The Freedom Trail: Exploring Boston’s Past

One of the best ways to explore Boston’s rich history is by taking a 2.5 mile walk along the historic Freedom Trail. This path leads you on a gorgeous journey to 16 of the city’s most historically significant sites. In my opinion, no first timer’s trip would be complete without taking the time to enjoy this informative, fun, & scenic trail. You will follow a brick pathway from the start in Boston Common to the finish at the USS Constitution in Charleston.

I walked this trail in its’ entirety long before moving to the region. After moving to the Providence metro, I am super familiar with the trail as I’ve walked in many times, both during the busy summer and slow winter season. I prefer the quiet nature of a winter walk, although I could see why tourists prefer the high energy vibe and more comfortable temps of the spring and summer season. No matter when you prefer to visit, I would definitely add this to your New England bucket list. It’s a piece of living history that is fortunately open for all to enjoy for free.

Below I have given an overview of the historic sites you will encounter on the trail, along with a bit of information explaining the significance of each. I hope you enjoy this virtual tour, however, it is by no means a replacement for taking the journey yourself!

1. Boston Common

Boston Common, established in 1634, is the oldest urban park in the US. The beautiful park has been used for numerous purposes over the years, ranging from Civil right rallies, a mass led by Pope John Paul II in 1979, and Anti-Vietnam protests. Today, you can enjoy numerous events here including the Boston Marathon, concerts, and the annual Christmas tree lighting) today.

One of my favorite things to do is ice skate at Frog Pond during the winter season. I have a lot of great memories here including skating while it was snowing on Christmas Eve. You can walk to a lot of great restaurants from here including the nostalgic Cheers pub on Beacon Street.

2. Massachusetts State House

The Massachusetts State House, established in 1798, is home to the General Court and the Governor offices. The building is located on top of Beacon Hill on 6+ acres of land. Great pictures can be obtained across the Street in Boston Common. This is truly a gorgeous building and I love the golden dome. Free tours are offered weekdays, from 10am to 3:30pm. Both self guided and guided are available – check the state house website for further details.

3. Park Street Church

Park Street Church, established in 1809, still operates today. The church housed the first Sunday School (1818) and first anti slavery speech by William Lloyd Garrison (1829). Whether or not you are interested in attending a service, I recommend simply appreciating the architecture. Tours are available during the summer season.

4. Granary Burial Ground

Old Granary Burial Ground, founded in 1660, is the oldest cemeteries in the US. It’s the most visited burying ground in the Northeast according to the trail website. Here you will find the gravestones of many prominent historical figures, including: Paul Revere, Samuel Adams, and Peter Faneuil.

I found this one of the more interesting historical stops; it was pretty cool seeing these gravestones of all these famous names that we have read about in history books. It was built as a means to combat overcrowding at King’s Chapel.

5. King’s Chapel

King’s Chapel, built in 1688, is an active Ecumenical Church. The architecture inside is supposedly the best example of a Georgian church in the US. Legend goes that those waiting to be hung could say their last prayers in pew 13.

I really love this building as the contrast between the old and new architecture is so stark. The old buildings are so much more ornate with so much more attention to detail than the more modern builds. The burying ground is located next to the chapel.

King’s Chapel Burying Ground, founded in 1630, is the oldest cemetery in the city. It is the final resting place of John Winthrop, the first Puritan Governor of Massachusetts.

6. Site of the 1st Public School

Boston Latin School, founded in 1635, was the first public school in the city. It still lives on today, although not in the same location (the original school was torn down in 1745). Out front, you will find a statue of Benjamin Franklin, one of several prominent figures who attended the school (he later dropped out).

The building pictured above is Old City Hall, which was home to the city council from 1865 to 1969. Currently, the building operates as an office and restaurant space. It’s such a gorgeous building, even more so in the winter with the barren trees so you can see the fine detail.

7. Old Corner Bookstore

This historic building was built in 1712 as an apothecary (similar to what a pharmacy is today), and later transformed into a bookstore in 1828. Most notably, this is the location where several famous books were published including The Scarlet Letter and Walden. It now stands as a Chipotle restaurant, so be on the lookout as there is only a small plaque designating the building.

8. Old South Meeting House

The Old South Meeting House, built in 1729, is most known for the meetings which eventually led to the Boston Tea Party. You can purchase tickets for a tour of the inside. They run from 10am-5pm. It’s an interesting experience to tour such a historic building that is surrounded by many modern businesses like a 7-Eleven.

9. Old State House

The Old State House, built in 1713, is the oldest surviving public building in the city. Up until 1798, it was the seat of the Massachusetts General Court. Today, it operates as a museum open to the public. You can purchase a combo pass to tour this house plus the Old South Meeting house mentioned above.

10. Site of the Boston Massacre

The Boston Massacre is the name for the street riot which took place in 1770 between the American colonists and the British. Tensions built up between the 2 groups and eventually escalated after a colonist insulted the “Redcoats.” In back of the Old State house, there is an emblem commemorating the incident. This is one of the most gorgeous buildings on the entire trail in my opinion.