Officially, there are sixteen stops along the trail, so each of those stops will be numbered below, along with all the information you need about them.

The entire tour is 2.5 miles (4 kilometers), but after all the walking you do at each individual location, you’ll easily double this.  It is best to start the Freedom Trail tour very early and well rested, because it will be a long day of exploring some of Boston’s and our Country’s most significant historic sites.

1. Boston Common

While you could start your tour at any stop along the Freedom Trail, this is the easiest place to start your tour.  Boston Common is quickly accessible via public transportation and has a great vibe about it to get you ready for a day of exploring.  It seems that Boston Common is bustling at any time of day, but on a weekend morning, among hundreds of other visitors, there were food trucks,  live bands playing music, and tour guides dressed up in costumes to look like colonists.

Learn while you walk.  Some facts about Boston Common:

• Established in 1634, making it the oldest public park in the United States.
• Boston Common was a place where local puritans could graze their livestock, but was also host to puritanical punishments.  Most notably, there was at one time a hanging tree and a whipping post stationed in Boston Common.
• During British Occupation of Boston in 1775, Boston Common served as a campsite for over 1000 British Soldiers.

Bonus Destination: Mooyah

While we were in Boston Common, we stopped at Mooyah, a build your own burger joint across the street!  Delicious burgers, with plenty of vegetarian options!, and best of all, it is not too far of a detour off the Freedom Trail

2. Massachusetts State House

Standing tall just at the edge of Boston Common, it is hard to miss the gold dome of the Massachusetts State House as you walk along the Freedom Trail.  From the official starting point of the trail, the Massachusetts State House is a 0.2 mile (0.32 kilometer) walk.  The building is closed on weekends and holidays, but can be accessed or toured Monday through Friday from 8:45am to 5:00pm.  Self-guided tours are available, or a guided tour is given, free of charge, Monday through Friday between 10am and 3:30pm.  Tours last approximately 30 – 45 minutes.

Learn while you walk. Some facts about the Massachusetts State House:

• The land that was bought to build the State House was owned by John Hancock.  Construction began two years after his death, on July 4th, 1795.
• The Gold Dome hasn’t always been there.  In fact, originally, it was covered in shingles, and then in 1802, it was copper coated.  It wasn’t until 1874 that the Gold leaf was added to the dome. 
• During World War II, the dome was painted grey to keep the city dark.  The Gold didn’t return to the dome until 1997. 

3. Park Street Church

Park Street Church is just 0.1 miles (0.16 kilometers) away from the Massachusetts State House.  This is a functioning church, and they ask that you please be respectful of their space.  The Church is open for tours June 18th through August 30th, on Tuesdays through Saturdays, between 9:30am and 3:00pm.

Learn while you walk.  Some facts about the Park Street Church:

• The first service was held here in 1810.
• Gunpowder was stored in the crypt below the church during the War of 1812. 
• The Song “My Country Tis of Thee” was sung publicly for the first time from the steps of this church in 1831.

4. Granary Burying Ground

Right next door to the Park Street Church is the Granary Burying Ground, it’s a quick 0.08 mile walk away (0.13 kilometers).  There should be someone standing up front, handing out guides to Granary Burying Ground.  Grab one of those to help you make sense of the 2,300 markers that stand here.

Learn while you walk.  Some facts about Granary Burying Ground:

• John Hancock, Samuel Adams, Robert Treat Paine, Paul Revere, and Ben Franklin’s parents are all buried here.
• It is estimated that there are between 5,000 – 8,000 people buried in this cemetery, although there are only about 2,300 headstones.

5. King’s Chapel & King’s Chapel Burying Ground

King’s Chapel is a 0.1 mile (0.16 kilometer) walk from Granary Burying Ground.  It’s open year round for free tours: 10am – 4pm Monday through Saturday, and 1:30 – 4pm on Sundays in the Summer.  It is only open Friday through Monday in the winter.  We were not able to make the tours at King’s Chapel, but everyone says it’s highly recommended.  While you’re walking through the King’s Chapel Burying Ground, you’ll notice a giant, caged in hole in the ground; that’s a subway vent!

Learn while you walk.  Some facts about King’s Chapel & King’s Chapel Burying Ground:

• The original chapel on this ground was built in 1689, and housed the first Anglican congregation in the colonies.
• This current chapel started construction in 1749.  Instead of tearing down the old chapel that stood in it’s place, they built the new chapel around the old one, and once construction was finished, they dismantled it brick-by-brick and passed it out the windows. 
• The bell hung in the tower of the chapel was cast by Paul Revere. 

6. Boston Latin School Site / Ben Franklin Statue

The next stop is the longest walk along the Freedom Trail so far; the Boston Latin School Site is a 0.3 mile (0.5 kilometers) walk away. One thing I love about the Freedom Trail is that everything is so close together so you can see all of these amazing destinations all at once.  At the Ben Franklin Statue by the Boston Latin School, there are large trees canopying a sitting area.  We grabbed a spot on a bench and took a minute to enjoy our surroundings. 

Learn while you walk.  Some facts about the Boston Latin School Site / Ben Franklin Statue:

• The Boston Latin School stood in the same spot that the Benjamin Franklin statue now stands.  It was opened in April of 1635.
• This was the first public school in the United States (yaay!)
• Students included: Samuel Adams, Benjamin Franklin, John Hancock, and Robert Treat Paine.
• A law was passed in 1647 that required elementary schools be established in any municipality of 50 or more families. 

7. Old Corner Bookstore

Perhaps the biggest disappointment along the Freedom Trail, I was very sad to see this historical site was turned into a Chipotle.  After some research, I learned that the building was set to be torn down until a group launched preservation efforts and proposed it get turned into commercial space instead of flattened and turned into a parking garage.  Even still, it is sad to see a place considered significant enough to be on the Freedom Trail now serving up build-your-own burritos.  The Old Corner Bookstore is just 0.06 miles (0.09 kilometers) away from the Boston Latin School Site / Ben Franklin Statue.

Learn while you walk.  Some facts about the Old Corner Bookstore:

• The most notable tenant of this building was publishing company Ticknor and Fields, who are best known for developing the royalties system for writers.  Before their time, all book rights were purchased for a set fee.
• Harriet Beecher Stowe, Nathaniel Hawthorne, and Charles Dickens were all published by Ticknor and Fields.

 Bonus Destination: Irish Famine Monument

Directly across the street from the Old Corner Bookstore, there is a monument to the Irish Famine.  Its a little park that has plenty of spots to sit and reflect on the history that the monument is depicting. 

8. Old South Meeting House

The Old South Meeting House is just across the street from the Old Corner Bookstore, a 0.04 mile walk (0.06 kilometers), if you were curious. This was the first stop we paid to tour along the Freedom Trail.  The Old South Meeting House was the place where talks of revolution began.  The Boston Tea Party was planned here.  It seemed like an important place to go visit, and we have AAA, so we got a discount to go inside.  What did we have to lose?  Honestly, it wasn’t my favorite stop of the day. 

Yes, it was an influential place, but there were so many things to read, and with our limited time span, I couldn’t fully enjoy and appreciate what we were reading, because I was too busy panicking that we wouldn’t have enough time for the other stops if we kept reading.  But we stayed, read all the information they had to share, and learned a lot about the specific people who lived in Boston during the time of the Revolution, which gave a face to some names I had heard before. Recommended stop if you have a few days to spend exploring the Boston area, but if you’re trying to see it all in a day, I’d skip the museum tour.

Learn while you walk.  Some facts about the Old South Meeting House:

• It was behind these very walls that the Boston Tea Party was launched. 
• During the British Occupation in Boston, the pews were ripped out, the room filled with dirt, and the space was used as a riding school. 

9. Old State House

Unfortunately, we didn’t get the chance to check out the Old State House.   It is another quick walk away from the Old South Meeting House, clocking in at 0.1 miles (0.16 kilometers) away.  This building is currently owned by the Bostonian Society and is home of museum exhibits about the Boston Massacre and the history of the building itself.  This is top of our list when we return to Boston.  We love exploring a place with unique artifacts.

Learn while you walk.  Some facts about the Old State House:

• This is the site of Boston’s first official town hall, dedicated in 1658. Unfortunately, this original building burnt down in the Great Fire of 1711.  It was rebuilt by 1713, and destroyed in another fire in 1747.  The current building was completed in 1750.
• This building served as British Government Offices during the British Occupation.
• On July 18th (MY BIRTHDAY!!) in 1776, the Declaration of Independence was read from the balcony on the back of the building for the very first time. 
• In the 1870s, the city of Chicago offered to buy the building, after it had fallen into extreme disrepair, and relocate it to Lake Michigan.  Embarrassed by this offer, the Bostonian Society was formed and the building was restored.

10. Boston Massacre Site

At the same stop along the trail as the Old State House, and just around back of the building, you’ll find a large circular marker for the Site of the Boston Massacre.  Flooded with people taking photos, the meaning of this site is all but lost.  Take a peak at a plaque that mentions the Boston Massacre which occurred near this spot on March 5th, 1770.  Maybe snap a photo with a few people’s feet in it, and keep moving!

Learn while you walk.  Some facts about the Boston Massacre Site:

• British soldiers killed five and wounded six angry Bostonians on this site.
• This was an important event in provoking Colonial unrest.

11. Faneuil Hall

Take a 0.2 mile, (0.32 kilometer) walk from the Boston Massacre Site, and you’ll find Faneuil Hall.  One of the most notable things about this destination for me is that the National Parks Service has an information desk in here!  They have tons of Passport stamps, maps, and knowledge to share.  In addition, the inside of Faneuil Hall is filled with tons of shops.  This might be a good place to grab a souvenir or a bite to eat.  When we were here, there was even live music going on outside.   Park Rangers lead talks here every 30 minutes or so.  The building is open daily from 9am – 5pm.

Learn while you walk.  Some facts about Faneuil Hall:

• Faneuil Hall was given to the City of Boston by Paul Faneuil.  Paul Faneuil earned his fortunes as a trade merchant (he was involved in a trading operation that shipped slaves from Africa to the West Indies.) He also inherited a large sum of money from his Uncle, on the condition that he never married. 
• Peter proposed building Faneuil Hall so that Boston had a central market where people could sell goods.  While they were a major seaport in the early 1700s, they didn’t have a central market in town for sales. 
• The construction was completed in September of 1743, only six months before the namesake’s death.
• In May of 1764, Faneuil Hall hosted the first protest against the Sugar Act. 
• So many other historic events happened here, surrounding the Revolutionary War, the Civil Rights Movement, and the Women’s Rights Movement.  Samuel Adams lead talks about the tea taxes here, and John F. Kennedy gave his final campaign speech here before he was elected President.  Ask a Park Ranger for more information about what happened in this building!

12. Paul Revere House

To get from Faneuil Hall to the Paul Revere House, you’ve got a bit of a trek.  The next stop is 0.4 miles (0.64 kilometers).  After walking and standing all day, this is the point along the Freedom Trail where it starts to feel like you’ve been walking and standing all day.

This house really stands out because it is the only one on this city block that appears to bow slightly, and because it is made of a dark wood and fenced in by an admission booth amongst modern Boston buildings.  We paid to get into this house too.  The lines to get into each room were incredibly long, so if you have trouble standing for any long periods of time, this may not be the best stop for you. 

I thought this place was really cool and am so glad we stuck it out to see what was inside.  Each room of the house was filled with artifacts of the time that help to illustrate what Paul Revere’s life looked like.  Each room was kept behind a gate, and at the gate were three or four signs that narrated what you were looking at.  That’s where the lines came in.  People were waiting to read the plaques, and eventually there was a bit of back up.  The whole building creaked with every step, but this only added to the feeling that you were somewhere important.

Learn while you walk.  Some facts about Paul Revere’s House:

• This is the oldest remaining building in Boston.  It is estimated that the original house was built around 1680, but purchased by Paul Revere in 1770. 
• The building was sold in 1800, and transformed into commercial space.  It was purchased by Revere’s great grandson in 1902 to prevent its demolition. 
• The building reopened in 1908 as one of the earliest historic home museums in the United States.

Bonus Destination: Mike’s Pastries

While we were walking around, it seemed that everyone was carrying around a box of pastries from a place called Mike’s Pastries.  Intrigued, we eventually went back to check out what all the hype was about.  Inside, there were huge lines, but at the end of the line, were some burrito-sized cannolis, cheesecakes, cookies, and every other sweet you could dream up.  The over 20 flavors of cannolis seemed to be what they were known for, and they didn’t disappoint.  If you’re curious about stopping, be sure to grab your box of Mike’s Pastries before you get too far away from this stop.

13. Old North Church

Continuing on the life of Paul Revere, this next stop, a 0.3 mile (0.48 kilometers) walk away, is the site of the infamous “One if by Land, Two if By Sea,” where Paul Revere started his midnight ride after seeing the signal “By Sea” from the top of the steeple.  Unfortunately we didn’t time our day out with enough time to see this spot before it closed, but the church is open for tours and offers a behind the scenes tour where you can climb up into the bell tower where the lanterns were hung.  Another spot on our list of places to see when we return.

Learn while you walk.  Some facts about Old North Church:

• This is the oldest church remaining in Boston, completing construction in 1745. 
• This was an Anglican Church (a church loyal to the British King) which meant it was very dangerous for Robert Newman to have hung the lanterns in the window signaling the British Invasion. 

14. Copp’s Hill Burying Ground

Continuing down the road just 0.1 miles (0.16 kilometers), you’ll find a small plaque identifying the Freedom Trail (a good photo opp) before entering the Burying Ground. 

Learn while you walk.  Some facts about Copp’s Hill Burying Ground:

• The Oldest Gave marker is dated 1661.
• During the British invasion, the soldiers used the tomb stones as target practice, and the bullet marks can still be seen on these markers today. 

Bonus Destination: the Smallest House in Boston

Directly across the street from Copp’s Hill Burying Ground is the smallest house in Boston.  Just to emphasize how tiny the house is, a car parked directly in front proves that this tiny house is indeed skinnier than the width of an average car.  The house is only 10.4 feet wide, and tapers off to be only 9.2 feet in the back of the building.  Wish we could have gotten a peek inside!

15. USS Constitution

I never thought this walk was going to end.  After hours and hours of walking and standing and touring the city of Boston, this 0.9 mile (1.45 kilometer) walk from Copp’s Hill Burying Ground was just about the death of me.  I whined the whole way there.  I just wanted to stop walking.  As soon as we got to the USS Constitution, all my pains and complaints fizzled away.  There are a couple places you can go around this area in the Navy Yard, but I highly recommend checking out the USS Constitution, the official stop along the Freedom Trail. 

The USS Constitution is run and maintained by the National Parks Service now, and tours of the boat are free.  You do have to check in at a security desk with a photo ID and put your bags through an X-Ray.  The lines for this moved very quickly (shockingly quick) and we were inside the gate in no time. 

Once inside, the whole thing is a free-for-all.  A large majority of the ship is open for exploration.  There are plenty of ladders to climb, windows to peek in, and cannons to trip over (okay, maybe that last one is just me…) Really cool stop, lots of knowledgeable Park Rangers around to answer questions or explain things to a naval novice like me.  If you’re tall, like Jason, be prepared to duck.  if I had to guess, judging by my own height, the clearance height for the lower decks is only about 5’4″. 

Learn while you walk.  Some facts about the USS Constitution:

• The USS Constitution was one of the original six ships of the US Navy. 
• In 1905, it was rumored that the USS Constitution was to be used as target practice and sunk to the bottom of the sea.  Public outcry saved her from destruction, and in 1907 she began her service as a museum ship open to the public. 
• In 1997, the USS Constitution took a celebratory sail in honor of her 200th birthday. 
• Each year, the USS Constitution takes a turn around cruise, where she leaves the harbor to, as the name implies, turn around, so that the waves weather on her evenly. 

16. Bunker Hill Monument

You’re on the last leg of the trip!  Bunker Hill Monument is a 0.4 mile (0.64 kilometer) walk from the USS Constitution.  It’s a beautiful, leisurely walk through neighborhoods.  Once you’re at the Bunker Hill Monument, you can either stay at the bottom of the hill and check out the Museum and Gift Shop, or you can walk to the top of the hill where the Monument stands.  The Monument also functions as an observation deck, free and open to the public.  The only catch is, you have to climb up each and every step to get to the top.  Remember when, at stop 15, I was saying that last stop was the death of me?  I had no idea what lay ahead for me at Bunker Hill. 

The monument is 294 steps to the top.  I had the bright idea, that after being on our feet for almost ten hours that we should climb to the top of the monument! We did it.  It was really, really hard.  There is hardly a place to stop the whole way.  There is barely any room to let anyone pass.  Mostly people passing you will be shimmying past you on their way back down.  But it would be almost impossible to let someone behind you pass while taking a break.  There just isn’t room.  Please know this before committing to climbing to the top.  Steep steps.  Tight Squeeze.  No resting areas.  The view (and the cold breeze) at the top is absolutely worth it though!  Highly recommend it. 

Learn while you walk.  Some facts about the Bunker Hill Monument:

• There were many funding delays to get this monument built.  In fact, a portion of the originally owned land for this monument had to be sold off in order to complete construction. 
• This monument transferred ownership in 1976, now being run by the National Parks Service.

Need a quick and easy printable guide of all this information?  There’s a download for that! I’ve created a printer friendly version of this guide, and it’s available for free in my resource library! Get exclusive access below!

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The post The ULTIMATE Guide to Boston’s Freedom Trail first appeared on Greetings From Kelly.

With the recent popularity of the Passport Program, there is more awareness now than ever before about the smaller parks managed by or affiliated with the National Park Service.  There are 90 parks in the United States that are “officially” designated National Historic Sites. 

While you may have visited the Grand Canyon or Yellowstone, or one of the other big-name parks run by the National Parks Service, you may not have visited Abraham Lincoln’s Springfield Home, or the Saugus Ironworks National Historic Site.  You might be curious about visiting these places, but unsure because you don’t really know much about them. 

The good news is you don’t have to know a thing!  Unlike Yellowstone, where not knowing what you’re getting into could be dangerous, at National Historic Sites, you can go in completely blind.  You don’t have to know anything about the site or the person that it was created for.  You can just go.  Which makes National Historic Sites even more exciting and accessible to Historic Park Newbies. 

While you’re more than welcome to go in knowing nothing, there are some things you can do to guarantee your trip to your first National Historic Site will be the best it can be.  

1. Do your Research Before you Leave

I know I said you don’t have to know anything before you go to a National Historic site, and that is completely, 100% true!  But you will get more out of your trip if you know the background of your destination.

Do they offer tours, and if so, what times?  Do they have audio tours?  Is the historic site mostly indoor or mostly outdoor exploring?  Will there be a place to grab some lunch?  How long will I need to spend here to see everything? 

There are so many things that are helpful to know, about the site that have nothing to do with the historical significance.  While you can learn more about why your chosen Historic Site is important once you get there, you cannot get there on a day they are closed and expect to learn something. 

Some parks, like the previously mentioned Saugus Ironworks, have certain days in the week that are different than others.  At Saugus, they do live demonstrations of the Ironworks Facility and how it functioned, but you aren’t able to see this every day of the week.  If your chosen park has something similar to this, know which day of the week you want to visit and plan accordingly. 

2. Bring a Notebook

Before you head to a National Historic Site, write down questions you have about the place you are visiting before you get there, and continue to write down questions that come up as you explore the site. 

You can also jot down notes about things you learned that you don’t want to forget, or other places that you might want to visit at a later date.  You could write down names of people that are also important, or maybe a specific battle that interests you.   You never know when you’ll hear something you want to remember, so be prepared!

3. Talk to a Park Ranger

Remember those questions that you wrote down in your notebook?  If you haven’t found answers for them yet, bring your questions to a Park Ranger and ask them!  Many of the Park Rangers spend years learning all there is to learn about the Historic Site they take care of.  They’ve read every book and they’ve told every story.  If you have a question that hasn’t been answered, now is your chance to get it!

You might also be able to talk to a park ranger about other historic locations nearby that are related to the site you’re at now.  At our local historic park, the Ulysses S. Grant National Historic Site, I love to talk to the Park Rangers about the other families in the area (the ones that all the streets are named after now!) and how they are related to Grant’s story.   This gives me opportunities to research more about other people that built St. Louis into what it was today.  There really isn’t an end to what you can learn from Park Rangers and the National Park Service.

4. Watch a Video at the Visitor’s Center

The History is typically dense at a National Historic Site.  The videos at the Visitor’s Center can help you to get your foundation before exploring the park deeper.  Visitor Center videos often give an overview of the history of the park, or will bring to life the specific moment that made this place relevant. 

Regardless of the topic discussed, watching the video will help get you oriented for the rest of the park you’re about to see.  Many parks have more than one video, so be sure to ask about all the video topics and find one that interests you most and fits your timeline best. 

5. Talk to the Gift Shop about Books

One of the best things I’ve ever done while visiting a National Historic Site was talk to the person working the gift shop about their favorite book they are selling.  Most of the time, the sales person is ecstatic to talk about their favorite topics. 

The gift shop attendant spends most of their day answering questions about t-shirt sizes, or giving directions to the bathroom, or being asked where the Passport Stamp is.  But it is important to remember that the person working the gift shop, often a volunteer, chose this park because it is a place they are passionate about.  Give them the chance to talk about their passions, and they will gladly share all that they can.

6. Take a Guided Tour

Not all historic parks are accessible without a park ranger, but if you have the option to explore the site on your own, I highly recommend you opt not to do that.  There is so much more you will gain by walking through the site and learning about it from a Park Ranger who spends all their time mastering it. 

If you have to go without a ranger, ask if they have a guided audio tour that you can listen to while you walk.   At the John F. Kennedy National Historic Site in Brookline, Massachusetts, Rosemary Kennedy, JFK’s mother, narrates the audio tour.  She walked through the house where her family grew up and recorded stories of things she remembered from the home.  They turned this into the audio tour, and it is truly unforgettable.  While the rangers are happy to share more stories and background in length, there is nothing like having Rosemary Kennedy give you a tour of her own house.

7. Take a Hike Before you Go

Many people who visit the National Parks love the parks because they love being active, getting outdoors, and connecting with nature.  Oftentimes, you won’t find this at a National Historic Site.  Many of the National Historic Sites are homes of influential people from history.  The extent of the walking will be within the home.   If you’re waning to stay active, get a hike in before you visit!

Some Historic Sites have hiking trails on the property that you can take advantage of.  At the Abraham Lincoln Boyhood Home, you can walk the paths between the Visitor Center and the house and walk the same places that Lincoln once walked.

If there aren’t any trails at the Historic Site you are visiting, it might be a great time to check for a nearby State Park and explore the hiking trails there.  It’s always a great idea, especially after a long car ride, to get your blood flowing before settling into learning.

8. Find a Connection to Another Park and Continue the Journey

The majority of historic sites can be seen in a couple of hours.  Which means if you plan it out just right, it is possible to visit more than one in a trip.  Check the map and see if there is another destination close by.

If you aren’t able to see more than one in a day or in a weekend, connect the park you are currently visiting to the next destination.  In the Midwest, it is very easy to link multiple Historic Sites that are all tied to Lincoln.  You can start at Lincoln’s Birthplace in Kentucky, visit his Boyhood Home in Indiana, and finish with his home in Springfield Illinois.  You can trace his steps from birth all the way to his presidency. 

The same could be said for battles of the Civil War, you can follow the stories of the Civil War from battlefield to battlefield.  You could pick a theme, like Black History, and visit all the parks that share that connection.  The possibilities are endless, but building on what you learn in one park by continuing learning in another is a great way to bring history alive and stay enthusiastic about what you’re learning.

Are you planning a trip to a National Historic site?  Where will you be visiting and what kinds of things will you be asking once you get there?   I’d love for you to share with me the questions you have and the answers you find.  The opportunities to learn are endless with our National Parks.  Where will you explore next?

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Brookline, MA

I like to fondly refer to our hotel in Brookline as the “shittiest hotel in the nicest neighborhood.”  Frankly, that’s where we always look to stay.  We look for the nicest, safest, cleanest, most top rated neighborhoods in a metropolitan area, and then we find the cheapest hotel that area will allow.  In Boston, even the worst hotels didn’t come cheap.

JFK National Historic Site

We landed for our long weekend in Boston in the early afternoon, and took a Lyft to our hotel.  We immediately dropped everything in our room and ran out the door to our first stop.  As avid National Park visitors, we pulled out our National Park Passport and ran to the JFK National Historic Site in Brookline, just a short walk away from our hotel.  We knew we would be too late for a guided tour, but the last hour of the day is set aside for self-guided tours.  They have an introductory video (which I highly recommend), a listening device with Rose Kennedy narrating life for the Kennedy’s in this home, and a ranger stationed on each floor to answer questions and tell additional stories.

At the information desk, they had a stack of maps of the Brookline area with suggested places for dinner.  We grabbed our map and headed to our next spot, a small place for a bite of pizza.

OTTO Pizza

Unbeknownst to us, we found ourselves at a place that actually originated in Portland, ME, one of our future stops for this trip.   There was a wait for a table, but the bar had full service and had plenty of seats open.  We grabbed a couple of slices of pizza — they mostly had New York style pizza (or maybe BOSTON style pizza, depending on who you ask) and one Detroit style pizza — we had a few beers, and continued down the road for dessert.

J.P. Licks

I’ll be honest, the name of this eatery piqued my interest.  J.P. Licks is an ice cream shop that had probably 40 different kinds of ice cream, and just as many toppings, creating a completely customizable experience.  We stuck with the standard flavors and skipped the toppings, but highly recommend this spot.  The ice cream was delicious and the service was even better.  We really felt welcome here.  Seating was limited this fall, I can only imagine what it looks like in the summer, but it is absolutely work the stop.

After dessert, we did two things that we always do on trips like these.  We bought a Metro Pass (in Boston, they call it a “Charlie Card”) and we bought some groceries.

Where to Buy a Metro Pass (Charlie Card)

Finding a Charlie Card proved more difficult that we originally thought.  Buying a one-time use pass was easy.  Nearly every stop along the route sold one of those.  But we needed a 24-hour pass so we could get around all day the next day.  Be careful, your Charlie Card day pass is good for 24-hours.  Don’t use yours to get back to your hotel for the night and then sleep off 8-hours of use.  Instead, buy a one-time ticket to get home and use your pass the next day so you have plenty of time to get where you need to go!

We used THIS LINK to help us locate a spot that sold a Charlie Card.  We ended up at a small liquor store a few blocks away from the main part of town.

For a long weekend in Boston, having this Charlie Card is an absolute must. Don’t rely on your feet for the entirety of this trip, especially if you’re staying in a suburb.

Trader Joe’s

Next stop was a Trader Joe’s on Beacon Street.  We grabbed some essentials for the remainder of our trip (bread, lunch meat, cheeses, breakfast muffins, yogurt, fruit leather, granola bars) We bought things we could use for quick and cheap snacks throughout the trip to tide us over.  This way we would be able to eat a quick breakfast in the morning (our hotel did not provide a free breakfast) then explore a bit, eat a lunch that we packed, and then splurge on dinner and treats along the way.

Boston, MA

That night, we took a trip into Boston to grab some dinner and drinks at a brewery near Boston Commons.

Democracy Brewing Company

We were ready for a low-key evening, and that’s exactly what Democracy Brewing was able to provide.  When we arrived, we settled into a corner booth, had a beer flight and a few appetizers to go with it, and enjoyed some time side by side with some locals (who were just getting their night started instead of just ending it.)

After dinner, we roamed around the area and found ourselves walking through Boston Commons in the dark (an experience that felt incredibly safe.  Tons of people were walking around this area still.) They had a carousel running and we just sat in the grass and watched the lights spin around for a while. It was such a wonderful way to end our evening.

Fenway Park

The next morning, we took the tram back into Boston for a tour of Fenway. We took the 9am tour, planning to spend the rest of our day on the Freedom Trail.  I cannot recommend the Fenway Tour enough.  Not only for baseball fans, but for anyone interested in learning a little bit more about the history of Boston. 

Baseball is such an integral part of this city, and our tour guide was so passionate about the history of Boston Baseball.  He told so many great stories, and we got to see the park from every angle imaginable.  Sitting on top of the green monster, sitting in the oldest seats in all of baseball, sitting in the press box, you can see almost every inch of Fenway on the basic tour, or upgrade to a tour that gets you on the field and inside the Green Monster.  You can buy tickets here.

The Freedom Trail

I’ve got a whole post, my ULTIMATE Guide to the Freedom Trail (going live in a couple days!)  Click here to read everything you need to know about walking the Freedom Trail from start, at Boston Common, to the finish at Bunker Hill Monument.

I was a little bit skeptical about doing something so touristy on a weekend, but I am so glad we took the time and fought the crowds to learn more about our country’s history.  I love incorporating history into travel, and Boston was the jackpot for that!

After a full day of walking, climbing, and standing in lines.  We were absolutely exhausted by the time the sun went down.  We settled back into our hotel (after dealing with a maintenance call…I told you, shittiest hotel in the nicest neighborhood…), got into some comfy clothes, and ate pastries in bed.  Where did the pastries come from, you ask?  You’re just going to have to check out my post on the Freedom Trail to learn more!

The next morning, I walked to pick up our rental car while Jason packed up our room and got us checked out.  Once we had everything taken care of, we drove down south to the Sam Adams Brewery and Tap Room. It’s a bit of a long haul if you would try to do this via public transportation.  I’d recommend driving here or taking a Lyft. If your time is limited to a long weekend in Boston, you do not want to waste any time.

Ula Cafe

We arrived a little early, so we grabbed coffee and a scone at Ula Cafe.  There were tons of people already busy working here when we arrived.  We found a table in the back and waited for the brewery to open.

Sam Adams Brewery and Tap Room

Unfortunately, the tours were cancelled for the day, but the Tap Room was open and they walked everyone through the tasting process and gave everyone a free beer for stopping by.  We grabbed a flight here, hung out for a while, and then left Boston.

Boston is such a fun city and it’s so easy to spend a weekend of non-stop moving here.  Know what you want to do before you go, and hit the ground running.

Do you have any favorite spots in Boston for my next visit?  Leave them in the comments below and let me know where to go next time we have a long weekend in Boston!

The post A First Timer’s Guide to a Long Weekend in Boston, Massachusetts first appeared on Greetings From Kelly.