20 great things to do in Boston

1. Defy gravity in a house of glass

The cube of metal and glass that houses the Institute of Contemporary Art is Boston's most daring piece of architecture and a hub for challenging art works. Inside the ICA's translucent glass skin are galleries, a theatre, a café and a bizarre downward-sloping mediatheque. View it from the harbour where the cube shape transforms into a cascading stairway topped by the cantilevered galleries and you can see how the boardwalk peels up from the ground to encircle it.

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2. Celebrate 'victory' on Bunker Hill

'Don't fire till you see the whites of their eyes' Yankee commander Colonel William Prescott ordered his troops at the Battle of Bunker Hill, the first major conflict of the American Revolution. While not technically a success for the Americans – the British won – they commemorate the first fight for American freedom with a 221ft granite obelisk. Tour guides, displays of weaponry, a 360-degree painting of the battle and an enormous diorama of fighting soldiers all attempt to recreate the atmosphere. Climb the monument's 294 steps for a breathtaking view of Boston.

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3. Hug a tree

Set in a beautiful sprawling 265-acre park, the Arnold Arboretum is a living museum of over 7,000 specimens of trees and plants. It's one of the world's leading centres for plant study and is also open to the public with free guided tours on designated days. In the spring, the Arboretum explodes with blossom. If you're there in May, don't miss Lilac Sunday, a day-long celebration of the fragrant, flowering shrub.

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4. Marvel at American art

Wander past Monets, Egyptian relics and modern American masterpieces in the neoclassical Museum of Fine Arts. American, French and Japanese art are trump cards in a rich globe-spanning collection. As well as the vast permanent collection, presented in an accessible way with a contemporary eye for design and placement, the MFA hosts major temporary exhibitions on such diverse themes as couture fashion and Spanish art during the reign of Philip III and Edward Hopper.

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5. Descend six feet under

With six 17th century burial grounds in the city alone, Boston is the final resting place for many ancient New England celebrities, from Benjamin Franklin's parents to a judge at the Salem Witch Trials. The gravestones of the Granary Burying Ground bear the famous names of the Declaration of Independence signatories John Hancock and Samuel Adams. Look out for the tombs of the victims of the Boston Massacre.

6. Order your pancakes fluffy and your lobster stewed

Chilli dogs, fluffy omelettes and fluffier pancakes are on the menu at Charlie's Sandwich Shoppe, a haven of old-school Bostonian cooking at its heartiest, and greasiest. It's not just the food that oozes old-style Americana, the restaurant itself is a memorial to a byone age: chrome stools line the counter, oilcloth covers the tables and yellowed photos of famous customers plaster the walls.

For more polished New England cuisine try Locke-Ober. All carved mahogany and polished silver, the dining room here looks much as it did when it opened 130-plus years ago. Other things have changed for the better. These days, curry, wasabi, guanciale and ancho chillies find their place among the escargots, filet mignon, calf's liver and dover sole. JFK was a fan of the lobster stew.

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7. Journey to the centre of the earth

One of Boston's oddest tourist attractions; the Mapparium at the Mary Baker Eddy Library is the world's largest walk-in globe. A three-storey high ball of coloured glass, it shows an accurate but now obsolete map of how the globe divided up in 1935. Countries have come and gone, but the Mapparium remains a special experience. Words, music, and a new lighting system, capable of generating 16 million colour combinations, mix with weird acoustics to make the experience hallucinatory but somehow uplifting.

8. Have an epiphany

Unabashedly ornate, Trinity Church's carved curved arches are the centerpiece of Copely Square, and a much-loved part of the Boston skyline. Enter and wonder at the colours, as light plays through the stained glass windows (designed by the English Pre-Raphaelite painter Edward Burne-Jones) onto the murals that cover practically every inch of the walls.

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9. Walk the line

Follow in the footsteps of history by walking the city's heritage trails. For first-time visitors the Freedom Trail (www.thefreedomtrail.org) is a must; a winding red line on the pavement takes you on a 2.5 mile urban tour of the key sites of the American revolution.

The Black Heritage Trail and the Irish Heritage Trail (get a map at www.irishheritagetrail.com) trace the histories of those communities. And the Women's Heritage Trail (www.bwht.org) celebrates Boston's foremost female citizens: passing by the homes of Louisa May Alcott, the suffragette and abolitionist who wrote Little Women, and Rebecca Lee Crumpler, considered to have been the first African American doctor.

10. Slip on the beer goggles

The American Revolution was plotted in alehouses and taverns and Boston has long had a love affair with fermented beverages. There are plenty of excellent breweries around, such as the Samuel Adams Brewery, the Boston Beerworks and the Cambridge Brewing Company. Their delectable products range from copper-coloured ales, to staid nutty classics and warming barley wines. Knock on the door for a fresh pint and taste for yourself how seriously Bostonians take their beer.

11. Shop for some new oldies

Vintage threads, Japanese denim, belly-dancing outfits and more(!) can be found in Boston's eclectic vintage shops. Whether you like your new clothes to have that worn-in look, or just have a thing for 1950s pyjamas, then make your way to the Great Eastern Trading Co, or Poor Little Rich Girl on Elm Street. Shuffle through History for a well-edited collection of frocks, Bobby from Boston throws up some classic menswear and Dollar-a-Pound in Garment District is a rummager's dream.

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12. Hang out with the literati

Boston is a city of intellectuals and if you hang around at the bookstores you'll probably run into a few. Not only do the clutch of excellent bookstores stock pretty much every book you could ever want, they host interesting events as well. The Brookline Booksmith organises readings for emerging authors and big names. Antiquarian bookshop Ars Libri hosts exhibitions, and at the Grolier Poetry Book shop, poets read their latest works in a room stacked to the ceiling with books of verse.

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13. Drop in on a socialite's salon

Kooky fin-de-siecle opulence is the order of the day at the Isabella Stewart Gardner Museum: a lavish reconstruction of a 15th-century Venetian palace. Its idiosyncratic mix of paintings, sculptures, tapestries, rare books and furniture reflect its glamourously eccentric patron, Isabella Stewart Gardner.

The blue-blooded heiress supposedly inspired the character of Isabel in Henry James' Portrait of a Lady, and was much discussed in her own time for borrowing lion cubs from the zoo and wearing a Red Sox headband to the Symphony Hall. In her honour, the museum offers free entry to all Isabellas.

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14. Crack open some native shellfish

America's oldest restaurant, the Union Oyster House established back in 1826, is still open, and still shucking oysters. We don't care much for the Yankee cooking, or the tourist-trap of a gift shop so stick with the historic raw bar and allow the shuckers to ply you with Blue Points and cherrystones, best paired with a pint.

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15. Get to the basics of booze

Don't go for the wine lists but these small-time watering holes give you what you came for: no-frills boozing. The Delux Café works for a cheap drink or two, the bartenders are friendly and there's a fake Christmas tree fixtured on the bar all year round. Ultimate dive bar Tam is a Boston classic with garish neon lighting, plenty of whisky and cheap beer. It draws an eclectic crowd of admirers.

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16. Pop goes the music

The fourth of July is not just Independence Day in Boston; it's also Boston Pops Day. If you're in town, make sure to catch this American institution – an off-shoot of the Boston Symphony Orchestra – playing rousing crowd-pleasing favourites at the Fourth celebrations. The concert culminates in glorious fireworks.

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17. Change tracks to retro

If a nightclub's named Roxy, it's got to be old school. This massive venue certainly looks the part: a grand stage, an elegant marble foyer and VIP balconies. Its fantastic sound system and 3D laser light show bring it into the 21st century. Roxy specials include The Chippendales Show, Roxy All Star Fridays and EPIC Saturdays.

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18. Cheer for Pride without prejudice

Boston is a bastion of gay culture and Massachusetts was the first state in America to legalise same-sex marriage, so it's little wonder Gay Pride takes up practically the whole month of June. The key event is the riotous parade through the South End, Boston's own gay mecca.

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19. Homerun to Fenway Park

Even if you can't get tickets to a Red Sox game, you can still soak up the baseball atmosphere with a tour of Fenway Park, the beloved home ballpark of Boston's favourite team. The match field has one of the last hand-operated scoreboards in the Major Leagues, something to look out for if the game gets a little slow. Additionally, each year on Patriots Day the Red Sox stride into the stadium for a rare morning game. If you're in town for the holiday, it's a must-see.

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20. Catch a rising star

The American Repertory Theatre is one of the country's top regional theatres, and has been making waves on the international scene since 1980. Spot a cutting-edge act before it becomes really famous, or the bright new stars of the writing and directing worlds. The Repertory hosts experimental works by local luminaries who have included David Mamet, Phillip Glass and Ann Bogart. Recently they collaborated with Brechtian punk cabaret artists The Dresden Dolls on hit show The Onion Cellar.

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