8 Best Sights in Boston, Massachusetts

Tides of students, tourists, and politically charged proponents are all part of the nonstop pedestrian flow at this most celebrated of Cambridge crossroads. Harvard Square is where Massachusetts Avenue, coming from Boston, turns and widens into a triangle broad enough to accommodate a brick peninsula (above the T station). The restored 1928 kiosk in the center of the square once served as the entrance to the MBTA station, and is now home to lively street musicians and artists selling their paintings and photos on blankets. Harvard Yard, with its lecture halls, residential houses, libraries, and museums, is one long border of the square; the other three are composed of clusters of banks, retailers, and restaurants.

Time in the Square raises people-watching to a high art form. On an average afternoon you'll hear earnest conversations in dozens of foreign languages; see every kind of youthful uniform from slouchy sweats to impeccable prep; wander by street musicians playing guitars and flutes; and wonder at how students reading textbooks out in the sunshine can get any work done among the commotion.

The historic buildings are worth noting. It's a thrill to walk though the big brick-and-wrought-iron gates to Harvard Yard on up to Widener Library, the University's flagship library. More than 50 miles of bookshelves snake around this imposing neoclassical structure, designed by one of the nation's first major African American architects, Julian Abele. It holds more than 3.5 million volumes in 450 languages, but is unfortunately not open to the public.

Across Garden Street, through an ornamental arch, is Cambridge Common, decreed a public pasture in 1631. It's said that under a large tree that once stood in this meadow George Washington took command of the Continental Army on July 3, 1775. A stone memorial now marks the site of the "Washington Elm." Also on the Common is the Irish Famine Memorial by Derry artist Maurice Harron, unveiled in 1997 to coincide with the 150th anniversary of "Black ’47," the deadliest year of the potato famine. At the center of the Common a large memorial commemorates the Union soldiers who lost their lives in the Civil War. On the far side of the Common is a fantastic park and newly renovated playground.

Between North and Hanover Streets, near the Haymarket, lies the Blackstone Block, now visited mostly for its culinary landmark, the Union Oyster House. Named for one of Boston's first settlers, William Blaxton, or Blackstone, it's the city's oldest commercial block, for decades dominated by the butcher trade. As a tiny remnant of Old Boston, the Blackstone Block remains the city's "family attic"—to use the winning metaphor of critic Donlyn Lyndon: more than three centuries of architecture are on view, ranging from the 18th-century Capen House to the modern Bostonian hotel. A colonial-period warren of winding lanes surrounds the block.

Facing the Blackstone Block, in tiny Union Park, framed by Congress Street and Dock Square, are two bronze figures, one seated on a bench and the other standing eye-to-eye with passersby. Both represent James Michael Curley, the quintessential Boston pol and a questionable role model for urban bosses. It's just as well that he has no pedestal. Also known as "the Rascal King" or "the Mayor of the Poor," and dramatized by Spencer Tracy in The Last Hurrah (1958), the charismatic Curley was beloved by the city's dominant working-class Irish for bringing them libraries, hospitals, bathhouses, and other public-works projects. His career got off to a promising start in 1903, when he ran—and won—a campaign for alderman from the Charles Street Jail, where he was serving time for taking someone else's civil-service exam.

Over the next 50 years he dominated Boston politics, serving four nonconsecutive terms as mayor, one term as governor, and four terms as congressman. No one seemed to mind the slight glitch created when his office moved, in 1946, to the federal penitentiary, where he served five months of a 6- to 18-month sentence for mail fraud: he was pardoned by President Truman and returned to his people a hero.

Every April thousands find a glimpse of Copley Square the most wonderful sight in the world: this is where the runners of the Boston Marathon end their 26.2-mile race. The civic space is defined by three monumental older buildings. One is the stately, bowfront 1912 Fairmont Copley Plaza hotel, which faces the square on St. James Avenue and serves as a dignified foil to its companions, two of the most important works of architecture in the United States: Trinity Church—Henry Hobson Richardson's masterwork of 1877—and the Boston Public Library, by McKim, Mead & White. The 200 Clarendon (Hancock) Tower looms in the background. To honor the runners who stagger over the marathon's finish line, bronze statues of the Tortoise and the Hare engaged in their mythical race were cast by Nancy Schön, who also did the much-loved Make Way for Ducklings group in the Public Garden. From May through October, a popular farmers' market draws crowds.

Two blocks north of Fenway Park is Kenmore Square, where you'll find shops, restaurants, and the city's emblematic sign advertising Citgo gasoline. The red, white, and blue neon sign from 1965 is so thoroughly identified with the area that historic preservationists fought, successfully, to save it. The old Kenmore Square punk clubs have given way to a block-long development of pricey stores and restaurants, as well as brick sidewalks, gaslight-style street lamps, and tree plantings. In the shadow of Fenway Park between Brookline and Ipswich is Lansdowne Street, a nightlife magnet for the trendy, who have their pick of dance clubs and pregame bars. The urban campus of Boston University begins farther west on Commonwealth Avenue, in blocks thick with dorms, shops, and restaurants.

Charming, and tucked around the corner from historic Acorn Street, Louisburg Square (don't drop the "s") was an 1840s model for a town-house development that was never built on the Hill because of space restrictions. Today, its central grassy square, enclosed by a wrought-iron fence, belongs collectively to the owners of the homes encircling it. The houses have seen their share of famous tenants, including author and critic William Dean Howells at Nos. 4 and 16, and the Alcotts at No. 10 (Louisa May not only lived here, she died here). In 1852, singer Jenny Lind was married in the parlor of No. 20. Former U.S. secretary of state John Kerry and his wife own a home here.

Known to many locals as The Prado, this makes a perfect time-out spot from the Freedom Trail. Bookended by two landmark churches—Old North and St. Stephen's—the mall is flanked by brick walls lined with bronze plaques bearing the stories of famous North Enders. An appropriate centerpiece for this enchanting cityscape is Cyrus Dallin's equestrian statue of Paul Revere. Despite his depictions in such statues as this, the gentle Revere was stocky and of medium height—whatever manly dash he possessed must have been in his eyes rather than his physique. That physique served him well enough, however, for he lived to be 83 and saw nearly all his Revolutionary comrades buried. Take a seat at one of the benches and enjoy your to-go treat from any of the North End Italian trattorias and bakeries.

About a mile northwest of Harvard Square lies Porter Square, an area that consists of several blocks along Mass Ave. that boast shopping centers and eateries. As you walk north (away from Harvard) past the heart of Porter Square, you'll find pretty much every ethnic eatery imaginable, many of them excellent and far cheaper than Harvard Square restaurants. There are also quite a few unique shops along the way, including thrift shops and music stores.

Reflecting a time when the South End was the most prestigious Boston address, this slice of a park is framed by lovely Italianate bowfront houses.