Favorite Ways to Spend a Fall Weekend in Boston & Salem

Favorite Ways to Spend a Fall Weekend in Boston & Salem

Fall is a fantastic time to visit New England.  The air is crisp, the leaves are changing into brilliant hues, and the temperatures are generally great for sightseeing.  A few years ago we spent fall break in Boston with a day trip to Salem.  We highly recommend this trip in the fall!

When we went

We visited in mid-October and had lovely fall weather with blue skies and abundant sunshine.  The leaves were a gorgeous palette of gold, red, and orange.  It was perfect!

Where we stayed

We stayed at an Airbnb in Somerville and were really happy with the location.  The Airbnb was located just outside of the city so it was a bit more peaceful to head back after a day of busy sightseeing.  It had a tiny fenced yard where the kids enjoyed running about and playing football, a kitchen to cook meals, and plenty of space to spread out.  We were also within walking distance to the train station which provided our transportation for our time in Boston.

Boston, Massachusetts

About Boston

If you grew up in the U.S. then you most likely learned about events that took place in and around Boston in history class.  Boston is the heart of historical America, having such important events that shaped the future of our country such as the settlement of the Puritans, the Boston Tea Party, and the Boston Massacre.  Today, Boston is a bustling, modern city while clearly still rooted in its historical past which makes it both an educational and fun place to visit.

A beautiful fall morning in Boston


The Freedom Trail

The Freedom Trail is a must during a visit to Boston.  You can walk this 2.5 mile route at your leisure, starting either from The Boston Common or The Bunker Hill Monument. 

We started from the Bunker Hill Monument, which is where most people will end.  Our reason for starting here is so that we would be in Little Italy in time for lunch, which worked out perfectly.  We arrived just as the restaurants were opening up and had our pick of tables for our party of 9.  Shortly after, a line was out the door and down the sidewalk!  The other reason we wanted to start here is so that we would end at the Boston Common.  This allowed our kids to run off their energy after a day of educational sightseeing.

The trail is easy to follow with its red brick path on the city’s sidewalks leading visitors along a route of some of Boston’s most important sites.  Visit cemeteries, churches, and meeting houses, walk through Paul Revere’s House, and stand at the site of the Boston Massacre.

Now, let’s walk the trail!

Five cousins ready to walk the Freedom Trail!

We started off at the Bunker Hill Monument, which is the site of the first battle of the American Revolution.  From here, we made our way past the USS Constitution, nicknamed “Old Ironsides” due to the fact that cannonballs fired at the ship seemed to bounce right off the ship’s sides.  The museum provides a hands-on experience for those who want to learn more about the history of the USS Constitution.  Our next stop was Copp’s Hill Burying Ground, the final resting place of many notables.  This cemetery is unique as it elevated and has lovely panoramic views. 

Look at these fall colors at Copp’s Hill Burying Ground!

Next up is Old North Church, where we spent some time learning about the importance of the box pews, notables who attended the church, as well as the part the church played at the beginning of the American Revolution. 

The interior of Old North Church

Continuing on, our favorite stop on the Freedom Trail was next, Paul Revere’s House.  Walking through this low-ceilinged house that Revere’s family lived in during the time of his famous ride was incredible.  It is the oldest standing building in Boston and sits juxtaposed right amongst modern buildings.

Paul Revere’s House, next to modern day buildings

The cousins in Paul Revere’s yard

Fanueil Hall is the next stop, one of America’s first meeting venues.  Continuing on, the site of the Boston Massacre is next where a plaque is erected on the sidewalk at the site of where five Bostonians were killed by the British. 

Checking out the site of the Boston Massacre

This site sits right in front of The Old State House, which is another historical building right in the midst of modern skyscrapers. 

The Old State House, juxtaposed next to modern buildings

You’ll soon pass The Old South Meeting House, where no tax on tea was famously declared.  I sure love Chipotle but it’s a bit disappointing that one is housed in what used to be The Old Corner Bookstore!  Many notable works by American authors were published at this bookstore so the building still plays an important part in American history.  Up next is the site of the Boston Latin School, which is the first public school where anyone of any financial means could attend.  A statue of Benjamin Franklin is also located here.  King’s Chapel & Burying Ground, New England’s oldest Anglican church, was founded in 1686 and houses America’s oldest continually used pulpit.  We spent a good bit of time walking through the next stop, Granary Burying Ground.  See the final resting places of Samuel Adams, Paul Revere, and the five victims of the Boston Massacre. 

This cemetery holds so much history

From here, continue on to Park Street Church, which has an important history in civil liberties, and the Massachusetts State House, sitting on what was originally John Hancock’s cow pasture, now the site of the state’s government.  The final stop is the Boston Common, a great way to end your time on the Freedom Trail.  Our kids ran off their energy playing tag and enjoying snacks from one of the many park vendors.  We adults sat on the benches watching them, happily resting in this beautiful park.  It was a great way to spend a day walking our way through American history.  

Boston Tea Party Ships & Museum

Kids (and sometimes adults!) are most eager to learn when there are hands-on and interactive experiences involved.   The Boston Tea Party Ships & Museum certainly delivers!

The museum is divided into sections to separate the different experiences one can do.  In Experience 1, a costumed interpreter taking on the part of John Adams acts as your guide.  Learn all about how the Boston Tea Party began.  In Experience 2, get your chance to throw tea into the harbor from an 18th century ship, just as those patriots did during The Boston Tea Party!  With Experience 3, enjoy a reenactment of the next day’s consequences for having been a part of The Boston Tea Party.  In Experience 4, view Robinson’s Tea Chest, the only surviving tea chest from the Boston Tea Party.  With Experience 5, head to the Minuteman Theatre to watch an award-winning, multi-sensory documentary.  And finally, stop at Abigail’s Tea Room, which serves a variety of drinks and snacks, but most importantly, TEA!

The Boston Common 

The Boston Common is the start (or in our case the end) of the Freedom Trail.  It is the oldest public park in the United States, dating back to 1634.  Initially, it was a grazing pasture for the Puritan’s animals.  Since then, it saw much activity during the Revolutionary War, bore witness to executions, including some from the infamous Salem Witch Trials, and in more modern times war protests and civil rights rallies have taken place here.

We found this historical park to be a beautiful respite after a busy day of sightseeing.  There are plenty of places to grab a snack and drink and park yourself on a bench to relax in the shade under trees with colorful changing leaves.  The kids had a great time playing an impromptu game of tag right on the grounds where so much American history has taken place.

If you’re here at a different time of year, there will be plenty of activities to keep you busy.  In the summer, Frog Pond acts as a splash park for those wishing to seek some respite from the heat.  In the winter, you can ice skate.  

Snacking, a game of football, and tumbling in the Boston Common

Candle Pin Bowling

Candle Pin Bowling is an activity that is found in America’s New England States and Canada’s Maritime Provinces.  It is similar to bowling, but the candle-shaped pins are longer and narrower than a traditional bowling pin and the ball is smaller and heavier.  Our kids found this much easier and more fun than traditional bowling.

We headed to Sacco’s Bowl Haven in Somerset to play a round of Candle Pin Bowling and followed up with a dinner of some delicious wood-fired pizza all under one roof.  It was a fun evening for the kids and the adults!

Playing a game of Candle Pin Bowling

Delicious wood-fired pizza followed our game of Candle Pin Bowling

 Take a Peek at Acorn Street

Do you want to visit one of the prettiest streets in America?  Then be sure to head to the Beacon Hill neighborhood of Boston and check out this quiet, residential street that is also often teemed with people snapping pics.  From its cobblestoned lanes to perfectly placed flower boxes and American flags, it is definitely worth a visit to get some lovely photos.

Acorn Street, one of America’s most beautiful streets

Salem, Massachusetts

About Salem

Salem is synonymous with the infamous Witch Trials which took place during 1692-1693.  During that time, 19 people were convicted of witchcraft and executed.  Soon after, public opinion changed and guilt over the executions ran deep within Salem.  Later, the Massachusetts General Court annulled the guilty verdicts, but of course it was too late for those put to death.

Besides its witchy past, Salem has a history steeped in whaling, due to its prominent location on Salem Bay Harbor.  Located just 15 miles northeast of Boston, it was a quick train ride for us to get there from where we were staying in Somerville. 

Salem, Massachusetts, on Salem Bay Harbor

Salem Trolley Tour

After we got off the train we walked a short distance to hop on the Salem Trolley Tour, our first activity of the day.  This one-hour narrated tour took us all throughout Salem, showing us the major sites all while narrating the journey with facts, both fun and historical.  

We highly recommend this as a great introduction into Salem.

Old Burying Point/Charter Street Cemetery & Witch Trials Memorial

Our favorite place in Salem was Old Burying Point, also known as Charter Street Cemetery.  This cemetery is Salem’s oldest and one whose gravestones are representative of simple Puritan design, free of crosses or angels.  Some inscriptions are barely readable anymore, having weathered 350 years.  

Old Burying Point in Salem

But the most moving part is just outside of the cemetery, along the perimeter of wall.  The Witch Trials Memorial pays homage to those executed after being convicted of witchcraft.  Nineteen rough hewn benches, one for everyone who died, are erected out of the wall with a name engraved, how they were put to death, and the date of death.  It really humanized this terrible time in Salem’s history.  It also was a good lesson for the kids to remember that we should always learn important lessons from history.  Flowers are still brought to the benches to honor the executed to this day.

The very moving Salem Witch Trials Memorial 

The House of Seven Gables

This famous house sits right near the harbor and does indeed have seven gables.  Made famous by Nathaniel Hawthorne’s book, The House of Seven Gables, it was built in 1668 and has been a standing solidly since.  Today, it is a non-profit historical museum and continues to be a symbol of Salem’s history. 

The Witch Dungeon Museum

There are a variety of kitschy museums and touristy haunts all trying to play into Salem’s witchy past.  But the most popular one is definitely the Witch Dungeon Museum.  

The museum reenacts a witch trial from 1692 and follows with a tour of a replica dungeon.  The real dungeon was just a few blocks away on Federal Street, though no longer standing.

A plaque is now erected where the witchcraft trials once took place

Peabody Essex Museum

Did you know that the Peabody Essex Museum is the nation’s oldest continuously operated museum?  It began in 1799 to showcase artifacts and curiosities from the far corners of the globe.  Today, it continues to boast a massive collection of art and prides itself on being a multi-dimensional museum:  a library, a museum, and an archive.  There is a lot to see here and it’s an incredible collection, one of the nation’s best.

Haunted Happenings – A Monthlong Festival

This fall festival runs during the month of October in Salem.  There are multiple events each day for a month of spooky fun!  Enjoy such events such as broom making, book binding, family movies, an open-air market, and magic shows.  We found the festival to be full of Halloween flair and got us into the spirit of Halloween!  We also got some great souvenirs!

Visiting Boston and Salem, Massachusetts in the fall should be on every traveler’s bucket list.  Not only will you get a good dose of American History but you’ll find fun for the whole family, from a unique game of bowling to a month long haunted festival!  


Dietary Notes

As always, everyone’s needs are different.  At press time my husband is grain-free and two of our kids are allergic to nuts and eggs.  Although we encompass a fair amount of dietary restrictions, we can only offer advice as to what pertains to our own family, as that is where our expertise lies!

We had an Airbnb during our stay in Boston.  We grabbed groceries from a nearby Trader Joe’s so we could eat breakfast, some lunches, and a dinner in.  

Our kids with allergies were able to eat the wood fired pizza at Sacco’s Bowl Haven in Somerset and Victoria Station in Salem (which is now permanently closed).

Dining out in Boston and Salem was relatively easy and they were always able to find meals they could safely eat.

For more on traveling with dietary restrictions, be sure to check out our guide:  On the Go with Allergies.

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