza, we made our way on the local ferry to eat lunch in Martha’s Vineyard and then ended up traveling to Boston overnight. We had found a tiny room for rent in a high-rise flat, and the price was infinitely cheaper than anything we had seen at a major hotel chain in the city. The location was ideal and right in the middle of the city. The spot was called The Beacon Street Inn. Though we had to walk down the hall to shower and the room was no bigger than a closet, it was an ideal place to stay, as we were only going to be there one night and wanted to spend the entire day exploring the city of Boston.

We started our morning by walking the Freedom Trail. Along the way, we saw many interesting and historic sights, lots of older buildings and the gravestone of Paul Revere. I was thankful that we had the interactive map downloaded onto our smartphones, as it made it quite simple to follow along and not get lost. The one thing we did not anticipate about visiting Boston was that it would be infinitely windier than anything we expected! Coming from the southern part of the area, we had packed warm clothing, but nothing was enough to prepare us for these freezing gusts. As you can see, it was also difficult to maintain any semblance of a hairstyle! Still, the more we walked, the warmer we became, so we just made it a point to keep moving.

We eventually made our way to the Cheers location! While we were a little young to really grow up watching the beloved and iconic television series, all four of our parents just adore it, so if only for their sake, we decided to take a short tour of the property. Though the original bar where many of the scenes were shot was closed to outside guests, they had built a replica of the set inside the same building, so we enjoyed getting an up close and personal feel for how it was! Turns out, it is actually a restaurant where the public can eat as well. When we got there, however, it was only around 10:00 in the morning so they were not open yet. Maybe next time!

Though it was still relatively early when we left Boston proper, we did have a short drive to get to the nearby Sam Adams Brewery. As my husband is an avid craft beer fan and has loved Sam Adams for years, we knew we wanted to make this a major stop while we were in New England. Overall, it was one of the best factory tours we have ever been on, and that is saying so much because we love a good factory tour

Our guide was informative, entertaining and interesting. She let us smell the grain and the hops. We could even taste one straight from the grain barrel! The tour ended with a tasting, wherein we sat around big tables and all shared a pint of Sam Adams with our new friends from the group. It was a wonderful way to cap off our time in Boston. Thankfully, we decided not to eat too much for lunch after that, because we were already full. Instead, we left the city and drove on to our destination for that night, Maine.

There, we stopped to eat dinner at Cook’s Lobster House in nearby Bailey Island. We had seen a view of Cook’s on a credit card commercial years ago and the atmosphere looked so perfectly New England that we made a mental note to check it out if we were ever in that neck of the woods. At the time, we thought it was only a pipe dream, but as soon as we found out we could take this trip, we decided to drive a little farther north and include Maine in our itinerary.

This meal was quite the experience. As two kids from North Carolina who have never traveled too far north and never really eaten lobster or crab, apart from the imitation stuff you can buy at the grocery store, we did not know how to start! The waitress brought us out bibs and metal utensils to begin with. We sat and stared at them for a while. The, she brought out the steaming hot lobster, along with a side of drawn butter. I have never felt so ill-prepared in my life! We had such a good laugh as we each tried to crack open the shell to get the delicate and delicious meat inside. Was it everything it’s cracked up to be (excuse the pun)? I’m not sure. It was incredibly decadent, but after all the work it took to reach it, we expected there to be more meat than there was. Still, the butter and lemon were delicious complements and the entire experience was so entertaining and downright fun that if we ever come back, this will once again be a stop on our trip.

Another reason why we will come back? The amazing blueberry pie that we got for dessert! We weren’t exactly filled up after the lobster and even though we rarely order dessert at a public restaurant, we decided to spring for it after our waitress and several nearby diners raved about the pie. It is a restaurant institution and one that people from all over the world visit just to try, so we were intrigued to say the least. Thankfully, it met every expectation and then some! The crust was flaky, the local berries were juicy, ripe and full of flavor and the ice cream on the side was just the icing on the cake.

Then, an interesting thing happened when we went to check into our hotel for the night. It was called the Cook’s Island Motel. From the outside, it looked very nice and clean. We were excited to check in and get unloaded. The only strange thing was that there was no one else in the parking lot! Our reservation confirmation said there would be someone at the office to show us to our room. The only problem was that the office was closed! It wasn’t exactly a busy season for the state, so I assume they only staff that location when tourists come in during the early summer. We sat there in the parking lot for a while unsure what to do, and then we noticed a light was on in one of the rooms. We walked over and opened the door, and sure enough, that was our room! There was a welcome letter on the front table with our names on it and everything! It was a beautiful room and we were thankful to be there! I’m just glad we thought to check out that light, and I’m also thankful no one else had decided to wander around in there while the room was unlocked.

That next morning, we explored Maine just a little longer before heading back down south. The water there was so blue and the myriad boats parked in the many harbors were so quaint and quintessentially northern! In our tour book on the area, we had read about a walking trail known as the Giant’s Stairs Trail in nearby Harpswell, Maine. After a quick breakfast at a local diner that turned out to be surprisingly delicious, we hit the road and decided to check it out. What a gorgeous view! The walk was a simple one that afforded us unbelievable views of the water below. There were also a few homes along the way that were rustic and beautiful and everything New England dreams are made of, with their cedar siding and distinct Cape Cod architectural style.

Afterward, we decided to head back. Along the way, as we traveled in our rental car, we noticed there was a little mini fair going on at the home of the Fryeburg, Maine fairgrounds. In October, the fair is in full swing, known across the state as “Maine’s Blue Ribbon Classic.” While we adore a fall fair and would have loved to have seen the event in full throttle, this was a smaller summer fair. Still, they were selling the area’s famous whoopie pies, so we had to try one! In short, these are two rich, dark chocolate cakes with a sweet cream sandwiched in the middle.

We grabbed two for the road, walked around just a bit to see the rides and the fairgrounds, and then got back in the car. We ended up stopping around the late afternoon for a quick appetizer platter at an Applebee’s we passed along the way. If we ever see one of these while traveling, we always try to hop in, even if it’s just for the jalapeno poppers and some sweet tea. It’s also a family favorite, as it’s one of the few places where kids eat free if you buy an adult entree. With two children under the age of five in tow, we often have to use that system when on the go!

The scenery as we drove was astounding. We had to pull over in many places just to take it in and snap a few pictures. As we drove on southward, I just kept looking out of my window, grateful for the chance to take this trip and see these sights. As New England is on the same coast as we are, this seems like a doable trip for the entire family to take, and I know that we will be back!


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