Best 5 Views in Boston

In my not at all humble opinion, Boston is the greatest city in the world. The Charles River, the old brick buildings, the leafy suburbs, the sublime climate that also happens to be excellent for building character– I could go on. . But, more than anything, more than Boston’s tremendous brainpower, artistic acumen, and otherwise fantastic personality,Boston is mind-blowingly handsome. I could sit on the MIT bridge and stare at the magnificent skyscrapers and supple curves of the winding Charles River from dawn to dusk, and I just might do that tomorrow, now that I’m getting all excited. Like any fine piece of artwork, the key to taking in Beantown’s beauty is viewing it from the right angle. With that in mind, I’ve compiled a list of the five best views of this spontaneous beauty of disorganized urban design so you can experience the rapture for yourself.

#5: Bunker Hill Monument

silhouette of high-rise buildings
Will Rhatigan | Lets Go Photo: Unsplash

While the main attraction of this Revolutionary War monument is the history of the battle that was fought here in 1776, a Boston skyline connoisseur will be most interested in the “hill” part of the monument. Standing atop on of the highest, steepest hills in the area, the monument, actually built on Breed’s Hill, provides a perfect view of the skyline from the Northeast, across the Charles river from nearby Charlestown.

#4: Longfellow Bridge on the Red Line

interior train
Will Rhatigan | Lets Go

This site is hardly worth mentioning, as Good Will Hunting has already made it famous, but no Boston views tour would be complete without it. Will Hunting looks at this view every day as he rides the Red Line from his home in Southie to his job as a custodian at MIT, often with a heavy heart as he reflects upon whatever calamities the filmmakers are putting him through. Looking out from this bridge in the middle of the city, you can see the Charles River on both sides, framing Beacon Hill and the Statehouse on one, and Back Bay and the skyscrapers on the other. This spot is best at sunset, when the Prudential and John Hancock building are framed in the orange light reflecting off of the river. For all its beauty though, I can’t help but feel somber every time I ride this section of the T– Good Will Hunting has made too deep an impact on my soul.

#3 Prospect Hill

aerial photography of pathways and tall trees at daytime
Will Rhatigan | Lets Go Photo: Unsplash

Prospect Hill is a bit further out of the city than the other views on this list, and is unfortunately best reached by car. For a panoramic, everything-at-once view of the city, though, this is far and away the best spot. Sitting in Waltham, several miles outside the city limits, Prospect Hill is quiet, and on most afternoons you’ll be all alone at the top making this a great place to bring your special someone for a romantic view of the sunrise.

#2 Arnold Arboretum

photography of brown wooden bench beside sakura tree
Will Rhatigan | Lets Go Photo: Unsplash

Walking through the thousands of different trees and flowers springing from the grass as you walk up the hill to the top of the Arboretum, you’ll already have had a beautiful day before you get to the main event. From the top you can sit at the base of an ancient maple and see a distant view of the city, smell the flowers and revel in the marvelous fact that this triumphant city of welded iron and steel is also home to some of America’s most peaceful public parks

#1 The Charles River Footpath between the Boston University and MIT Bridges (Cambridge Side)

white motorboats on dock during daytime
Will Rhatigan | Lets Go Photo: Unsplash

Easily accessible and a staple of many morning runs, this stretch of the riverside trail is simply the most beautiful view of this most beautiful city.. Across the wide Charles River Basin from Boston, this small sliver of grass lets you absorb the entire iconic skyline at once, all while sailboats and crew shells peacefully drift by. With the Prudential, John Hancock, Statehouse, and Citgo sign all in the frame, a view from this spot is one the finest works of art known to man. Enjoy the show and learn to love Boston, and remember, Boston loves you too.

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