From the cobblestones of the Freedom Trail to the roar of Fenway Park, Boston blends centuries of American history with world-class museums, lively neighbourhoods, riverside parks and harbour adventures, making it one of New England's most rewarding cities to explore.
Massachussetts: Boston – The Freedom Trail
🚶 About the Freedom Trail
We’d been to Boston more times than we could count on one hand, but somehow we’d never got round to doing the Freedom Trail properly, start to finish, the whole 2.5 miles of it. It’s a route that takes you past most of the places where the first proper grumbling against the British colonial government started to turn into something rather more serious. We’d dipped in and out of a few of the sights on previous trips, the way you do, but this time we said right, no half measures, we’re doing the lot. Walking boots on, and off we trotted, full of good intentions, the way the English always are before our feet start aching.
The trail itself is dead easy to follow, in theory, because someone had the sensible idea of painting a continuous red line right through the pavements and streets of the city, so all you have to do is keep your eyes down and follow the breadcrumbs, except they’re made of paint rather than bread. We have to say, it really is hard to lose the thing, though we did manage to wander off it once or twice, usually because we’d got distracted by a shop window or a coffee smell, so don’t go thinking it’s entirely foolproof, because nothing involving us and a map ever is.
Along the way there are sixteen separate historic sites to tick off, and they vary enormously in scale and significance, from grand monuments you could spend the best part of an afternoon in, to a simple marker on a pavement that you could walk straight past if you weren’t paying attention. Several of them let you go inside, usually for a small entry fee, and that’s where you really get the meat of the history rather than just a plaque and a photo opportunity. We’d recommend doing your homework before you set off, because on the day we walked it a fair few of the buildings were shut, the Paul Revere House among them, and there’s nothing more deflating than trudging all that way only to find the one place you were most looking forward to has its shutters down. Ring ahead, check the website, save yourself the disappointment.
We gave ourselves about half a day for the whole walk, starting up at Bunker Hill and working our way down through the city, and we did stop properly at a handful of the bigger sites, paying our way in and having a proper look round rather than just snapping a photo and moving on. If you wanted to do it justice and see absolutely everything in depth, you could easily turn this into a full day’s outing, and nobody would think you peculiar for doing so. Below are ten of what we’d call our own personal highlights from the whole trail, the bits that stuck with us long after we’d taken our boots off and put the kettle on.
⚔️ 1. Bunker Hill Monument
The Battle of Bunker Hill, fought on the 17th of June 1775, was the first proper set-piece battle of the Revolutionary War, and in many ways it told you everything you needed to know about how the rest of the conflict was going to play out. It took a force of around 3,000 British Redcoats, under Major General William Howe, three separate assaults to finally shift the Colonial militia out of a redoubt they’d thrown up overnight on Breed’s Hill in Charlestown, just down the road from the hill the battle is actually named after. Colonel William Prescott had been given orders to fortify Bunker Hill itself, but for reasons nobody has ever fully nailed down, he and his officers chose Breed’s Hill instead, which was lower but closer to Boston and altogether more provocative. A British Army lieutenant called Page then drew up a map of the action that managed to swap the names of the two hills around, and between his confusion and Prescott’s change of plan, the mix-up stuck for good, so the fight has gone down in history under the wrong hill entirely, which strikes us as a very British sort of muddle to leave behind.
Although the Redcoats technically won the day, they paid an eye-watering price for it, with over a thousand casualties against roughly half that on the American side, and it left the British high command rattled rather than triumphant. It’s the battle that gave us the famous line, “don’t fire until you see the whites of their eyes,” supposedly barked out by Prescott to stop his men wasting precious gunpowder on men still too far away, though historians these days reckon nobody can say for certain who actually said it, or indeed whether anyone said it at all. What the battle did prove, beyond any doubt, was that the Colonial forces could stand toe to toe with the finest army in the world and give them a properly bloody nose, even while losing. Fifty years on, in 1825, the Marquis de Lafayette himself laid the cornerstone for the granite obelisk that stands there today, and the whole thing was finally finished in 1842, standing 221 feet tall over the hill where it all began.
⚓ 2. USS Constitution
A short stroll on from Bunker Hill brings you down to Boston’s old naval dockyard, and that’s where you’ll find the USS Constitution waiting for you, looking every bit as proud as her history suggests she should. She was launched in Boston back in 1797, making her the oldest commissioned warship still afloat anywhere in the world today, and she picked up her famous nickname, “Old Ironsides,” during the War of 1812, when she took on the British frigate HMS Guerriere and came out the better of the two, much to everyone’s surprise at the time given how lopsided most naval encounters with the Royal Navy tended to be in that era.
Before you even reach the ship herself, you’ll come across a museum dedicated entirely to the Constitution’s story, and it’s well worth a wander through, covering everything from the long sweep of her naval service to what daily life was actually like for the sailors who served aboard her, the cramped quarters, the rough rations, the strict discipline, the lot. She got her famous nickname during that scrap with the Guerriere when British cannonballs were said to simply bounce off her thick oak hull, hence “Old Ironsides,” a name that stuck for good and turned her into something of a national symbol of defiance long before anyone had thought to coin the phrase “national symbol.” We only had about twenty minutes to spare, which we’ll admit was a bit of a rush job on our part, us being creatures of habit who always seem to leave ourselves short of time, but if you’ve got the luxury of a slower pace, you could happily lose an hour or more in there poring over the exhibits and getting properly absorbed in the maritime history of the place.
Once we’d finished in the museum, we headed down to see the great lady herself, and even tied up at her berth, with all her sails furled away and not so much as a breeze to fill them, she’s an absolutely commanding sight. You can only begin to imagine what she must look like out on open water with a full head of canvas up, the timbers groaning and the wind doing its proper work, because there’s something about a tall ship at rest that only hints at what she’s capable of underway. The good news is you’re allowed to climb aboard and have a proper poke around, wandering the main deck among the rigging before heading below to explore both of the lower decks, ducking your head as you go if, like us, you’re not built to eighteenth-century proportions, and it all gives you a real feel for the cramped, creaking world the crew would have called home for months on end.
⚰️ 3. Copp’s Hill Burying Ground
From the Constitution’s dockyard, we crossed back over the water and made our way along to Copp’s Hill Burying Ground, a spot named after a local shoemaker by the name of William Copp who once owned the land on which it stands, back when this whole patch of the North End was nothing more grand than orchards and pasture. It’s the final resting place of a great many of the merchants, craftsmen and ordinary working folk who made up that close-knit North End community in Boston’s earliest years, the sort of unremarkable working people whose names rarely make it into the history books but without whom the city would never have functioned at all, and walking among the old leaning headstones, with their worn lettering and crumbling slate, gives you a real sense of just how long people have been calling this particular patch of the city home.
Among the rather more notable names buried there are Cotton Mather and his father Increase Mather, two formidable fire-and-brimstone Puritan ministers who were closely tied up with the dark and shameful business of the Salem witch trials, a chapter of New England history that still casts a long shadow today, and Prince Hall, the founder of Black Freemasonry in America, a man whose legacy stretches a long way beyond Boston itself and into the wider story of civil rights. You’ll also find Robert Newman resting here, the sexton of the Old North Church who famously climbed the steeple on the night of Paul Revere’s ride and hung the two lanterns that set the whole alarm in motion, along with Edmund Hartt, the shipbuilder responsible for constructing the very USS Constitution we’d just been clambering around minutes earlier.
⛪ 4. Old North Church
Just along from Copp’s Hill stands the Old North End Church, and this is genuinely the spot where you could argue the American Revolution properly got going. Built in 1723, it’s the oldest church still standing in Boston, and it owes its fame almost entirely to one single night in 1775, when sexton Robert Newman hung those two lanterns in the steeple to warn that British troops were coming by sea rather than by land, giving us the immortal phrase “one if by land, two if by sea,” a line that’s been quoted in classrooms and pub quizzes ever since.
🏠 5. Paul Revere House
We made our way over to the Paul Revere House, fully expecting it to be shut, and shut it duly was, that day at least, which by this point in proceedings was starting to feel like a running joke at our expense. The house is run by an independent non-profit organisation these days rather than any official body, so it’s well worth checking their website before you set off, to make sure you don’t end up staring forlornly at a locked door the way we did. Built around 1680, in what was still very much a young and modest colonial settlement, the house was owned by the legendary patriot himself from 1770 right through to 1800, the same three decades that took in his famous midnight ride and the birth of the new nation, and it has the distinction of being not only the oldest surviving structure in downtown Boston but also the only official Freedom Trail site that’s actually somebody’s old home rather than a church, hall, monument or burying ground.
🕯️ 6. The New England Holocaust Memorial
This particular memorial isn’t officially part of the Freedom Trail itself, though we’d happily argue it has every bit as much to do with the idea of liberty and human dignity as anything else on the official route. It sits right alongside the trail as you walk, so it would be easy enough to stroll straight past without a second glance, but as you’re passing we’d thoroughly recommend pausing for a few minutes to take it in properly, because it’s a quietly powerful and moving place, and well worth the short detour from your stride, however eager you might be to get to the next stop.
🏛️ 7. Faneuil Hall
Faneuil Hall has earned itself the nicknames “the home of free speech” and the “Cradle of Liberty,” and with very good reason too, since it played host to America’s very first Town Meeting and went on to be the stage for countless rallies and gatherings in the years that followed. None of that grand political destiny was part of the original plan when the building first went up back in 1742, courtesy of a wealthy merchant called Peter Faneuil who funded it as a marketplace, mind you, but over the years it grew into the stage for a whole string of momentous events that helped shape the course of the nation’s history, which just goes to show you never quite know what a building’s going to end up being remembered for. Sadly for us, it was closed on the day we wandered past, much like the Paul Revere House, which by now seemed to be something of a running theme on our visit. The hall itself is owned by the City of Boston but operated as a visitor centre and historic site by the National Park Service, with their visitor centre occupying the bustling market level on the first floor and the lower level of the building, while the Great Hall proper, with all its grand portraits and panelling, sits up on the second floor for anyone lucky enough to get inside.
💥 8. Old State House & Boston Massacre Site
We’ve lumped these two together, partly because they sit right next to one another, practically sharing a doorstep, and partly because they’re so closely tied up in the same story that it would feel daft to separate them. The Boston Massacre site itself is marked at the junction of State and Congress Streets in the heart of downtown Boston, right outside the Old State House, with a small ring of cobblestones set into the pavement to show where it all happened. On the 5th of March 1770, after months and months of simmering tension over British military occupation and the various taxes being imposed on the colonists without their consent, things finally boiled over into open violence in the streets, when a crowd of angry Bostonians confronted a small detachment of British soldiers, and shots rang out. By the time the gunfire stopped, five civilians lay dead: Crispus Attucks, Samuel Gray, James Caldwell, Samuel Maverick and Patrick Carr, names that every Boston schoolchild learns by heart. Their deaths galvanised ordinary Bostonians against the Crown and forced the temporary withdrawal of British troops from the city, who didn’t dare show their faces again in any numbers until 1774.
Through massacre, revolution and the odd devastating fire that has periodically swept through the old city, the Old State House has somehow managed to survive as the oldest public building left standing in Boston. Built in 1713, long before anyone had any inkling of the trouble brewing, it once served as the beating heart of the city’s civic, political and business life, hosting everything from council meetings to public proclamations, and these days you can either explore it yourself on a self-guided wander through its creaking rooms or join an organised tour if you’d rather have someone else do the talking and the storytelling for you.
⚱️ 9. Granary Burying Ground
The Granary Burying Ground was established in 1660, making it one of the older corners of the city, and it’s the final resting place of some of America’s most celebrated historical figures, the sort of names you’ll recognise from school history lessons, which makes it well worth a slow, respectful walk through. It takes its name from a 12,000-bushel grain storage building that used to stand right next door, supplying the city in leaner years, and today the burial ground holds roughly 2,300 visible headstones, though there’s a curious mismatch between that figure and the actual number of bodies lying beneath the ground, with historians reckoning the true total runs to somewhere over 5,000 Bostonians who’ve ended up calling the Granary home in the end, packed in layers below the surface. The site was originally part of Boston Common itself, back when the boundaries between burial ground and public space were a good deal blurrier than they are now, and in the early years the livestock that grazed freely on the Common did the job of keeping the grass down around the graves as well, which is a charmingly low-tech approach to landscaping that we rather admire, even if it wouldn’t pass muster with health and safety today. It wasn’t until the Victorian era that someone finally decided to tidy the whole place up properly, rearranging the headstones into neat orderly rows so that the newfangled lawnmower, the height of horticultural technology at the time, could finally get to work without anything getting in its way.
🏢 10. Massachusetts State House & Boston Common
Our walk along Boston’s Freedom Trail came to its natural conclusion at the Massachusetts State House and Boston Common, which felt like a fitting and rather gentle place to finish, given how much weighty history bookends the whole site we’d just spent half a day traipsing around. Designed by the celebrated architect Charles Bulfinch, the ‘new’ State House, as it’s still rather quaintly known even after well over two centuries, has served as the seat of the Massachusetts state government ever since it first opened its doors in 1798, housing both the legislative and executive branches of government under its handsome golden dome, which gleams rather splendidly when the sun catches it, and standing right next to where the historic Hancock family mansion once stood before it was sadly demolished.
Directly across the road from the State House lies Boston Common, and this is no ordinary patch of municipal grass. Established way back in 1634, only a handful of years after the city itself was founded, it has the distinction of being America’s oldest public park by a considerable margin, predating anything comparable elsewhere in the country. The Puritan colonists who founded it bought the land rights to the Common’s 44 acres from William Blackstone, an Anglican minister who’d arrived in the area before any of them and earned the rather grand title of the first European settler in these parts. These days it’s the perfect spot to flop down on the grass and treat yourself to an ice cream or a cold drink once you’ve finished trudging the length of the Freedom Trail, and frankly, by that point, you’ll have thoroughly earned it.
In summary …
If you’re planning on walking the entire Freedom Trail and want to make proper stops along the way to get the full flavour of the more significant sights, then you’ll want to set aside the best part of half a day to do it justice, and possibly a good deal longer if you’re the sort who likes to linger over a good museum rather than skim past the exhibits the way some folk do. The trail itself is mercifully flat from start to finish, so there are no hills to worry about huffing and puffing your way up, which is more than can be said for some of the city walks we’ve done over the years, though you will be pounding hard pavement for several hours solid, so do yourself a favour and wear something sensible and comfortable on your feet rather than anything you’d normally save for best, however smart you might fancy looking for the photographs. Boston’s weather, it has to be said, is a fickle old thing, swinging from properly bitter, snow-laden conditions in the depths of winter to thick, sweaty humidity come the summer months, with absolutely everything else in between thrown in for good measure depending on which week you happen to turn up, so it really does pay to check the forecast carefully and pack accordingly before you set off.
Planning Your Visit to the Freedom Trail
How you choose to tackle the Freedom Trail is entirely up to you, and there’s no single correct way of going about it, despite what some of the guidebooks might have you believe. We opted to walk the whole thing in one go, starting at Bunker Hill up in Charlestown and finishing down at Boston Common, but you could just as easily flip that around and do it back to front, starting where we finished, or pick a spot somewhere in the middle and spread the whole adventure out over several days if you fancied taking things at a more leisurely pace, perhaps breaking it up with a pub lunch or two along the way, which is very much our preferred approach to most things in life. We also chose to go it alone as a self-guided tour, working things out as we went along with nothing more than a map and a bit of common sense, but if you’d rather have someone walk you through the finer points of the history and explain exactly how each individual site fits into the bigger story of the Revolutionary War, then you can just as easily book yourself onto an organised tour group instead and let them do the legwork of the storytelling.
The Best Time to Visit Massachusetts
🌸 Spring (March to May)
Spring is changeable, starting cold and slushy in March and warming into blossom by May. It’s quiet and cheaper, but weather can be unpredictable, making it best suited to flexible travellers.
What to pack: layers, a warm jacket, waterproofs, sturdy waterproof shoes, a few light tops, and a jumper.
☀️ Summer (June to August)
Summer is warm to hot, with humidity rising in July and August. Long days are perfect for beaches and trails, but this is peak season, so expect crowds and higher prices.
What to pack: breathable clothing, swimwear, sun cream, a hat, trainers, a light rain jacket, and sunglasses.
🍂 Autumn (September to November)
Autumn is widely considered the best season, with mild temperatures and spectacular foliage across the Berkshires. Crowds thin after summer, though leaf-peeping season draws its own visitors.
What to pack: a jumper or fleece, a medium jacket, layers, walking boots, a scarf, and a light hat.
❄️ Winter (December to February)
Winter brings cold, snow, and a festive atmosphere, especially in Boston. It’s the quietest and cheapest season, and good for skiing, though travel can be disrupted by snowstorms.
What to pack: an insulated coat, thermal layers, a woolly hat, gloves, waterproof boots, and a scarf.
Overall Best Time to Visit
Autumn is the overall best time to visit, combining mild weather, stunning foliage, and fewer crowds than summer. Summer suits beach lovers, winter suits festive and ski enthusiasts, and spring works for budget travellers happy to brave variable weather.
Other Things to do Whilst in Boston
1. The Isabella Stewart Gardner Museum
This museum is housed in a building modelled on a Venetian palace, built around a beautiful indoor courtyard garden that changes with the seasons. It was created by Isabella Stewart Gardner herself, who arranged every painting, tapestry and sculpture exactly as she wished, and the collection has stayed largely the same since her death in 1924. Inside you’ll find work by artists such as Titian, Rembrandt and Sargent, displayed without the usual museum labels, so visitors are encouraged to look and form their own impressions rather than read plaques on the wall. The museum is fairly compact, so a visit of an hour or two is usually enough to see the highlights, though art lovers could easily spend longer. It’s a quieter, more personal alternative to Boston’s larger museums.
- Location: 25 Evans Way, Boston, MA 02115
- Website: gardnermuseum.org
- Telephone: +1 617 566 1401
- Opening hours: Wed–Sun 11am–5pm (Thu until 9pm); closed Tuesdays
- Entry fees: Around $20 for adults, $13 for students, free for visitors aged 17 and under
2. The Boston Tea Party Museum
3. Boston Duck Tour
A Duck Tour is a sightseeing trip around Boston in a brightly painted amphibious vehicle, originally built as a WWII landing craft, which drives through the city streets before splashing straight into the Charles River for the final stretch. The land portion takes in major sights such as Boston Common, the Massachusetts State House and Faneuil Hall, while the river section gives a different view of the skyline from the water. Tours last around eighty minutes in total and are narrated by a guide, often with a fair bit of humour mixed in with the history. It’s a popular choice for families and first-time visitors, since it covers a lot of ground without much walking. Tours run from spring through to late autumn and depart from a few different locations around the city.
- Location: Departs from Prudential Center, Museum of Science, or New England Aquarium, Boston, MA
- Website: bostonducktours.com
- Telephone: +1 617 450 0068
- Opening hours: Daily, roughly 9am until an hour before sunset, late March to late November
- Entry fees: Around $50–$60 for adults, with reduced rates for children and seniors
Where to Stay in Boston
🌳 Back Bay
Boston’s most elegant district, known for Victorian brownstones, leafy streets and upscale Newbury Street shopping. Walkable to Copley Square, the Public Library and Public Garden — ideal for first-timers wanting charm with convenience.
- ⭐⭐⭐⭐⭐ Four Seasons Hotel One Dalton Street – the city’s luxury benchmark. Booking.com
- ⭐⭐⭐ Hotel AKA Back Bay – stylish rooms, top guest scores. Booking.com
- 🛏️ Newbury Guest House – cosy and affordable on Newbury Street. Booking.com
🏛️ Downtown / Faneuil Hall
Boston’s historic, central core, packed with Freedom Trail sights like Faneuil Hall and the Old State House. The best base for walking everywhere, with excellent transport links.
- ⭐⭐⭐⭐⭐ The Langham, Boston – grand former Federal Reserve building. Booking.com
- ⭐⭐⭐ Hyatt Regency Boston – modern comfort near Boston Common. Booking.com
- 🛏️ HI Boston Hostel – popular, well-rated budget pick. Booking.com
🍝 North End
Boston’s “Little Italy” — cobbled streets, Italian trattorias and Revolutionary history along the waterfront. Charming and great for food lovers and families.
- ⭐⭐⭐⭐⭐ Battery Wharf Hotel – luxury harbourside, private airport water taxi. Booking.com
- ⭐⭐⭐ The Bostonian Boston – boutique character near Quincy Market. Booking.com
🏮 Beacon Hill
Quintessential old Boston — gas-lit cobblestones, red-brick townhouses and famous Acorn Street, right beside Boston Common. Quieter, residential, yet close to everything.
- ⭐⭐⭐ The Whitney Hotel Boston – characterful converted hospital building. Booking.com
⚓ Seaport District
A modern waterfront area with the ICA museum, convention centre and a growing dining scene along the HarborWalk. Best for contemporary design and harbour views.
- ⭐⭐⭐⭐⭐ Omni Boston Hotel at the Seaport – sleek, top-rated waterfront stay. Booking.com
- ⭐⭐⭐ Residence Inn Boston Downtown Seaport – spacious, apartment-style rooms. Booking.com
🎓 Cambridge (Harvard Square)
Across the Charles River — home to Harvard and MIT, with bookshops, cafés and a relaxed academic vibe. Well connected by the Red Line.
- ⭐⭐⭐⭐⭐ The Charles Hotel – Harvard Square’s classic luxury choice. Booking.com
- ⭐⭐⭐ Kimpton Marlowe Hotel – stylish riverside boutique. Booking.com
- 🛏️ Harvard Square Hotel – simple rooms right in the square. Booking.com
More to Explore
