A Walking Tour of Boston’s Waterfront

The Harborwalk, the JFK Library to the Wharf

The magnificent Boston skyline. Photos by Pinaki Chakraborty.
The magnificent Boston skyline. Photos by Pinaki Chakraborty.

By Esha Samajpati

Clear blue skies and a day to spare prompted my husband Pinaki and me to explore the largest city in New England, that is, Boston. The city has maintained its urban growth without compromising on its natural beauty.

Boston stands proud as the birthplace of the American Revolution and the present day hotbed of art, education and culture. For baseball fans, the city offers a taste of Red Sox history at Fenway Park.

With so much to see and do, we set off early in an effort to reach Boston by 9 a.m. Our primary intention was to walk along Boston’s scenic Harborwalk, which has been constructed to provide easy access to the Harbor and connect the waterfront neighborhoods. Some parts of it are still undergoing extension.

Getting There

John F. Kennedy Presidential Library and Museum
John F. Kennedy Presidential Library and Museum

You can fly down to the Logan International Airport or ride the Amtrak into Boston. As a cheaper alternative, you could check out bus schedules and fares at gotobus.com. If you are driving down as we did, be prepared with some change or your EZ Pass for the toll booths. It took us 2 hrs 50 minutes from our home in Danbury, Connecticut.


As we all know, parking in a bustling city is a nightmarish experience but thankfully, we found a place to park at the John F. Kennedy Presidential Library and Museum, which incidentally was our first stop.

JFK Presidential Library and Museum

Stepping into the cool interiors of the modern building overlooking the blue waters of the Dorchester Bay, we were overcome by a sense of awe and pride. Kennedy’s legacy lives there in the form of sight, sound and the occasional memorabilia.

Bikers along Dorchester Bay. The Boston Harborwalk sign-board in the forefront with the Boston skyline in the distance.
Bikers along Dorchester Bay. The Boston Harborwalk sign-board in the forefront with the Boston skyline in the distance.

For followers of fashion, there is plenty of space dedicated to Jackie Kennedy and her sense of style, apart from her various other accomplishments. The entry fee is $12 for an adult. For further information, please check out the following link jfklibrary.org.

Dorchester Harborwalk

On walking down the steps of the Presidential Library leading towards the Bay, we came upon a blue sign-board of “Boston Harborwalk” and decided to follow the paved path.

Runners, bikers, joggers, walkers, rollerbladers and dogs greeted us at every step. We followed the harborwalk right up to Fort Independence Park overlooking the Pleasure Bay and passed a few parks, cafés and beaches along the way.

It is a 5.4 mile round-trip so make sure you have the right shoes on before you start. The lovely scenery around the walk and the Boston skyline in the distance more than made up for our tired feet.

The Daily Catch

Esha at The Daily Catch with the Boston skyline in the background.
Esha at The Daily Catch with the Boston skyline in the background.

Not surprisingly, by the time the sun was overhead, we were famished. Picking up our car from the Presidential Library, we drove down to Fan Pier.

We parked there for $12 (the rate applies to the entire day) without any hassle and set off towards the John Joseph Moakley United States Courthouse which houses a famous sea-food restaurant – The Daily Catch.

On our way, we saw banners brandishing the Volvo Ocean Race but we were hungry enough to walk past the greatest sailing event in the whole wide world.

Undeterred by the sea-breeze, my husband was all for an alfresco brunch so we sat on the patio of the courthouse with the Boston skyline to provide us company.

Crews work on the gorgeous sailboats in the Volvo racing village at Fan Pier.
Crews work on the gorgeous sailboats in the Volvo racing village at Fan Pier.

My shrimp on linguine pasta with a white clam sauce was a safe choice compared to what my husband ordered. His salad plate was filled with every sea-food imaginable.

A handful of greens could be seen peeking in between heaps of calamari (squid), shrimp, mussels, scallops and clams. A dream come true for a sea-food afficionado like my husband.

By the way, my pasta was served in an ancient-looking pan with a handle, the very pan it was cooked in. I was told that it was the restaurant’s signature style. The place is owned by a friendly Sicilian family and the food is great.

Life at the Extreme

With some “extreme” sea-food inside us, we made our way into Fan Pier, right into the heart of extreme adventure.

Dubbed the world’s premier global race, the event is all about skill, endurance and passion. It is a nine-month-long event which started in Alicante, Spain in October 2008 and will conclude in St Petersburg, Russia, during late June 2009.

Sights along the Boston Harborwalk
Sights along the Boston Harborwalk

The teams sail over 37,000 nautical miles of the world’s most dangerous seas via Cape Town, Kochi, Singapore, Qingdao, around Cape Horn to Rio de Janeiro, Boston, Galway, Goteborg and Stockholm.

As you can see, Boston is the only stopover in North America. For three weeks, Fan Pier was transformed into a race village with live entertainment, information booths, interactive race experience, in-port racing and of course, the beautiful boats being worked on in full view of us awestruck land-dwellers.

Some of these boats had endured more than thirty days of sea at a stretch and needed to be repaired and touched up with precision and care. For more details on the event, you could check out volvooceanrace.org.

The Institute of Contemporary Art

The Institute of Contemporary Art
The Institute of Contemporary Art

One of the iconic structures on Boston’s waterfront, the ICA is home to ideas that have refused to follow the beaten path. Stop by for a visit and you won’t be disappointed. Visit icaboston.org for details on hours and fees.

Rowes Wharf and Central Wharf

Stepping out from the ICA, we started walking towards Rowes Wharf and found ourselves in the midst of the bustle of Boston.

We realized that the solitude of Dorchester Bay had been replaced by a busier neighborhood, adding a touch of variety to the harbor walk.

Soon we reached the New England Aquarium in Central Wharf which boasted of whale watching, 3D shows and much more. Founded in 1969, the New England Aquarium is a global leader in ocean exploration and marine conservation.

The brick-walled splendors of Long Wharf
The brick-walled splendors of Long Wharf

But the long line of tour buses made us change our mind so we continued walking on the red-bricked pavements soaking in the spirit of a city steeped in history, yet modern in every step of life.

Long Wharf

Before long, we came upon The Chart House Restaurant on Long Wharf with its identical shutters and old European charm.

Walking past delightful sidewalk cafes filled with people laughing and eating, we stopped to take in the luxury yachts, cruise boats and commuter boats dotting the calm cool waters of the Boston Inner Harbor.

Emack & Bolio’s Ice Cream

Time flies in Boston and, sure enough, it was nearly 5 p.m. so we headed back into State Street and got ourselves chocolate ice-creams from Emack & Bolio’s. They have recently been voted the best by Zagat and certainly have no trouble living up to their reputation.

Emack & Bolio's Ice-cream shop on State Street
Emack & Bolio’s Ice-cream shop on State Street

There is one problem though. They don’t accept cards so make sure you have enough cash or else you could hop across the street to an ATM.

Walking with an ice-cream cone on a sunny afternoon is not a smart move for someone wearing a white t-shirt. Sure enough, I found myself struggling with melted chocolate.

A passerby noticed my predicament and handed me a packet of wet-tissue, a very nice gesture coming from a perfect stranger. After thanking her and wiping myself free of gooey chocolate, we walked back by the majestic arches of the Boston Harbor Hotel in Rowes Wharf.

Minutes later, we were back to our car in Fan Pier.

Leaving Boston

It is not easy to leave behind a city filled with wonders of both land and sea, nature and man. There were lots left to explore but nonetheless, the day did offer us a brief glimpse into “America’s Walking City,” surely a deserving nickname.

Esha Samajpati


Esha Samajpati is an advertising consultant who loves to travel and write. She authors a blog on advertising trends called The Business of Advertising and a travel blog called Miles to Go.

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