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15 Ultimate Things to Do in Boston

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It’s a wicked good guide!

Narrowing down what to do in Boston can be a challenge, but while historic sights beckon left and right–and shouldn’t be missed–there’s plenty more to see and do. Bostonians are justifiably proud of their revered ballpark, their delicious food, their world-class museums and their outstanding outdoor attractions. Here are some of the ultimate things to do in the Hub.

Bunker Hill Monument, Boston, Massachusetts, USA
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Walk the Freedom Trail

One of Boston’s most famous, not to mention free, attractions is the Freedom Trail, a 2.5-mile line alternately painted red or paved in red brick which guides visitors to some of the city’s most important historic sights. Highlights along the trail, which officially includes 16 sites, are Faneuil Hall, Old North Church, the Paul Revere House, King’s Chapel and the Bunker Hill Monument. Begin a self-guided tour from Boston Common (pick up a map or download one); sign up for a free guided tour given by the National Park Service at Faneuil Hall; or book a tour with the Freedom Trail Foundation, where 18th-century costumed guides lead the way.

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Catch a Game (or Take a Tour) at Fenway

Without a doubt, Boston is a town that takes its sports seriously. Very seriously. From the New England Patriots to the Boston Bruins, from the Boston Celtics to the Boston Red Sox, this is a city of super fans. Of all the venues where sporting events are held though, none can compare to Fenway Park, which locals hold in absolute reverence. The nation’s oldest Major League Baseball ballpark, where the Red Sox have played since 1912, seems like a throwback to more innocent days, where legendary games have played out over the decades. If you can’t make it to a game, excellent tours run year-round and even get you onto the hallowed ground of the field.

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Eat a Cannoli in the North End

The North End, often called Boston’s “Little Italy,” has an assortment of riches for food lovers, and for anyone with a sweet tooth, it’s heaven. Practically every storefront in the neighborhood has something to do with food, be it a coffee shop, café, gelateria, food store, restaurant, or bakery. The classic Italian pastry, the cannoli, which is a rolled, fried pastry shell filled with sweet ricotta cheese, can be found at any number of bakeries, though every local has their favorite to recommend. Why not sample several and you be the judge? A walk down Hanover Street, the main stretch through the neighborhood, will bring you to two of the most popular, Mike’s Pastry at 300, and Modern Pastry Shop at 257.

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Eat a Lobster Roll

Nothing says “New England” more than seafood, and nothing says it better or tastier than a lobster roll. Every seafood restaurant from Maine to Massachusetts claims to have the best one, so the only thing to do is to eat as many as you can so you can decide for yourself. Whether you’re a purest and only want fresh lobster meat with butter on a hot dog roll (a classic preparation), or you prefer a little mayo and more seasonings, there’s a lobster roll for you.

Head to Boston’s waterfront where any number of restaurants beckon, from the old school James Hook & Co., which has which been selling seafood since 1925, to Legal Harborside, the flagship restaurant of Legal Sea Foods, one of Boston’s most famous restaurant companies.

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Walk Down Acorn Street in Beacon Hill

It is said that Boston’s most photographed street is Acorn Street, located in historic and picturesque Beacon Hill. While that may be simply anecdotal, it can’t be denied that the charming one-lane cobblestone street, complete with 19th-century rowhouses and gas lamps, looks like it belongs on a movie set. No matter what time of year, it’s picture-perfect. Gorgeous flowers spill from window boxes in spring and summer, carved pumpkins line the brick steps in fall, and stunning winter greens frame the houses in winter.

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Take the Architecture Tour at the Boston Public Library

Most people go to libraries to check out books, and perhaps visiting one is not on the top of your list when you’re a tourist. Don’t make that mistake in Boston. The magnificent main branch of the city’s library system, located in Copley Square, is in an 1895 Renaissance Revival building. Among the treasures hidden behind its doors is a mural series painted by none other than John Singer Sargent on the Triumph of Religion.

Other highlights, all of which are pointed out on a free tour given by the library, include murals depicting the nine muses by French artist Puvis de Chavannes; Edwin Abbey’s mural interpretation of the Holy Grail legend; and Bates Hall, the stunning 218-foot-long main reference reading room with its 50-foot-high barrel-arch ceiling.

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Ride a Swan Boat in the Public Garden

Boston’s Public Garden, located in Beacon Hill, is America’s oldest botanical garden. The 24-acre park boasts beautiful formal plantings, the world’s smallest suspension bridge, and its main attraction, an almost 4-acre pond, home to Boston’s famous Swan Boats. Astoundingly, these foot-pedal powered boats shaped like giant swans have plied the waters of the pond since 1877. No visit to Boston in the warm weather is complete without taking a ride on one (a captain supplies the foot power).

A natural follow-up to a ride is to pay a visit to the Make Way for Ducklings bronze sculptures, done by Nancy Schön, as a tribute to the 1941 classic children’s story by Robert McCloskey.

Book a Hotel

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Ice Skate on the Frog Pond in the Boston Common

The winter equivalent to a summer Swan Boat ride in the Public Garden is to take a spin on ice-skates on the Frog Pond in the adjacent Boston Common. To ice skate on the pond at night with the golden dome of the State House and twinkling lights in the trees as a backdrop is one for the memory books. The 50-acre park, founded in 1634, is the oldest public park in the United States. Locals grazed their cattle on it until 1830. The Frog Pond is situated on the site of a former natural pond, which in 1848 was turned into a fountain to celebrate the city’s new public water system.

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Spend the Day at the Museum of Fine Arts, Boston

One of the most highly regarded museums in the world, the massive Museum of Fine Arts boasts about half a million objects spanning the centuries from ancient Egypt to present-day artwork. The museum officially opened its doors in 1876, with a little over 5,500 objects. What a difference a century-plus makes! It’s best to make a game plan of what you want to see because tackling the museum in a few hours, or even a day, is impossible.

Highlights include more than 70 works by John Singleton Copley and major paintings by Winslow Homer, John Singer Sargent and Edward Hopper. Paintings aren’t your thing? African masks, Native American pottery, mummies, musical instruments, and practically any other media you can think of have a home at the museum. Daily free one-hour guided tours give a good overview.

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Visit the Boston Tea Party Ships and Museum

This hands-on interactive museum lets you channel your inner rebel and toss (fake) tea overboard in a re-enactment of the Boston Tea Party. Exhibits at the museum (which is located on Griffin’s Wharf, close to where the actual Tea Party occurred in 1773) include 3-D holograms, talking portraits, and replicas of two of the three ships on-hand that fateful night, the Beaver II and the Eleanor. Actors clad in Colonial period costumes offer commentary and lead you through the museum. If you have time, stop by Abigail’s Tea Room for a cuppa and a great view of the harbor.

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Visit Faneuil Hall

Visitors can be forgiven for thinking that Faneuil Hall Marketplace is Faneuil Hall, but it’s not; the marketplace is a complex of buildings which include Faneuil Hall, Quincy Market, North Market and South Market, all situated around a cobblestone promenade. Restaurants, shops, and buskers make it a lively scene.

Faneuil Hall was built in 1742 as a public meeting space and market. The original building burned down in 1761 and was immediately rebuilt. Over the years, many significant speeches took place there, from colonists protesting the Sugar Act in 1764 to George Washington toasting the nation on its first birthday. To this day, Massachusetts politicians hold speeches here. Inside, park rangers offer tours and advice, visitors can check out dozens of paintings of famous Americans, and there are interactive displays about Boston sights.

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Get out on the Charles River (Kayak, Canoe, Duck Boat)

Besides serving as a watery landmark between Boston and Cambridge, the Charles River offers a wealth of activities on the water, from kayaking to canoeing to splashing down in one of the city’s ubiquitous Duck Boats. You can even ride along a channel of the river in a handcrafted Venetian gondola if you choose! Other activities include learning to sail, stand-up paddle boarding, taking a leisurely riverboat tour or an architecture tour. Whatever activity you decide, it will definitely give you a different perspective on the city.

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Stroll Down Newbury Street in the Back Bay

Whether or not you’re a big shopper, Newbury Street, Boston’s version of New York’s 5th Avenue, is worth a visit. The eight-block-long street is jam-packed with upscale shops, trendy cafés, quirky boutiques, and some of the best people-watching around. Park yourself at an outdoor café, order a drink, and watch the world go by.

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Visit the Isabella Stewart Gardner Museum

One of the city’s most charming attractions is the small but lovely Isabella Stewart Gardner Museum. Isabella Stewart, a New York socialite, came to Boston in 1860 to marry John Lowell Gardner, one of Boston’s prominent citizens. In short order, Isabella set to building herself a Venetian palazzo to hold her extensive art collection. Just like she was, the collection is eclectic, with masterpieces by Titian (Europa), Giotto (Presentation of Christ in the Temple) and John Singer Sargent (El Jaleo), to name a few.

Isabella left strict instructions in her will that the building remain exactly as she left it, so visitors today can almost picture her enjoying the gorgeous gardens in her Venetian courtyard or warming her hands by one of the Renaissance hooded fireplaces.

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Eat Oysters at the Union Oyster House

Locals like to give it a bad rap, but there’s something to be said for this National Historic Landmark, which the National Park Service designated as the oldest continually run restaurant and oyster bar in the United States and the oldest standing brick building in Boston’s Georgian architecture (it was constructed in 1717).

Before it opened as a restaurant in 1826, it was a private home. Diners over the years include a veritable who’s who of the rich and powerful including Franklin Roosevelt, John F. Kennedy, and William Clinton, as well as governors, athletes, and movie stars. It is highly recommended to follow the example of Daniel Webster, a regular in the 1840s and 1850s, who sat at the raw bar and downed oysters with a brandy and water. Make sure to chat with the shuckers, some of whom have worked there for decades.