Massachusetts – Thanksgiving 2025

Plymouth

We’ve been enjoying our trips with our friends for the past few Thanksgivings. We were considering where to go to next – and chose Boston / Massachusetts as a good, viable option. Unfortunately, our friends weren’t available this weekend, but we still chose to enjoy a quick getaway. Although we had a half day of school Wednesday, most places were closed on Thursday because of Thanksgiving, plus we anticipated a lot of traffic. We decided to leave Thursday morning and head straight to Plymouth, MA for an authentic Thanksgiving experience. Plymouth is where the Mayflower landed in 1621 with the Pilgrims who had arrived from Europe. We commemorate their feast with the Wampanoag natives with the annual Thanksgiving celebration. 

The Plymouth Museums have 3 parts. On the harbor, you can see Plymouth Rock and tour a replica of the Mayflower ship. (The original boat sailed back to England once it dropped the Pilgrims off in Massachusetts.) It was interesting to see how the Pilgrims lived on the ship, the food they ate, and how they slept. We then headed to the Plimoth Museum, about 10 minutes away. The museum transports you back to Plymouth in 1621 – houses are built and heated as they were back then and the guides are all personas of people who lived back then. They speak as if it’s the 1620s and only have knowledge of life during that time. There were also many demonstrations of cooking, children’s games, and musket marches. It was very cool to see what life would have been like for the Pilgrims, especially on Thanksgiving Day. The last stop was the Grist Mill, where we learned how the town used the mill for food and energy. We then drove an hour to Boston and ate at the Kosher Wok. Funnily enough, we saw some friends from Brooklyn at Plymouth and the restaurant, who had the same idea as us for the weekend. 

Boston

Friday was a very short and freezing day in Boston. Sam and Rita had visited Boston ten years ago, but the kids had never been. Therefore, nothing felt urgent to visit, and we wanted to show the kids, especially Allen and Joseph, some of what they would be learning about the American Revolution. 

The day centered around the Boston Freedom Trail – a red road that runs through the city of various historical sites. We visited the MA State House, Boston African American NHS, Old State House, and Faneuil Hall. We also stopped at the cemetery of some of the Founding Fathers. The Old State House is the site of the Boston Massacre of March 5, 1770, an important step on the road to the American Revolution. We went inside and explored the related exhibits. Faneuil Hall has tons of food stands, souvenir shops and small stores, making it the perfect place to eat our lunch. Despite the cold, we even watched a street performer do a daring act. After warming up in a Dunkin Donuts, we drove to Bunker Hill, the site on a Revoltuonary War Battle. There, we learned about the battle (it really is located on Breed’s Hill) and climbed the 291 steps to the top of the monument. We were all exhausted and freezing and we made it to the hotel just before Shabbat was starting. 

Luckily, we got upgraded and had 2 connecting suites, which was very helpful on Shabbat, in terms of meals and hanging out. 

On Shabbat morning, we walked about 30 minutes to the Harvard Art Museum, which has free entry. We enjoyed looking at the artworks and historical artifacts. On the way, the boys enjoyed hearing about our college experiences. It was a great way to break up the (short, but long) day. After lunch we played games, I closing mahjong and Moose Match Mayhem until Havdalah. After Shabbat, we drove to Boston Common to watch the Boston Holiday Drone Show. Instead of fireworks, the sky was lit with drones in different colors to form various shapes, including a dreidel, Paul Revere’s ride, Boston 250 and others. We’ve never seen a show like that and it was pretty cool. 

Springfield

By Sunday we felt like we had done most of the activities in Boston and made other stops in MA on the way home. In our quest to hit as many national sites as possible, we stopped at the Springfield Armory NHS. Starting in the times of the Revolutionary War, this site stored many weapons, rifles and guns throughout our history. It was particularly interesting to see the type of rifle used in trench warfare. We then stopped as the collection of Springfield Museums, among them the Dr. Seuss museum. This has been on our radar for a while, but was honestly a major letdown. The museum itself is quite dinky and smalls and the activities are basic and run down. The sculpture garden outside the museum with famous characters of Dr. Seuss was much cooler. We stopped briefly at some of the other museums, if only because they were included in the overpriced ticket. 

Our last stop was the Norman Rockwell museum, which houses some of his most famous paintings and prints, including the Freedom series. It was not a necessary stop, but Rita had been teaching some of his paintings, so she was curious to see. 

Overall, this was a great weekend getaway and we recommend it for couples or families who are looking to learn some of our country’s history.