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MASSACHUSETTS · USA

  • chrissihuf
  • Dec 19, 2025
  • 7 min read

Updated: Jan 4



Statue of Paul Revere's Midnight Ride, with the Old North Church in the back


Brief History/Information

The state of Massachusetts is bursting with so much history, so I’ll keep this to a minimum. The geographical area of Massachusetts, was booming with at least five Native American tribes. In 1620, the Pilgrims founded Massachusetts, and in 1630, it became one of the largest and most influential early English settlements. It contained a mecca of revolutionary leaders like Samuel Adams, John Adams (2nd U.S. President), John Hancock, and Paul Revere. It is home to some of the United States’ most prestigious universities.

Here are some of the major roles Massachusetts participated in that started the American Revolution:

  • Boston Massacre (1770)

  • Boston Tea Party (1773)

  • Battles of Lexington and Concord (1775) – “The shot heard ’round the world”

  • Battle of Bunker Hill (1775)


The best way to ensure you see as much as you can is really to walk. Make sure you have some good and comfortable walking shoes, as well as proper clothing for the weather.


We’ve been to Massachusetts twice together (2006 & 2025), 19 years apart, both times different.


Brief History/Information

Boston was founded in 1630 by Puritan settlers. Boston played a central role in the events leading up to the American Revolution, starting with the Boston Massacre in 1770, the Boston Tea Party in 1773, battles of Lexington & Concord/Bunker Hill in 1775.


What we did

November 2006

This was a Thanksgiving trip when our kids were small and we covered a lot of historical places! We landed in Boston and stayed at the Courtyard by Marriott Boston Downtown. This hotel was really cool even with a jazz bar and an area for kids to play! We ate at MJ O’Connors Irish Bar & Restaurant which was really good. We also ate at L'Osteria on Salem Street, Trani Dessert which sadly is no longer open, and Regina Pizzeria… triple yum!

May 2025

Our second trip, was all about Boston! We arrived in the evening, so we didn’t have much ‘exploring’ time. We stayed at the Historic Liberty Hotel, that used to be a jail. What a great place! Very centrally located and able to walk to many sites (make sure you have good walking shoes). We walked to the Cheers Bar (from the TV series ‘Cheers’) and got a beverage and an appetizer. We then walked back to the Liberty Hotel and wandered in their bar, called The Alibi. The remainder of our Boston vacation followed the below, Places of Interest and Walking Tour w/ Bar Crawl; this can be broken up in as many days as you wish.


Places of Interest  (see Walking Tour w/ Bar Crawl for detailed information)


Walking Tour w/ Bar Crawl

BARS/RESTAURANTS/SITES (see above for detailed information)

  • Bell in Hand - established in 1795. Opens at 11.

  • Benjamin Franklin‘s Birthplace- Benjamin Franklin was born and lived in Boston on One Milk Street. The actual building burned down in 1811, a statue of Franklin's head now marks the birthplace. When you get there… LOOK UP!

  • Black Rose - opens at 11, nice Irish bar. They usually have a beer and shot special.

  • Boston Tea Party & Museum - this place is great and so much fun! I learned so much (and I taught it before I retired from teaching!)

  • Boston Common & Public Garden- this is Americas oldest public park. It’s a huge green space with plenty of sitting areas, play areas, and historical information

  • Boston Massacre Site - where it all happened… now it’s just a marker on the sidewalk. When you get there… LOOK DOWN!

  • Bunker Hill - opens at 1:00. This is a beautiful monument that you can walk up to the top.

  • Cheers Bar (from the TV series ‘Cheers’) - great tv show and you can sit at the actual bar!

  • Dubliner Bar - opens at 11, really nice Irish bar

  • Durty Nelly’s - opens at 11am. In the same area as Bell in Hand. This is just a bar. Nothing fancy, but great bartenders.

  • Faneuil Hall- this was once a famous meeting spot, but now it’s a food and shopping hall.

  • The Fill A Buster - for a fabulous (and inexpensive) breakfast

  • Freedom Trail - this is about a one mile marked walking path of American History, you can start anywhere on the trail. This is a Must Do!

  • Granary Burying Ground - Opens at 9. A lot of famous burial plots Ben Franklin's parents - Sam Adams - Victims of Boston Massacre, etc.

  • Green Dragon Tavern -established in 1654. It was a favorite hangout of Paul Revere and John Hancock.

  • L'Osteria - really good restaurant

  • Massachusetts State House

  • MJ O’Connors Irish Bar & Restaurant - really good!

  • Old City Hall - in 1635, it was The Boston Latin School (Boston’s first public school and the oldest educational institution in the country). In 1810, it was The Suffolk County Courthouse. Now it’s a Ruth's Chris Steak House

  • Old North Church - Reserve in advance. Includes a guided tour of the bell ringing chamber where Paul Revere rang bells as a teenager

  • Old South Meeting House- this is right where history happened! There’s a fee to get in, but totally worth it.

  • The Paul Revere House - a very unassuming and small house for a man that had eight children! Totally worth it to go in and see how he lived.

  • Regina Pizzeria - hands down the best pizza I ever had! Get there before they open- there’ll be a wait and it’s worth it.

  • Sam Adams Brewery Downtown - opens at 11, good food, good beer

  • Statue of Robert G Shaw -

  • Sullivans - opens at 4:30. Apparently this is Bostons oldest sports bar (1933-the day after Prohibition ended).

  • Tremont Temple Church - haunted??

  • Union Oyster - Americas oldest restaurant, opens at 11. You can sit at JFKs special table.

  • USS Constitution & Museum - open from 10:00 am – 5:00 pm. This is ‘Old Ironsides’! Remarkable.

  • Warren Tavern - oldest bar in MA! What a great place. So old and historic.

  • Wicked Craft Co.- this is a swanky place! Great craft cocktails.


Cape Cod & Plymouth


Brief History/Information

Cape Cod was originally inhabited by the Wampanoag tribes. In 1620, the Mayflower first anchored at Provincetown Harbor, making Cape Cod the Pilgrims’ first landing site in New England.


Plymouth, was originally called Pawtucket and inhabited by the Wampanoag tribe. The Pilgrims landed in Plymouth December 1620, after stopping in Cape Cod first. Before the Pilgrims touched the ‘New World’ soil, they signed the Mayflower Compact, which was their form of self-government.


Cape Cod and Plymouth do not disappoint… it is beautiful, historic, and lots to do.


What we did

November 2006

We drove 1 1/2 hours from Boston to Middleboro and stayed at the Fairfield by Marriott Inn & Suites Raynham Middleborough/Plymouth. We then drove to Cape Cod, Hyannis, saw the JFK monument, and the Korean War monument. Drove to Historical Hyannis and saw the Kennedy compound, snack/drink at Common Ground Cafe, unfortunately it is no longer in operation, but it was an amazing place; the interior was a forest/mystical place.


We then drove to Plymouth, and went aboard the Mayflower II-an exact replica to scale of the original Mayflower! Then went to the actual 1620 Plymouth Rock where the Pilgrims landed. We ate at Mamma Mia's Restaurants… really good!


On Thanksgiving day it was cold and raining… lots of rain, we drove to the Wampanoag Indian Village and were able to interact and talk with the actual Wampanoag Native Americans. We sat in their huts and teepees, enjoyed a nice warm fire with them, as they explained and talked about the days of the English settlement and what happened as they know it to be. Some of them were dressed in regular everyday street clothing, and some of them were dressed in Native American clothing. All of us were able to talk and ask questions, it was very nice, informative, and educational.

We then went to the Pilgrims’ 1620 English Settlement village area. All of this was rebuilt, all of the people working there dressed, talked, and acted as if in the 1620s. In spite of the cold and rain, it was amazing to be there. We were able to go to many different houses and talk and interact with them, and they never broke character.

For our Thanksgiving Dinner, we reserved a seating for a Victorian style meal. Again here, all of the people working there dressed, talked, and acted as if in that time period. The time period was from 1863, when President Abraham Lincoln proclaimed Thanksgiving a holiday. We sat in a ‘family style’ table with other people. The food was plentiful and delicious. I highly recommend this experience, with our without children, it is truly amazing.


Places of Interest


Salem


Brief History/Information

When you hear the words, Salem, Massachusetts, most often immediately think of the Salem Witch Trials in 1692, where over 200 people were accused and 20 people were executed. Salem was inhabited by the Naumkeag Native American tribe, prior to the English colonists in 1626. It was one of the first permanent English settlements in Massachusetts. In the American Revolution, Salem strongly supported the Patriot cause.


What we did

November 2006

We drove 1 1/2 hours from Boston to Salem. Started at the Salem Visitor Center and watched a movie about Essex County. We then proceeded to do all of the things on the below ‘Places of Interest’. We ate at The Derby Restaurant & Bar and had soups and lobster rolls… Yum! We also went to Ye Olde Pepper Companie this is Americas oldest candy company!


Places of Interest


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May 04
Rated 5 out of 5 stars.

So awesome!

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