What to See in Boston Today: Freedom Trail, Free Events & Walking Tours

Boston: One of America’s Greatest Cities

Bostonians may tell you that the long-lived nickname of this historic city, “Beantown”, isn’t particularly endearing to them, but there is one thing that Boston residents and visitors can agree on – this small and energetic city is one that all Americans can be proud of.

The Beantown name comes from the dish of slow-cooked, molasses-sweetened bean dish that was a staple back in colonial times. While visitors may still use it on occasion, Boston locals prefer to talk about their sports teams including the Red Sox baseball team and Celtics of the National Basketball Association, and the more than 100 colleges such as Harvard, MIT, Wellesley, and Tufts that call the Boston area home.

With a storied history dating back to 1630, nearly 150 years before American independence, Boston offers a multitude of things to see and do to satisfy every kind of traveler.

The Best Things To See & Do in Boston - Freedom Trail

Walking the Freedom Trail ranks right up there with the best things to do in Boston, for individuals, couples, or families with kids who can handle the 2.5 mile walk. There is no better way to learn about the American Revolution than to visit the 16 historic spots including meeting halls, churches and other landmarks that comprise the walk.

Following the Freedom Trail is easy on your own simply by following the red brick path at your feet. The trail starts at Boston Common, ending at Bunker Hill and the USS Constitution. While there are guided tours of the Freedom Trail, making use of your smartphone and perhaps a little pre-walk research makes this experience free of charge. Some of the attractions along the way may require an admission fee, but the trail can be completed without them if you choose.

In addition to the Boston Common/Public Garden area, walkers will pass through downtown and the North End, site of the North Church of Paul Revere fame (“one if by land and two if by sea….”), before ending in Charlestown. Especially interesting is the Granary Burial Ground where Benjamin Franklin, John Hancock, Samuel Adams, Paul Revere, and many other notable early Americans are buried.

USS Constitution

Visit the USS Constitution, also known as “Old Ironsides”, at the Charlestown Navy Yard on Boston’s waterfront. The three-masted wooden hull U.S. Navy frigate was launched in 1797 and is best known for capturing numerous British merchant and warships during the War of 1812. While the ship was retired from active service in 1881, she made a 90-port, three year tour of the U.S. in 1934. In 1997, at the age of 200, the Constitution sailed in various presentations to honor her service to the nation. Today, the ship is the central focus of the USS Constitution Museum which offers tours hosted by active service Navy sailors.

Tour Fenway Park(or attend a Red Sox game)

The oldest stadium in Major League Baseball, Fenway Park opened in 1912 as the new home of the Boston Red Sox. Whether you are a baseball/sports fan or not, you will find the hour long tour of this historic facility to be utterly amazing.

The public guided tour is available daily during non-game days, and up until three hours prior to the first pitch on game days. Visitors are led throughout the ballpark with stops at the 37-foot high Green Monster wall in left field, both outside and inside the scoreboard which is to this day maintained by a person stationed inside during games. The unique outfield bleachers and Pesky’s Pole in right field, named for former player and manager Johnny Pesky, and the Red Sox historic museum are other points of interest.

If you are lucky enough to plan your Boston visit when the Red Sox are in town, grab some tickets (purchase online in advance to avoid disappointment) and prepare to have the time of your life.

Shop on Beautiful Newbury Street

Whether you’re more of a window shopper or want to find something special to take home, the mile-long stretch of Newbury Street from “Mass Ave” to the Public Gardens is the place to go. Historic brownstones dating from the 19th century are home to dozens of upscale local shops, trendy cafes, restaurants, and world-class luxury brands.

Visit Some of Boston’s Incredible Museums

The Museum of Fine Arts is considered to house one of the premier art collections in the world. Size-wise it is the 20th largest art museum in the world, with more 450,000 works of art in its inventory. Included in this massive collection are 8,161 paintings, many of which are on display in the museum’s ten primary galleries. More than 1.2 million art lovers visit the museum annually, clearly making this someplace you may want to consider touring during your Boston vacation.

Located on the UMass Boston campus, the John F. Kennedy Presidential Library and Museum is fully dedicated to honoring the memory of the 35th President of the U.S. The building overlooks the water south of downtown Boston, the city where JFK launched his political career on the way to historic greatness.

JFK’s life, which was cut short by an assassin on November 22, 1963, was dedicated to leadership and public service. Permanent exhibits include Young Jack, the creation of the Peace Corps, the Nixon-Kennedy television debate, his family – wife Jackie, daughter Caroline, and son JFK, Jr., the Robert F. Kennedy (his younger brother) years as the U.S. Attorney General, and Liftoff: the US Space Program.

Not to be overlooked is the incredible Isabella Stewart Gardner Museum, considered one of the most important personal art collections in the world. Works acquired by Gardner were first exhibited in 1903, including Italian Renaissance art, textiles, French paintings from the 19th century, and am amazing array of Chinese sculpture. When she died in 1924 she left explicit instructions that no changes be made to the permanent art displayed and that the museum should forever be accessible for the “enjoyment and education of the public forever.”

Boston Central Library Building in Copley Square

Bibliophiles won’t want to miss the opportunity to see this architectural masterpiece which is the main branch forthe oldest public library in the U.S. Opened in 1848, the incredible interior is open to self-guided tours during public access hours. It’s amazing how quiet a building with hundreds of visitors that is also a favorite of local students, can be.

Explore the North End Neighborhood

Boston’s North End is where you want to be if Italian food is your plan. One of the oldest neighborhoods in town, you will find a vast array of cafes, full-service restaurants, pizza places, and bakeries.

Three of our long-time favorites are Tre Monte which has another location in suburban Woburn, Carmelina’s, and Mamma Maria. But no matter where you end up, you will enjoy some of the finest Italian cuisine outside of Italy. We cannot emphasize enough…..MAKE YOUR DINNER RESERVATIONS AS EARLY AS POSSIBLE, to avoid disappointment.

Faneuil Hall Marketplace and Quincy Market

As one of the ten top tourist destination in the U.S., Faneuil Hall Marketplace and the adjacent Quincy Market Colonnade are a must-visit part of Boston. This is the top spot for visitors and locals to congregate for a diverse shopping experience and to enjoy a fantastic meal. With more than 80 retailers including local shops and national brands, you won’t have any difficulty finding gifts to bring home and of course, something special for yourself, too.

As the first food hall in the country, Quincy Market offers so many dining options that you may have to come back here multiple times. With 30 casual and sit-down restaurants in-house, there is something for everyone to satisfy everyone’s appetite. The vibe here is beyond energetic, with live musicians frequently performing in the central rotunda.

Some of our favorites include the Boston & Maine Fish Company, The Boston Chipyard, Boston Chowda, DalMoros Fresh Pasta to Go, mmMac N Cheese, Regina Pizzeria, and Wicked Lobsta. If you’re still looking for something different there’s sushi, Asian food, Greek food, an Irish pub, and Mexican specialities, pokey bowls, babka, organic options, and much, much, more. Come very hungry as this place is a foodie heaven.

Hang Out at Boston Common and the Public Garden

The oldest public park in America is a beautiful 50 acres of lawn and trees in the heart of Boston. There are beautiful paths to stroll, several historical landmarks, and the gold plated dome of the Massachusetts State House directly across the street will enhance your visit, and photo opportunities.

The adjacent Public Garden is another beautiful area to savor, especially during the warmer months. From April to September there are swan boat rides that kids will especially enjoy. On the west side of the pond is the bench made famous in the Robin Williams film, “Good Will Hunting”. And don’t miss the “Make Way for Ducklings” sculpture in the northeast corner of the park. The Freedom Trail passes through both parks.

The New England Aquarium

The New England Aquarium, home to more than 20,000 residents of the sea, is a highly recommended museum that is especially enjoyable if you are bringing the kids to Boston. There’s a floor-to-ceiling saltwater ocean tank filled with hundreds of sea creatures, and the open-air penguin exhibit is always a crowd favorite.

Museum of Science

Across the Charles River in Cambridge is the world-class Museum of Science that offers exhibits that educate and fascinate visitors. An especially popular venue for families traveling with kids, the MOS offers an array of permanent and temporary exhibits that are perfect for an indoor day while in Boston. Visitors marvel at the triceratops dinosaur fossils, Hall of Human Life, Arctic Adventure, Exploring AI, and many other incredible exhibits.

Harvard University and Massachusetts Institute of Technology

It isn’t often that taking a student-led tour of a famous university is even an option for vacationers. But that is exactly what Harvard University and MIT offer visitors. Harvard is the oldest (1636) in the U.S., with a stunning campus in the heart of bustling Cambridge.

We highly recommend booking the hour-long tour, as well as leaving ample time to explore the local neighborhood. Dozens of boutiques and dining spots are nearby, and the Harvard/MIT Coop, a store operated jointly by the two schools, is the place to purchase clothing and other items with the school’s logos.

Time permitting, Harvard’s four museums are well worth a visit and located within five minutes of each other. Choose your personal interests: Harvard Museum of National History, the Peabody Museum of Archaeology & Ethnology, the Harvard Museum of the Ancient Near East, and the Collection of Historical Scientific Instruments.

Walk along the Charles River

If you’re in the mood for some outdoors quiet time, a walk or bike ride along the Charles River is highly recommended. The 80-mile-long river forms a natural boundary for three miles between Boston and Cambridge, offering picturesque views of both cities and an ideal way to spend part of a day away from the tourist venues.

Named for King Charles I of England, the adjacent park known as the Esplanade offers views of downtown Boston, MIT, and frequent rowing teams on the water. Best of all, this is a free activity, or quite affordable if you choose to rent a bike.

Beacon Hill

Considered by many to be Boston’s most attractive neighborhood, Beacon Hill’s historic homes date back as far as the mid-1600s. Its narrow streets are ideal for a morning stroll or stop in at one of the many local cafes on Charles Street for lunch or a beverage.

Two of the most photographed streets in Boston are located on Beacon Hill. Be sure not to miss Mount Vernon Street and Acorn Street, where stunning townhomes and elegant decorations will surely catch your attention.

The Beacon Hill Historic District is on the U.S. National Register of Historic Places and is a U.S. National Historic Landmark District.

Union Oyster House

Not only is the Union Oyster House the oldest restaurant in Boston, but it’s also the oldest restaurant continuously serving in the entire United States! Located along the Freedom Trail, the historic dining spot has been frequented by Daniel Webster, John F. Kennedy (check out the “Kennedy Booth” upstairs), Franklin D. Roosevelt, and many other dignitaries and celebrities. Best known, of course, for their oysters, the restaurant offers a wide variety of seafood, and an incredible New England clam chowder.

View Boston Observation Deck

High above the city is View Boston, a 360-degree observation deck with indoor and outdoor viewing platforms with stunning views of downtown, the Charles River, MIT and Harvard, Logan International Airport, and the sparkling coastline that stretches indefinitely to the north and to Cape Cod to the south. Located on floors 50-52 of the Prudential Center which is known locally as “The Pru”, floor to ceiling glass allows for panoramic views during the day or at night.

Nearby Places to Visit in Suburban Boston

Lexington is known as the place where the first shot of the American Revolution was fired. The suburban Boston town can be found about 30 minutes northwest of downtown. Tour Lexington Common, also known as Battle Green, and see the Minuteman Statue and Revolutionary Monument that commemorates the opening salvo with the British Army.

Concord, also in the northwest Boston suburbs about 15 minutes by car beyond Lexington, is also known for its role in the American Revolution. In April 1775, the “Shot Heard Round the World” was fired here at the Old North Bridge. The British retreated but the war for independence had just begun.

Salem, home to the Salem Witch Museum and the world renowned Peabody Essex Art Museum is a fun excursion to the north. Located 30 minutes from Boston, you can learn about the 1692 Salem Witch Trials while visiting here.

Where to Stay to Get the Most Out of Boston

Boston is a compact city of just 700,000 residents, but with a metro area population just shy of five million, it ranks as the 10th largest urban center in the U.S. Choosing where to stay for a Boston vacation can seem overwhelming, but our suggestion is to stay as close as possible to the city center as so much that the city offers is walkable.

Using Travelated as our preferred hotel booking website, visitors can find scores of hotels in all price ranges, and no, Boston doesn’t have to cost you an arm and a leg. While the city can certainly be pricey with no shortage of five-star luxury properties such as the Boston Harbor Hotel or the Hotel Commonwealth, there are also an abundance of mid-range hotels that are noticeably more affordable. Consider the Studio Allston Hotel Boston, AC Hotel by Marriott Boston Downtown, or the Revolution Hotel, which are convenient to the myriad of Boston attractions.

Whatever your travel budget looks like, Travelated has a hotel that will fit your style and not empty your wallet.

History and Incredible Food Awaits You in Boston

Boston is one of the most historic cities in the U.S. and is well worth a visit for American history buffs, art lovers, foodies, sports fans, and anyone who likes to travel. Its compactness means that having a car isn’t a necessity unless you plan to head to some of the suburban sites, and there is more than enough to keep you busy in the city for many days.

Ride the metro transit system, the “T”, to get around, or make use of Uber or Lyft ride-sharing apps to arrange transportation when needed. And most importantly, have a pair of extremely comfortable walking or athletic shoes for everyone in your party. Walking around Boston is the best way to get to know this amazing city.