Now that my time living in Boston has come to an end, I thought I’d reflect on all of my favourite things to see and do in the city.

I loved Boston. The city is laid back and charming, yet full of history, beautiful architecture, and so much to do. There is a sports fanaticism that is contagious, an easy-going spirit that lets you get into any restaurant in a sweatshirt, and yet the composed elegance of being home to Harvard and a well educated crowd. It is homey, while still being exciting.

One of my favourite things of all was how walkable the city is. Even though I lived “on the edge” of town in Fenway – I leisurely strolled downtown on the weekends, could surround myself in nature within seconds, and walk to work in 12 minutes flat. Lacking a car was never an issue, and I somehow managed to never step foot on the train.

This makes Boston a very accessible city, with the attractions of a big cosmopolitan city, but the cozy feeling of a small town. There are countless things to do in Boston, but below are some of my favourites:

 

1. Boston Public Garden: Nature in the City

Right in the heart of Boston are two adjacent parks, Boston Public Garden and Boston Common. With one street separating them, it’s easy to see both. My favorite was Boston Public Garden, which I loved to stroll through every weekend with its blossoming flowers and huge willow trees draping over the lake.

Boston Public Garden is lovely in every season. The well-manicured bushes flower all summer, but are just as beautiful in autumn when covered with fallen colored leaves.

 

2. Beacon Hill: Fanciest Place in Town

Heading north from the park is Charles Street, the main thoroughfare through Beacon Hill. Beacon Hill is perhaps the most well known neighbourhood in Boston. It is one of the most desirable (and therefore most expensive) places to live.

There’s nothing specific to do in Beacon Hill other than to go for a relaxing stroll through the charming neighbourhood. The brick row townhouses, neatly decorated facades, and cobblestone streets give it an air of dignity.

And the residents sure know how to embrace a holiday, with appropriately decorated doorsteps for every occasion:

 

3. Walk the Esplanade: Action Along the River

Hitting the end of Charles Street takes you to a wide pedestrian walkway that follows the Charles river. The Esplanade was a favourite walk of mine, meandering from Fenway to Beacon Hill or vice versa. On summer days, we would lounge on the floating docks built out onto the water to enjoy some sun. In the fall, biking or jogging below the yellow canopy of trees was a pleasure.

The Esplanade is also the place to be for many events. The Hatch Memorial Shell is an open air amphitheatre just off the Esplanade where many concerts and plays are held. On July 4th, the famous Boston Pops Orchestra performs for onlookers laying out on the grass, followed by a magical firework show. Friendly tip: there is a rehearsal on July 3rd that is much easier to get into and just as delightful!

There are also worthy stops along the Esplanade if you feel you need a rest. Night Shift Owl’s Nest is a beer garden located in a grassy patch right off the walkway. It’s common to see joggers, bikers, and rollerbladers stopping in for a refreshing drink mid-ride. Sometimes a food truck arrives to provide some snacks!

 

4. Freedom Trail & Faneuil Hall: Delve into History

Brick buildings and cobblestone streets are constant reminders that Boston is one of America’s oldest cities. The city is like a big outdoor museum, with countless statues and historic sights commemorating the city’s role in the American fight for Independence (among other events).

One easy way to see the main historic sites is by following the Freedom Trail. This 4-km walking trail is denoted by a strip of bricks you can follow from one site to another.

Boston Common and the Massachusetts State House are memorable stops along the self-guided tour, as well as Faneuil Hall. Faneuil Hall is known for hosting the first town hall meeting in all of America, and hosting many important meetings during America’s Revolutionary War involving star players like Samuel Adams.

Today, Faneuil Hall is part of a larger marketplace of four buildings which are full of various shops and fast food stalls. The grounds host numerous city festivals and daily street performers. There is no shortage of action here if you are looking for some excitement!

The numerous food stalls serve a variety of meals meant for a quick bite, most of which are pretty average. However, this is a good place to try a bowl of Boston’s famous New England Clam Chowder. Though not necessarily the city’s best clam chowder, something about eating this creamy soup out of a messy bread bowl feels very Bostonian.

 

5. The Seaport: Trendy Neighborhoods, Breweries, and Views

Not far from Faneuil Hall is Boston’s Seaport. I was told that only 5 years ago, the seaport was a huge industrial parking lot. In a short period of time, this area has been completely revitalized into the trendy neighbourhood that everyone wants to be in.

Apart from numerous restaurants and Boston’s famed breweries, the Seaport is a great area to go for a walk and appreciate sweeping views of downtown Boston.

It helps that two of Boston’s famed breweries are located here, including Trillium (which boasts a large rooftop patio which is packed every day of the summer) and Harpoon (known for its delicious pretzels – or is that just me?).

A newcomer to the group is a temporary set up by Nantucket’s Cisco Brewery. For the summer months, Cisco turns a parking lot into an outdoor beer garden with green turf, lawn games, live music and a food stand to fulfill your summer dreams. Wine and ciders are also on the menu! Even if you don’t care for a beer, it’s a great place to hang out with friends and enjoy a local band playing live.

 

6. The North End: Visit the Oldest Part of Boston

Just north of Faneuil Hall and the Seaport is Boston’s North End. This is Boston’s oldest residential neighborhood, and is sort of a “Little Italy” given its predominantly Italian population. Overall this neighborhood (as well as the Freedom Trail sites) are the most tourist heavy and crowded areas in Boston. Thus, this is an area I generally avoided.

However, I think it’s worthwhile to wander through the North End at least once to appreciate the old architecture and historic sites. Not to mention the yummy Italian bakeries such as Boca’s (which is open 24h!). Note that some will recommend dining in the North End, but I think there are better choices in Cambridge or the South End.

 

7. Isabella Stewart Gardner: If You Could Pick Only One Museum

The Isabella Stewart Gardner Museum of art is one of the more unique museums in Boston. It is the original home of art collector Isabella Stewart Gardner who, upon passing, requested for her art to be shown “for the education and enjoyment of the public forever”.

The house, which was designed as a Venetian palace, is beautiful. What makes it so special is that it was carefully designed and curated by Isabelle, and left untouched after her death. Every room is a different color and different theme, and you feel like you’re moving from one world to another as you go room to room.

The courtyard on its own is a sight to behold. I was there while the “Sonic Blossom” exhibit was underway. An operatic singer selects a visitor in the gallery at random, asking them: “May I give you the gift of song?”. If accepted, the visitor is guided into a chair in the courtyard and treated to a personal performance. The singer’s voice fills the courtyard and spills into every open window of the museum, letting you listen even if you weren’t part of the event. Every time the singing began, I felt I was part of a truly special moment!

On another note, the museum is also known for the famous 1990 unsolved heist. Two thieves, disguised as police officers, broke into the building and stole works of art valued up to $500 million dollars. They cut the art pieces right out of their frames. These empty frames have been left as is, and can still be seen in the museum today:

The stolen art included works by Rembrandt and Vermeer, felt now to be the most valuable unrecovered paintings in the world.

 

8. SoWa Open Market: A Sunday Favorite

If you ever spend a Sunday in Boston, then heading to the South End is a must. The SoWa Open Market is a huge outdoor and indoor market. Inside, you can view artist studios, galleries and vintage shops. Outside is a beer garden featuring live music, lawn games, and numerous food trucks. Several large farmers markets cover everything from food to clothing to home decor, etc.

Even if we weren’t shopping, we found ourselves at SoWa most Sundays of the summer to enjoy live music in a relaxed setting. It’s great with a group of people, as everyone can satisfy their own cravings from the rotating food trucks and featured local breweries.

 

9. Watch a Game: Sports Fanaticism at its Best

It took only a few weeks in Boston to realize the city has only two dress codes. Option 1: Sports paraphernalia, including a Red Sox jersey, Patriots hoodie, or Bruins cap. Option 2: College gear, including a sweatshirt with one’s school logo or a Patagonia zip-up engraved with your name and hospital emblem.

The endearing part of this all is the underlying unified spirit of the city. Boston is full of true sports fanatics and college kids/alumni brimming with school spirit. It’s contagious! And for this reason, attending any sports game in Boston is a thrill.

For this reason, I attended more sports games in Boston than I ever have. The first time we were in Boston a few years back, we watched our first NFL game with the New England Patriots vs the Atlanta Falcons, a rematch of the 2016 Super Bowl. We got there hours early to enjoy the most enthusiastic tailgating we’ve ever seen – complete with big screen TVs and full-sized smokers – followed by an action packed game from the 11th row (never once sitting down!).

The second time we were in city we watched a Boston College football game (a more budget friendly alternative). Crowds formed hours before the game to see the marching band lead the players across the grounds to the stadium. Students and families tailgated outside, turning the game into a whole day event. We enjoyed watching the festivities, as well as taking in the beautiful grounds of Boston College:

Of course, there is no shortage of sports teams in Boston. Hockey fans can watch the Boston Bruins, rowing fans the annual Harvard regatta, and baseball fans can enjoy the magic of Fenway Park. Which we did, on one warm summer day when the Boston Red Sox played the New York Yankees:

We watched the game in the famous and beloved Fenway Park, which is a site in itself…

 

10. Fenway: America’s Most Beloved Ballpark

Even if you are not a sports fan (ie. me), Fenway Park is definitely worth visiting. It is as much for the sports lover as the history buff. As the oldest ballpark in Major League Baseball, Fenway hasn’t changed much since it was built in 1912. The ballpark has retained a classic vibe, with its manual scoreboard, retro advertisements, and intimate seating.

The blue grandstand stadium seats are the last wooden chairs left in baseball. Admist the sea of blue is a single red chair, signifying the longest ever home run hit in Fenway in 1946.

Most famously, the park is known for the “Green Monster”, a big 37 foot high wall in left field. It was originally built because a few tall buildings near Fenway allowed fans to watch the game from their windows or rooftop. The wall was erected to prevent those who hadn’t bought a ticket from watching.

In recent years, seating was created on the Green Monster to cash in on the hype. Seats atop the wall are now some of the most expensive in the whole ballpark!

Whether you decide to take in a Boston Red Sox game or not, there are daily tours of the ballpark that we would highly recommend. The 45-minute tour is a great way to appreciate all the history contained within those green walls!

 

11. Boston Public Library: The Library That Makes You Want to Study

Speaking of notable historic buildings, the Boston Public Library is another grand work of architecture. The library was built in 1848, and was the first free city library in America.

 

12. Bow Market: Off the Beaten Path

Technically just outside of Boston in Somerville is an off-the-beaten find, the Bow Market. Bow Market was created out of an old storage building, and now features a small assortment of chefs and boutique owners around a central courtyard. There are often weekly events, such as the one we stumbled upon where they were giving away free ice cream!

 

13. The Emerald Necklace: For Nature Lovers

Draped around the cities of Boston and Brookline, just like a necklace, is a chain of parks and greenways termed the “Emerald Necklace”. The chain extends from the center of the city at Boston Common through to the Franklin Park zoo. In between are lush stops such as Jamaica Pond, Olmstead Park and the Harvard Arnold Arboretum. If you are in the mood for a peaceful stroll or a nice bike ride through the city, this is a great place to go.

Note that even if you don’t have your own bike, there are Blue Bike rentals all over the city. For just a couple of dollars, you can rent a bike and traverse the entire Emerald Necklace. Stopping off at the Samuel Adams Brewery on your way back into the city center is recommended!

 

14. Timeout Market: An Industrial-Chic Hangout

Newly opened in 2019 (on the day I arrived in Boston!) is the Timeout Market Boston. Located in a grandiose building in Fenway, this market is an indoor food hall with multiple restaurants and a bar to serve drinks. In the center are long wooden benches for communal seating, with a stage up front for various DJs and live music acts on the weekends.

Outside the Timeout Market is a large green space for lounging and weekly activities (such as free yoga, live bands, and contests). In the winter, this turns into an outdoor skating rink with rentals included!

 

15. Newbury Street: Shop Till You Drop

Newbury street is a highlight of Boston: a mix of residential, local boutiques, and well known commercial shops. On specific weekends over the summer the whole street is closed down to only pedestrian traffic, making it a pleasure to walk down.

There are numerous great stops along Newbury, many of which are favorite Boston chains. JP Licks serves delicious ice cream for those hot summer days, Flour bakery has every dessert you’ve dreamed of, and Tatte cafe is a must do. It won’t take you long to understand why all these places have long line ups during peak hours!

 

16. Eat New England Cuisine: Lobster Rolls & Clam Chowder

Boston is right on the New England coast, meaning that seafood is in no short supply. Typical cuisine consists of lobster, fresh oysters & clams, mussels, and the previously mentioned clam chowder. Bostonians take their lobster rolls seriously, and it’d be sinful to leave Boston without trying one.

Some of the best seafood places are the waterfront shacks downtown and in the Seaport. James Hook – a simple trailer with an outdoor eating space – served our favorite lobster roll.

Other places like the Barking Crab serve average food but in a lively outdoor setting (pictures below). For higher class dining, Island Creek Oyster Bar and Row34 serve great seafood as well.

 

Miscellaneous

There is no shortage of activities in Boston, and this posts lists only a few. A few other miscellaneous options include:

Explore the world renown education sites of Harvard University or MIT. Meander through the campuses on your own, or take the free student-guided tours.

Though not known for its beaches, there are plenty of options in and around Boston given its waterfront location. Castle Island is short car or bike ride from the city center, though be aware that planes do fly overhead!

You will never be lacking a place to go for a walk, including the aforementioned Beacon Hill and Esplanade. Straddling the already recommended Newbury Street, is Commonwealth Avenue (a peaceful treelined walkway through a residential area) and Boylston Street (a bustling street full of stores and restaurants, including the Prudential Mall).

If you visit Boston, I hope you have a great time enjoying the wonderful city. If you find some new sites you would recommend, feel free to share them below!