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The Ultimate Guide to Boston's Freedom Trail

We’ve had the pleasure of visiting Boston a handful of times in the past year and we find something new to love about this beautiful city every time. One of our favorite things that we’ve gotten to experience is the Freedom Trail. You get to see so much of the city along with some of the most significant historical sites in the entire United States. If you’re visiting Boston and have half a day or full day to spare, we highly recommend it! You can choose to go on a paid, guided tour, or do what we did and get a map (PDF version) and take the trail at your own pace! If you’re reading this and wondering “What is the Freedom Trail?”, here's a little run down...

The Freedom Trail is a 2.5 mile long walking path that winds through downtown Boston, Massachusetts, and passes by 16 historically significant sites along the way. Marked by a red brick pathway (2 bricks wide), it runs from Boston Common to the Bunker Hill Monument in Charlestown. Most of the sites are free of charge or suggest donations, but the Old South Meeting House ($6 for adults, $5 for seniors and students, $1 for children 5-17), the Old State House ($12 for adults, $10 for seniors and students, $0 for 18 and under), and the Paul Revere House ($5 for adults, $4.50 for seniors and students, $1 for children 5-17) charge admission.

Now that we’ve covered the basics, here’s all the fun details and our recommendations and tips to make your Freedom Trail experience as amazing as ours!

*Be sure to watch our "Massachusetts: Boston for a Day" vlog for a closer look at our time on the Freedom Trail*

The best way to get started on your Freedom Trail Adventure is to take the Green or Red Line to Park Street Station, which is the closest station to Boston Common and the beginning of the Freedom Trail. Or you can take the Blue or Orange Line to the State Street Station and you’ll have a 5-7 minute walk.

1. Boston Common: Serving as the starting point to the Freedom Trail, this beautiful central public park dates back to 1634, making it the oldest city park in the United States. From 1634 to 1830 the Boston Common was used as a common space for the grazing of cattle and is now a place for visitors and locals to meet up with friends, relax, and enjoy a day in the park.

Once you’ve spent some time taking in the sites and beauty of Boston Common you’ll make your way up the trail and through the park to the next stop on the trail...

2. Massachusetts State House: Built in 1787, this is where the state legislature meets and is the oldest continually running state capitol building in America. The dome was originally made of wood and in 1802 it was covered in copper by Paul Revere. It is currently gilded in 23k gold! During weekdays the State House offers free guided tours of the inside of the State House. Tours run on the half-hour, Monday through Friday from 10:30 am to 3:30 pm. You can make your reservation by calling 617-727-3676. Directly across the street from the State House, you’ll find the Robert Gould Shaw Memorial which is worth seeing. It shows Gould-Shaw and his men of the 54th regiment of the Union Army. The 54th Regiment is the first all-volunteer African American unit in the US Army which was formed in 1863 during the American Civil War.

We decided not to do the free State House tour in order to allow more time for some of the sites later on since we only had a half day, but that is totally up to you. Once you’ve taken in the beauty of the golden dome State House and the Civil War Monument, you’ll follow the trail back through Boston Common and take a left on Tremont Street to find your third stop...

3. Park Street Church: Built in 1809, Park Street Church is an active Congregational church in Downtown Boston. And while it has a strong theological history, it is probably best known for its role in social justice and human rights. This congregation was among the first to grapple with prison reform, education, women’s suffrage, and anti-slavery.

Now you can continue down Tremont street for a short walk to the next site...

4. Granary Burying Ground: The Granary Burying Ground is the city of Boston's third-oldest cemetery, founded in 1660. It is the final resting place for many notable Revolutionary War-era patriots, including Paul Revere, the five victims of the Boston Massacre, and three signers of the Declaration of Independence: Samuel Adams, John Hancock, and Robert Treat Paine. The cemetery has 2,345 grave-markers, but historians estimate that as many as 5,000 people are buried in it.

This was one of our favorite stops on the trail. Getting to see the grave sites of people that had such a huge impact on US history was surreal. We spent 20 minutes or so just roaming the beautiful cemetery taking in the history that was right in front of us. After leaving the burying grounds, you’ll make your way back onto Tremont street, then make a right on School Street toward your next site...

5. King's Chapel and Burying Ground: Founded in 1686 as Boston’s first Anglican church, King’s Chapel is home to over 330 years of history. The 1754 granite building still stands on the church’s original site: the corner of King’s Chapel Burying Ground, Boston’s oldest English burying ground (est. 1630)

While they do offer crypt and bell tower tours, we chose to continue making our way down School Street to stop number 6…

6. Benjamin Franklin statue and former site of Boston Latin School (now Old City Hall): Founded on April 23, 1635, it is the oldest public school in America. It offered free education to boys - rich or poor - while girls attended private schools at home. Until the completion of the schoolhouse in 1645, classes were held in the home of the first headmaster, Philemon Pormont. A mosaic and a statue of former student Benjamin Franklin currently marks the location of the original schoolhouse. Currently the Old City Hall (est. 1865) stands in place of the schoolhouse and now serves as office and commercial space.

While this may be the historic Old City Hall building, it currently serves as office space to some of Boston’s leading professional firms as well as houses Ruth's Chris Steak House. We didn’t go inside, but we did stop to get some photos of the beautiful French Second Empire architecture. One of the interesting things about Boston is that many of these historical buildings are used as commercial space, and the next stop is no exception...

7. Old Corner Bookstore: Constructed in 1718, the Old Corner Bookstore is downtown Boston’s oldest commercial building and was home to the 19th-century publishing giant Ticknor and Fields, producer of many venerable American titles including Thoreau’s Walden, Hawthorne’s The Scarlet Letter, Longfellow's Midnight Ride of Paul Revere, and the Atlantic Monthly including Ward Howe's Battle Hymn of the Republic. Saved from demolition in 1960, the building’s leases help subsidize important historic preservation projects in Boston’s neighborhoods.

The Old Corner Bookstore is currently home to Chipotle Mexican Grill. While we opted to grab food at a more unique-to-Boston establishment, you could always stop in for a snack and be able to say that you ate at what is likely the most historic Chipotle location! Once you’ve gotten your fill of history and mexican food at The Old Corner Bookstore, you’ll hang a right onto Washington Street to your next stop...

8. Old South Meeting House: Built in 1729, Old South Meeting House is a historic church building that gained fame as the organizing point for the Boston Tea Party on December 16, 1773. Five thousand or more colonists gathered at the Meeting House, the largest building in Boston at the time.

9. Old State House: Built in 1713, it was the seat of the Massachusetts General Court until 1798, and is one of the oldest public buildings in the United States. It is the oldest surviving public building in Boston, and now serves as a history museum.

10. Site of the Boston Massacre: This cobblestone ring marks the site of the 1770 civilian massacre & Revolutionary War precursor.

11. Faneuil Hall: Opened in 1743, Faneuil Hall was the site of several speeches by Samuel Adams, James Otis, and others encouraging independence from Great Britain. Now, it is a shopping center with many stores & restaurants comprising 3 historic market buildings & a promenade.

On top of holding such historic value, Faneuil Hall/Quincy Market is a great spot to take a break from all the walking and grab a bite to eat or do some shopping. There are tons of shops and restaurants to choose from. We especially love Boston & Maine Fish Co. for their Lobster Rolls, but if you want to deviate a little from the trail you can head to Union Oyster House.

Being the oldest operating restaurant not only in Boston, but in the entire US (est. 1826), we felt that it was worth a visit. Fun fact, the Kennedy family were regulars here and JFK had a favorite booth (now appropriately named “The Kennedy Booth”). While we did enjoy and appreciate the history of the place, we did feel that it was a little bit of a tourist trap. The food was ok and overpriced in our opinion and the service was average. Our recommendation would be to stop in for drinks or maybe an appetizer, because it is worth the visit, but get lunch at Faneuil Hall or wait until you get into the North End where you’ll find some amazing Italian food!

12. Paul Revere House: Built c.1680, this was the colonial home of American patriot Paul Revere during the time of the American Revolution.

This is our favorite area of Boston… The North End. We’ve never done the official Paul Revere House Tour, but it’s amazing just seeing a piece of history with that significance standing in the middle of a busy city. The North End is rich in history, culture… and food! Every time we visit Boston we find ourselves in the North End eating pasta and pastries! We just can’t resist! Many amazing restaurants and bakeries are right on the trail or just a short detour. We’ve enjoyed La Famiglia Giorgio's Restaurant and Al Dente on our most recent trips, and you have to try Mike’s Pastry and/or Modern Pastry while you’re there. Some of the best desserts you’ll ever have!

13. Old North Church: Old North Church (officially, Christ Church in the City of Boston), is the location from which the famous "One if by land, two if by sea" signal is said to have been sent. This phrase is related to Paul Revere's midnight ride, of April 18, 1775, which preceded the Battles of Lexington and Concord during the American Revolution.

14. Copp's Hill Burying Ground: Named after shoe maker William Copp (originally named "North Burying Ground") this cemetery was established in 1659, making it the city's second oldest cemetery.

From here you have a little bit of a walk (or drive) to your next stop (.9 miles to be exact), but it doesn’t come without some nice scenery. You’ll leave the North End and walk across the North Washington Street Bridge which passes over the Charles River. Your last two sites are in the neighborhood just on the other side of the river, Charlestown.

15. USS Constitution: Also known as Old Ironsides, the USS Constitution is a wooden-hulled, three-masted heavy frigate of the United States Navy. She is the world's oldest commissioned naval vessel still afloat. She was launched in 1797, one of six original frigates authorized for construction by the Naval Act of 1794 and the third constructed. The name "Constitution" was among ten names submitted to President George Washington by Secretary of War Timothy Pickering in March of 1795 for the frigates that were to be constructed. Joshua Humphreys designed the frigates to be the young Navy's capital ships, and so Constitution and her sister ships were larger and more heavily armed and built than standard frigates of the period. She was built at Edmund Hartt's shipyard in the North End of Boston, Massachusetts. Her first duties were to provide protection for American merchant shipping during the Quasi-War with France and to defeat the Barbary pirates in the First Barbary War.

Getting to step aboard a ship that is nearly as old as America is kind of mind boggling when you think about it. It was one of our favorite stops on the trailI and it is definitely worth taking the time to do the tour. There is a security checkpoint with a metal detector that you have to go through, so just keep that in mind when planning your visit. When you’ve finished your time at the USS Constitution, you’ll take a short half mile walk to the final site on the trail...

16. Bunker Hill Monument: The Bunker Hill Monument was erected to commemorate the Battle of Bunker Hill, which was among the first major battles between British and Patriot forces in the American Revolutionary War, fought there June 17, 1775. The 221 foot granite obelisk was erected between 1825 and 1843 with granite from nearby Quincy, conveyed to the site via the purpose-built Granite Railway, followed by a trip by barge. There are 294 steps to the top, and while we didn’t have time to make the climb, we definitely plan to on our next visit.

And THAT is how you do the Freedom Trail! And you’ve put in enough miles to justify a second stop at Mike’s Pastry or Modern Pastry! We hope that this blog has helped you plan your next trip to Boston. Please, tag us (@AdventuresofMattandNat) in any photos and let us know your favorite part of the Freedom Trail!

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