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I will show you how, Boston Massachusetts NOW! (Part 1) The Freedom Trail

Updated: Jan 23

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One of my favorite cities in the world, and I've been there several times because of the history, colleges, and food. Boston Massachusetts Freedom Trail is a history buff's dream. Today we will explore, eat, and talk about a few places to stay, on a budget along the Freedom Trail. (Except when you eat Italian in the North end, it can be pricey).


Flying into Boston is neat to see through the airplane window, all the water, marshes, and tiny islands, I was not expecting it. Usually, it is cheaper to fly here and rent a car then most of the other cities in the Northeast. The only downside to the airport is finding the car rental spot. I was confused for a bit trying to find it and taking shuttles to get to it.

Side note, fly into here if you are visiting southern Maine, New Hampshire, Vermont, or Rhode Island. Trust me you will save some bucks doing so. Plus, now there are cheap direct routes from Charlotte NC to Boston.

Cruise Critic

The start of the Freedom trail area

Beautiful houses and streets of Boston
Beautiful houses and streets of Boston

I just love walking in Boston, beautiful houses, the freedom trail, and several parks to choose from. All of this is free, and it covers basically 2 days or more depending how in depth you are or how fast you walk. Save money by touring on your own or buy some tours. Whichever you choose, it will be wonderful. Most can do more than me because of my bad knees and achy feet, but even though I am sore at the end, it's worth it. I know when to stop and start again the next day for my body.

You are stepping back in time here to the American Revolution. Just think about how many historic figures walked these streets around 250 years ago. Samuel Adams, Paul Revere, Benjamin Franklin just to name a few.

Beacon Hill and the parks at the bottom of Beacon Hill

First Visit Beacon Hill, it is the best place to start a walk and you can continue on to many other places from right here. Grab a quick coffee or eat breakfast here. Just starting your walk around Beacon Hill, you will be overwhelmed by its beauty. Start behind the Massachusetts State House, or up Charles Street near Boston Common. The hill behind the State House is steep (but did you notice how impressive that building is with its gold dome). The brick streets, and the beautiful houses with flower boxes out front. Words cannot describe how this neighborhood looks and feels. The Boston Brahmin, as it's known by, the architecture is Federal and Georgian in style and America's first professional Architect Charles Bulfinch is responsible for many of the homes here. Check out the Sunflower Castle on Mt Vernon Street, it is neat to see, and closer to 2 of my favorite eateries. There are several cute shops to check out too.

Random fact about picture above, The Massachusetts State House. In 1802 Paul Revere covered the dome with Bronze. Also free guided tours inside the building happen every weekday from 10:30 to 3:30 at every half hour mark of the hour. That's 6 tours a day.

Food at Beacon Hill

  • The Paramount- (Pancakes, Bacon egg and Cheese sandwich, or Avocado Sunrise) most items are under $15 bucks and service is fast so you can get moving on with your day. Located on Charles Street. It may be closer for you to get to from Boston Common or Public Garden

  • Tate Bakery and Cafe- (Lamb Hash, or Croissant Sandwich for breakfast, Prosciutto and Fig Panini for lunch), also on Charles Street but farther on into the Beacon Hill area. Great fast Service and the bakery part is amazing too.

  • Heads up if you are farther up near Cambridge Street, check out B Nutritious, Flour Bakery, The Tip Tap Room, or for lunch Anna's Taqueria.

As you come back down the hill and pass the State Building. you see a large park across the street on the right. Boston Common is massive, with a pond called the Frog Pond, a visitor center, Carousel, bandstand, and plenty of statues to see, as you walk around. Depending on when you are in Boston you can see live performances in the park too.

While in the park you can find some food, Earl of Sandwich is a great cheap place to eat, sandwiches, wraps, soups, salads and desserts. My favorites are The Original 1762 and the Buffalo Chicken Wrap.

Now before you cross the street to the park or after just as long as you stay near Beacon Street, 4 Blocks down Beacon Street, on the right is a TV landmark. the outside shot of the show Cheers. You know what I am talking about, the entrance to the Cheers Bar with the Stairs going into the bar. (Neat huh!) Stop in this bar and rest your legs and grab a quick drink or bite to eat if you would like. But if you do, try the Sam Adams Brick Red, it is only sold in Boston and money made from the sale goes to the local community. Wish I could get it where I live.

Skyline view from The Public Gardens
Skyline view from The Public Gardens

After you leave Cheers, cross the street to the park, and you will see another park right beside Boston Common, Called the Public Gardens, there is a huge pond, statues (one of George Washington) and plenty of places to stop and look around. This is the park where Robin WIlliams and Matt Damon sat on a bench and talked in Good Will Hunting. You can easily find the bench because there are always flowers laid on the bench because of Robin Williams death a few years ago. Bring some flowers if you like.

Also, side note, at the corner of Boylston Street and Washington Street is Chinatown, take a left out of the southern end of Boston Common on the Boylston and Washington is 2 blocks away.

Whichever Park you are in, Boston Common, or the Public Gardens, make your way to Boylston Street and turn left on Tremont. or back to Beacon Street, turn right on Park, then left on Tremont. Tremont is where you want to be at the edge of Boston Commons. At this point you have already seen 3 spots on the trail. The State Building, Boston Common, and the Statue at the corner called Robert Gould Shaw and the 54th. (The first all-Volunteer African American Unit in the US Army). This is a good place to start the rest of the Freedom Trail, at the far-left edge of Boston Common on Tremont Street. Next stop is Park Street Church, and you can see it from where you are standing. This is where abolitionist William Lloyd Garrison made his first anti-slavery speech in 1818.

Aluity Insurance sells Allianz Travel Insurance
Aluity Insurance sells Allianz Travel Insurance

The Granary and Beyond

Now we continue on to right beside the church is the famous Granary Burying Ground. Several famous people from the Revolutionary war era are buried here and even Mother Goose. Check out the graves of Paul Revere, Samuel Adams, John Hancock, and the parents and siblings of Benjamin Franklin. Continue on up Tremont Street and take a left on School Street (just a couple blocks away). On the corner is Kings Chapel, open daily to look around. The first woman to step off the Mayflower is buried in the graveyard in the back of the church, Mary Chilton. As you travel down School Street stop at the Boston Latin School (the oldest school in America, 1655) and see the Statue of Benjamin Franklin. Just a few steps down for that is the statue of Josiah Quincy III. (it's at the corner of City Hall Avenue. Turn left for a second to see Old City Hall, then turn back to School Street and continue on to the Old Corner Bookstore. Across the street from the bookstore is the Boston Irish Famine Memorial and Reader Park check it out since it is on your way, and from there you can see the Old South Meeting House on Washington Street, The Old South Meeting House is where The Sons of Liberty walked out in 1773 and started the Boston Tea Party.

The Old State House and Beyond

Boston- near Faneuil Hall and Old North Church
Boston- near Faneuil Hall and Old North Church

Walk North on Washington Street, if you need a stop there are a few places to stop along the way for food or drink or just take a rest. One of my favorites is right here on Washington Street. Falafel King, I just love. Another one that is as good as the name says it is, B Good. You can stop at Starbucks, Dunkin or my favorite is The Well Coffee Shop for a quick coffee if that is all you need. (Sidenote take a quick trip down Water Street to see the Winthrop Building, then turn around and head back to Water Continue on Washington Street and take a right on the trail in front of the Old State House, (if you made it to State Street you went too far, but you are right beside the Old State House). Random Fact, did you know that from the balcony on this building in 1776 the Declaration of Independence was read out loud for the first time, causing a riot.

Continue onto Devonshire Street and take a left and you will come to the Boston Massacre site. Cross Devonshire Street and Congress Street at the same time and stop to look at the marker of John Winthrop's First House Site. Now cross State Street and walk north on the right side of Congress Street. On the same block you will see the Samuel Adams statue, Sam Adams Downtown Taphouse is where you want to turn right to continue the Freedom Trail.


Faneuil Hall and Beyond

Old State House
Old State House

If you miss the path like I did, just follow Congress Street to North Street (it's right there) and you can get anywhere from there. Faneuil Hall and Quincy Market is a huge area. Many little side streets to look at all the little stores close by. You can go inside and shop, and there are also tons of shops and places to eat all around this area. You can spend hours here just shopping, eating, and people watching. By the time I got here it was late afternoon and there was music, vendors, and performers on the street. In this area, just North of Faneuil Hall. Last Note....Look for the grasshopper on top of Faneuil Hall, the man that made it is buried in Copp's Hill Burying Ground (part of the Freedom Trail, on down the trail).

The New England Holocaust Memorial and Union Oyster House are close by, go check them out as well. The Union Oyster House is the oldest Restaurant in the United States.

Paul Revere Statue and Beyond

After leaving the Faneuil area you will head a good bit north, it will be a walk from here. Paul Revere Statue, Paul Revere House, and Old North Church are what's next to see and you will be in the Italian area of Boston. All the Pasta, Pizza, and Cannoli's a girl can dream of are in this area. Travel up North Street, and you will pass through a beautiful garden called The Rose Kennedy Greenway and Wildflower Meadow. First you come to Paul Revere House, it's beside Rachel Revere Square and North Square Park. You can tour the house for $5.

Next take a left on Prince St, then a right on Hanover Street and you will come to the Paul Revere Statue on the left, but you will pass St Leonardo's Peace Garden on the way. At the Paul Revere Statue, walk through the Paul Revere Mall and you will come out at Old North Church, and the Saint Fransis of Assisi Garden.

After leaving the Old North Church, traveling down the Freedom Trail Road is Copp's Hill Burying Ground. It's not too far away to see. Many early Americans are buried here along with many Puritans. Robert Newman, who hung the lanterns in the Old North Church as a signal for Paul Revere to do his ride, is buried here. On one side of the Freedom Trail Road here is the Skinny House, check it out, it sure is skinny.

After all the walking I had done at this point I gave up on the tour, I couldn't do anymore of the Freedom Trail in one day. Plus, I knew if I continued on, I would miss eating in Little Italy. There are still 2 more stops that are quite a large walk away, so I quit and got dinner and called it a day. I started fresh the next day and finished the trail. With Beacon Hill, Boston Common, and Public Garden before the trail, it was just too much.

My favorite Italian places In the North area where you are near Old North Church or Paul Revere House are. (Heads up most are a little bit pricey up here, $20 to $30 a plate, some even $50 to $100).

Carmel Limo

Food in Little Italy near the Old North Church

Yummy pasta
Yummy pasta

*Lucia Ristorante- (Calamari Pirata). It's a little Pricey, but amazing. Located directly Across from Paul Revere Statue on Harris Street.

*Dino's Cafe-(Lobster Ravioli) Most menu items are under $20 Located on Salem Street,,,,, after you leave Old North Church walkout the back to Salem Street and walk south 3 blocks.

*Assiago- (Amalfi market Price) that tells you a lot about the prices here, but I love lobster. It is located on Prince Street near Leonardo's Peace Garden.

*Mike's Pastry-(Cannoli), The best Cannoli in Boston and desserts are always cheaper than most dinners anyway. Located on Hanover Street, just South of St Leonardo's Garden, and they have been open since 1946. Long enough to have perfected the Cannoli in my opinion.

*Rina's Pizzeria and Cafe-(Chicken Parm Ziti, Pizza by the slice, and Nutella Pizza) North on Hanover Street, on the right before you get to Paul Revere Statue. This is on the Freedom Trail. As you can tell I have been there often. It's Cheap.

Last part of Freedom Trail

I took an Uber to the USS Constitution the next day because of the distance between Copp's Hill Burying Ground, to the USS Constitution. is 1.2 miles and I knew I still had lots to see and walk to that day. Also, for those of you that hate bridges, you would have to walk over the North Washington Street Bridge which is over water. The USS Constitution is the oldest warship in US history, and you can tour for free. And the USS Constitution Museum is located there also, you can enter for a donation ($5 to $10) to learn more about the ship's history.

The last stop of the Freedom Trail Bunker Hill Monument, and only about a 5-minute walk away. Follow the signs that help you pass over the road that is a toll road to Tremont Street that takes you to Monument Square. Bunker Hill Monument was built in 1843, where the famous Bunker Hill Battle took place. The Bunker Hill Museum is located at the base, and it is free.

This concludes part 1 of Boston, I will continue onto part 2 next which will include Harbor Walk, aquarium, food and The Secret. I hope you have enjoyed the walk of The Freedom Trail as much as I did. So much history, food, and walking in the city of Boston.

Hilton Honors

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