Boston

A modern American city that proudly trades on its colonial past, BOSTON is about as close to the Old World as the New World gets. This is not to say it lacks contemporary attractions: its cafés, museums, neatly landscaped public spaces and diverse neighbourhoods are all as alluring as its historic sites. Boston has grown up around Boston Common, a utilitarian chunk of green established for public use and “the feeding of cattell” in 1634. A good starting point for a tour of the city, it is also one of the links in the string of nine parks called the Emerald Necklace. Another piece is the lovely Public Garden, across Charles Street from the Common, where Boston’s iconic swan boats paddle the main pond. Grand boulevards such as Commonwealth Avenue lead west from the Public Garden into Back Bay, where Harvard Bridge crosses into Cambridge. The beloved North End, adjacent to the waterfront, is Boston’s Little Italy, its narrow streets chock-a-block with excellent bakeries and restaurants. Behind the Common rises the State House and lofty Beacon Hill, every bit as dignified as when writer Henry James called Mount Vernon Street “the most prestigious address in America”.

364.4 Smoots (+ 1 Ear)

If you walk from Back Bay to Cambridge via the scenic Harvard Bridge (which leads directly into MIT’s campus), you might wonder about the peculiar marks partitioning the sidewalk. These units of measure, affectionately known as “Smoots”, represent the height of Oliver R. Smoot, an MIT Lambda Chi Alpha fraternity pledge in 1958. As the shortest pledge, part of Smoot’s initiation included the use of his body as a tape measure, all down the Harvard Bridge – resulting in the conclusive “364.4 Smoots (+ 1 Ear)” at the bridge’s terminus. While the marks continue to be repainted each year by LCA, the “Smoot” itself has gone global and even appears on a Google conversion calculator.

Accommodation in Boston

Good-quality, inexpensive accommodation is hard to find in Boston – any hotel room within walking distance of downtown for under $175 has to be considered a bargain. Room rates range wildly depending on the season and the day – if the rates below seem high, it’s worth calling to check the current price. On the plus side, the city has a number of good hostels, and there are some well-priced B&Bs.

To get more information about accommodation options - read our guide to the best areas to stay in Boston.

Beacon Hill

No visit to Boston would be complete without an afternoon spent strolling around delightful Beacon Hill, a dignified stack of red brick rising over the north side of Boston Common. This is the Boston of wealth and privilege, one-time home to numerous historical and literary figures – including John Hancock, John Quincy Adams, Louisa May Alcott and Oliver Wendell Holmes. As you walk, keep an eye out for the purple panes in some of the townhouses’ windows (such as nos. 63 and 64 Beacon St). At first an irritating accident, they were eventually regarded as the definitive Beacon Hill status symbol due to their prevalence in the windows of Boston’s most prestigious homes.

The Black Heritage Trail

Massachusetts was the first state to declare slavery illegal, in 1783 – partly as a result of black participation in the Revolutionary War – and a large community of free blacks and escaped slaves swiftly grew in the North End and on Beacon Hill. The Black Heritage Trail traces the neighbourhood’s key role in local and national black history and is the most important historical site in America devoted to pre-Civil War African American history and culture.

Pick up the trail at 46 Joy St, where the Abiel Smith School – the first public building in the country established for the purpose of educating black children – contains a Museum of African American History (Mon–Sat 10am–4pm; $5; 617 725 0022, afroammuseum.org). Adjacent, the African Meeting House was built in 1806 as the country’s first African American church; Frederick Douglass issued his call here for all blacks to take up arms in the Civil War. The trail continues around Beacon Hill, including a glimpse of the Lewis and Harriet Hayden House. Once a stop on the famous “Underground Railroad”, the home was owned by the Haydens who sheltered legions of runaway slaves from bounty hunters in pursuit.

The best way to experience the trail is by taking a ninety-minute National Park Service walking tour (late May to early Sept Mon–Sat 10am, noon & 2pm; mid-Sept to Nov 2pm only; free; 617 742 5415, nps.gov/boaf; Park St T).

Boston spectator sports

Boston is undeniably a sports town. Ever since the Boston Red Stockings scored their first run in 1871, the city’s devotion to baseball has raged to a nearly religious fervour. There’s no shortage of Patriots football (patriots.com), Bruins ice hockey (bruins.nhl.com) or Celtics basketball (nba.com/celtics) fans either. Baseball is treated with reverence in Boston, so it’s appropriate that the city’s team, the Red Sox (redsox.com), plays in one of the country’s most celebrated ballparks, Fenway Park. Though they compete in a stadium a long drive away, seeing a Patriots game live is a rare treat for non-season ticket holders. Both the Celtics and Bruins light up massive TDBanknorth Garden, a stadium in Boston’s West End.

Charlestown

Across Boston Harbor from the North End, historic Charlestown (“Chucktown” to residents) is a very pretty, quietly affluent neighbourhood that stands considerably isolated from the city. Most visitors only make it over this way for the historic frigate the USS Constitution (if at all), which is a shame, because the neighbourhood’s narrow, hilly byways, lined with antique gaslights and Colonial- and Federal-style rowhouses, make for pleasant exploration and offer great views of Boston. As you make the uphill climb to the Bunker Hill Monument – Charlestown’s other big sight – look toward the water for jaw-dropping vistas.

Boston drinking and nightlife

Boston has a vibrant nightlife scene that offers everything from tried-and-true neighbourhood taverns to young, trendy lounges. The live music is dominated by the very best local and touring indie bands. The free weeklies Boston Phoenix (thephoenix.com) and Dig Boston (digboston.com) are the foremost sources for up-to-date listings. Note that most establishments are officious in demanding ID.

Eating in Boston

Boston is loaded with excellent restaurants. While boiled lobster, shucked oysters and clam chowder are local favourites, the city’s dining scene also mirrors the increasing diversity of its population, with a rainbow of Indian, Mexican, Greek and assorted Asian cuisines. Studenty Cambridge has the best budget eats, while the historic north end is king of Italian – some of its bakeries and pizzerias are nearly a century old. Tremont Street, in the stylish South End, is known as “Restaurant Row”, beloved of foodies.

Fenway Park

Home to Boston’s beloved Red Sox baseball team, Fenway Park was constructed in 1912 in a tiny, asymmetrical space just off Brookline Avenue, resulting in its famously awkward dimensions. The 37ft left-field wall, aka the Green Monster, is its most distinctive quirk (it was originally built because home runs were breaking local windows); that it is so high makes up for some of the park’s short distances.

Tours of the ballpark are fun and deservedly popular, but your best bet is to come to see a game. The season runs from April to October, and tickets are reasonable.

The Freedom Trail

Delineated by a 2.5-mile-long red-brick (or paint) stripe in the sidewalk, the Freedom Trail (thefreedomtrail.org) stretches from Boston Common to Charlestown, linking sixteen points “significant in their contribution to this country’s struggle for freedom”. About half the sights on the trail are related to the Revolution itself; the others are more germane to other times and topics.

Though some of the touches intended to accentuate the trail’s appeal move closer to tarnishing it (the costumed actors outside some of the sights, the pseudo-antique signage), the Freedom Trail remains the easiest way to orient yourself downtown, and is especially useful if you’ll only be in Boston for a short time, as it does take in many “must-see” sights. Detailed National Park Service maps of the trail can be picked up from the visitor centre. Thrifty travellers take note: most stops on the trail are either free or inexpensive to enter.

Old South Meeting House

On the morning of December 16, 1773, nearly five thousand locals met at Old South Meeting House, awaiting word from Governor Thomas Hutchinson on whether he would permit the withdrawal of three ships in Boston Harbor containing taxed tea. When a message was received that the ships would not be removed, Samuel Adams announced, “This meeting can do no more to save the country!”. His simple declaration triggered the Boston Tea Party. Considered to be the first major act of rebellion preceding the Revolutionary War, it was a carefully planned event wherein one hundred men, some dressed in Native American garb, solemnly threw enough British tea into the harbour to make 24 million cuppas.

Public Garden

Boston’s most beautiful outdoor space, the Public Garden is a 24-acre botanical park first earmarked for public use in 1859. Of the garden’s 125 types of trees, most impressive are the weeping willows that ring the picturesque man-made lagoon, around which you can take a fifteen-minute ride in a swan boat. These elegant, pedal-powered conveyances have been around since 1877, long enough to have become a Boston institution.

Sweet wave

The granite Copp’s Hill Terrace, on Charter Street across from the Copp’s Hill Burying Ground’s northern side, was the place from which British cannons bombarded Charlestown during the Battle of Bunker Hill. Just over a century later, in 1919, a 2.3-million-gallon tank of molasses exploded nearby, creating a syrupy tidal wave 30ft high that engulfed entire buildings and drowned 21 people and a score of horses. Old North Enders claim you can still catch a whiff of the stuff on exceptionally hot days.

The North End

Hemmed in nearly all around by Boston Harbor, the small, densely populated North End is Boston’s Little Italy. Though the above-ground highway that once separated the area from downtown has been removed (replaced by the landscaped Rose Kennedy Greenway), the area still has a bit of a detached feeling, making it all the more charming.