Bucket List Boston 🇺🇸

Boston (or ‘Beantown’) is the Capital of Massachusetts, the most populous city in New England and the oldest city in America! Despite being a bustling hive of activity, the underground highways allow for vast, protected green spaces and a distinct lack of car horns, smoke and smog. New York City it is not. In fact, Boston comprises 17% green space.

Whether you have a couple of days or an entire week in Boston, there’s so much that you’ll want to see and do – all of it within easy reach on foot or via a quick hop on the train. But if time is tight, you’ll need to be a little picky to make sure you get the most out of your trip.

Here’s my ‘wicked smaaht’ (pretty cool) must see, must do Boston Bucket List…

1. Soak up the sun at Boston Common and Public Garden.

If relaxation is the first port of call, then head straight to the lush green, 50-acre Boston Common. This is slap bang in the centre of the city and renowned as the very first public park in the USA, founded way back in 1634. It was once the camping ground for British troops during the Revolutionary War, but is widely used today as a meeting place where people can sunbathe, people-watch or sledge when the winter snow arrives. You can even grab free WiFi in the park, if you plan to use it as an office!

Boston Common is where you can expect to find the pretty Brewer Fountain featuring bronze Greek gods, impressive statues, refreshment carts selling traditional lemonade and a fabulous tourist information office – complete with tour guides dressed in Colonial costume. It’s also the best place to start walking the Freedom Trail (more of that in a minute).

Next door to the Common is another top tourist favourite – the Public Garden. By contrast, this is a smaller (24 acre), mini oasis amongst the city skyline. It’s arguably the prettier of the two parks, with rose gardens, botanical flowerbeds, a shimmering lake and more weeping willows than you could shake a stick at. If this makes your list, then why not take a ride on one of the iconic paddlewheel swan boats – each steered with skill by operators who get a pretty hefty leg workout. The swan boats date all the way back to 1877 so they really are part of Boston’s history!

If that doesn’t appeal, or the boats aren’t operating (April to August only) – simply say hello to the bronze ‘Mrs Mallard and her ducklings’ – a piece of public art that’s almost as popular as the park itself.

Going in May? We happened to be in Boston on Memorial Day (the last Monday every May) and were lucky to see 37,000 flags at the foot of the Soldiers and Sailors Monument, paying tribute to those who died in the Civil War. The display of flags has been a city tradition since 2010.

2. Walk the Freedom Trail

Got your walking shoes? Great – you’re ready for Boston’s biggest attraction! As we all know, Boston is steeped in American history and no visit is complete without walking the Freedom Trail! And guess what – it’s completely free!

The Freedom Trail is a 2.5 mile, self-guided walk that takes you past 16 historical markers, ending up over the river in Charlestown. Red bricks mark the way and copper plates indicate the locations of each historical site. You really can’t go wrong.

The perfect place to join the walk, in my opinion, is at Boston Common (itself, one of the historical markers). Of course, you can pick it up anywhere along the route, but here you can buy a helpful guide book at the Tourist Information office, for just a few bucks.

You can expect to see the impressive, dome-roofed Massachusetts State House, the 1809 Park Street Church which stored gunpowder during the 1821 War and the Granary Burial Ground where famous Boston residents such as Paul Revere and Samuel Adams are laid to rest. You can also spot a fantastic statue of Samuel Adams on his horse outside Faneuil Hall – another marker on the trail.

Keep on walking and you’ll also see the Old North Church (Boston’s oldest place of worship), the Kings Chapel, Copp’s Hill Burying Ground covered in bullet holes, the site of the Boston Massacre, Paul Revere’s House and the Old Corner Bookstore where literary greats such as Charles Dickens used to gather during revolutionary times! The latter is rather bizarrely, now a fast-food Mexican restaurant called Chipotle!

Near to the ‘Chipotle restaurant’ is the Old State House – one of the oldest buildings in America and the site at which the ‘Declaration of Independence’ was first read to the crowd from the balcony.

The Old South Meeting House is another particularly interesting site where the Boston Tea Party was organised. For those reading this who don’t know the story, 90,000 lbs of tea was literally dumped into Boston harbour by the ‘Sons of Liberty’ in protest against the high taxation. If you have time on the itinerary, you can visit the site of the Boston Tea Party to learn more and participate in it’s rather gimmicky reenactment!

The last two stops on the Freedom Trail (assuming you set out at Boston Common) are across the river in Charlestown on it’s gorgeous waterfront.

The USS Constitution is said to be the world’s oldest commissioned warship and is a pretty spectacular sight amongst the much smaller tour-operating boats! Visitors can jump aboard the USS Constitution and see firsthand what life would have been like aboard – try not to bang your head as you climb the deck ladders! I speak from experience.

After you’ve seen the ship, don’t forget to stop by the museum to learn the history and see some exhibits. Why not grab yourself a cheeky sailor hat souvenir from the gift shop whilst you’re at it? You’re a tourist, after all!

The final stop of the Freedom Trail is at the huge Bunker Hill Monument where the American Revolutionary battle took place in 1775. If you still have steam left in you, it’s worth the 294 step climb up to the top of the Monument as it’s here where you will get fantastic, panoramic views of Boston, below.

Watch my video of the Freedom Trail.

3. Feast on New England seafood!

After all that walking, you’ll be in need of some calories – and when in Boston, you have every excuse to sample a variety of yummy seafood, including hot or cold lobster rolls, massive oysters and the famous ‘New England chowda’.

You’ll find these delights almost anywhere in the city, but arguably, the best place is the Seaport District for the freshest feasts in town!

Despite seafood being big in supply and demand, a cheap treat it is not. As far as 2022 prices go, you are looking at around $35 for a lobster roll, $5 for a single oyster and $10 for a very small tub of chowda. Of course, prices vary according to whether you buy from a roadside food truck or a fancy harbour-side restaurant – but the rule of thumb is that it will cost you a pretty penny regardless.

Did you know? Lobster wasn’t always expensive in Boston – in fact, it was once so plentiful that lucky prisoners used to be served it for dinner! Who says crime doesn’t pay?

One of the best places to stop for a quick seafood lunch is at Quincy Market – a popular food court with around 40 stalls in one place. And it’s not just seafood up for grabs, you’ll find all manner of burgers, hot dogs, bagels, cakes and ice cream too.

4. Enjoy brunch and beers in Beacon Hill

With its tree-lined, red-brick, cobblestone streets, Beacon Hill is a super-pretty historic neighbourhood in Boston that you absolutely have to see. It’s certainly one of most prestigious areas to live too, with multi-million dollar town houses, fancy boutiques and (in the warmer months) window baskets full of flowers.

If a lazy meander is just what you’re after, then Beacon Hill fits the bill. There’s a real cafe culture here, with cosy coffee shops serving avocado toast with flat whites, and intimate restaurants providing the perfect spot for date night. Expect to book ahead or have a lengthy wait in many of the eateries.

If an afternoon beer is more up your street, the Bull and Finch pub is also in the Beacon Hill district. This is the original Cheers Bar and a top tourist spot for a bit of 1980s Ted Danson nostalgia. You really should pay a visit if you can – whether you go inside for a pint or just have your photo taken outside! If you do choose to venture in, you will see the original set that now doubles as a functioning bar and a rather bizarre gift shop. Definitely expect queues at this one!

Did you know? Drinking alcohol is not a cheap past time in Boston (little is). Forget any hope of a ‘Happy Hour’ in Beantown because the law prohibits bars and restaurants from having timed deals on alcohol! But don’t let that put you off because the Bostonians pour a ‘wicked’ pint.

5. Take in the culture of North End

Think 1920s Chicago vibes and it pretty much sums up North End. It’s definitely got a different feel to the rest of Boston. If you plan to walk the Freedom Trail (and why wouldn’t you?), you’ll pass through North End when you visit the Paul Revere house, Old North Church and the Copp’s Hill burial ground.

North End is Boston’s ‘Little Italy’ and home to huge families of Italian Americans. Here you will find countless Italian restaurants, tasty delis and takeaway joints offering the perfect pizza pie – like Mama used to make. You’ll never go hungry in this part of town, that’s for certain.

If there’s one stop you must make, it’s to Mikes Pastry’. Here you can grab a delicious cannoli treat filled with any flavour your heart desires – plain ricotta, espresso, limoncello, mint choc chip – you name it, Mike has it! Again – expect very, very long queues!

If you get time, venture across to take a look at the ‘West End’ of the city too. It’s literally alongside North End. This is where you will find the transport hub and North Station, where you can catch trains up the coastline and to the likes of Salem (more of that in a bit). North End also has the huge TD Garden, home to the Boston Celtics basketball team.

6. Catch a baseball game at Fenway Park

Whilst on the subject of sport and in case you weren’t aware – it’s actually baseball that’s the biggest deal in Boston. The city is proud home of the Boston Red Sox – 2018 World Series champs, no less.

If you happen to be in town during game season, then you owe it to yourself to buy a ticket! Even if you don’t like baseball. Why? Because Fenway Park is an attraction in itself – it’s the USA’s oldest Major League baseball stadium, built in 1912.

Fenway Park is the only baseball stadium to remain exactly as it was when it was first built. As such, it’s retained the natural charm, as well as the nickname ‘The Green Monster’ since all the walls are painted green to match the ball park.

It’s no exaggeration to say that you’ll see Red Sox logos and memorabilia all over Boston – on cars, in shops, in bars, on shirts and on hats. In or on pretty much anything, in fact.

Check out my vid of the game!

7. Graffiti geek? Get down to Ink Block!

The Underground at Ink Block is Boston’s arty effort to repurpose the underneath of the South Boston overpass and bring some colour to the otherwise abandoned area.

The area is now filled with 150,000 square feet of murals and graffiti by artists from Boston, Los Angeles, New York and Puerto Rico. If you’re a street art nerd like me, you can spend hours here. If you’re not, the space also includes bike paths, boardwalks and a dog park.

You don’t have to go to Ink Block to spot impressive murals, however, as there are loads dotted around the city – Chinatown, especially. Equally, Boston is brimming with indoor art galleries, such as the Institute of Contemporary Art and the Museum of Fine Arts. So if art is on the itinerary, there’s lots to go at in this colourful city.

8. Take time out at the Reflecting Pool in Back Bay

You may have gathered by now that Boston is a city of many personalities – whether it’s laid back park life, harbour lights or sporting arenas, it’s fair to say that Boston has something for all.

Located just between the Prudential Center and the Christian Science Center in the Back Bay area sits the glimmering 670 foot Reflecting Pool. On a sunny day, this is quite a sight to behold and most definitely a great place to take a break from sightseeing and just enjoy the view for a while.

It’s in this area where you can find some of the best architecture that Boston has to offer, from the Public Library, to Trinity Church and the John Hancock Tower. Be sure to look up!

The Charles River Esplanade is also in Back Bay and another nice place to chill the day away, provided the weather is right. To walk it in it’s entirety is three miles, with dedicated paths and cycle lanes. You’ll probably see canoeists and artists along the journey, as well as sun worshippers on the dedicated bathing decks dotted along the river.

9. Visit Harvard campus

Founded in 1636, Harvard is America’s oldest University. Everything seems to be given the title of being the oldest, or a first, in Boston! Around 140,000 brainiac students call Boston home and attend school at Harvard. It’s famous the world over with thanks to its frequent mention in films such as The Social Network’, ‘Legally Blonde’ and ‘Good Will Hunting’.

For those of us British folk, Harvard is the American equivalent to our Cambridge University. Strangely, the town that Harvard is in is actually called Cambridge. Go figure.

Harvard may be a train ride outside of Boston – but only a short one – and one worth taking. Jump off at Harvard Square and you’ll easily find the campus – just look for the red brick buildings, lush green lawns and student-types carrying satchels.

Don’t miss the John Harvard statue in the centre of Harvard Yard – apparently if you give his left shoe a rub, it brings you good luck…supposedly.

10. Get your spook on in Salem

Last but most definitely not least, a day trip to Salem (‘Witch City’) is a 20 minute train ride/ 1 hour bus journey that you’ll be glad you took!

Any history buff will know that Salem is the infamous site of the 1692 witch trials where 19 alleged ‘witches’ (women AND men) were hanged as a result of witch-hunt hysteria in the town. The infamous trials began after a group of young girls claimed to be possessed by the devil and accused several locals of witchcraft.

There are a number of ‘attractions’ relating to this in Salem, but we opted to visit the Witch House as this is the only ‘actual’ historical site. The house is really creaky and very creepy and once belonged to a local magistrate who investigated the witchcraft claims. It is believed that the examinations of those accused took place on the first floor bedroom! Enter if you dare….

But Salem is not just solemn, it’s a fun town that really plays up to the whole witchcraft thing with shops selling spooky souvenirs, bakeries selling witchy delights and a statue of Elizabeth Montgomery as Samantha in Bewitched (filmed in Salem) taking pride of place in the centre.

There’s also opportunity to visit the filming locations from Hocus Pocus and channel your inner Sanderson Sister!

Away from the witchiness, Salem has a rich maritime history and there’s no better place to grab lunch than the Sea Level Oyster Bar for fabulous harbour views and wonderful seafood! My other half even said it was his favourite meal of the entire trip! High praise indeed.

Take a virtual tour of Salem in my video!

So, there you have it – my Top Ten Bucket List Boston! I hope it helps inspire your trip to Beantown. Let me know in the comments below 👇🏻