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The city of Boston is one that encompasses many things; extensive history, impressive academics, world-class health care and that infamous thick accent that screenwriters across the country have come to know and love. While Boston is known for many “touristy” things, such as Faneuil Hall and the Freedom trail, there are so many other hidden gems in Boston that only locals typically frequent. 

While COVID-19 has affected us, like the rest of the world, Boston is opening its doors and the city is starting to come alive again.  As we are living in unprecedented times, please remember to follow any local COVID guidelines and double check to make sure everything is open prior to arrival!

Off the Beaten Path around Charles Street

In terms of restaurants and bars, some of Boston’s best kept secrets are in the heart of the city, right on Charles Street. Running down the middle of Beacon Hill, Charles Street is a quaint yet bustling street that connects down to the Boston Common.

One of my favorite breakfast spots of all time is The Paramount. It’s a small place but be careful, it gets packed on the weekends so head there early. It’s cafeteria style, but the food is top notch. After grabbing breakfast there, you can head on down to the common and walk through the Boston Public Garden

Explore hidden gems around Boston Public Garden

The Boston Public Garden

If you’re looking for more of a true Boston bar in that area, then you have to stop at The Sevens, also on Charles Street. It’s a small bar that perfectly encompasses the intersection of dive bar and historical haunt, and is always overlooked by tourists. If you’re looking for one of those hidden gems in Boston with a true pub room feel, The Sevens definitely is a bar for you.

Exploring Around Newbury & Boylston Street

After exploring the area around Charles Street, you can head on over to Newbury and Boylston streets to do some shopping (window or otherwise), check out the Boston Marathon Finish Line and see the map room at the Boston Public Library

Hidden Gems in Boston: Newbury Street - eight blocks filled with salons, boutiques, and dining.

Boston’s Newbury Street – eight blocks filled with salons, boutiques, and dining.

If you’re exhausted from your shopping and want to grab some food or a drink, there are plenty of great spots along Newbury and Boylston. One of my favorites is Sonsie on Newbury. Sonsie is more of an upscale place but they have a cute bar with great food.

Boston overall is a very casual town though, so even “upscale” here really just means put on your jeans instead of your COVID-friendly sweatpants. Stephanie’s on Newbury also is great and has a cute front patio if you want to relax and people watch as well. 

Hidden Gems and Boston Harbor Views in the Seaport District

If you don’t want to get up early for breakfast, then starting your trip in the Seaport District is another great way to go. There they have the Barking Crab, which is a seafood restaurant with a unique atmospheric blend that’s casual, but with fantastic waterfront views.

Hidden Gems in Boston - The Barking Crab in the Seaport District

The Barking Crab in Boston’s Seaport District

Nearby is the Envoy Hotel which has more of a high class feel. There you can go to the roof and check out the Lookout Rooftop and Bar. While the drinks are on the pricier side, the scenery is gorgeous, and they even have COVID-approved igloos that you can rent as well.

In that area, you also can walk down the street to the rooftop at Legal Seafood, or you can get a true Boston experience by going to Harpoon Brewery for a brew tour and a few beers.

Breweries and Dive Bars off the Beaten Path in Boston

If our city’s watering holes are one of the reasons that brought you here, then look no further. Boston’s food scene is still up and coming, but our alcohol scene has been top level since the Revolution!

If you want a brewery feel in downtown, then I would suggest Trillium Brewery which has a Fort Point location and also has an outdoor spot in their Garden on the Greenway. They have great hazy IPAs and are typically rated some of the best beers in the country. 

If you’re looking to take more of a self-guided brewery tour, then I would suggest heading outside of downtown and going into the neighboring town of Somerville. There you can do your own “brew tour” and hit up places like Aeronaut, Remnant Brewing, and the Winter Hill Brewing Company. These places have more of a hipster vibe than the breweries downtown and also can tout some of the best hazy IPAs in the state. 

The Craft Beer Taps at Night Shift Brewery - Everett

The Craft Beer Taps at Night Shift Brewery – Everett

If you’re staying slightly outside the city, I also would always suggest checking out Nightshift in Everett. They have a great outdoor spot and often times have a lot of fun beers relating to classic 80s and 90s themes.

They too have a satellite location called Nightshift – Lovejoy Wharf, which is right near the TD Garden and is a perfect spot to stop at if you’re in town checking out a game.

To continue the fun after the game, look no further than Sullivan’s (Sully’s) right down the street from the garden. This is true dive bar atmosphere but is a perfect place if you’re not ready to go home after watching a good Bruins or Celtics game.

Hidden Gems in the Boston North End

Close to the Garden lies Faneuil Hall and Quincy Market. This you need to check off your list if you’re coming to Boston, but personally I feel like it’s over touristy and doesn’t really give you a glimpse into the city.

After making a quick pit stop there, head over to the city’s famous North End. If you can catch it on a feast day, which occur sporadically throughout the summer, then I would highly suggest checking it out. 

Walk through the city’s old cobblestoned narrow streets and experience our Little Italy, either with friends or on a date night. They have amazing restaurants there, my personal favorite being Bricco, which has incredible food and a dark moody, yet modern, atmosphere. Ristorante Fiore is also fantastic and has a beautiful roof deck for the summer months. 

The Improv Asylum is a great little comedy club right on Hanover Street and makes a perfect pairing with some good Italian food later in the night. After you’ve gone to dinner and checked out a comedy show, then you have to head over to the original Regina Pizzeria at 11 ½ Thatcher Street, just a few minutes’ walk from Hanover. The pizza is truly amazing and is perfect if you need a late-night snack.

Staying Active In Boston

At this point, if you’ve drunk all you can drink and eaten all that you can eat, then I would suggest taking a walk along the Charles River Esplanade to burn off some of those calories.

It’s also a great place to bring a picnic and watch the sunset over the river if the weather is nice enough. Parking in that area can be difficult, but you can park at the Boston Common (along the Beacon Street side) and walk over. 

The Charles River Esplanade - A favorite spot for Boston locals

The Charles River Esplanade – A favorite spot for Boston locals

If you want more activity than just a casual stroll and don’t mind waking up early, then you have to check out the November Project. This is a great work out and is free, which is even better! All you need to do is show up.

They offer workouts Monday, Wednesday and Friday mornings at varying locations across the city. Typically, these workouts involve things like doing the stairs at Harvard Stadium or running hill sprints in Brookline. More information can be found on november-project.com and I highly recommend joining their community if fitness is top of your priority list!

If you want to do an activity that doesn’t involve acting like Rocky Balboa running up and down stairs, then check out Boda Borg which is a combination of an escape room and an obstacle course.

It’s fun and easy for all levels, perfect for an afternoon with friends. You also could bring your skates and go skating at the public rink in the North End which has a partial glass wall where you can see the harbor. 

Lastly, the city’s location in beautiful New England makes it a great jumping-off point for some amazing day hikes near Boston. This four-season guide includes 60 great trails in Eastern Massachusetts to help you get even further off the beaten path when visiting Boston.

Boston’s Lesser-Known Guided Tour

Now at this point, I don’t know about you, but I’d be pretty tuckered out and would want someone just to show me around. While the Duck Tours are the most popular tour of the city, I always recommend something a little spookier.

The Ghost and Gravestones tour of Boston is fantastic, albeit a little gimmicky. They give you a great tour of the city while also enlightening you to some of the spookier aspects of Boston, such as the Boston Strangler, the Great Molasses Flood and the ghosts of the revolution that haunt our streets. You’ll need to make reservations in advance, but I always suggest this as I feel like it’s a little more off the beaten path and a fun way to explore Boston.


Truly, Boston is an amazing town full of a lot of character, grit, and plenty of hidden gems. Of course, if this is your first time visiting, be sure to also take a look at the top things to do in Boston to make sure you’re not missing out!

The history here is fantastic and there are enough things to do in and around the city to last a lifetime.  Once you’ve been once, you’ll understand why we Bostonians think our city is “wicked” cool. Have fun! 

 

Hidden Gems in Boston – A Local Insider’s Guide

Boston is an excellent place for history buffs. As the site of such famous events like the Boston Tea Party, Paul Revere’s midnight ride, and the first American Revolutionary War battle, it’s no wonder that many of the things on our historical Boston bucket list revolve around historical events. Walking around the city will bring stories and characters to life. When deciding things to do in Boston, the most critical question is how to incorporate everything into your schedule!

1. Talk a Stroll on the Boston Freedom Trail

One of the first things on your historical Boston bucket list has to be walking the Boston Freedom Trail. It is best to do this at the beginning of your trip since it will take you past some of the most important historical sites in the city. It’s also a great way to get your bearings at the start of your trip.

The Freedom Trail starts in Boston Common and ends at Bunker Hill on the river. The trail is 2.5 miles (4km) long and takes you past 16 markers on the Freedom Trail. Red bricks mark the way, and copper plates indicate the locations of historical sites.

Boston Freedom Trail - one of the best things to do in Boston

A bronze plaque of a historic stop on the Freedom Trail

A walk along Boston’s Freedom Trail is likely to take a full day, as it includes visits to many historical sites. Once you reach the end of the Freedom Trail, you can head back to the city on foot or via the Charlestown Water Shuttle.

You can walk the Independence Trail on your own, or take one of the Independence Trail trips. Your guide might even wear 18th-century costumes and explain everyday life using historical information and stories.

Stops on the Boston Freedom Trail

Along the Freedom Trail, you will encounter 16 stops. We recommend finishing the trail in one day and then spending more time in Boston’s major attractions later.

  1. Boston Common – The Freedom Trail begins in America’s oldest park, which has a rich history and, to this day, is a popular meeting place for locals.
  2. Massachusetts State House – The Governor of Massachusetts still conducts his work in this historic building. The dome of the building was originally built by Paul Revere out of bronze and was later covered with gold.
  3. Park Street Church – This landmark was founded by orthodox Trinitarians in 1809 and is still an active Boston church.
  4. Granary Burying Ground – In this cemetery, you’ll be able to visit the final resting place of famous Boston residents like Samuel Adams, John Hancock, Paul Revere, and Mary Goose (mother goose).
  5. King’s Chapel and Burying Ground – This was the first Anglican church to be built in the colonies.
  6. Benjamin Franklin statue and the Boston Latin School – Take a photo with Mr. Franklin and visit the first public school in the USA.
  7. Old Corner Bookstore – literary greats such as Charles Dickens, Ralph Waldo Emerson, Nathaniel Hawthorne, and Henry Wadsworth Longfellow used this bookstore as a gathering place during revolutionary times.
  8. Old South Meeting House – Many revolutionary leaders attended the religious services here, but it’s more famously known as the place where they organized the Boston Tea Party.
  9. Old State House – Built in 1713, this is one of the oldest buildings in America. The Declaration of Independence was first read to the crowd from the balcony of this historic building.
  10. Site of the Boston Massacre – Often cited as the triggering event for the American Revolution, this was the site where British troops killed five unarmed colonists during the fighting. 
  11. Faneuil Hall – The Faneuil Hall is in itself on of the things on our historical Boston bucket list. It’s a famous market for food, boutiques, and street performers.
  12. Paul Revere’s House – Visit the colonial home of the great American Revolutionary figure.
  13. Old North Church – A place where the famous lamps that signaled “one by land, two by sea” were hung to warn the colonists.
  14. Copp’s Hill Burying Ground – A resting place for many early settlers in Boston.
  15. USS Constitution – A historic naval ship that can be viewed and toured today. The vessel saw the war on both American and British shores during the War of 1812.
  16. Bunker Hill Monument – The site of the great American Revolutionary battle on June 17, 1775.

2. Spend Time at the historic Faneuil Hall Market

Faneuil Hall Marketplace is a group of buildings that include Faneuil Hall, Quincy Market, North Market, and South Market.

It is a great place to try the traditional food available in the Boston market. Throughout Faneuil Hall, you will find first-class restaurants and small shops along the Quincy Market Colonnade. Faneuil Hall Marketplace is a popular meeting place for locals and tourists and one of the best places for street shows in the world.

Boston Faneuil Hall Marketplace Things to do in Boston

There is much to discover near Boston Faneuil Hall Marketplace

Faneuil Hall is called “Cradle of Liberty” because of the many important speeches made here. At Faneuil Hall, James Otis declared “no taxation without representation” against British rulers. You can also take a tour to learn more about the history of Faneuil Hall.

A widespread curiosity and thing to see in Boston is to see the Faneuil Hall Weathervane and its famous Gold Grasshopper. This icon has been in the Boston market since 1742. The Grasshopper has watched over the birth of the nation and centuries of American history. There is even a time capsule in the body of the Grasshopper that contains historical newspaper debates, coins, and letters.

3. Relax at the Boston Common park

Boston Common is a beautiful city park and one of the places in Boston where locals love to hang out. This vast green space is America’s oldest public park and was founded in 1634.

Boston Common is one of the top things to do in Boston

Boston Common is a green oasis in the city center

In the early days, it served as a training ground for colonial troops, until British troops took over in 1768. Throughout history, many protests and celebrations have taken place at Boston Common.

Boston’s main attraction is usually the Frog Pool. In hot weather, it becomes a water fountain and is a great place for children to stay cool during the humid summer months. During the winter, the Frog Pong freezes over, and ice skating here is one of the best things to do in Boston during winter.

4. Immerse yourself in art and culture in the Museum of Fine Arts

The world-renowned Museum of Fine Arts in Boston has an extensive collection that ranges from Egyptian artifacts to Contemporary Art. Visiting this museum is one of the best historical bucket list activities for Boston.

They have an impressive collection of French impressionist paintings and frescoes. The most famous fresco on display at the Museum of Fine Arts was acquired from the Villa des Contrado Bottaro in Pompeii, Italy. You can even see samples of Paul Revere’s silver work. Before he was an art historian, he was a worker in silversmith by profession.

A visit here can be one of the best things to do in Winter when the weather is too cold to do much else. The museum is large, but fortunately, if you have a ticket to the museum, you have a full day of entry plus free entry for another visit within ten days. The museum opens its doors free of charge after 4 pm Wednesday and some public holidays.

5. Walk around Boston Public Garden

Boston Public Garden was the first public botanical garden. The garden has a Victorian flair with a lake and meandering paths, and many locals consider Boston Gardens to be their favorite place in the city.

Boston Gardens is home to more than 80 plant species from the region, as well as many imported species. It also includes a 4-hectare lagoon. And while you’re at it, let’s add taking a ride on the swan boats to our Boston historical bucket list. These famous and vintage boats have been in use for over 100 years.

6. Stroll along the waterfront at Boston Harbor

Boston is surrounded by water, with a beautiful harbor and plenty of water-based tourism opportunities.

Boston skyline as seen from Boston Harbor

Boston skyline as seen from Boston Harbor

Take a tour of the floating museum dedicated to the Boston Tea Party. The museum does a beautiful job of bringing these historical events and characters to life. There are examples of former tea boats and interactive displays, making Boston Harbor one of the most obvious activities on your historical Boston bucket list. You can even throw tea overboard and join the ranks of revolutionaries.

Another unique activity would be a harbor cruise in Boston or a ride on one of the Duck Boats. From the water, you get a different view of Boston. To get the best deal, check in advance on sites like can check the prices Get Your Guide and Tiqets, two websites of which work directly with local operators. While you’re at it, you might as well check for other activities and skip the line tickets for other attractions in Boston.

7. Tour the John F. Kennedy Presidential Museum and Library

This museum is located on the coast overlooking Boston and offers a beautiful view of the city center. The location of the museum was a deliberate decision because of how much Kennedy loved his city of Boston.

The memorial is dedicated to John F. Kennedy and includes research, collections, and exhibitions on the life of the late president. The building is an attraction in itself and was designed by the famous architect I. M. Pei.

Anyone interested in fashion will also love to see some of Jackie Kennedy’s iconic outfits on display.

8. Dive into the history of the Old North Church

The old North Church is the oldest church still standing in Boston. The famous lamps, which signaled “one by land, two by sea,” were hung on the bell tower of this historic Boston church.

You can take a tour of the church and learn all about the history from a resident historian. The tour is free, but donations are always welcome to help maintain this historic building.

9. Tour Fenway Park (or attend a game!)

Fenway’s historical park is almost synonymous with Boston. The stadium is the oldest stadium of the Major Leagues.

Boston’s historic baseball stadium in Fenway Park

Boston’s historic baseball stadium in Fenway Park

With a little bit of planning ahead, you can add watching a baseball game at Fenway Park to your historical Boston bucket list. Doing so is undoubtedly one of the most quintessential things to do in Boston. Or visit the historic stadium and visit the Bleacher Bar at the stadium level. On game days, tours begin 3 hours before the game, and you can see the players while they warm up on the field. On non-game days, you can take a one-hour tour anytime from 9 am to 5 pm.

10. Take a beer tour at a local brewery

One fun thing to do in Boston is to visit a local brewery. Historically, beer has been a big part of the city of Boston, and visitors have the chance to visit historical and massive points of interest like the historical Sam Adams brewery, along with smaller modern microbreweries.

How to get around in Boston

Fortunately, the city’s historic center is very small and very accessible. Many of the most popular things to do in Boston are only 20 minutes from downtown. Public transport is easy to find, so a car is not required. The public transport system is called the MBTA and is well-managed with good connectors throughout the city.

Boston also has a public bike service called Blue Bikes, which is a great way to get around the city. To use a bike or car-sharing service, all you have to do is sign up for an account in advance. Once you have an account, it is straightforward to use.

As you can see, there is no shortage of things to add to your historical Boston bucket list. Enjoy your time at the center of American history!

Things to do in Boston - The Ultimate Guide