A Weekend Guide to Boston for History Lovers and Foodies

I have visited the US many times however it only took one weekend for Boston, Massachusetts to become my favourite US city. Boston reminds me of a clean and organised version of Europe. The city is full of history but it is laid out in a methodical way. The architecture is dated but well put together. But the real reason why I love Boston is because it is full of surprises. From the friendly people and amazing food, to the bustling markets and happening night life. The city has a lot to offer and its citizens are immensely proud. If you are travelling the East Coast, make sure you visit Boston as it will surely be a highlight. This weekend guide to Boston covers all the main historical and foodie stops.

When I visited Boston I stayed at the Friend Street Hostel, which provided me with a very cheap and clean bed somewhere central. Staff at the hostel were friendly and they organise group outings for visitors as well.

Getting around Boston is easy as it is compact and easy to navigate by foot. For longer distances I used their train system, as the routes are easy to understand and the trains look charmingly old-fashioned. I took the below video of the green line train arriving at Copley station.


Boston played a significant role in American History, notably starting the American Revolution and establishing America’s independence from Imperial British rule. They have created the Freedom Trail, which is a well marked route on Boston roads that tells the story of key events that took place in 1700’s Boston. I’ve highlighted some favourite stops and stories of the Freedom Trail below.

The Old State House

The Old State House was built in 1713 in the Georgian style and was the centre of political life in colonial Boston. It was a place where people exchanged political and economic news. The Merchants Exchange, The Council Chamber of the Royal Governor and the Massachusetts Assembly occupied the building and the balcony was used to read important declarations to the public from. On 18 July, 1776 the citizens gathered in the street to hear the Declaration of Independence read here.

An old illustration of the Old State House in Boston

Today the Old State House is a museum containing original artefacts and is worth visiting for its retelling of the Boston Massacre history by great method actors. As the story goes, it all began on the cold wintery evening of 5 March, 1770. At the time, Boston was an important shipping hub under British colonial rule. The Townshend Act had recently passed which meant items produced in England and exported to the colonies were subject to high import tariffs. That evening, a group of American colonists went to the nearby Customs House to protest against the occupation of British troops who had been sent to enforce these unpopular taxes. The British Captain, Thomas Preston ordered his troops to fix their bayonets on the crowd. When the colonists began to throw snowballs and other items at the guards, it led to soldiers firing their weapons instantly killing five people and injuring many others.

A method actor at The Old State House in Boston

Following the event, a lot of articles and propaganda served to heighten tensions in the area. The engraving by Paul Revere of the event popularised the massacre and depicted the colonists as helpless and downtrodden against belligerent troops. There are many inaccuracies in the picture including the fact it appears daylight and the setting is all too well-organised for what was actually a riot that occurred in the evening.

The Boston Massacre as portrayed by Paul Revere

Thomas Hutchinson, acting Governor at the time, led the investigation of the massacre and by the next day Preston and eight soldiers had been arrested. However the trials were delayed by Hutchinson until more than 6 months later. The defendants stood accused of murder and were represented by future US President John Adams. In his speech to the jury Adams asked them to look beyond the fact the soldiers were British, and that if they had been endangered by an unruly mob they had the legal right to defend themselves. You can read the whole speech here. The jury acquitted six of the men and two were found guilty of manslaughter, based on evidence submitted which included a testimony from one of the victims on his deathbed delivered to his doctor. Those convicted had their sentences reduced from capital punishment by the Benefit of the Clergy ruling, thereby receiving a branding on the thumb in open court instead.

The Old North Church

The Old North Church is a beautiful white building and the oldest church in Boston, which has been preserved for almost 300 years. It is notorious for its eight ringing bells, which were originally cast in Gloucestershire, England in 1744 and hung in 1745. A visit to this great building is one of the stand-out stops on the Freedom Trail. Famous people to have prayed at the pews of this church include Theodore Roosevelt and Paul Revere.

A pew in the Old North Church taken during my weekend in Boston

The Old North Church is fondly remembered by locals for being the object of Paul Revere’s famous instruction “one if by land and two if by sea” given in the wake of the American Revolution. In April of 1775, Revere along with William Dawes planned a midnight ride from Boston to Charlestown to warn patriots there of the movements of the British Army. However before departing, he also asked Boston patriots at the Old North Church to hang lanterns in the steeple to signal to their compatriots across the river in case they were to be caught before the message was delivered. The lanterns were to be raised for just under a minute so as not to raise suspicion with one lantern indicating the troops were marching over the Boston Neck and Great Bridge, and two lanterns indicating troops were crossing the Charles River by boat. “One if by land and two if by sea” became the inspiration for the poem Paul Revere’s Ride by Henry Wadsworth Longfellow, which is still recited by American school children today.

weekend guide to Boston
A portrait of Jesus in the Old North Church
The courtyard of the Old North Church

To read about more stories about the Old North Church, visit the page on the official website: If these pews could talk here.

Boston Common

Boston Common is a park located in the middle of Boston city centre. It is also the oldest park in America, dating back to 1634. Today you will find many locals and tourists alike enjoying the abundant seating and greenery when the weather is fine, as well street performers, snack vendors, and people celebrating special occasions such as weddings.

It is one of the stops on the Freedom Trail because of its colourful history. In its earliest days, the grounds were used by locals for grazing herds of cows. From the late 1700’s until 1817 it was an arena for public hangings utilising a great elm tree that once stood there and was affectionately referred to as The Oldest Inhabitant in Boston and The Hanging Elm. Convicted criminals, pirates, and witches were among the many hung there as well as Quakers who were considered the most heinous of heretics to the English Protestants in Boston during those times. One of the most well-known religious martyrs of the period was Mary Dwyer. Mary and her husband William Dwyer were English Protestants who departed England for Boston in 1635. However they soon became involved in the religious and political debates occurring in Massachusetts and were denounced for supporting considered heretics Anne Hutchinson and John Wheelwright. Around this time Anne gave birth to a stillborn deformed baby, which she attempted to bury in secret however the truth came out and it was used by the Puritans as evidence of her misaligned faith. Mary and her husband were ousted from the city however Mary returned in defiance several times and was ultimately hanged in 1660 on the great elm in Boston Common. The elm tree no longer is in the park, as it was destroyed by a great gale in 1876. A chair was carved out of the remaining tree and now resides in the Boston Public Library. Today now stands a plaque on the site where the tree once stood in the park.

weekend guide to Boston
Mary Dwyer walks to her death

Boston Common has been the location of many significant events throughout the years and a popular place for people to gather. In 1965 and 1969 anti-Vietnam war protests were staged, in 1967 Judy Garland gave a concert, and Martin Luther King Junior and Pope John Paul II have made speeches at the park.

weekend guide to Boston
A statue of Washington at Boston Common

Today there is a strict curfew on the park, since an altercation that took place in 2007 after 10pm which resulted in two teenagers being shot. In the lead up to this the park had become an after-hours hub for drug activity and crime. The park closes daily at 10pm however this continues to be protested against by Boston’s homeless population.

Faneuil Hall

Faneuil Hall is one of Boston’s most visited tourist sites. It is often called the Cradle of Liberty since it has been host to many speeches advocating freedom from the British Empire from notable figures including Samuel Adams and James Ortis. The hall was built in 1742 and since then has been both a market place and meeting hall. It was built in the style of an English country market and there is a grasshopper weather vane that sits atop it, which is now one of the key symbols of Boston.

weekend guide to Boston
The famous grasshopper weather vane atop Faneuil Hall

Faneuil hall is always a hub of activity and has many indoor and outdoor food markets and restaurants providing a great opportunity to sample local Bostonian food. You can also purchase products such as nuts, sweets, chocolates and hand-made crafts as souvenirs. The second floor of the hall still serves as a meeting room for political debates and the third floor is a museum and armoury of the Ancient and Honourable Artillery Company of Massachusetts.

weekend guide to Boston
Faneuil Hall on a busy sunny day

Boston Tea Party

One of Boston’s favourite stories is of the Boston Tea Party during which colonists finally put their foot down against the British Empire. Discontent had become rife in colonial Boston after the passing of the Townshend Act in June 1767, which increased taxes upon all goods entering the colonies from Britain to help subsidise the salaries of colonial British judges and governors and ensure their continued loyalty and enforcement of British rule.

The Boston Tea Party museum

In 1773 the British government then passed the unpopular Tea Act, which granted the British East India Company a monopoly on the export of tea to the colonies to help shift surplus product and emerge from their economic difficulties and inefficiencies. When colonial American’s found out they became further enraged with the British Government, perceiving it as another example of taxation enforced without representation and fearing such a monopoly could also extend to other products. Seven ships of the East India Company departed England tin September and October of 1773 and bound for Boston, New York, Charlestown and Philadelphia however angry protests from locals saw all except the four boats bound for Boston abandoning course. When three ships full of tea arrived at Boston harbour, a local mob of up to 100 men, some dressed as American Indians, took over the vessels and dumped 342 chests of tea into the water. Following the event, drinking tea became seen as unpatriotic and led to America’s preference for drinking coffee.

Famous picture of the Boston Tea Party

The location of where the Boston Tea Party took place is at the foot of Pearl Street on the harbour. Today you can visit the Boston Tea Party museum to watch actors reenact key scenes. For a birds-eye view of the harbour head to 470 Atlantic Avenue, Independence Wharf where there is a free observation deck on the 14th floor. At the ground floor of the building there is also a mini exhibition about the history of Boston harbour.

The view from the free observation deck at 470 Atlantic Avenue
Selfie from the observation deck


Fenway Park

A guided tour at Boston’s baseball stadium, Fenway Park that is home to the local team the Red Sox, is a must when visiting Boston even if you are not a baseball fan. The Park was built over 100 years ago and remains little changed since the first baseball match was played on 20 April, 1912.  It is one of the smallest baseball stadiums today, seating just over 37,000 spectators and since 2009 almost every game held there has sold out.

weekend guide to Boston
The baseball pitch at Fenway Park

Upon entering the stadium you will see the framed baseball shirt of Boston Strong number 617 (the area code of Boston) in support of the Boston Marathon explosions which killed four people and injured many others in April 2013. In the aftermath of the explosions, Boston city refused to be frightened by the attack and regular life continued. Red Sox players had B Strong patches sewn into their jerseys in support of the city, which they wore to every game. On the one year anniversary of the explosions Fenway also held a special pre-game ceremony in which survivors and first responders on the scene were invited onto the pitch while the band played Highland Cathedral to commemorate all those impacted by the attack.

The guided tour will talk you through the various changes that have occurred at the stadium as well as show you all of its iconic features and behind the scenes, including the dressing room (known to be one of the least glamorous in the USA) and the media boxes. Ownership of Fenway Park has changed three times, with each successive change making various changes to increase capacity or improve the park, which has led to a few quirks including the infamous Green Monster, a left-field green wall located only 310-315 feet from home plate to the benefit of right-handed batters, and which contains a manually operated scoreboard. The tour also tells the stories of baseball players and fans alike that have left their impression on the history of this stadium. My favourite story was of the Lone Red Chair. This was where the longest ever homerun was hit by Ted Williams on 9 June, 1946 and ended up hitting innocent spectator Joseph Boucher on the head. Boucher later commented: “how far away must one sit to be safe in this park”?  The chair was painted red to commemorate the feat and many, many years later his son and grandson visited the park, each sitting on either side of the red chair to save a space for his memory, as they watched a game together.

The Public Library

The Boston Public Library is an impressive building in the business district of the city. It was designed by architect Charles Follen McKim who created this Palace for the People, which first opened its doors in 1895. The library’s collection contains over 23 million items that include rare books, manuscripts, musical compositions and maps.

Outside the Boston Public Library

It is a free public building for all to enjoy as well as a place of study for students and a warm haven for the city’s homeless population. When I visited in September 2014 I enjoyed the exhibition they hosted on maps and geographical aids in American classrooms during the 18th century. This included beautifully crafted handmade maps constructed in classrooms, original photographs and the humorous prints in William Harvey’s book Geography is Fun depicting Scotland and Germany as seen below.

weekend guide to Boston
Maps of Europe by William Harvey

The Public Library also host many events and tours that occur throughout the year including talks on architecture and music concerts, you can see what is happening on their official website here.


It’s the bar where everybody knows your name, according to the famous sitcom Cheers which ran from 1982 to 1993. The TV show was about the life of the workers and patrons of the fictitious Cheers Bar and it starred Ted Danson, Shelley Long, Rhea Pearlman, Kelsey Grammar, Woody Harrelson and Kirstie Alley among its key characters. Contrary to popular belief, the filming for the series mostly took place at a studio in front of a live audience, however exterior shots taken of the bar for television were of the Bull & Finch Pub that was renamed Cheers in 2002 and which is located at 84 Beacon Street, Boston MA 02108. A second Cheers pub has also been established near Faneuil Hill to capitalise on the shows fame.

Outside the famous Cheers pub

A visit to the pub on Beacon Hill is worthwhile and it is located opposite the Boston Common. You will recognise the facade immediately if you were ever a fan of the show and the interior has also been done up to resemble the bar as it appeared on TV, including plaques designating where the key characters sat. There are three different areas within the pub, the downstairs restaurant, the upstairs bar and the gift shop. Although most of the patrons are tourists, the drinks are reasonably priced. For more information about the history of the pub, visit the official Cheers Pub website here.

weekend guide to Boston
The cast of Cheers


Boston has one of the most famous city skylines in the world. What makes it interesting is it is historically colour-coded so you can roughly guess what era the buildings are from based on their colour and style. In simple terms, red-brick buildings are from the 1700’s till late 1800s, the white more elaborate buildings from mid 1800’s to early 1990’s, the harsh looking concrete buildings are mid 1990’s whilst the glass buildings are the most modern, dating late 1990’s onwards.

weekend guide to Boston
The Boston skyline by boat

Whilst in Boston I took the Architectural Boat tour, which departs from the CambridgeSide Galleria through the Charles River Boat company daily, subject to weather. The tour lasts 90 minutes and includes detailed commentary on the key buildings, bridges and sites. You can view my video of the tour below.

What struck me most about Boston’s skyline was the amount of Brutalist architecture present, which to me looks like old-fashioned concrete slabs at first glance. Brutalist architecture is one of those controversial styles that people love or hate, but mostly hate for is lack of obvious aesthetic. It is characterised by angular geometric shapes, blunt and exposed details, lack of adornment and the use of concrete. During the mid 1990s concrete had become the main choice of material for architects in Boston as opposed to in New York where new buildings were being constructed in steel. Concrete was seen as a more affordable option and Boston-based architects were highly influenced by Europe, which was also going through a concrete phase, especially in the UK. According to architect Michael McKinnell who created the Boston City Hall, there was a strong feeling for using concrete at the time because “we were particularly interested in imbuing architecture with authenticity…. concrete was the appropriate material to achieve this”. McKinnell’s Brutalist City Hall is a perfect example of how this architecture strikes chords. As seen in a recently written Boston Globe article available here, the building is described as an “atrocious waste of space… is [sic] so ugly that its insane upside-down wedding-cake columns and windswept plaza distract from the buildings true offence.” In the past decade there have been two serious proposals made to the city to demolish the building, although neither were successful.

weekend guide to Boston
Boston City Hall is an example of Brutalist architecture

Brutalist architecture prizes function over aesthetic and at first glance can be quite ugly. However I felt drawn to its lack of imagination and harsh lines as a reflection of an era past, a time where harsh reality dictated the day and poverty, race issues, gender equality, and the cold war were key themes that occupied this American society rather than frivolous decoration. My favourite example of Brutalist architecture in Boston are the Harbour Towers, two great big blocks of white concrete with symmetrically lined black-looking windows dotting each building face and a row of balconies running down the corner side which look like a chunky black zipper. They were designed by Henry N. Cobb and erected in 1971, originally as affordable housing in a poor, warehouse district close to the city. However due to its prime location on the harbour and stunning views they have now become expensive luxury condominiums.

weekend guide to Boston
The Harbour Towers in Boston

What I found to be a most odd specimen of architecture was the new headquarters of EF Education First, which was at the time undergoing construction and close to completion during my visit. The facade of the building appears cut and twisted to resemble a waterfall, which looks altogether very odd given the overall shape of the complex is a perfectly unimaginative white square.

EF Education First building has an interesting waterfall design feature
EF Education First building has an interesting waterfall design feature


Of all the US cities I have visited, the food and cuisine in Boston is the best. Located on Massachusetts Bay and connected to the North Atlantic Ocean, the specialty here is seafood. Dishes you must try include the famous Lobster Roll, which is a bread roll stuffed with fresh lobster meat that can be served hot with melted butter or cold with mayonnaise, a quahog cake which is a stuffed large clam deep fried in breadcrumbs, clam chowder, fresh and fried clams, oysters, and Boston cream pies and donuts. Many of these dishes were staple foods for the immigrants that originally settled here from England. Modern-day Bostonians love their food and there are many food trucks, food markets and food stalls where people queue to purchase their lunch and snacks throughout the day. Most of these take-away food vendors serve very well-prepared and fresh cuisine, although Faneuil Hall tends to be a little more touristy, crowded and overpriced.

weekend guide to Boston
Food trucks are popular in central Boston

Mike’s Pastry

300 Hanover Street
Boston, MA 02113

Located in the Italian district of Boston, if you’re a fan of tiramisu or cannoli this place is a must. Did I mention the cannoli? They have more than 20 different flavours of cannoli both traditional and fanciful including peanut butter, chocolate chip, strawberry, pistachio, amaretto, Oreo cookie, original ricotta and many more. They also serve a wide variety of pastries, cakes, cupcakes and gelato as well as a decent cup of coffee. The service is a little rough and slow so I’d recommend ordering to take away and sitting in the nearby courtyard of the Old North Church or outside Paul Revere’s old house to enjoy your sweet treats.

weekend guide to Boston
The best cannoli in the world is at Mikes Pastry

Neptune Oyster

63 Salem Street
Boston, MA 02113

This is the best restaurant for fresh seafood and oysters although prices tend towards the fine dining spectrum. The interior is cosy with only a handful of small tables and there is a great raw seafood bar set at the window that you can sit at and watch the chefs prepare cold seafood platters and oyster plates. Neptune Oyster is incredibly busy and they don’t accept any phone or online reservations, although you can put your name on a “waiting list” if you pop in and the restaurant is busy. As a result, consider yourself exceptionally lucky to get a table here in the evening and you will observe many other trying patrons being turned away. To ensure you don’t miss out on this great restaurant, a lunchtime visit is a safer bet.

weekend guide to Boston
The cold seafood bar at Neptune Oyster

As the name suggests, Neptune Oyster specialises in oysters and boasts over 12 varieties from the US East and West coasts costing between $2-3.5 per oyster. They have an impressive selection of other local seafood available at their raw seafood bar such as clams, razor clams, shrimp, blue crab, Maine lobster and anchovies that are served cold with various home-made sauces and dips. If you are after a simple traditional Boston meal I would recommend the hot lobster roll as it is to die for! They are incredibly generous with the lobster portion that has been perfectly cooked so it is succulent and not dry, and it is lightly coated in warm butter to complete the taste, served with a tangy yet light rocket salad. It is also worthwhile checking their daily special as well, which features a different hot fish dish for each day of the week.

weekend guide to Boston
The card for ordering your favourite oyster varieties

Salty Dog Seafood Grill & Bar

Quincy Market Building
Boston, MA 02109

If you absolutely must dine at Faneuil Hall, try the Salty Dog restaurant. Although it sits within a prime location in a big tourist trap, it has a rustic atmosphere and the food and drink is simple yet good. The restaurant has been established for more than 40 years and seats over 100 guests with indoor, outdoor and bar seating areas. If the weather is nice try sitting at the outdoor bar as the bartenders are friendly and will advise on the best dishes of the day. In terms of drinks, I just had to go for their famous Bloody Mary, which was average at best because the tomato juice was watery and there was no horseradish, although it came served with a shrimp and extra Tabasco on the side. However my meal more than made up for it. It was here I tried the Boston specialty quahog cake, which was a large, breaded and fried clam of sorts that was very tasty. I also had a platter of various fresh local oysters and clams that tasted of top quality. Whilst I didn’t order a hot main course, I observed their hot fish dishes looked tasty ad were good-sized portions.

weekend guide to Boston
Fresh oysters and quahog cake
weekend guide to Boston
A Bloody Mary at the Salty Dog


Boston has a very happening social life. The Boston Calendar is a regularly updated website that is fantastic for helping to plan your visit as it tells you of all events, concerts and happenings occurring in the city each day. One of the highlights of my visit was Friday night at the Science Museum, where you can visit the observatory on the rooftop for free to view the stars with trained staff. The view of the Boston skyline is also pretty stunning from here. I also got to catch a great local musical act, HiFidality who performed his Sounds for Freedom: Jazz for Peace Love and Prosperity at the Museum of African American History and talked about his music-making philosophy (see small clip below).

Boston also attracts many well-known comedians and I was fortunate to see the hilarious Orny Adams at Laugh Boston, located at the Westin Waterfront hotel, during my weekend in Boston. Orny is a born and raised Bostonian who has gone on to become a famous international comedian and TV celebrity and it was the first time he had returned to perform in Boston in many years. For Brits you will be able to catch Orny in London at the Wolf’s Bane Origins Convention in March 2015. Below is a YouTube video of one of his acts.

Last but not least, for art buffs don’t forget that the Boston Museum of Fine Arts is free every Wednesday evening from 4pm onwards.

I spent only a weekend in Boston but I managed to see all the main sites and enjoy a lot of great food. I hope you enjoy my weekend guide to Boston, which is a marvellous city!

One reply on “A Weekend Guide to Boston for History Lovers and Foodies”

Leave a Reply

Your email address will not be published. Required fields are marked *