10 Essential Boston Experiences


Those of us from Boston know that the Massachusetts capital can be a confusing place to get around. A city of just over 650,000 people — according to the latest census data — there is seemingly little rhyme or reason to the city’s layout. While city lore states that Boston’s architects laid the roads on top of preexisting cow paths, in truth, the metropolis’ winding streets are simply a product of a lack of city planning. Those who originally settled here never imagined that the city would grow to such importance, and thus didn’t apply the kind of forethought to the laying of streets that those in cities like New York or Chicago did.


As a result, wandering around confused has become a regular part of Boston living. In turn, whether you are moving to Boston, already living in Boston or are just visiting, there will always be essential experiences that you likely have missed while trying to figure out where you are.

So while life in Boston is a wonderful combination of cosmopolitanism and classic New England charm, we can think of no other city more in need of a top 10 list of essential experiences.

While tourists are sure to find this guide useful as they explore Boston for the first time, this guide is as much for the resident as it is for the guest.

Therefore, without any further ado, here is our guide to the 10 most essential Boston experiences.

A Brief History of Boston

Before we get to our essential experiences, it’s worth quickly exploring Boston’s illustrious history. As one of the oldest settlements in the United States, Boston is a city that keeps its history front and center. Therefore, understanding Boston’s history is just as essential as exploring any of its locals. In fact, many of the places listed in our guide are there because of their remarkable historical importance.

English Puritans founded Boston in 1630 as a “city on a hill,” an example of Godly living for the rest of the world. However, while religious commitment continued to define the city, it quickly grew into an important seaport, becoming one the English colonies’ most crucial sites for importing and exporting goods and foodstuffs. Not only were wares such as tea and textiles exchanged in Boston’s ports, but so too were the latest political ideas. It’s no wonder that leading political thinkers in Boston began to contemplate the future of the colonies. By the 1760s, many in Boston deemed British rule to be a burden rather than a benefit and began to advocate for the radical notion of independence. Inspired by these ideas, Bostonians famously dumped a shipment of tea from the East India Company into Boston Harbor in 1773, causing the British to send troops to occupy the city. Tensions caused by this occupation soon led to the first clashes between Massachusetts “Minutemen” and British regulars at the small towns of Lexington and Concord just outside of the city. With those “shots heard round the world” the American Revolution began.

After the Revolution, the city continued to thrive. New England became the center of 3-irishAmerica’s textile industry as well as fishing and whaling industries. Ships continued to carry goods both in and out of Boston Harbor, transforming this small Puritan settlement into a cosmopolitan hub. When the potato famine struck Ireland in the 1840s, many Irish immigrants began to arrive in Boston, establishing the city’s multicultural roots. Later, waves of Chinese and Jewish migrants further diversified Boston’s citizenry.

Moving into the present, Boston has maintained a firm grasp of its history while tackling the problems of the future. Boston continues to be an American leader in culture, technology and urban living. World-renowned institutions of higher education, such as Harvard, MIT, Boston University and Boston College help keep the city on the cutting edge. This mix of contemporary economic opportunity and a sense of timelessness makes Boston an inviting place for young professionals looking to start their careers, even as lifelong residents trace their Boston heritage back generations.

Top 10 Essential Boston Experiences

Now that you have a sense of the deep and ever-present history of the city, we offer you our 10 most essential Boston experiences. Whether you have lived here for years or are just moving to Boston, these experiences are a must if you really want to know the city. Those who’ve already been to these places should consider wandering through them again, as they’re all worth years of repeat visits. So whether you are looking for culture, great food, history, or some of America’s most storied sporting traditions, Boston is a city worth exploring — even if it is an easy place to get lost.


The Freedom Trail

This isn’t so much one place but instead a trip through many of the attractions that highlight the ways in which Boston became the starting point for the Revolution. Some of the stops along the way warrant more in-depth exploration — in fact, we’ll highlight some of them separately on this list — but the best part of the Freedom Trail is that you don’t have to do it all at once. While guided tours are available, you can walk it any time on your own and at your own pace.

The whole trail is 2 and half miles and takes you past 16 important revolutionary sites. These include the site of the Boston Massacre, Faneuil Hall, the Bunker Hill monument and the Paul Revere House. There is an easily downloaded Walk in History audio guide, which is handy for those unfamiliar with the area. However, even a longtime resident will find the historical insights provided informative.

The official tour begins at Boston Common, but you can start anywhere if you are up for exploring on your own. And while the full tour takes anywhere from 2 and half hours to half a day, residents can easily do a portion one day and return to finish the rest later. For more information, check out the Freedom Trail website.


Museum of Fine Arts

This is without a doubt Boston’s premier fine arts institution. In fact, it is one of the most important art museums in the world.

The founding of the MFA on July 4, 1876, marked the 100th anniversary of the United States. It now is home to half a million works of art, ranging from contemporary art to ancient Egyptian artifacts. The museum continues to expand, recently adding an “Art of the Americas” wing — which connects pre-Columbian art to the contemporary American greats. They’ve also recently renovated their contemporary art wing, while also adding to the European, Asian and African art collections.

The MFA is also associated with the School of the Museum of the Fine Arts, which is a partnership with Tufts University. In this sense, the MFA is not only displaying countless artistic riches but also incubating the great art of the future by offering both undergraduate and graduate art programs.

If you are going to give the MFA its due, you need to make sure to block off most of the day. Its depths of artistic treasures cannot be taken in just a couple of hours. Additionally, the price of admission — $25 for adults — reflects the scale of its collection, so while the cost is fair, it isn’t worth it if you only plan to rush through. However, on Wednesday evenings, they offer a pay what you want admission, giving budget visitors an opportunity to explore.

Finally, if you want to get the full experience, take a complimentary tour. Guides will point out the significance and history of the works, giving you an even deeper understanding of the collection’s grandeur.


Fenway Park

If you are a baseball fan, no matter which team you root for, you know about Fenway Park. It is the oldest ballpark still being used in Major League Baseball, and its various design quirks are renowned throughout the sport.

The most striking feature of Fenway is the “Green Monster.” While most outfield walls are somewhere around shoulder high, the left field wall at Fenway is over 37 feet tall. Because of space limitations in the the area occupied by the park, the left field wall is much closer to home plate than in any other park. To compensate, the wall is also much higher, meaning any ball that bounces off the wall is still in play rather than being a home run.

However, Fenway is also notable as a baseball time capsule. It celebrated its 100th birthday in 2012 and its age is on display every time the score changes, as the scoreboard is still hand turned.

Of course, if you enjoy baseball, taking in a game among the rabid Red Sox faithful is a must. However, it is worth touring even when a game isn’t being played, as it is a wonderful landmark to America’s favorite past time. With the exception of maybe Chicago’s Wrigley Field, no ballpark in America comes close to honoring the storied history of this wonderful game the way Fenway does.

If you do want to see a game, you’d be wise to get tickets early as Fenway is one the smallest ballparks in the MLB as well as being the oldest, and Bostonians don’t miss many games, meaning tickets sell out fast — even more so if the hated Yankees are in town.


Boston Common

Who’d have thought a former cow pasture could grow into such an engrossing experience? Such is the case of Boston Common. After cows ate all the grass, the Common became a camp for British soldiers prior to the Revolutionary War. Today, it is the oldest public park in the country.

If relaxation is in order, you can’t do much better than Boston Common. People, birds and great scenery gently mingle here. It’s the perfect locale for a picnic lunch or a nice jog.

However, if you want to explore in-depth, there are a considerable number of interesting venues in Boston Common as well. Buried in the Commons are many of the soldiers who died at the famous Battle of Bunker Hill. Fittingly, this place is where the Commonwealth of Massachusetts chose to honor those fell during the Civil War in the form of the Soldiers Monument.

The Commons is also the site of many cultural events, including live theater and music performances. The frog pond in the middle of the park is a favorite location for waterside relaxation during warmer months and it transforms into an ice rink during the winter.

For those who work downtown, this is a great location to add to your daily rhythm and it is an integral part of the cultural life of the city.

8-churchOld North Church

As Henry Wadsworth Longfellow famously penned, “one if by land, two if by sea.” This line commemorates Paul Revere’s famous ride, in which he rode his horse to the outskirt of Boston to warn Americans of the impending arrival of British soldiers. As the story goes, the sexton of the church was to hang a lantern or two in the steeple of the church in order to indicate the manner of the British’s arrival.

As the British were observed leaving the Common and boarding rowboats in the Charles River, the sexton hung two lanterns from the steeple. Since they were taking the quicker route towards Concord, Revere had to ride as fast as he could to alert the Minutemen. As he road, he cried out “The British are coming! The British are coming!”, giving the American colonists enough warning to take up arms and meet the advancing troops at Lexington Bridge.

The church itself is a wonderful relic of colonial architecture. The church features America’s longest running public clock. You can even see pew number 54, which, according to the custom of the time, was reserved for the Revere family.

Old North Church is a part of the Freedom Trail, but it’s also worth a dedicated visit in its own right. It is still an active congregation, so you can even attend a service on Sunday. It is free to visit on weekdays, though donations are encouraged, and you can hire a guide if you want a more in-depth tour.


Faneuil Hall Marketplace

Throughout its history, Boston has been a commerce-driven city. As one of America’s most important shipping hubs, the merchant class held an important position in Boston society. No wonder then that Faneuil Hall, originally built as a marketplace in 1742, become a central part of the Boston ethos.

Although the marketplace and the wares it offers have changed over the years, Faneuil Hall continues to occupy the same role as it always has. It is a gathering place where one can shop, exchange ideas and enjoy the company of others.

According to the official website, Faneuil Hall Marketplace is home to over 70 retailers occupying 200,000 square feet of retail space.

The cobblestone walkways hearken back to the market’s storied history. As you stroll, live music and street performers, who all give the marketplace that rich noisy bustle that has filled the area for over a quarter of a millennium, will regale you.

While it is a great place to get some shopping done, it is also a wonderful destination for meeting friends for a bite to eat or cocktails. Alternatively, you could just people watch as you walk along, basking in the romantic energy of this historic commercial center.


Samuel Adams Brewery

Although branded after one of the founding fathers, Samuel Adams Brewery is 18th-century in name only. Despite this, it’s still a revolutionary brewery. Along with a few other breweries, Sam Adams (the beer) is often cited as kickstarting the craft beer industry.

The Boston area brewery can no longer keep up with the insatiable demand of America’s beer drinkers — commercial brewing has moved elsewhere. However, this location is still the primary laboratory where new recipes and techniques are tested. It is therefore still a fully functioning brewery, even if the bottle you enjoy at a cookout didn’t originate there.

The tours, directed by charismatic chaperons, are free, though donations are encouraged. You do have to reserve a space and tickets are on a first come first served basis.

Although tour guests of all ages are welcome, the best part — the tasting at the end of the tour — is obviously for those 21 or over.

So while the history of the brewery isn’t nearly as lengthy as the rest of the city, it is nonetheless a site of the commercial innovation that is so quintessentially Boston.

Boston Symphony Orchestra 

On October 22, 1881, the Boston Symphony Orchestra gave its first historic performance. 132 seasons later, the BSO continues to be one of the most important symphony orchestras in the United States. In fact, the BSO has long held a position as a member of the “Big Five,” a collection of the 5 most important symphony orchestras in the United States.

The orchestra performs in Boston Symphony Hall, which has earned nearly as much praise as the orchestra it houses. It is widely considered one of the most perfectly acoustically designed music halls in the world.

The Boston Pops, a division of the BSO, has long been a fan favorite and are especially well suited for young attendees. In fact, the holiday classic, “Sleigh Ride,” originally composed for the Boston Pops in 1946, is a mainstay of any holiday concert.

For Boston residents interested in being a regular part of this cathedral of high culture would do well to purchase a seasonal subscription. Those interested in select performances should purchase tickets well in advance, as performances tend to sell out quickly. Tickets are available on the BSO’s website.

Boston Children’s Museum

The youngest Bostonians among us have a place designed just for them. The Children’s Museum exists to evoke a childlike wonder among its guests while piquing their interest through exciting educational exhibits.

Any trip to the Children’s Museum begins at the iconic giant bottle of milk that rests outside the building. Inside, kids and their adults will find countless displays of science, culture, wellness and art, all designed to be hands on and child-friendly.

This is an especially good rainy day option for parents who need to get their kids out of the house. It also undergoes enough constant transformation that warrants repeat visits. Located in the heart of downtown, the museum isn’t far from other places worth exploring for the inquisitive young mind.

Boston Public Garden

Founded in 1837, the Boston Public Garden is located right next to Boston Common. It is America’s first public botanical garden, and the many grounds keepers work tirelessly to maintain the tree and flower specimens. A four-acre pond sits in the middle of the park, which you can explore by swan boat.

There is also statuary worth viewing, including a famed statue of our first president, George Washington. Those familiar with the famous children’s book, “Make Way for Ducklings,” will also recognize the statues of the same name.

More Information on Boston Living

Now that you have a sense of the cultural and historical wonders of Boston, there’s no better time to discover just how easy it is to call this city your home. Here at Boston Luxe, we are committed to finding you the best home in this our favorite town. So whether you are looking to rent or buy, we want to make your Boston real estate experience as stress-free as possible. Contact us today and take the first step toward your new Boston home.

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