The 9 Best Things to Do in Boston

By PokerPilgrim | Aug 7, 2019
North America > United States > Massachusetts > Boston

When you grow up near a city, you sometimes take it for granted. You may figure you have all the time in the world to see the sites. That has certainly been true for us, living 30 minutes outside of Boston for the past two decades. Every time we get up the energy to make the trip into the big city, we're reminded how much we love Boston. The scope of entertainment, cultural, and scenic pleasures in the greater Boston area seems limitless. If you find yourself heading for the "Hub" (of the Universe, of course), these are our picks for the nine best things to do in Boston.

While we could share dozens of favorite activities in and around Boston, we'll stick to the highlights. One caveat: Boston is not the easiest city to drive in (an understatement of the greatest magnitude). Do yourself a favor and leave the car at home. Instead, take advantage of the aging but sufficient rail system (MBTA or the "T"). Or if budget allows, use Uber/Lyft or cabs. Nothing ruins the Boston experience more than driving in it.

Boston Common/Public Garden

The Boston Common is not only one of the best things to do in Boston - it's also free! A bucolic space in the middle of a dense urban area is always refreshing. Starting your visit to Boston in the Common will help you get a sense of the scope of the city while enjoying its more pastoral side. While the Common lacks the massive scope of New York's Central Park, it provides a similar respite from the bustling city scape. Beside the lush greenery, features include the Frog Pond, which operates in various seasons as a reflecting pool, children's spray pool, and ice rink. The Public Garden houses not only a plethora of seasonal floral offerings, but the iconic Swan Boat rides and the bronze ducks made famous in the classic children's book Make Way for Ducklings. At Christmas, the Common is transformed into a magical landscape of lights and winter cheer. Finally, if you ignored our advice to leave your car at home, some of the most reasonable parking in Boston can be found in the giant lot that lies beneath the Common.

Boston Common

Boston Common

Shopping Near the Common

Beyond its inherent beauty, the Common provides a convenient entree to Boston's high end shopping scene. The famous Newbury Street, the fashion hub of the city, intersects with the west side of the Public Garden. Here you can explore fancy boutiques, buy a $12 cupcake, or get the haircut of a lifetime. Running parallel to Newbury is Boylston Street. Boylston Street, famous as the finish line for the Boston Marathon, and for the fabulous Boston Public Library (definitely worth a walk inside), also offers Apple's flagship store, a number of large retail outlets, and some amazing dining experiences. Boyleston Street runs into the Copley Square/Prudential Center area which houses an upscale mall experience. You can peruse the chain retail stores and grab something at the food court. Or you can take a trip up to the Prudential's Skywalk Observatory and get the best view of the city from on high.

On the Common's east side, you can access the always busy Downtown Crossing. There you'll find a large Macy's and The Corner Mall, which has a very nice diverse food court. Discount shoppers will enjoy the Downton Crossing span of Primark, Old Navy, TJ Maxx and Marshalls.

Freedom Trail

The Boston Common also represents the western terminus of Boston's Freedom trail. This 2.5 mile walk, helpfully marked by a red brick line in the street, winds through much of historic Boston. Starting at the Common, you immediately come to the historic Granary Burial Ground where John Hancock, Samuel Adams and several other historical notables rest. Along the first half of the route are The Old State House, the site of the Boston Massacre, and Faneuil Hall (see below for more).

Cross into the North End, and you start the second half of the trail. Paul Revere's house and the Old North Church, of "one if by land, two if by sea" fame are a couple of the notable sites. While you're in the North end, take a break and grab a cream filled cannoli from one of the many great Italian bakeries, or stop for pizza or pasta at an Italian restaurant. Finally, you'll cross the Charles River into Charlestown, pass the USS Constitution (aka "Old Ironsides"), and end at the Bunker Hill Monument. For history junkies, there are few stretches in the country that can compete with this 2.5 mile stroll.

The Freedom Trail Foundation offers regular daily guided tours. You can also find a self-guided tour and map online at Free Tours by Foot.

Faneuil Hall/Quincy Market

Quintessential Boston pretty much starts and ends with Quincy Market.

Beyond its long history stretching back into the mid-1700s, the Faneuil/Quincy Market area provides more retail shopping and casual dining. Most enjoyable is the variety of street entertainment (e.g., jugglers, dancers, magicians) who perform here when the weather is good. Walking through the narrow corridor of the rectangular central building is a Boston requirement. Walk the full length and take it all in, and then make your dining decision. An array of cuisines are offered at Faneuil Hall, but we'd personally go the seafood route, particularly Boston chowda.

You can shark for a table in the two story rotunda in the middle of the market. Not an easy get in busy times. You may want to send a scout ahead to grab the first available table while others get the food. Sit down restaurants line the outer ring of the building, as well as others across the outer brick walking area.

On a more somber but moving note, right around the corner from Quincy Market is the New England Holocaust Memorial. Walking slowly through the six glass towers, each representing one of the major death camps embossed with the numbers of victims, provides a powerful meditative experience. Reading the quotes from victims extracts overwhelming empathy and respect for casualties and survivors of this terrible time in history.

Museum of Fine Arts

If you visit a city that boasts a world class art museum, skipping it should be a fineable offense. If you go to Chicago and skip the Art Institute, shame on you, please pay your $25 to the city clerk! Boston's Museum of Fine Arts is such an institution. While it lacks the grand scale of the Metropolitan, the unique structure of the Guggenheim, or the thematic certainty of MOMA (New York City's pacesetter 200 miles southwest), the MFA offers a comprehensive collection of both American and world art that makes it noteworthy. Consistent with Boston's place in history, it especially excels in the American notables: Sargent, Copley, Homer and the like.

Coolidge Corner Theater

If you're a movie lover, Coolidge Corner theater is definitely one of the best things to do in Boston. Coolidge Corner is a short ride on the green line to the close suburb of Brookline. While the neighborhood is a treat in itself, the Coolidge Corner Theater is a true non-profit treasure. Coolidge Corner dedicates itself to supporting both the best in current mainstream and independent film as well as historical treasures. With only three screens, Coolidge has to be selective about its films. Its main screen is a beautiful high ceilinged testament to great theaters and cinema houses of the past. Watching a film in the main theater downstairs will transport you 60 years back into the heyday of live cinema. No cushy, space-aged reclining seats here, just a wondrous environment for the film lover. If you are lucky enough to be visiting at the right time you can attend one of Coolidge's special screenings accompanied by presentation and discussion. These programs include Science On Screen, the Sound of Silents, Rewind, and Dance on Screen. So if you have time to take in a movie while visiting Boston, be sure to check out Coolidge Corner Theater's schedule while you're here.

Boston Museum of Science/New England Aquarium

If you're doing the tourist arc, the Museum of Science and the Aquarium are the two non-art "museums" that stand out. Both reside in great locations, easily accessible by T or by walking from Quincy Market or the Freedom Trail. The Museum of Science sits atop a bridge over the famed Charles River, while the Aquarium sits at the edge of Boston Harbor. We can pretty much guarantee that these two experiences will thrill everyone in your party.
The Museum of Science offers exhibits ranging from the dinosaurs to the cosmos. All elements of scientific pursuits are covered and the exhibits are meant to be enjoyed and absorbed by all. The enormous Van de Graaff generator distinguishes the Boston Science Museum from those in other cities and really must not be missed. The Science Museum also has a planetarium, IMAX theater, and even a laser show for those who would like to get off their feet for an hour.

New England Aquarium

New England Aquarium

Meanwhile, the New England Aquarium has one of the best penguin displays outside Antarctica. Who doesn't love penguins? The aquarium is a nice, moderate size: not overwhelming but with some great exhibits and an IMAX theater of its own.

Be forewarned for both the Aquarium and Science Museum: midweeks during the school year the places will be mobbed with elementary school classes.

Fenway Park

After 30 years of watching the Red Sox, I retired as an active fan when they broke The Curse in 2004. Baseball is not my favorite sport to watch, and other aspects of my life demanded my time. Having said that, Fenway Park is a magical experience for even a casual sports fan. The tradition and unique architectural aspects of Fenway make it an aesthetic pleasure, and seeing a game there is definitely one of the best things to do in Boston. The vibe of the passionate, perhaps maniacal, Red Sox fanbase truly highlights the Fenway experience. Just don't try to park there. Take the Green line and enjoy the stroll through the Fenway designed by Frederick Law Olmstead.

Harvard Square

Is Cambridge Boston? We'll let others decide. Either way, we suggest jumping on the T's Red Line and taking a peek. Harvard University, one of the world's most famous higher ed institutions, is worth the trip in and of itself. You can wander through Harvard Yard (pronounce that as you wish) and see the wild Harvard Lampoon building. Harvard has multiple museums, highlighted by the Peabody Museum of Archaeology and Ethnology and the Harvard Museum of Natural History.

Harvard Square is also a retail and dining center, although frankly not our favorite area for either in Boston. A walk through the Square on a sunny day, however will offer up some great buskers and street entertainers. The Brattle Theater may also be worth a visit if you want a couple of hours off your feet. The Brattle is a single screen old movie house that shows mostly classic domestic and foreign films, some fairly obscure.

Immediately I look at this list and say "How did I not put the JFK Library in this article?" Or the Isabella Stuart Gardner Museum? And how about venturing out on a commuter rail west to Lexington and Concord or north to Salem or Gloucester? Suffice it to say, Boston is immensely rich on so many dimensions. While we recommend the above as some of the best things to do in Boston, truly the list is endless.

Things to do North America Massachusetts United States Boston

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Written by PokerPilgrim
Our names are Paul and Heather. We are both avid poker players with a love for travel. Our dream is to spend a year traveling the country, seeing the sights, and visiting every decent poker room that we find along the way. A poker pilgrimage, if you may. In the meantime, we are dreaming, preparing, and travelling whenever we have the chance. Come follow our journey at .

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