A wonderfully walkable city, Boston is not shy about revealing its many delights to those who leave their hesitation at the border and dive straight into one of the oldest cities in the United States.
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Simply strolling the streets and listening to the famed accent emanating from locals is a worthwhile experience, but a little exploration will uncover a culturally diverse destination filled with a mix of historical havens and modern marvels. So lace up some comfortable shoes and begin ticking off authentic Boston activities like the ten that follow.
10 Drain a pint at the Black Rose
In a city known for its pubs, the Black Rose stands alone as a beacon of Irish hospitality and traditional fare that provides the perfect experience every time. First opened in 1976 and still yet to take a day off, this is the place to spend an evening enjoying live music with a pint in the hand and stars in the eyes.
Guinness is poured by staff experienced in the art, the cuisine stays true to its roots while branching off inventively and the stage is occupied by musicians 365 days a year, all combining to make the Black Rose an essential stop for a drop during every Boston visit.
9 Gain inspiration from the Museum of Fine Arts
One of the largest museums in North America and proudly showcasing over 450,000 pieces of striking beauty, the Boston Museum of Fine Arts rivals museums the world over thanks to its spectacular collections and regular special exhibits. Founded in 1870, the museum eventually found its home at its current location in 1909.
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Some breathtaking highlights include Ancient Egyptian artifacts, French impressionist and post-impressionist works by geniuses of the form and the largest collection of Japanese works outside of Japan. It is possible to spend days lost amongst the splendor of this incredible museum so be sure not to miss that dinner date you’ve made!
8 Take to the skies on the Skywalk Observatory
There is no second choice when it comes to finding the best view of Boston, the Skywalk Observatory atop the Prudential Tower is where the debate begins and ends. The city’s only vantage point offering a full 360-degree view, it is an awe-inspiring sight and the perfect way to cap off a trip to Boston.
It is possible to ascend to the astounding view both day and night, but the evening is generally the most popular option thanks to the stars and moon bathing the city lights in a beautiful glow that brings Boston to life.
7 Get your fix at Thinking Cup
Casting a watchful eye over the Boston Common, Thinking Cup is one of the best places in Boston to savor lovingly-crafted coffee. Serving delicious Stumptown beans in every variety - including pour-over, drip, and iced - coffee lovers won’t be able to find a single fault in this immaculate cafe.
Enjoy a light breakfast or lunch among the crowd of caffeine-cravers or grab a takeaway brew to sip slowly while walking around the enchanting surrounds that seem to brighten with every mouthful of the dark and emboldening liquid.
6 Pick a winner and cheer them on
When in Boston, do as the Bostonians do. Which means attending sport. Lots of sport. With the Red Sox playing ball at Fenway Park and the Celtics and Bruins regularly taking to TD Stadium, there will always be elite-level sport waiting to be enjoyed.
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Boston is a successful city and will not accept anything less, so get ready to be swept up in the excitement and passion of a sporting event in this truly mad city. If you aren’t seeing your own team play, it is best to just get behind Boston, who are quite likely to get the win no matter the opponent or sport.
5 Follow the founding footsteps of the Freedom Trail
Who doesn’t love a 2.5-mile walk through a beautiful city? It just so happens that this one passes alongside or through no less than 16 nationally significant historic sites in that relatively small distance.
Walkers will experience over 250 years of history along the iconic Freedom Trail, a Boston institution since 1951. It is a wondrous amalgamation of museums, churches, graveyards, parks, and historic markers that bring stories to life from the American Revolution and beyond. Each step along this trail truly does place visitors in the shoes of America’s founding fathers.
4 Join the buzz of Quincy Market
Serving the public since 1826, Quincy Market’s official name is actual Faneuil Hall Market but it’s more common title stuck in 1989 when a sign was put up to commemorate the contributions of Mayor Josiah Quincy. The market is comprised of three buildings that were designed to help with overcrowding issues in the early 19th Century.
Today it has turned into a vibrant and bustling marketplace showcasing local food, handicrafts, art, and performance spaces. It is a great meeting point for locals and tourists to bathe in the atmosphere of old-town Boston while hunting down a bargain in the food halls.
3 Just breathe in Boston Common
The oldest park in the United States, the centrally-located Boston Common dates back to 1634 and consists of 50 acres of beautiful green space always bursting with activity.
A perfect place to spend a morning before a day of exploration, it is also ideal to relax midway through that adventure or rest at its completion. There is no better time of day to spend in the Common than right now. Chat with the fearless squirrels, hang out by the frog pond or recline on a hill and enjoy one of the many events that take place here all year round.
2 Get your fill of Beacon Hill
A favorite of both Bostonians and those just visiting, Beacon Hill is a maze of ivy-covered brick buildings and cobblestones that almost feels like stepping through the wardrobe and into another time. The streets are gaslit and deceptively steep in several places, making a journey here quite the workout for curious explorers.
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You won’t be the only one taking hundreds of photos along the picturesque alleyways and pathways like the charming Acorn Street, so be prepared to wait for that perfect, unobstructed image. There is a reason so many people come here though, it is simply marvelous.
1 Sample the tastes of Little Italy
Two things need to be done when strolling the streets of Boston’s enchanting Little Italy, and they both revolve around food. First on the agenda is to grab a slice from an authentic pizzeria like Regina’s before crossing the road for a cannoli made the traditional way by Italian families for centuries.
The North End is actually the oldest Boston neighborhood and has evolved over the years from a secluded village to a settlement for American Revolutionists before becoming home to the Irish population and finally coming to rest as one of the best Little Italy’s in North America. Absolutely not to be missed thanks to its history and charm, not just the incredible food.