The Freedom Trail: Exploring Boston’s Past

11. Faneuil Hall

Faneuil Hall has been used as a meeting place since 1742. In 1806, the space was expanded. Today you will find several restaurants, including the most famous “Cheers” (the pub/restaurant where the TV show was filmed), along with the Quincy Market, which is the largest US food hall (here you will find over 36 international vendors) In addition, you will find numerous shops. Street performances and live events take place throughout the year. We had a great time watching the eclectic free shows.

Update: Cheers is now closed. However, you can visit the location where exterior shots of Cheers were filmed on Beacon St. You will find a number of cafes where you can enjoy chowder or fresh seafood. Ned Devine’s Irish Pub is a long running city staple where you can enjoy authentic Irish fare while catching a Red Sox or Patriots game.

12. Paul Revere House

The Paul Revere house was built in 1680, which makes it the oldest building downtown. Paul Revere, whom is most famous for alerting colonists of the British arrival, resided here from 1770 to 1800. That’s me in the pic enjoying the historical sights all to myself on a blistering cold winter’s day. If you are seeking a low-key, more personal experience, I definitely recommend a winter stroll.

13. Old North Church

Old North Church, built in 1723, is the city’s oldest church building. The location is famous for the for being the origination of the “One if by land, and two, if by sea” phrase. From its’ tall steeple (191 feet) Robert Newman signaled Britain’s arrival to Paul Revere – 2 lanterns lit up to announce the Britain’s arrival by sea.

The interior is supposedly gorgeous, unfortunately Sunday mass was taking place during our trip. Make sure to check mass times if you plan on touring the interior. It’s 5 bucks for a general tour, although crypt tours are also available for 10 bucks.

14. Copp’s Hill Burying Ground

Copp’s Hill Burying Ground, founded in 1659, is the second oldest cemetery in the city. Robert Newman, who signaled The Britain’s arrival to Paul Revere from Old North Church, is one of the notable figures buried here.

The Dupee monument, built in 1846, is the most elaborate in the cemetery.

15. Bunker Hill Monument

Bunker Hill Monument, a 221 foot granite monument, est. 1827-1843 to commemorate the Battle of Bunker Hill. Visitors are able to go inside and climb the 294 steps to the top. I highly recommend planning a stop here along your journey.

The views of the skyline are incredible. It’s a steep climb, however, well worth it in my opinion for the amazing views. Plan for an exhausting workout if you decide to add the climb to an already hilly 5-6 mile walk. You could always visit on a separate day if it would be too much. I admit the walk itself is exhausting as you are reading so much and taking in so much info.

The Statue of Colonel William Prescott, est in 1881. Prescott was an important figure in the Battle of Bunker Hill.

This is one of the best places for a great city view. Not the best skyline in my opinion, but this view is about as good as it gets. If you are up for a hike, there is a wonderful reservation near the city called Blue Hills. I recommend hiking the Skyline Trail for awesome views and an incredible workout.

16. USS Constitution

The USS Constitution is the world’s oldest commissioned warship. Today you can walk around the ship and take a tour to learn more about its’ history. The ship which launched in 1797 is also commonly referred to an “Old Ironsides” because cannonballs bounced off the hard sides of the ship during the War of 1812.

The views of the skyline are pretty great. I am not a huge war buff, but we took a quick self guided tour. I appreciated that there were many informative plaques so you could learn some more.

What a view!

Free attractions along the trail

One of the things I love most about Boston is that there are so many freebies lurking about. Even if your hotel is pricey, you can make up for some of the costs with the many free activities to enjoy. Not only is the trail free (and an all day activity), but there are so many historic sites and museums to explore. Plus, if you are willing to drive, there are great parks in the metro.

Massachusetts State House: Free tours are provided on weekdays from 10:00am-3:30pm. You will need to call (617) 727-3676 for reservations.

Park Street Church: Open from late June-August for tours from 9:00am-4:00pm.

Granary Burying Ground: Open daily from 9:00am-4:00pm.

King’s Chapel Burying Ground: Open daily from 9:00am-4:00pm.

Faneuil Hall: Open daily from 10:00am-9:00pm (7 on Sundays), with historical talks offered every half hour.

Copp’s Hill Burying Ground: Open daily from 9:00am-4:00pm.

Bunker Hill Monument: Hours vary for the museum depending on the time of the year. Climbing is open from 1:00-4:00pm. See the monument website for more info.

USS Constitution: It is free to walk around this 200+ year old ship. Even if you aren’t interested in history, I recommend a walk around to enjoy the beautiful harbor views. The hours are as follows: 10:00am-5:00pm (closed Monday and Tuesdays). There is an adjacent museum which operates on a pay-as-you-wish format with suggested donations. See the Constitution Museum website for more details.

Trail attractions with a small admission fee

Old South Meeting House & Old State House – You can visit 2 attractions for one low price. Open for tours daily from 10:00am – 5:00pm. Adult admission costs $15, while children 6-18 are $8. Students and senior citizens get a discounted rate of $13.

Paul Revere house – Take the opportunity to tour the oldest downtown building. Admission to the tour the house is $6 per adult and $5 for seniors and students with ID. Hours are 10:00am-5:15 (closes at 4:15 from Nov 1-April 14th, closes Mondays from Jan-March)

King’s Chapel – Various guided tours offered including art and architecture tours for $5 and special tours of the crypt for $10. Visit the chapel website for more details.

Old North Church – Various tours available included general tours for $5. For $10, you can see the bell ringing chamber or tour the crypt. Additional details on the church’s website.

Other notable attractions along the way

Boston Public Garden – This beautiful 24 acre park built in 1837 is amazing any season, even during the winter months. The park is adjacent to the Commons, the starting point of the trail. There’s a lot of history to explore and the space is beautiful for walking around in any season. For all the movie buffs out there, you can also see the famous bench where Robin Williams and Matt Damon shared their heart to heart.

Bell in Hand Tavern – The oldest tavern in America (located in the North End neighborhood is conveniently located right along the trail. The food here was surprisingly delicious. We really enjoyed the Fisherman’s Platter app which included all sorts of fried goodies including shrimp, calamari, haddock, and fries! As a Patriots fan, (I know I am from Chicago but always loved Brady and the Patriots), I had a great time kicking back and watching the game for a while before continuing on the trail.

The Dog Tag Memorial (next to Old North Church) honors those who lost their lives in the Iran and Afghanistan wars.

Boston’s North End neighborhood – More than 80 authentic restaurants are packed together in Little Italy. My personal favorite is Giacomo’s for their amazing lobster ravioli and pumpkin tortellini. I have taken several out-of-town friends here and they loved it too!

Also, if you need a pick me up, I recommend a stop at the city’s first Italian cafe. It’s a gorgeous cozy little space to enjoy a coffee and dessert called Caffe Vittoria. Conveniently, it’s also located in The North End, so a great place to take a relaxing break before continuing on. It’s actually right near Giacomo’s, so you can walk right over after your meal.

A view of TD Garden from the Charlestown Bridge (home to the Boston Celtics). We recently bought tickets to a game here and enjoyed the local pride even though were were in the second to last row. I haven’t been to a basketball game in years (since seeing the Bulls play in the 90’s) so it was a great time!

St. Stephen’s Church – The only city church designed by Charles Bulfinch still in existence (located in the North End).

Best time to plan your walk

We typically arrive downtown by 7am. At this time, parking is easier to find and our pictures are not obstructed by large crowds. We prefer walking in the winter although temps can be very cold and windy. To me, enjoying a bit of peace and quiet is worth putting on a big jacket and hat and gloves.

Tips for a smooth experience

*Plan at least half a day to give yourself time to explore all the wonderful attractions along the way.

*Check operating hours of each attraction. Hours vary depending on day, time, and season. I have included hours for each of these attractions for you in the section above. Note that hours and fees may change at any given time.

*Bring with plenty of water. The trail is not a loop, so you will end up walking roughly 5 miles.

*Plan for lunch or dinner in the North End. This is a great opportunity to test out one of the city’s fabulous Italian restaurants. As mentioned earlier, Giacomo’s is the best.

*Plan on a Sunday morning walk for the fewest crowds and least traffic.

*Free parking is available on side streets and by parking meters on Sundays. Parking in the city can be pretty pricey, so head out early in the morning on a Sunday for your best shot at free parking. The best place to find free parking is around the Boston Common area, which is the starting point for the trail.

*Follow the red brick road and you won’t get lost. The path is visible throughout the entire trail.

Directions, tours, and a handy Map

Tours are available for a small fee ($17 per adult, $15 per student/senior, & $8 per child). Visit the Foundation Tours site for more information.

Directions: The trail starts downtown at the Commons Visitor Center (139 Tremont Street).

Trail map: As with most tourist activities, there is a fee for the map. I have created a printout map of the trail that includes photos of each of the sites. Click the link below to download the PDF map to your computer then print it out so you don’t have to pay for one of less quality.

Our Map to guide you along the way. Have fun and enjoy your trip through history. It’s one of my favorite cities in the country and I know you will love it just as much as me!