Road Trip to Boston

Robert Cekan
Robert Cekan Travels
8 min readAug 14, 2017

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Who doesn’t enjoy a road trip? In recent years, nearly all of my travel destinations were reached exclusively by plane; road trips were pushed aside as viable alternatives. This streak was about to be broken when my girlfriend Jessica and I discussed how she had never visited the USA. That kick-started early planning of a USA road trip and by August, we set off to the East coast!

A drive from Hamilton, Ontario to Boston, Massachusetts is approximately 8 hours non-stop. Once you’ve included breaks (i.e. food and gas refills) it’ll be around 10 hours until you reach Boston. It’ll also cost you about $20 in tolls if you take the direct route, which can be avoided by detouring through Pennsylvania and adding an extra 2 hours of travel time (I don’t recommend this as gas alone will neutralize any savings). The drive itself was really scenic and overall very enjoyable; a good reminder as to how underappreciated road trips are.

Since it takes nearly an entire day to travel to Boston, we arrived in the evening and would begin exploring first thing next morning. The first of which was visiting the Harvard University campus in Cambridge. Harvard University, as you are likely well-aware, is the oldest institution of higher learning in the United States (this comes just after visiting the oldest university in the world in Bologna, Italy). As we passed by Harvard Square on our way to the university campus, we noticed a group of people congregating in the square and decided to check it out. As it turns out, it was a group of visitors gathered around a tour guide for a free tour that was just about to begin!

The number of short stories and history our tour guide shared are far too expansive to write about in a single blog post, but I’ll highlight some of the most interesting landmarks found on this longstanding campus. As we approached the main entrance point of the campus, we learned that even the gate has a story!

Apparently Harvard students are only supposed to walk through the main gate twice in their life; once when are admitted and once upon graduating otherwise misfortune will fall upon you. The main gate is closed (presumably to uphold this tradition) and so visitors funnel to the much narrower side gate.

The John Harvard statue can be found in Harvard Yard, the oldest part of the campus, which is alternately called “the Statue of Three Lies” since the only things written on the statue — JOHN HARVARD • FOUNDER • 1638 — are all incorrect. The face of John Harvard is unknown since all portraits of him were lost in a fire (the face was depicted after another student), John Harvard was not the founder (the school was named after John Harvard after he donated his famous book collection) and the school was founded in 1636, not 1638 (the latter year was the date John Harvard’s “endowment” occurred). Students and visitors alike rub the toe of the shoe for good luck and from constant contact, now reveals the bronze underneath.

The Memorial Church was built to honour the men and women of Harvard University who died in World War I. It is located across Widener Library as a reminder to the university’s spiritual background.

Widener Library had one of the most interesting backstories, however. The building was named after Harry Elkins Widener who travelled the world collecting rare and interesting books but tragically died in the sinking of the Titanic. Harry Elkins’ mother donated her wealth to build a library in her son’s honour with very strict stipulations as to what could and could not be done to the building. If these rules were not followed, Harvard can lose possession of the building to the city of Cambridge. The most notable of these stipulations was the disallowance of any alteration or expansion of the library to make it taller or wider. But as Harvard’s library collection outpaced available shelving space, the library had to expand in some form. This was cleverly resolved by the university exploiting a loophole regarding downward expansion. By digging down, the school was not in conflict with any stipulations in the agreement and now has a tunnel that connects to even more library space. Widener Library now houses an impressive 3.5 million books and “holds one of the world’s most comprehensive research collections in the humanities and social sciences” (source).

As a business graduate myself, I naturally had to visit the Harvard Business School (HBS) campus before I left the university. I explored Baker Library, the heart of HBS, and read up on its history through various exhibits inside.

It only takes a few moments indoors for the level of prestige to become apparent.

Let’s move away from Harvard now and explore the city of Boston. One of the easiest methods to explore this city is to follow the Freedom Trail, which starts in the city park: the Boston Common. Adjacent from this is the other city park known as the Public Garden, which we’ll explore first. It’s a fresh breath of air from all of the tall, surrounding buildings and a pleasant walk as well.

Any big fan of the movie Good Will Hunting will recognize the above picture as a scene from the movie where Robin Williams delivers a powerful speech to young Matt Damon in the Public Gardens. This visit to Boston was only days after news of Robin Williams’ death. As a result, hundreds of people wrote messages on the pathways around the bench featured in the movie in memory of the actor. This was certainly an incredible thing to witness first-hand.

What I particularly enjoy about the Boston Trail is how easy it is to follow. A line of red bricks are inserted into the sidewalk that winds throughout the city as a way to guide visitors. It’s so subtle yet so effective.

The Freedom Trail is entirely within the city, highlighting various landmarks and structures that hold historical significance to both Boston and America. On the trail, you’ll come across the new and old State House, new and old City Hall, burial grounds, marketplaces, monuments and various churches. It’s a great way to skim through some of Boston’s richest history.

The trail ends at the Bunker Hill Monument, which marks “the site of the first major battle of the American Revolution fought on June 17, 1775” (source).

An attraction in Boston that isn’t on the Freedom Trail but worth checking out is the Mapparium. It’s a giant, indoor stained-glass globe of the world (with country borders) as it was in the year 1935. The globe is backlit to light up certain regions during a presentation as you stand on a 30 foot long bridge in the centre of this sphere. It’s something truly unique and as an avid traveller, I greatly appreciated my visit here. Unfortunately you can’t take pictures indoors (not that you could capture the globe properly anyway) but you can read more about the Mapparium on their official website.

Next door to the Mapparium is a stunning church called The First Church of Christ, Scientist. It’s actually a combination of two structures, the original being in grey stone. The larger attachment is known as the Mother Church. As if the size of this church wasn’t impressive enough, the structure stands beside a giant pool of water that’s a full city block in width; it’s a real head-turner!

After eating at some very American restaurants such as Dunkin’ Donuts and IHOP, the final attraction Jessica and I made time for was an hour-long ride on an old-timey sail boat in Boston Harbour.

At one point the captain asked me to take over, to which I unquestionably agreed to.

Few things in life are more relaxing than being out on the water. This boat ride also made for a great view of the city’s skyline.

That concludes the Boston portion of this trip. The next leg of the trip was Cape Cod! Stay tuned!

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This blog entry is part of the publication Robert Cekan Travels & was originally written on October 6, 2014

Robert Cekan is a young entrepreneur and proud Hamiltonian. He is the founder of the Hamilton discovery website True Resident, as well as Cekan Group, a property management group. He is also a Hamilton REALTOR® with Ambitious Realty Advisors Inc., Brokerage and an active blogger.

For all of Robert’s projects, please visit robertcekan.com

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Robert Cekan
Robert Cekan Travels

Creator, writer, real estate agent, entrepreneur, Hamiltonian, husband.