Things to Do in Boston: A First-Timer’s Guide

Boston is the easiest big city in America to fall for on a first visit. It is compact enough to cross on foot in an afternoon, old enough that the story of the American Revolution is written into its street plan, and young enough, with a quarter of a million students in the metro area every fall, that it never feels like a museum. In a single day you can follow a red-brick line past the meeting houses of the 1770s, eat cannoli in the North End and watch a game in the oldest ballpark in the major leagues. This guide covers the sights that earn a day, the neighborhoods worth a half-day, the museums, the sports and the food, the day trips that make Boston the natural base for New England, and the practical details that turn a checklist into a trip.

If you are still comparing cheap flights to Boston, read this alongside our guides to the best time to fly to Boston and whether you need a car (for the city itself, you do not). Between the three you can plan the whole trip.

Boston at a glance for first-timers

• Airport: Boston Logan International (BOS), in East Boston across the harbor, only about 5 km (3 miles) from downtown, one of the closest big-city airports in the country. The Silver Line bus, the Blue Line subway, a water taxi or a cab gets you in. See our Logan airport guide.
• Getting around: the MBTA, known to everyone as the T, runs the oldest subway in the country, and its Red, Orange, Blue and Green lines reach nearly every sight. The historic core is small and walkable, and most visitors never need a car; our car-versus-transit guide explains why.
• Money: US dollars. Massachusetts adds a 6.25 percent sales tax at the register, restaurant meals in Boston carry a slightly higher meals tax, and most clothing under a set price per item is exempt. Tipping 18 to 20 percent in restaurants is expected.
• Weather: four real seasons: cold, snowy winters with the occasional nor’easter, a late and changeable spring, warm and humid summers cooled by the harbor breeze, and a fall that is the best in the country. Our month-by-month guide has the detail.
• Where to stay: Back Bay for Newbury Street, Copley Square and the easiest all-round base; downtown and the Financial District for the Freedom Trail; the Seaport for new hotels and harbor views; Cambridge for Harvard, MIT and slightly lower weekend rates. Our Boston hotel search covers them all.

The Freedom Trail: Boston Common to Bunker Hill

The Freedom Trail is where nearly every first visit starts, and for good reason. It is a line of red brick and paint, about 4 km (2.5 miles) long, that links sixteen sites of the Revolutionary era, and you can walk it on your own for free or join one of the guided walks led by costumed guides. It begins on Boston Common, laid out in 1634 and the oldest public park in the country, and climbs past the gold-domed Massachusetts State House to Park Street Church and the Granary Burying Ground, where Paul Revere, Samuel Adams and John Hancock are buried. From there it runs past King’s Chapel and the Old South Meeting House, where the mass meeting that set off the Boston Tea Party began, to the Old State House, the oldest surviving public building in the city, with the Boston Massacre site marked outside. Faneuil Hall and the Quincy Market food hall behind it are the halfway point and the obvious lunch stop. The second half crosses into the North End for the Paul Revere House, the oldest house in downtown Boston, and the Old North Church, where two lanterns were hung in the steeple on the night of April 18, 1775, then crosses the bridge to Charlestown for the USS Constitution, the oldest commissioned warship afloat in the world, and the granite obelisk of the Bunker Hill Monument, whose 294 steps repay the climb with a view back over the city. Allow a full day. Several of the sites are part of Boston National Historical Park, whose rangers run free talks and whose visitor center at Faneuil Hall is a useful first stop.

Beacon Hill, the Public Garden and the Charles River

Next to the Common, the Public Garden is the country’s first public botanical garden and the prettiest few acres in the city: a lagoon crossed by a miniature suspension bridge, weeping willows, formal flower beds and, from spring until the end of summer, the pedal-powered Swan Boats that have been gliding around the pond since 1877. Children head straight for the bronze Make Way for Ducklings statues. North of the Common, Beacon Hill is the Boston of postcards: steep, narrow streets of red-brick row houses with black shutters and gas lamps, cobbled Acorn Street, the private green of Louisburg Square, and Charles Street at the foot of the hill with its antique shops, cafés and restaurants. Walk down from the hill to the Charles River Esplanade, the riverside park that runs west along the Boston bank, with boathouses, lawns and the Hatch Shell, where the Boston Pops play their free Fourth of July concert.

Back Bay and Copley Square

Back Bay was tidal marsh until the nineteenth century, when the city filled it in and laid it out as a grid of French-style boulevards, and it is now the most elegant neighborhood in Boston. Commonwealth Avenue runs through it with a tree-lined mall down the middle, and the brownstone mansions on either side are among the best-preserved Victorian streetscapes in the country. Newbury Street, one block south, is eight blocks of boutiques, galleries and café terraces. At Copley Square, H. H. Richardson’s Trinity Church faces the Boston Public Library, whose McKim Building is open to everyone: climb the marble staircase to Bates Hall, the grand reading room with its barrel-vaulted ceiling and green lamps, and find the courtyard with its fountain and café. The finish line of the Boston Marathon is painted across Boylston Street just outside. For a view from above, the observation floors at the top of the Prudential Tower look straight down over the whole city, the river and the harbor.

The North End, the waterfront and the Seaport

The North End is Boston’s oldest neighborhood and its Little Italy: narrow streets, laundry lines, espresso bars, bakeries and red-sauce restaurants along Hanover and Salem Streets, and, in July and August, the religious feasts where statues of the saints are carried through the streets. Come for dinner and stay for a cannoli. Below it, the Rose Kennedy Greenway is the ribbon of parks, fountains, a carousel and food trucks laid over the path of the elevated highway that was buried in the Big Dig, and it leads to the harbor. The Harborwalk follows the waterfront past Long Wharf, where ferries leave for the Harbor Islands and Provincetown, to the New England Aquarium and its giant ocean tank. Across the Fort Point Channel, the Seaport has grown in twenty years from parking lots into a district of glass towers, restaurants and the Institute of Contemporary Art, whose cantilevered building hangs over the water. On the channel itself, the Boston Tea Party Ships and Museum lets you board replica ships and throw a crate of tea into the harbor.

Neighborhoods worth a half-day

Cambridge: Harvard and MIT

Across the river and a few stops on the Red Line, Harvard Square is a crossroads of bookshops, cafés and street musicians at the gates of Harvard Yard, where you can walk among the red-brick buildings, rub the foot of the John Harvard statue and visit the Harvard Art Museums and the Harvard Museum of Natural History. MIT, two stops closer to Boston, has the Great Dome, Frank Gehry’s Stata Center, a campus full of public sculpture and the MIT Museum in Kendall Square.

The South End

The largest Victorian row-house district in the country, with bow-fronted brownstones on leafy squares, many of the city’s best restaurants along Tremont Street and Washington Street, and the SoWa Open Market of artists, food trucks and vintage stalls on Sundays from spring to fall.

Fenway and the Kenmore area

Beyond the ballpark, the Fenway neighborhood holds the Back Bay Fens, the first link of Frederick Law Olmsted’s Emerald Necklace of parks, the Fenway Victory Gardens, and two of the city’s great museums, all within a short walk of Kenmore Square.

Charlestown

Across the harbor from the North End, Charlestown has the Navy Yard, the USS Constitution and quiet colonial-era streets climbing to Bunker Hill; the small MBTA ferry from Long Wharf is the cheapest harbor cruise in town.

Chinatown and Jamaica Plain

Chinatown, between downtown and the South End, is small, dense and the place for dim sum and late-night noodles. Jamaica Plain, on the Orange Line, is leafy and relaxed, with Jamaica Pond and the Arnold Arboretum, Harvard’s living collection of trees, famous for its lilacs in May.

Museums, culture and family attractions

The Museum of Fine Arts is one of the great encyclopedic museums of the country, with outstanding Egyptian and Japanese collections, a wing of American art that includes John Singleton Copley and John Singer Sargent, and one of the best collections of Impressionist painting outside Paris; plan half a day. Around the corner, the Isabella Stewart Gardner Museum is a Venetian-style palace built around a flowering courtyard and left exactly as its founder arranged it, which is why empty frames still hang where the paintings stolen in the unsolved 1990 heist once were; anyone named Isabella gets in free. The Institute of Contemporary Art in the Seaport is the place for modern work, and the Harvard Art Museums reward a detour to Cambridge. The Museum of Science, on the Charles River Dam, has a planetarium and a famous indoor lightning show. The John F. Kennedy Presidential Library and Museum, in a striking I. M. Pei building on Columbia Point overlooking the harbor, tells the story of the Kennedy presidency. Symphony Hall is home to the Boston Symphony Orchestra and the Boston Pops, and the theater district hosts touring Broadway shows and the Boston Ballet. Our Boston events page lists what is on stage and in the arenas during your dates.

Sports

Fenway Park, home of the Red Sox since 1912, is the oldest ballpark in the major leagues, with the 37-foot left-field wall known as the Green Monster, a manual scoreboard; the season runs from early April to late September, and the ballpark offers guided tours year-round. The Celtics (basketball) and the Bruins (hockey) share TD Garden, built above North Station, from October into spring. The Patriots and the New England Revolution play at Gillette Stadium in Foxborough, about 40 km (25 miles) southwest, reached by special commuter trains on game days. The Boston Marathon, the world’s oldest annual marathon, runs on Patriots’ Day, the third Monday of April, and the whole city turns out along the route. In October, the Head of the Charles Regatta fills the river with rowing crews from around the world over a weekend. Check what is on sale in Boston for your dates before you book flights.

What to eat, and where

Boston’s food starts with the sea. Clam chowder, thick, creamy and made with quahogs, is on every menu, and the version at the oyster bars is the one to try. The lobster roll comes two ways, cold with mayonnaise or warm with butter, and everyone has an opinion. Raw bars serve local oysters from Wellfleet, Duxbury and the rest of the Massachusetts coast, and fried clams, scallops and cod are summer staples. The North End is the place for Italian, from pizza and pasta to the cannoli and sfogliatelle in the bakeries. Chinatown has the dim sum, the South End and the Seaport the ambitious new restaurants, and Cambridge and Somerville the best neighborhood spots. For something quick, Quincy Market behind Faneuil Hall is a busy food hall, the Boston Public Market near Haymarket is an indoor market of New England producers, and the open-air Haymarket produce stalls beside it run on Fridays and Saturdays. Boston cream pie was invented at the Omni Parker House hotel, which still serves it.

Boston through the seasons

Boston changes completely with the calendar, and what you do depends on when you come. Winter (December to March) is cold, often snowy, and cozy: skating on the Frog Pond on Boston Common, the holiday lights on the Common and along Commonwealth Avenue, the Celtics and Bruins at the Garden, long afternoons in the museums, and First Night celebrations on New Year’s Eve. Spring (April to May) arrives late but with a rush: the Marathon, Opening Day at Fenway, magnolias on Commonwealth Avenue, the Swan Boats back on the lagoon, lilacs at the Arnold Arboretum and, in late May, college commencements that fill every hotel. Summer (June to August) is harbor season: ferries to the Harbor Islands, the Fourth of July concert and fireworks on the Esplanade, outdoor movies and concerts, the North End feasts, and day trips to Cape Cod and the North Shore beaches. Fall (September to November) is the reason many people come: crisp days, the foliage in New England from late September to late October, the Head of the Charles, Salem’s Halloween month, pennant races at Fenway and the students back in town. Our month-by-month guide has the fare patterns that go with each season.

Boston with kids

Boston is one of the best cities in the country for children. The New England Aquarium, with its four-story ocean tank, penguins and harbor seals, and the Museum of Science are full days on their own. The Boston Children’s Museum, on the Fort Point Channel under its giant milk-bottle landmark, is excellent for under-tens. The Swan Boats and the duckling statues in the Public Garden, the Frog Pond spray pool in summer and skating rink in winter, the carousel on the Greenway and the Boston Tea Party Ships fill the rest. Older children enjoy the USS Constitution, climbing Bunker Hill and the amphibious duck tours that splash into the Charles. In summer, the ferry to the Boston Harbor Islands, where Georges Island has a Civil War fort to explore and Spectacle Island has a beach and trails, is the best day out. For families adding a road trip to Cape Cod or the mountains, our family car rental guide covers the vehicle question.

Boston on a budget

Boston hotels are among the most expensive in the country, especially in the fall, but a surprising amount of the city costs nothing. The Freedom Trail, Boston Common, the Public Garden, Beacon Hill, the Esplanade, the Greenway and the Harborwalk are all free; so are Harvard Yard, the MIT campus, the Boston Public Library, the USS Constitution and the Bunker Hill Monument. Several museums offer free or reduced-price evenings or days, and the Institute of Contemporary Art has long offered free admission on Thursday evenings; check each museum’s site before you go. Eat well for less in Chinatown, at the food trucks on the Greenway, at the Boston Public Market and in the North End’s pizza places. Stay in Cambridge, Brookline or near a T station outside the core for lower rates, and visit in January, February or early March, when rooms can cost half their October price. Compare rates by neighborhood on our Boston hotel search.

Day trips from Boston

Lexington and Concord, 30 to 40 minutes west by car, are where the Revolution’s first shots were fired on April 19, 1775: Minute Man National Historical Park links the battle road, the North Bridge and the visitor centers, and Walden Pond, Henry David Thoreau’s retreat, is a few minutes further. Salem, half an hour north by commuter rail or, in summer, by ferry, has the witch trial history, the excellent Peabody Essex Museum and a month-long Halloween festival every October. Cape Cod is the classic summer escape: beaches, lighthouses, dunes, clam shacks and, at its tip, Provincetown, reachable by fast ferry from Boston in season. Plymouth, an hour south, has Plymouth Rock, the Mayflower II and the living-history museum of Plimoth Patuxet. Newport, Rhode Island, with its Gilded Age mansions, is about an hour and a half by car, and Portland, Maine, about two and a half hours by the Amtrak Downeaster. The White Mountains of New Hampshire, two to three hours north, are the heart of leaf-peeping country in early October. Salem, Concord, Rockport and Providence are easy by train; Cape Cod, Newport and the mountains are best by car, so see our Boston car rental page. Visit Massachusetts, the state tourism office, covers the whole region, and our guides to New York and Philadelphia cover the next cities down the Northeast Corridor.

Two sample itineraries

Three days, first visit

Day one: the Freedom Trail from Boston Common to Faneuil Hall in the morning, lunch at Quincy Market, the Paul Revere House and the Old North Church in the afternoon, and dinner in the North End with a cannoli to finish. Day two: Charlestown for the USS Constitution and Bunker Hill in the morning, the Public Garden and Beacon Hill at midday, Newbury Street, Copley Square and the Boston Public Library in the afternoon, and a Red Sox game or a concert at Symphony Hall at night. Day three: the Museum of Fine Arts or the Gardner in the morning, the Red Line to Harvard Square for the afternoon, and a seafood dinner in the Seaport.

Five days, with New England

Add a day on the harbor, with the Aquarium, the Harbor Islands ferry and the Tea Party Ships, and a day trip: Lexington and Concord or Salem by train, or pick up a car for Cape Cod or Newport and return it before you head to the airport.

Practical details

• Transit: tap a contactless card or phone at subway fare gates and on buses, or use a reloadable CharlieCard; subway fares are flat and buses are cheaper. The MBTA has maps, fares and service alerts; our transit-versus-car guide goes into detail.
• From Logan: the Silver Line SL1 bus to South Station, a free Massport shuttle to the Blue Line at Airport station, a water taxi across the harbor, or a taxi through the tunnels. The Massport site covers ground transport.
• Weather: layers in spring and fall, a real coat, hat and waterproof boots from December to March, light clothing and an umbrella in summer. The National Weather Service’s Boston office has the forecast.
• Time zone: Eastern, the same as New York, Washington and Toronto.
• Entry requirements: visitors from Visa Waiver Program countries need an approved ESTA before boarding; most others need a visa. The State Department’s travel site is the authoritative source.
• Safety: one of the safest large cities in the country; the usual awareness applies around the busiest stations late at night.

Frequently asked questions

How many days do you need in Boston?

Three full days covers the Freedom Trail, Beacon Hill, Back Bay, one museum, Cambridge and a game or a show; add a fourth or fifth for the harbor and a day trip to Salem, Concord or Cape Cod.

What is the number one thing to do in Boston?

Walk the Freedom Trail, at least from Boston Common to the Old North Church. If you have one evening, make it a game at Fenway Park between April and September.

Is Boston walkable?

Extremely. The historic core, Beacon Hill, Back Bay, the North End and the waterfront are all within a half-hour walk of each other, and the T covers Cambridge, Fenway and the Seaport.

Do I need a car in Boston?

No. Parking is expensive, the streets are notoriously confusing, and the T and your feet are faster for nearly everything. Rent one only for Cape Cod, Newport or the mountains.

Is Boston expensive?

Hotels are, particularly from September to November and during graduation season in May. Many of the best sights are free, and winter rates are dramatically lower.

What is Boston known for?

The American Revolution, Harvard and MIT, Fenway Park and passionate sports fans, the Marathon, clam chowder and lobster rolls, and the most beautiful fall in the country.

Ready to go? Compare flights to Boston, find a place to stay with our Boston hotel search, and see what is on at Fenway, the Garden and Symphony Hall for your dates on our Boston events page.