You guys, I am obsessed with Boston. And not like oh my gosh it was so fun , I mean it in the I want to literally move there one day type of way. And I know, I know, I wasn’t there in the winter. I thought about that, and Joey and I want to visit in the Winter one day so that we can really get a taste and see if we could weather it (no pun intended). We literally talked about it, maybe one day when our kids are in college we’ll turn into Bostonians! So yes, we really loved it there to say the least.

Let’s rewind a little bit. How exactly did we end up in Boston? Well, we have this problem where we’re always itching for something to do/somewhere to go. Our favorite season is Fall and going somewhere that has a real Fall has always been something in the back of our minds (we live in California if you’re new here!) One night, Joey just casually goes- let’s go somewhere for Fall. I pulled out the Bucket List (yes I have one), and Salem, MA has been on my bucket list FOREVER (if you know me, you know I’m a Halloween girlie), and visiting during October specifically has been on the list. SO Joey goes, why don’t we go to Boston? And well, that was it! I want to say we literally had the trip booked like a week before leaving. It was the most spontaneous thing I’ve ever done I think in my life lol. I’m definitely the type of person who likes to be packed for a trip like at least 2 weeks prior to leaving. So this was a little testy for me!

Let’s get into the details!

+ Trip Dates : Thursday, October 22nd- Sunday, October 25th

+ Where We Stayed: Intercontinental Boston // cannot recommend this hotel enough! We stayed at the one in Monterey Bay and immediately fell in love with it, so finding out there was one in Boston, it was a no brainer.

We flew direct out of San Diego and got to Boston at around 5 pm on Thursday night.

After landing and checking into our hotel, we walked to dinner not far from the hotel where I had the BEST clam chowder EVER! We ate at the Broadside and it was amazing! After dinner we walked to Faneuil Hall Marketplace where we got some ice cream at a Ben&Jerry’s counter inside. Then we walked back, did showers and got cozy in bed!

Day I

Our first full day in Boston started off in Salem!!!! Like I mentioned, visiting Salem in October has been on my bucket list for a long time, so I was SO excited to finally be making this dream come true. There is a museum there, The Salem Witch Museum, and during October, they’re so busy that they change their hours to accommodate the increased number of visitors AND tickets go on sale for the day you want to visit, at 10pm the night before.

I was hooked to my phone by like 9:30 pm to make sure I was ready to grab tickets as quickly as I could! There are reservation times that you have to choose from, our train left downtown Boston at 7:30 am the next morning, and I knew we would be getting into Salem by around 8:15 am. I booked our tour for 10 am and bought two tickets- the kids were free.

We took an Uber to the train station, got on the train, and then got off in Salem! We took the first train out of Boston to make sure we had enough time in Salem 🙂

We walked around town a little bit first which I highly recommend if you’re visiting Salem in October- the later it gets in the day, the more and more packed it gets! We went straight to Town Hall (where the famous I Put a Spell on You party scene in Hocus Pocus) and were able to take pictures without anyone else around, we did circle back to this area later in the day and it was nearly impossible to walk through because of all the people! I’d say if you’re visiting and you know your points of interest, try to get them done as early as possible, especially if you know you’re going to take pictures and not want thousands of people in the background.

After walking around, we found a place for breakfast- Red’s Sandwich Shop (which in 1698 was the meeting place of patriots before the American Revolution- sorry I’m a history nerd!!) There was a line, so while we waited I walked around and got my daughter and I hot chocolate from a nearby coffee shop- it was like 50 degrees outside, so very cold for us. It was about 9:30 am when we were like 3rd in line to get seated and my reservation was at 10 am for the Salem Witch Museum, I was supposed to check in at least 10 minutes before, soooooooo I ended up walking to the museum by myself while my husband and kids waited and then went to breakfast.

I’m so glad I did though because the museum was a little intense. The tour is broken into two parts- one is a retelling (using animatronics) of how the Salem Witch Trials started and why the hysteria around “witches” was warranted- the puritans had deep deep beliefs and a fear of the devil and anything abnormal was seen as an attack by Satan on their community. This was pretty dark so I think it would have been scary for my kids.

The second part of the tour was all about the imagery of witches and how we got from regular human beings being convicted of witchcraft to the very cartoonish witch images we know today- green skin, riding on broomsticks, etc. The museum also had some items from the houses of a few people convicted of witchcraft, along with some books and bibles from the Judges presiding over the trials and from people who lived in the town at the time.

After my tour ended, I caught up with my family, they were walking around and shopping down Essex Street. My husband got my daughter a witch hat and it was SO cute on her!

We had a few more places to hit before ending our time in Salem, I’m going to briefly list them below. Also, little note- we walked everywhere in Salem and didn’t bring a stroller. If you have kids, I’d recommend not bringing a stroller, around the main streets in Salem, the sidewalks and walk ways are very tight and a lot of the older buildings and homes that you might want to visit, were built in the 1700s, so hallways are TIGHT and most places will not let you bring a stroller. I researched and read this prior to our trip, so just passing it along because I did find it to be true!

+ walk/shop down Essex Street

+ Ropes Mansion & Garden : this is Allison’s House in Hocus Pocus! You can purchase tickets to tour the inside or just wait in line to take a picture in the front of it! Tours are only available Saturday and Sundays, it was Friday when we were in Salem, so we didn’t do the tour, but you can still walk around the gardens in the back for free!

+ Witch House ( The Jonathan Corwin House) : one of the last surviving structures in Salem with direct ties to the Salem Witch Trials of 1692. Jonathan Corwin was a judge overseeing the Salem Witch Trials. Tickets for tours can be bought online, unfortunately for me, tickets were sold out when I tried!

+ Salem Police Department : you have to visit! They have a vending machine inside where you can buy patches!

+ House of Seven Gables : a 1668 Colonial Mansion made famous by Nathaniel Hawthorne’s book of the same name. I just got the book in the mail!

+ Salem Witch Village : a street where they have haunted houses, mazes, and festival like booths set up. It was so cool!

+ Salem Witch Trials Memorial : this is located right next to the cemetery (we did not walk directly through the cemetery because I didn’t think my kids needed to have that memory), but the memorial you can walk essentially in a circle around granite stones with the names of those who were wrongfully convicted of witch craft. The stones also have their manner and date of death on them.

+ Bewitched statue!

I absolutely loved learning all the history within Salem (plan on doing a deep dive on the trials next!!) and walking within this city during October was just a VIBE!! It was literally like walking through Halloweentown (the Disney classic). There were characters everywhere, walking around, playing music, posing for pictures- it was truly so much fun.

Afterwards, we walked back to the bus station and caught a bus back to Boston! I highly recommend NOT staying too late if you plan on taking the train! I saw videos of the lines to get on that last train out of Salem and it looked INSANE!

When we got back into Boston, we decided to hit some things that were actually on the itinerary for the next day, but it was only 3 pm so we figured we had plenty of time to keep exploring!

We ended up walking through Boston Common (one of many parks), where my children chased squirrels and ran around the open space. It was beautiful out and seeing the city behind all the Fall colored trees was really spectacular. Afterwards, we walked straight on thru to Beacon Hill to check out their Halloween decorations, which we’d seen all over social media- and let me tell you, being there in person is just WOW.

There’s also a little bookstore in the area called Beacon Hill Books & Cafe, we stopped by and ended up leaving with our fair share of books! It was getting dark so we started to walk back towards our hotel and stopped at High Street Place Food Hall for dinner and dessert!

I went to bed so happy that night and so excited for day II!

DAY II

After having an early wake up call for our first full day in Boston, we decided no alarm was necessary for day #2. We ended up naturally getting up at around 8:30 am Boston time, which was a little shocking because that’s 5:30 am California time lol. We took our time getting up and ready while deciding where to go for breakfast. We loved the Beacon Hill area so much, we decided we wanted to have breakfast somewhere over there so that we could kinda explore that area more. We took an uber this time and ate at The Paramount. 10/10 food was DELICIOUS! I got banana smore’s pancakes which were absolutely amazing.

After breakfast, we took one more stroll through the Beacon Hill neighborhoods, of course stopping for a picture in front of the famed Acorn Street. Then we made our way to Boston Public Garden. This park was so stunning! And truly, this was my favorite morning possibly of all time. I loved taking our time walking through the garden and enjoying the beautiful scenery; ducks playing in the water, the leaves on the trees changing colors and falling to the ground, it literally felt like I stepped into a romcom and I was loving every minute.

There was a photographer on one of the bridges taking photos of people and then printing them out on a vintage Boston newspaper type print, of course we had to do it! We posed for the photo and then continued our walk throughout the Garden and eventually hit Newbury Street- this is a street full of cute little boutiques and eateries! We stopped in at Central Perk for some coffee and continued our walk! For this day, we knew we’d be walking quite a bit so we did bring our stroller with us.

We walked into the Boston Public Library for a peek and then decided to hit the New England Aquarium to let our kids run around. I ALWAYS stress that with trips, it’s so important to also let your kids be kids and to plan something specifically for them. For this reason, I always look up a local aquarium or zoo when we’re traveling.

We got an uber from the library that dropped us off right in the front of the aquarium. Of course, my son fell asleep on my lap on the drive over, so we transferred him to the stroller and let him sleep as long as he wanted (which was only about 30 min). The New England Aquarium is so fun, and since it was Halloween, they had decorations and carved pumpkins in the tanks for all the fish! It was so cute!

We took our time at the aquarium and really let the kids lead the whole time. After the aquarium, we hit the gift shop, if you know my daughter, you know she doesn’t leave ANYWHERE without getting a little something- and her motto on vacation (which she says repeatedly) is “we’re on vacation, we can get what we want.” And if thats not the best vibe for being on a vacation, I don’t know what is.

Once we left the aquarium, we walked over to James Hook & Co, which was not too far away. I had to try their lobster rolls! Last year they celebrated 100 years! It was so good, the kids got some hot dogs to eat as well. Then we hopped in another Uber to take us to the Boston Public Market!

I’m not going to lie to you guys, when we got there I immediately wanted to turn around. It doesn’t look like it’s in the best area of town and there was also a huge farmer’s market going on right outside and the smell of seafood was really grossing me out. But Joey convinced me to at least go in (I literally told him it looked like a food pantry), and well, I’m so glad we went inside! It was such a cute little place filled with counters for different bakeries and eateries. We went to a donut shop and grabbed a bunch of donuts to snack on and then some for the next morning so that we’d have something to eat prior to our very early flight! I also got THE BEST hot cider from a separate counter for an apple farm!

I’m going to list what we did next down below to simplify!

+ walked part of The Freedom Trail to Paul Revere’s House and the Old North Church! If you don’t know who Paul Revere is, you might need to repeat middle school history class. But I’ll sum it up here- Paul Revere played a critical role in the American Revolution for his famous midnight ride throughout Boston alerting minutemen that the British were coming (one if by land, two if by sea ring a bell?) Paul Revere arranged a code with a friend (a sexton of the Old North Church) to signal how the British were coming- one lantern hung in the church meant by land, two lanterns meant by sea. When you walk the Freedom Trail, you walk from Paul Revere’s house to the Old North Church, which still has one of the lanterns inside! The other lantern is housed in the Concord Museum in Massachusetts. The Freedom Trail as a whole is a 2.5-mile-long walking path that connects 16 historically significant sites tied to the American Revolution and the founding of the United States. It was so cool for me to see all these places, especially because I recently watched The American Experiment on Netflix which was basically about the start of America and delved into all the details of how our country started, which literally happened right in Boston, MA. I was in every single location the documentary talked about, I loved it!

+ walk around the North End : we walked the Freedom Trail to the Old North Church and then actually walked into another church which was having Mass. We sat in the church and listened and prayed for a little bit before heading out. We like to visit churches when we can when we travel!

+ dinner in the North End : we ate an Italian restaurant that was OUT OF THIS WORLD! For the life of me I cannot remember the name of it, although if my husband were home right now, he’d be able to tell me lol. It was soooo good though!

+ Mike’s Pastry : we waited in a line that was literally down the block and then realized once we reached the inside portion of the line that it was cash only and we spent the last of our cash at the aquarium buying a stuffed turtle LOL. SO that was a big fail, but if you go- bring cash and buy a cannoli for me! I’ve heard they’re incredible!

+ ended up walking back to Faneuil Hall Marketplace for dessert and then back to our hotel!

By the time we got back to our hotel it was around 8:45 pm, we showered and got the kids in bed, they watched a movie while my husband and I packed everything up for our flight out the next morning! We had to be at the airport by 6 am Boston time, so it was definitely an early morning for us!

The entire trip was just 10/10 and I definitely want to go back!! Being from California, we don’t really get “real” seasons, so being somewhere that was the perfect picture of Fall, was really special and amazing, especially for someone who adores the Fall as much as I do.