21 Wonderful Things to Do in Boston As Told By A Bostonian

The Best Things To Do In Boston Are All Over the City!

Want to explore one of America’s classic cities? You must be thinking about Boston then! From a rich history to great sports teams and great American culture, today, Boston has something for everyone.

The city really does have a ton of character around every single corner.

Eric has actually been to Boston – twice. Both times, however, were when he was a teenager… so best to say that his Boston memory is a little rusty!

He certainly wouldn’t be a great resource for talking about the best things do to in Boston for adults or at night! But Boston left a lasting memory – and we wanted to write about it to help others trip plan.

So, we asked our local connection, Gwyn, if she would dish the details about her city. Eric and Gwyn went to university together and have remained close friends ever since.

With Gwyn’s help, Eric was able to remember quite a bit and put together a comprehensive list of the most classic, fun, and free things to do in Boston!

Things to Do in Boston: To Do, See, and Eat

Okay – the piece you’ve all been waiting for – here is the list of the best things to do in Boston. Now, these are in no particular order so have a scroll through to find the things that might interest you when you visit!

If you plan on doing A LOT of attractions, consider buying a Boston Card to save up to 55% on over 40 to attractions in the city.

You can choose the card length from 1 to 7 days depending on your trip length so it’ll pay for itself if you do lots of the things below! It’s easy to use and you get a guidebook.

Explore Faneuil Hall and Quincy Market

A great place to start your exploring of Boston is the original marketplace downtown! Faneuil Hall has been a market hall/meeting place since 1742.

Sometimes called Cradle of Liberty (for its role in the American Revolution), the building is located near the waterfront and Government Centre.

These days, it’s a well-known stop on the Freedom Trail (which we will definitely mention below). It’s also one of the most visited tourist sites in Boston and in all of the US!

It’s a good area for shopping but easy to walk through and just see as well. The Hall houses shops, places to eat, a museum, and even meetings rooms. 

It’s been said that it’s not the best area to go out at night unless you want to party like you’re 21.

Faneuil Hall Marketplaces also includes three other long buildings called North Market, South Market and Quincy Market. Quincy Market is located right next to Faneuil Hall so it’s super easy to explore these two attractions together.

It’s a market with lots of stalls selling souvenirs, small trinkets as well as delicious food. This is the perfect opportunity to try out some local treats.

That said, they also have a lot of generic food places you’d find at any mall in North America so if you’re pressed for time don’t spend too much time there!

Address: 4 S Market St, Boston, MA 02109

Pro Tip: Hop on the Hop On/Hop Off Boston Trolley Tour to See the Most Popular Boston Sights!

Enjoy The Charles River

The Charles River is a relatively short river (only 80 miles in total length) that extends through the eastern part of Massachusetts until it reaches the Atlantic Ocean.

The river is actually the divider between the city of Boston from the city of Cambridge.

One of the best things to do in Boston is to explore the city from the river! Once on the river, you can go rowing, canoeing, or paddle-boarding among other activities depending on the season.

If you don’t want to spend time in/on the water, the Charles River Bike Path which runs along the banks of the river is perfect for biking, running or a simple walk.

There is a path known as Esplanade (three miles long) which is a great walk especially if you travel with kids as there are lots of playground along the way.

Try Clam Chowder at Legal Seafoods

You can’t go to Boston without trying Clam chowder at least once. It’s almost like a rite of passage. Make sure you have New England Clam Chowder at Legal Seafood. 

This chain has been serving its fresh seafood in restaurants since the 1960s!

If you go to Long Wharf you can have chowder, explore seafaring trade history, and catch a ferry for the “Boston trifecta”.

Overall, there are more than 10 Legal Seafoods locations in Boston alone so you’ll surely find a location not too far away. To see all of them, check the Legal Seafoods website.

Address for Long Wharf Location: 255 State St, Boston, MA 02109

Do a Boston Harbour Cruise

Get great views of the cityscape from the water and learn about the maritime history, too. There are quite a few different companies offering different kinds of harbour cruises – you can find some great options below.

You even get the chance to go on a whale watching cruise if that’s something you’re interested in.

If you’re set on sitting outside in the spring make sure to bring a warm jacket or windbreaker (like Eric’s black North Face) as it can get quite chilly on the boat. However, most boats also have indoor seating.

Here is the exact harbour tour with Boston Harbor Cruises that Eric did years ago (and loved) and here is a guided boat tour on the USS Constitution  – the ship you see in the photo which is also known as “Old Ironsides”!

Go for a Drink at “Drink”

You have to go to Drink for the experience. A bar dedicated to cocktails, there is no drink menu at Drink – you simply tell the bartender what you enjoy and they’ll make you a cocktail that won’t disappoint.

If you’re not into cocktails don’t give up on the bar just yet – they also offer a great collection of wines and craft beer.

This place is perfect for evening drinks with friends. It’s a bit on the pricier side but you’re paying for more than just your drink.

If you want to learn more about the bar beforehand, you can check out their website here.

Address: 348 Congress Street Boston, Massachusetts 02210

Explore the Boston Tea Party Ships and Museum

If you are going to Boston, you need to learn about the Boston Tea Party. The famous political protest from 1773 played a vital role in the grand scheme of the Revolutionary War.

Now, you can learn all about the events and relive the history!

Now, this is not your typical museum. In addition to seeing artefacts that played an important role in history, you can also enjoy a multi-sensory experience which makes it a perfect place to go with kids.

The floating museum and tour with interactive exhibits and restored tea ships among other attractions. You even get the chance to throw the tea overboard.

The immersive tour lasts approximately an hour. You can also visit the Meeting House where you can learn more about events that lead to the Boston Tea Party through a colonial town meeting.

Overall, this is a great attraction for those who are interested in (sailing) ships since you can see some full-scale restored sailing vessels from the 18th century. You can visit the official website to learn more.

Address: 306 Congress Street, Boston, Ma 02210

Relive the Freedom Trail

This is something Eric remembered doing and felt that it was vital it made the list. After all, this is one of the most popular activities in the whole city!

Walking the famous Freedom Trail is considered a must-do because this is how you learn about the city’s role in the American Revolution!

The approximately 2.5 mile walk is filled with 16 historic sites that played a role in the American Revolutionary War.

A few of these stops include The Paul Revere House, North End, and the Monument on Bunker Hill to commemorate the battle in 1775.

You can walk the trail yourself with a downloaded map or you can choose to take a guided tour of the Freedom Trail. Eric had a tour guide and remembers (over a decade later) it being an amazing experience. Honestly.

Wander Through Charlestown Neighbourhood

While it’s slightly further away from downtown, Charlestown is worth checking out! The old shipyards have been turned into a really cute little area of the city.

This is actually the oldest neighbourhood in Boston – it was its own city before and became part of Boston in 1874.

To get there, head for the peninsula north of the Charles River – close to the Boston Harbour area. Today, the area is home to many historic sites but is also a large residential area with many places along the water.

The area has become more and more popular in the last years (and as such more expensive)!

While over there, be sure to walk up the hill and visit the Bunker Hill Monument. The Hill also allows for a great view of the water below.

In fact, while you are there you can climb the monument all 294 steps to get amazing 360 degrees views of the city below. Eric climbed to the top with his friends and remembers it like it was yesterday!

Also handy – the USS Constitution is close by (at the end of the Freedom Trail) so of course also have to walk along the water!

Go Brewery Hopping

Boston has a rich history when it comes to beer. Exploring Boston through beer is a must-do – and the breweries in Boston are ready to welcome you with full glasses.

If you want to stay mobile, you can actually do a historic pub crawl along the Freedom Trail. That way, you get to learn about Boston’s patriotic history AND enjoy a few beverages along the way!

Check out Harpoon Brewery since it’s on the water, has tours and a big patio.  Good place to spend an afternoon if it’s nice out. It’s also free to tour – So that’s great on the wallet.

The other big name you’ll hear if you’re out and about in Boston is Samuel Adams. As such you should do a Sam Adams Brewery Tour.

The brewery does a really cool brewery tour that you get free samples at. We suggest taking the “party bus” to Doyle’s afterwards. If you order a Sam Adams beer you get to keep the beer glass!

Do a Tour of Historic Fenway Ballpark

Even though Fenway is generally well known, those not interested in North American sports – especially baseball – might not know that Fenway Ballpark is home to the famous Boston Red Sox baseball team.

Fun Boston Fact: Fenway Park is the oldest ballpark in the league!

Because of its long existence, there is a lot of history to this ballpark. As such, taking a guided tour is a great way to learn more about it.

Since the Fenway Ballpark is in the centre of the city it is quite easy to get to without a car since it’s within walking distance of public transport. This is when you’d refer to that Boston transit map we talked about!

The area around the ballpark is full of bars and pubs that are also very lively before and after games so head on down even without a ticket to take in the buzzing Boston sports atmosphere.

You can learn more about visiting Fenway and even catching a game at the official website.

Address: 4 Yawkey Way, Boston, MA 02215, USA

Visit a Concert at the House of Blues

As Boston’s main entertainment venue, catching a concert at the House of Blues is something to be experienced. There is even a restaurant & bar onsite along side the famous music hall.

There are all different kinds of concerts and events so be sure to check the website to see what is going on and enjoy a great night out! Oh, and don’t forget t buy tickets in advance if you DO find something you like!

Address: 15 Lansdowne St, Boston, MA 02215

Catch a Professional Sports Game

Boston is considered one of the best sports cities in North America – with all the top teams in their sports being really good, usually. There’s also a passionate fan base for each team so any game is a treat to go to and cheer along.

Catch a Bruins (ice hockey), Celtics (basketball), or Red Sox (baseball) game depending on the season (all venues are downtown). You can even catch an American Football game at Gillette Stadium out in Foxborough.

The New England Patriots or Revolution (soccer) play there. There is transit that brings people out to the stadium which is handy!

Relax in the Boston Common / Public Gardens

Want to relax in the park for the day or even just the afternoon? The Public Gardens are the place for you then! The Public Gardens were created in the 17th century and thus they are quite old. 

Of course, they have been changed over the years with new plants being introduced! The really big park is perfect for families since they have swan boats that you can rent to enjoy a fun afternoon on the lake.

Address: 4 Charles St, Boston, MA 02116

Visit the Brattle Bookstore (Boston Downtown)

As one of America’s oldest and largest antiquarian bookstores, you should probably visit the Brattle Bookstore if you’re in exploring more of America’s rich history.

Founded in 1825, you’ll find three storeys of used books – some of them are quite rare.

Officially, the store carries over 250,000 books, maps, prints, postcards, etc. So stop by and have a look – maybe you’ll find a hidden gem or one of your childhood favourites!

They are open from 9 am to 5:30 pm from Monday to Saturday but you can double check the website if you are planning a visit!

Address: 9 West Street, Downtown Boston, MA 02111

Meet the Daily Catch on Commonwealth Pier

Looking for the freshest of seafood? Like, “caught earlier that day” fresh? Then head down to Commonwealth Pier to greet the daily catch making it to shore.

Located in South Boston, the Pier is home to parks, shops, and other restaurants. After you check out the catch, you can check out the “Spirit of Boston” and then walk to No Names for a lunch or dinner of chowder and fish!

Address: 200 Seaport Boulevard, Boston, MA 02212

Visit the Old North Church Crypt

Having been closed for basically a century, visiting the Crypt in the Old North Church is a recently new activity. It reopened in 2017 and visitors can now do a tour of the lower areas.

To be exact, you can walk through 37 tombs that were built below the church floors between 1732 and 1860!

The church itself is Boston’s oldest surviving church building and the most visited historic site in the city! If you want to learn more about the church and the tours they run, check out the website.

Address: 193 Salem St, Boston, MA 02113,

Shop the Historic Haymarket Farmers’ Market

Open every Friday/Saturday, the Historic Haymarket Market has been going at that location since 1830!

Located in the centre of the city (quite close to Faneuil Hall Marketplace), this farmers’ market is where you will find the cheapest produce in the city.

That’s basically a known Boston fact. There are no set hours – vendors show up early and stay until dusk! You can learn more about the Haymarket Farmers’ Market here.

Address: 100 Hanover Street 

Explore the Boston Public Library

Founded in 1852, the Boston Public Library isn’t just any old library – it’s the second-largest library in the United States by volumes. There are over 19 million!

The library building today is beautiful and you can take a free tour with one of their trained volunteer guides to learn more about the history and architecture of the library.

The tour lasts approximately one hour and they take place frequently. You can check the exact tour schedule and more information here. Gwyn’s advice for visiting? Have a snack in the Inner courtyard!

Address: 700 Boylston Street Boston MA 02116

Eat Cannoli in the North End and Settle the Dispute

If you are feeling hungry, the North End is known for Italian food. Mike’s Pastry and Modern Pastry both make amazing Italian traditional pastries.

So, since these two family-owned and run shops have been at it for decades – there’s a big fight over if Mike’s or Modern’s cannoli are better. We guess you’ll have to go taste test and see for yourself!

Address for Mikes: 300 Hanover St, Boston, MA 02113 and Address for Modern’s: 257 Hanover St, Boston, MA 02113

Discover the World at Mapparium

Hands down one of the neatest attractions around! Want to go inside an inside-out glass globe from 1935? Technically an attraction at the Mary Baker Eddy Library, this three-story-tall globe is illuminated with light and you are able to walk in the middle with a walkway.

Fun Fact: It’s the only place in the world in which the surface of Earth can be seen without distortion (since you look from the centre of the globe outwards – your eye is the same distance from every point).

Remember, it was built in 1935. The size of the continents is accurate, but the countries’ borders are a TAD out of date. Makes for a great history lesson, though!

Another cool trick while you’re there is trying to speak or whisper something from one end to the other. You’ll be surprised how much you can hear! You can read more about the Mapparium here.

Address: 200 Massachusetts Avenue, Boston, MA 02115

Bonus: Take A Day Trip to Cape Cod, Portsmouth or Lowell

While there is so much to do and see in Boston, there are lots of great day trip destinations from the heart of the city.

From the classic places like visiting the beaches of Cape Cod by ferry to the historic houses of Portsmouth, you’re sure to find an attraction that suits your interests.

If you want to stay closer to Boston, you can also check out Lowell National Historical Park and learn more about the industrial history.

You can check out their website here. Like we mentioned up top, we’re writing a whole post just on day trips from Boston so watch for that – we’ll link to it here when it’s ready!

Things to Consider When Visiting Boston

Here is a short section on a few important things that you should know while you are planning a trip to Boston!

General Information About Boston

Boston was founded in 1630. With over a half million people as the population, Boston is the largest city and the capital city of Massachusetts.

Located on the East Coast, it’s easy to get to from Europe. In fact, many major European cities fly direct to Boston in a few hours!

Boston is a very important city in American History. Boston was/still is a port city and this made it of strategic importance. As such, the city played a key role in the American Revolution against the British.

Today, the city is known for amazing sports teams, clam chowder, and top-world-ranking universities like Harvard and MIT (the Massachusetts Institute of Technology).

Harvard is actually located in Cambridge – which is a separate city very closely tied to Boston and separated only by the Charles River!

Best Time to Visit Boston

The best time to visit Boston really depends on the weather you want and the activities you’re interested in doing. The summer months from June to September are the warmest and surest bet for sunshine – but also the busiest months for visitors.

From outdoor events and markets to baseball games and harbour cruises, the busy warm months are definitely worth the trip.

That said, the spring and the fall are also good times to visit Boston. Spring is shorter overall – stick to May (this is when Eric visited) for nice temperatures with fewer crowds. The fall – like October – also allows for cooler temperatures.

Of course, the classic New England fall foliage is on display in late September and October – so that might be a reason to go then!

Getting Around Boston

Overall, Boston is a pretty walkable city. That said, if you wanted to venture out a little further – e.g. to Cambridge – you might consider taking public transportation. For that, you have the MBTA.

The Massachusetts Bay Transportation Authority is the official name but locals call it “The T”. There is a pretty good system of subways (known as rapid transit) and buses to take you around downtown and then light rail trains to get you a little further out.

If you want to take the T around the city, you should check out the maps and schedules at the official MBTA website.

You might also be interested in exploring areas away from the city centre on a day trip from Boston. If this is the case, then you should consider renting a car. We’ve covered a few ideas for day trips in the above section!

Where to Stay in Boston

There are lots of great neighbourhoods to check out and stay in while you are visiting Boston. These neighbourhoods include: Back Bay, South End, Beacon Hill, North End (especially at night), and Fenway (good for sports bars, obviously).

All of these areas are “classic Boston”- lots of brownstones, cobbled streets, and beautiful overall scenery.

For a boutique hotel option, The Godfrey Hotel Boston is a short walk to Boston Common and close to downtown. The Westin Copley is a super convenient, central hotel that is well-located and easy to get to by car.

If you want to have a deeper look at hotels and other accommodations, check here for hotels in Boston and check here for hostels in Boston if you are interested!

And there you have it – a few great ideas for the perfect trip to Boston. Whatever you end up doing, you can’t really go wrong in Boston.

While history dominates the activities (for good reason), that doesn’t mean that there aren’t plenty of other themed things to do to keep you busy!

Are you planning a trip? What interests you the most? Drop us a line and let us know! And a huge shout out to Gwyn for helping us out with this one!

As always, Happy Boston Waddlin’,
-L&E

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