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North America Travel United States


November 9, 2017

I couldn’t help falling in love with Boston, Massachusetts. It’s one of the oldest cities in America and its intriguing history, captivating architecture, liberalism and undeniable coolness has made it my favourite city in the United States (don’t tell New York).


Boston is a patchwork of neighbourhoods that used to be individual towns. For this reason it is remarkably diverse and fascinating to explore. Because it is such an old city, Boston is rather small compared to newer, planned cities. The streets are twisty and curvy, as opposed to a grid, and the wealth of historic architecture interspersed with nature makes it feel like a European town rather than a bustling metropolis.

The neighbourhoods of Boston reflect a high degree of multiculturalism. It has the fourth largest Chinatown in the country, one of the highest Irish populations outside Ireland, and a robust Italian community. These are some of my favourite neighbourhoods:

Beacon Hill

With brick sidewalks, gas street lamps, and Federal-style row-houses, Beacon Hill is easily one of the most gorgeous (and expensive) neighbourhoods in the city. It’s a wonderful place to explore on foot and soak up the historic ambience.

Back Bay

Affluent Back Bay is famous for its Victorian brownstone homes – some of the best-preserved examples of the style in the country. Back Bay has some fantastic shopping areas and is also home to the breathtakingly beautiful (on the inside) Boston Public Library.

North End

This small neighbourhood is the city’s oldest residential area and home to a lively Italian community. Here you will find some of the best gelato outside of Italy and Italian religious feasts, such as the Feast of Saint Anthony, are held in the streets to be enjoyed by all.

Jamaica Plain

One of Boston’s most diverse neighbourhoods, Jamaica Plain is inhabited by people representing a multitude of ethnicities, income levels, and sexual orientations. There’s an air of social consciousness and progressive thought is widely accepted.

South Boston

This neighbourhood is home to a large Irish population who immigrated to Boston following the Great Famine in Ireland. Needless to say, this is where you want to be for authentic Irish pub hopping and, if you’re lucky, a St. Patrick’s Day celebration.


Boston is definitely a walking city – it’s clean and safe and relatively compact. It also has a great subway system called “the T”, which can take you anywhere you want to go. I could spend a year in Boston and still not experience all it has to offer but here is a list of highlights I enjoyed and you might too:

The Boston Marathon

Happening since 1897, The Boston Marathon is the oldest marathon in the world. Participants run from Hopkinton to Copley Square, the midpoint being the affluent neighbourhood of Wellesley, home of the historic Wellesley College (America’s foremost academic institution for women). The students form a “scream tunnel” for athletes to run through for motivation, encouragement, and luck. Even if you’re not a runner, it’s still tons of fun to cheer on the participants from the sidelines. I’m considering doing a half marathon here to complete my 30 before 30.

The Freedom Trail

This 2.5-mile route is marked by red lines along the sidewalk and takes you through sixteen of Boston’s most historically significant sites. It’s a great way to see the city, get some exercise, and learn about Boston and the role it played in shaping the history of the country. You can do it with a guided tour or download a map or audio guide and enjoy it at your own pace.

Quincy Market

A perfect place to stop for lunch along the Freedom Trail. It’s a lively indoor market hall with over a hundred shops, including dozens of food stalls. You can get every kind of food imaginable here but I recommend seeking out some Boston specialties like Boston Cream Pie (shocker: it’s actually a cream-filled cake, not a pie) or New England Clam Chowder (“chowda” as it’s called in the local vernacular) or a lobster roll.

Faneuil Hall

Adjacent to Quincy Market, Faneuil Hall is another great place to eat, drink, or shop. It’s been a marketplace and meeting hall for hundreds of years and several historically significant events occurred here, earning it the nickname “The Cradle of Liberty”. If you stand outside and look up to the roof, you’ll see a unique weathervane featuring a giant grasshopper. It’s been there for over 250 years and there’s actually a time capsule inside its stomach containing newspapers, coins, and letters from various mayors.

Bunker Hill Monument

This monument commemorates a battle between British and Patriot forces during the American Revolution. It’s the final stop of the Freedom Trail and the view of Boston’s skyline from here is unbeatable. Take an extra moment to drink it in because after scaling the 294 steps to the top, you might need a rest.

Boston Common

Founded in 1634, Boston Common is the oldest city park in America. It has 50 acres of green grass, shady trees, running and walking paths, a graveyard, a bandstand for concerts, and even a pond that you can skate on in winter.

Boston Public Gardens

Next to Boston Common are the enchanting Boston Public Gardens. Romantic pathways meander through magnificent flower gardens overflowing with brightly-coloured, sweet-smelling blossoms. An adorable highlight of the park is the Make Way for Ducklings sculpture, which was inspired by the children’s book of the same title. Mrs. Mallard and her eight ducklings are cast in bronze and sometimes get dressed up in seasonal outfits (or sports jerseys if the Red Sox or Patriots are doing well).

Arnold Arboretum

If you find Boston Common or Public Gardens too crowded, check out Arnold Arboretum in Jamaica Plain as an alternative. It’s quieter, bigger (260 acres!) and has a wider variety of plants.

Newbury Street

If you like shopping, eating, reading, walking, or people-watching, Newbury Street is for you. It’s one of the prettiest streets in Boston and offers eight blocks of super trendy shops and boutiques. It’s a great place to blow the next three months of your travel budget or just sit in the shade of a sidewalk cafe with a latte and watch the people go by.


Something a little different than the usual tourist activities is a visit to Mapparium inside the Mary Baker Eddy Library. It’s a 30-ft diameter stained glass sphere illustrated with a scale map of the world that is illuminated from outside. From your viewpoint in the centre of the sphere, you can really understand the true size and shape of landmasses because there’s no distortion as there is on flat maps. But the cool thing is that it was built in 1935 and hasn’t been updated since then. You’ll see the now-defunct Soviet Union, Thailand labelled as “Siam”, Indonesia is simply a Dutch colony, and there’s no Israel.

Fenway Park

Home of the much-loved Boston Red Sox, Fenway Park is the oldest ballpark in Major League Baseball and one of the few remaining parks to still have real grass. The park is full of quirky features and interesting historical stories, so it might be fun to take a guided tour. Otherwise, grab a beer and a hot dog and take in a Red Sox game (just make sure you don’t even whisper the name of their sworn enemy, the New York Yankees).

Cambridge and Harvard

North of Boston, on the other side of the Charles River, is the intellectual magnet city of Cambridge. It’s home to two of the most prestigious universities in the world: Harvard University and the Massachusetts Institute of Technology (MIT).

Harvard University is the oldest university in America. It’s actually older than America itself, having been founded in 1636 while the Declaration of Independence was signed a solid 140 years later in 1776. The university offers free student-led tours of the campus and buildings, or you can grab a coffee and head out on your own. Harvard Square is a must: listen to the emerging talent of street musicians, join an outdoor chess game, or have lunch at a cafe.

If you’re really hungry, check out Bartley’s Burgers – they’ve been serving up Boston’s best burgers since 1960. You might even remember seeing it in Good Will Hunting or The Social Network. And make sure to swing by The Harvard Coop Official Bookstore to pick up some Harvard paraphernalia to decorate your home/car/dog. On the upstairs level you can feel really smart by perusing the textbooks students buy.

Cambridge is a lovely town to explore. It has lots of great bookstores – some of which double as coffeeshops – and is a very cycle-friendly city. There’s a paved pathway along the Charles River and if you go for a ride or walk along it, you might catch the MIT or Harvard rowing teams getting in a practice on the river.


Boston bars come in two flavours – Irish and sports – and it’s not hard to find a combo of both. Try the neighbourhood of South Boston to search for your favourite Irish Pub. Here’s a few to start with: L Street Tavern (scenes from Good Will Hunting were shot here), Murphy’s Law (no frills, just friendly staff and affordable pints), and JJ Foley’s Cafe (over 100 years old, it’s the oldest family-run pub in the city).

Happy hour has been illegal in Massachusetts since 1989 (an effort to prevent drunk driving), so don’t expect to see any signs for “buck a brew” specials. But there’s plenty of other ways to enjoy imbibing in Boston. For example, take a tour of one of its numerous local craft breweries. Samuel Adams is a popular one and they offer free tours (suggested donation of $2 goes directly to charity) including samples.

Another way to get your drink on without breaking the bank is to drink where poor people drink and who’s usually poor? Students. So head over to Cambridge and get drunk with the Harvard kids at any of the bars along Mount Auburn Street. This may be a good time to mention that Boston also has really good coffee, so after your night on the town, head straight to the closest Boston Common Coffee Co. for a cup of something to revive and refresh you for another day experiencing this awesome city.