Boston in a Day – The Freedom Trail & Fenway Park

While in Scarborough, we wanted to make the 2-hour trip to Boston, but we didn’t want to have to worry about parking The Beast there. We decided to take the Amtrak Downeaster, and we were so glad we did.

Be sure to check out the video below for all the photos we took during the day.

Take the Amtrak Downeaster

Aside from the fact that we decided to take the 5:15 a.m. train from Portland, this was the best way to go. We could relax, eat, and even sleep during the 2+hour trip and not have to worry about getting around Boston once we got there. All for less than $60/ticket. And all-day parking at the Portland station was just $5!

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Amtrak Downeaster has several stations around Scarborough, including one at Old Orchard Beach, just 3 miles from Wild Duck Campground. Unfortunately, the earliest we could get there from Old Orchard Beach was 8:22 a.m., and we had a lot of things planned once we got to Boston.

The Freedom Trail

Our first adventure of the day was following The Freedom Trail. The website was a wealth of information, including maps and descriptions of the various locations around Boston, so be sure you can access it from your phone. HINT: I took screenshots of tickets, maps, and other important info and saved it to my phone.

Follow the Red Brick Road

As strange as this may sound, there is a path on the sidewalks around the city where the Freedom Trail goes. You can start from anywhere along the red brick road.

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We chose to start across the Charlestown Bridge at the U.S.S. Constitution and Bunker Hill before continuing on to the rest of the trail in the main part of Boston. While the U.S.S. Constitution Visitor’s Center wasn’t open yet as it was around 8:00 in the morning, we were still able to experience so much.

We continued on to Copp’s Hill Burial Ground, where we saw graves from prominent citizens and even those who had been involved in the Boston Tea Party.

The Spite House

Across from Copp’s Hill is The Spite House. As you’ll see from the video, this house is the smallest house one could possibly live in. Legend has it that one brother got into a fight with another brother and decided to build his house to block the other brother’s view of the harbor. Thus the name ”The Spite House” was born.

More of the Trail

We continued on to Old North Church, through Little Italy to Paul Revere’s House, and then to the Old State House. Be sure to check out the video below to see the sights along the trail.

While we wanted to continue on the trail, we were running short on time for another bucket list event we had tickets for at 1:00.


Of course, we had to find Cheers, home of the famous bar from the television show, while we were exploring Boston. Our plan was to have lunch there, but unfortunately, the wait was too long. So we opted for a photo of the sign instead.

Fenway Park – Indians vs. Red Sox!!

As luck would have it, the Cleveland Indians were playing the Boston Red Sox while we were there! Being lifelong Indians fans, we were so excited. Not only did we get to check out Fenway, but we were also able to see a game.

We purchased two cheap-seat tickets near the Green Monster, and enjoyed the first four innings, including one of the Indian’s hitting a home run over the Green Monster.

Why didn’t we stay for the whole game? Because we had to catch the 5:15 train back to Portland. We took the T (Boston’s metro train) back to the Amtrak Station. I must say that Boston’s transit system was very easy to use.

We arrived early for the trip home, and knowing that the train ride would be over two hours, we decided to head to Little Italy for an early dinner. We found a little pizza place with lots of people around it, so we figured that meant it was good. We weren’t disappointed. We sat at the bar, and the bartender told us that Regina Pizza had been voted #1 in the country by Tripadvisor for best pizza. We could see why.

Boston in a Day – The Freedom Trail & Fenway Park


We highly recommend taking the Amtrak Downeaster to Boston if you get the chance. It is so much more relaxing that driving the highways and paying unbelievable prices to park. And, after walking over 10 miles, we were more than happy to relax and leave the driving to someone else on the way home!

Be sure to follow us for more of our adventures as we see America one mile at a time!

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