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Boston Freedom Trail Itinerary (How to Do It in One or Two Days)

Boston Freedom Trail Itinerary (How to Do It in One or Two Days)

Lizzie

Introduction

The Shaka Guide Freedom Trail Tour in Boston, Massachusetts, literally walks you through the historical events that led up to the American Revolution and our country's ultimate freedom from British rule.

The Freedom Trail is the birthplace of American liberty and is historic in many ways.

We've divided the Freedom Trail into two tours. The first one covers 14 of the 16 official stops on the Freedom Trail.

The second tour covers the final two, located in the distant neighborhood of Charlestown.

We begin our tour at the Boston Common and end in the historic North End neighborhood.

DAY ONE Itinerary

Illustrated map of the Boston Freedom Trail Part 1, highlighting key historic sites like Boston Common, Old North Church, and Faneuil Hall.

1. The Boston Common

The Freedom Trail leads to Park Street Church in Boston, with people walking along the historic path on a clear day.Lizzie G

  • Duration: 15 minutes

When Puritans established the city of Boston, they designated a common area for gathering and for livestock to graze. Today, it's a central park with fountains, ponds, and the start of the Freedom Trail.

2. Massachusetts State House

The Massachusetts State House in Boston, with its iconic golden dome, stands against a bright blue sky, with the American flag waving nearby.Matt Caracciolo

  • Duration: 30 minutes

Constructed in 1798 and designed by noted Boston architect Charles Bulfinch, the Massachusetts State House is actually the "new" state house.

Enter the building through the General Hooker Entrance, which is just to the right of the front of the state house. Guided tours are available 10 am-3:30 pm, but advance registration is required.

Self-guided tours are available from 8:45 am to 5 pm. For more information, visit here.

3. Park Street Church

  • Duration: 5 minutes

Park Street Church is an active Congregational church, and the inside is not open to the public outside of church services.

For more information on church services and events, visit their website. 

4. The Granary Burying Ground

The Granary Burying Ground in Boston, featuring historic tombstones and the prominent Franklin family obelisk, surrounded by lush green trees.Matt Caracciolo

  • Duration: 15 minutes

This cemetery is the final resting place for over 2,000 Bostonians, including famous patriots like Samuel Adams and Paul Revere.

5. King's Chapel and Burying Ground

King's Chapel in Boston, a historic stone church with grand columns, visitors exploring its grounds, and modern skyscrapers towering in the background.Matt Caracciolo

  • Duration: 15 minutes

King's Chapel is considered one of the finest examples of Georgian architecture. A small fee gets you inside the building, but there are also guided tours available for areas off-limits to the public.

For more information on tours, click here.

The Burying Ground is the oldest cemetery in Boston and is accessible from the street outside the chapel.

6. Boston Latin School Site

  • Duration: 5 minutes

The former site of the Boston Latin School, which educated many of the Revolution's most ardent patriots. Today, it's the site of the old Boston City Hall and a statue of Benjamin Franklin.

7. Old Corner Bookstore

  • Duration: 5 minutes

This commercial building was once home to several major booksellers and publishers in the 19th century. Today, modern first-floor retail subsidizes the historic building's upkeep.

8. Old South Meeting House

Old South Meeting House in Boston, a historic red brick church with a clock tower, surrounded by modern skyscrapers and bustling visitors exploring the area.Matt Caracciolo

  • Duration: 30 minutes

The largest church/meeting house in Colonial Boston, the Old South Meeting House was a place where Bostonians gathered to discuss the politics of the day. One fateful meeting here led to the Boston Tea Party.

Purchase your tickets at Revolutionary Spaces. Admission covers both the Old South Meeting House and the Old State House.

9. Old State House

Old State House in Boston, a historic red brick building with ornate details, surrounded by modern skyscrapers, with pedestrians and tourists nearby.Matt Caracciolo

  • Duration: 30 minutes

The oldest surviving public building in Boston, the Old State House was built in 1713 and was the seat of government for the colony.

The bottom floor is a subway station, but above is a museum housing artifacts from colonial Boston.

Purchase your tickets at Revolutionary Spaces. Admission covers both the Old South Meeting House and the Old State House.

10. Boston Massacre Site

  • Duration: 5 minutes

A circular emblem in the pavement marks the approximate spot where the infamous Boston Massacre took place in 1770. The emblem is located on the east side of the Old State House, between State and Devonshire streets.

11. Faneuil Hall

Statue of Samuel Adams in front of Faneuil Hall in Boston, a historic red brick building with arched windows, symbolizing the American Revolution.Matt Caracciolo

  • Duration: 15 minutes

Faneuil Hall is a meeting hall and marketplace that opened in 1742. It was the site of several speeches by Sam Adams and others encouraging independence from Great Britain. It's sometimes referred to as the "Cradle of Liberty."

12. Quincy Market

  • Duration: Your own discretion

Open since 1826, Quincy Market is also known as Faneuil Hall Marketplace and has been a central market for Boston for 200 years.

The bottom floor of Faneuil Hall was later incorporated into the market. Today, the market is primarily a food hall rather than a series of produce stands.

For more information on vendors, visit Quincy Market.

13. The New England Holocaust Memorial

  • Duration: Your own discretion

This memorial is dedicated to the Jewish people who were murdered by Nazi Germany during the Holocaust.

14. Boston Public Market

  • Duration: Your own discretion

An indoor marketplace with coffee, food, desserts, craft vendors, free WiFi and charging stations, and restrooms, open seven days a week.

15. Paul Revere House

Paul Revere House, a historic wooden structure in Boston's North End, with diamond-paned windows and visitors walking by, showcasing colonial architecture.Matt Caracciolo

  • Duration: 30 minutes

Circa 1680, this was the colonial home of American patriot Paul Revere during the era of the American Revolution.

It's located in Boston's North End and is now operated as a nonprofit museum.

You can tour inside for a small admission fee. For more info, click here.

  • Entry Fee: Adults $6, Seniors & Students $5.50, Children $1

16. Paul Revere Mall & Statue

Paul Revere statue in Boston’s Revere Mall, showing the patriot on horseback with Old North Church’s white steeple framed by lush green trees in the background.Matt Caracciolo

  • Duration: 30 minutes

This statue is located in the Paul Revere Mall, a brick park in the North End with plenty of benches, historic plaques to read, and shady trees in the summer. It connects to the back of the historic Old North Church.

17. Old North Church

Old North Church in Boston, a historic red-brick building with a tall white steeple, famous for its role in Paul Revere’s midnight ride during the Revolution.Lizzie Gerecitano

  • Duration: 30 minutes

This is the church from which the famous "One if by land, and two if by sea" signal was sent to coincide with Paul Revere's midnight ride on April 18, 1775 before the Battles of Lexington and Concord leading up to the American Revolution. The church is a mission of the Episcopal Diocese.

  • Entry Fee: View the church and its surrounding courtyard free of charge. To enter the church requires you take one of the many tours available, ranging in price from $-$10.

18. Copp’s Hill Burying Ground

Copp’s Hill Burying Ground in Boston, a historic cemetery with weathered gravestones and lush greenery, known for its ties to the American Revolution.Lizzie Gerecitano

  • Duration: 15 minutes

A historic cemetery in the North End of Boston circa 1659.

End of Day One

Now that you've finished Part One of Shaka Guide's Boston Freedom Trail, we hope you continue with Part Two.

Don't miss the rest of the story, including the Battle of Bunker Hill, the American Revolution, and the USS Constitution, Old Ironsides!

download shaka guide for free

DAY TWO Itinerary

Illustrated map of the Boston Freedom Trail Part 2, featuring sites like Bunker Hill Monument, Prescott’s Statue, and the USS Constitution in Charlestown.

Welcome to Part Two of Boston's Freedom Trail. Hopefully, you've already taken Shaka Guide's Freedom Trail Part One.

This part of the tour takes you through the Battle of Bunker Hill beneath the monument.

Then, visit the Charlestown Navy Yard to see the USS Constitution while continuing the story of Boston’s role in the Revolutionary War.

1. Charles River Pedestrian Bridge (William Felton Bill Russell Bridge)

A modern pedestrian bridge in Boston with white steel beams creating a striking geometric pattern against a blue sky with scattered clouds.Lizzie Gerecitano

  • 15 minutes to walk across

This is a modern pedestrian bridge leading from the North End into the Charlestown neighborhood of Boston along the Freedom Trail.

2. Charlestown City Square Park

A peaceful city park with a decorative fountain surrounded by lush green trees and brick pathways in Boston, offering a relaxing urban retreat.Matt Caracciolo

  • 10 minutes

This small 'pocket park' welcomes you to the Charlestown neighborhood on your way to Bunker Hill.

It contains the Cod and Corn Fountain, a tribute and symbolic representation of the area's reliance on both the land and sea for early survival.

3. Winthrop Square

A quiet urban park with green lawns, shaded benches, and historic brick buildings in the background, providing a peaceful space for relaxation.Matt Caracciolo

  • 10 minutes

Winthrop Square is a historic park and former training field in Boston's Charlestown neighborhood.

4. Bunker Hill Monument

The Bunker Hill Monument, a tall granite obelisk, stands against a blue sky, framed by bare tree branches and historic buildings in the background.Lizzie Gerecitano

  • 45 minutes

The Bunker Hill Monument is erected at the site of the Battle of Bunker Hill, which was among the first major battles between the United Colonies and the British Empire in the American Revolution.

5. Prescott's Statue

The statue of Colonel William Prescott stands in front of the Bunker Hill Monument, holding a sword and extending his arm, with a bright sky above.Lizzie Gerecitano

  • 5 minutes

Col. William Prescott served in the Massachusetts militia and led the Battle of Bunker Hill. This statue honors him.

6. Bunker Hill Museum

The entrance to the Bunker Hill Museum, a red brick building with a blue sign hanging above the doorway, featuring the words "Bunker Hill Museum.Lizzie Gerecitano

  • 30 minutes

Learn more about the Battle of Bunker Hill and the monument that was built to honor that battle through the exhibits at this museum.

7. Paul Revere's Landing Site

A historical plaque marking the site where Paul Revere landed on April 18, 1775, to begin his midnight ride, surrounded by small American flags.Lizzie Gerecitano

  • 5 minutes

On the night of April 18, 1775, Paul Revere set out to warn of the march of British troops on Lexington and Concord. He departed Boston by water and rowed to this spot in Charlestown, where he landed before borrowing a horse to gallop through the countryside.

8. The USS Constitution at the Charlestown Navy Yard

The USS Constitution, a historic wooden-hulled warship, docked at the Charlestown Navy Yard in Boston, with its masts and rigging set against a clear blue sky.Matt Caracciolo

  • 45 minutes

The USS Constitution, also known as Old Ironsides, is a three-masted wooden-hulled heavy frigate of the US Navy and the world's oldest commissioned naval warship still afloat.

9. USS Cassin Young

The USS Cassin Young, a World War II-era destroyer, docked at the Charlestown Navy Yard in Boston, showcasing its anti-aircraft guns and smokestack.Lizzie Gerecitano

  • 30 minutes

The USS Cassin Young was built in 1943 and was a destroyer ship built during World War II.

Conclusion

Congrats on journeying through the American Revolution and learning about the bravery of our Founding Fathers. The Freedom Trail is a nod to the patriots whose fight for life, liberty, and the pursuit of happiness is a gift we still treasure today.

Explore Boston Freedom Trail with Shaka Guide

Plan your visit to the Boston Freedom Trail with Shaka Guide! Walk through history, see famous sites, and hear exciting stories about America’s past. Our tour is easy to follow and packed with fun facts. Don’t wait—download the tour today and start your adventure!

download shaka guide for free

Ready to take the tour? Check out Shaka Guide's Boston Freedom Trail Tour!

We hope that we’ve given you all the information you need to make the most of your day. Your vacation is extremely important to us so if you have any questions feel free to reach out at aloha@shakaguide.com.

For more detailed information to help you plan, check out our Boston Freedom Trail Know Before You Go article for Part One and Part Two!

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