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Boston Memorial Day Weekend

For us, a lot of Memorial Day Weekends have been an invite to pool parties or a drive out to the beach, but a few years ago, I felt it was time to broaden our summer kick-off routine with a Boston Memorial Day weekend. We absolutely love that city, so when looking through old photos and previous blog posts I was shocked we hadn’t been there since the summer of 2015! Furthermore, while researching family fun accommodations. I stumbled upon Hotel Commonwealth. Located in Kenmore Square, the hotel is a short walk to Newbury Street shopping district, and close to countless other Boston attractions. Ideal for my clan on the run!

Big thanks to the Hotel Commonwealth for hosting us a wonderful Bostonian Weekend!

Boston Video!


Boston mdw trip

Boston Memorial Day Weekend

Firstly, anticipating loads of traffic, we opted to take the train after the kids finished school. We did pull them slightly earlier to catch a train that got us into Boston Memorial Day weekend at around 4 pm! Honestly, this was probably one of the best ideas we’ve had in a while, because Jason and I enjoyed the ride just as much as the kids, relaxing along the way. Moreover, I knocked off a ton of work, leaving my weekend completely free for fun with kiddies!

Boston mdw trip

Boston mdw trip Boston mdw trip

About the Hotel

Moreover, for our family of five, the Hotel Commonwealth suggested adjoining rooms to make our stay a bit more comfortable. To our surprise, the kids were greeted with two pop tent beds in the room, with a plush Teddy for each, books, and a welcome basket full of sweets for their stay; all part of their Bedtime in Beantown package. For example, the tents even had the girl’s names written on a sign above- love that little detail, because it mitigated their urge to tussle over who slept where. And it gave Jason and me a room totally to ourselves!

Boston mdw trip

Boston mdw tripBoston mdw trip Boston mdw trip

Boston Red Sox

Furthermore, as the official hotel of the Boston Red Sox, I especially enjoyed how the Hotel Commonwealth “tipped a hat” to the Sox in so many ways with its decor. One of the elevators is painted white with red stitching to mimic that of a baseball. This alone kept Gemma busy all weekend, tallying the number of times she rode in the Baseball Elevator- 11 to be exact. For instance, other nods to their Commonwealth Avenue neighbors can be found throughout the hotel, like their Boston Terriers mascot around the property, and Boston University themed Terrier Suite! 

Boston mdw trip

Boston mdw trip Boston mdw trip

Where to Eat

Specifically, our first stop on our Boston Memorial Day Weekend Friday evening was dinner. My friend is the owner and chef at TABLE in the North End of Boston, which is an absolute MUST if you happen to be in town. A 32-seat, family-style restaurant, TABLE offers nightly seatings Thursday through Saturday evenings. Henceforth, with a set menu, there is no need to order or feel the urge to eat off anyone’s plate. Eggplant parmesan, gnocchi bolognese, mussels Italiano were just a few of her amazing dishes. We left busting at the seams, and while I may seem biased because Jen is a dear friend, but it was hands down one of the best meals I’ve had in ages.

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Exploring the City

The next day we wasted no time getting up and out, to enjoy the streets of Boston with picture perfect weather. Our waiter from the previous night offered a couple of tips, mentioning that Castle Island was definitely worth checking out! We’d never been, so this was our first stop after breakfast. Castle Island combines history and recreation, where we toured and walked the perimeter of Fort Independence, watched the kids romp in the playground, and enjoyed calm beaches along the Bay. Such a beautiful spot and I totally recommend it for kids!

Boston mdw trip Boston mdw trip Boston mdw trip

Boston mdw trip

Lobster Rolls

Last time in Boston, Jason really enjoyed The Barking Crab, so we decided to head back for a late lunch. The outdoor patio situated right on the Bay is a fun, laid back vibe, with yummy lobster rolls, the kids loved it too! It’s near the seaport, so afterward we checked out Boston’s Childrens’ Museum and the Boston Tea Party ship too.

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Boston Commons

Finally, on Sunday, we explored Boston Commons and Boston Public Gardens, walking from Hotel Commonwealth through the Commonwealth Avenue Mall. For instance, all along the strip, you will find statues paying homage to Bostonians who left their mark in history. We stopped at each to read their stories and take photos.

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Swan Boat Tour

No trip to the Public Gardens would be complete without a lap around the lake on a Swan boat tour. We road the same swan boats back in 2015, so I was excited to compare the photos and kids reactions, now a little older.

Boston mdw tripBoston mdw trip

Boston mdw trip

Honoring Those Who Have Served Our Country

In the park, we came across a spectacular tribute. 37,000 flags planted in the garden, to honor fallen soldiers in the state of Massachusetts, dating from The Revolutionary War to the present. It was quite daunting to see the sheer volume of these flags to put into perspective how many people lost their lives to make the country what it is today. How fortunate we were to witness this Boston Memorial Day weekend tribute.

Boston mdw trip Boston mdw trip

Each night upon our return to the hotel, the concierge had a little basket of goodies that they offered the kids. What kid will turn away candy or chocolate almonds!


Boston mdw trip Park

Since we were walking distance to Fenway, it only seemed fitting to go see a game, so we bought tickets for the Monday night game against the Indians. Fenway is one of the last original ball fields in all of the US and you can totally feel the vibe and history when you enter. The Red Sox may be our opposing team here in New York City, but we totally rooted for the home team (well, Jason didn’t!). The perfect end to a lovely holiday.

Boston mdw trip Boston mdw trip Boston mdw trip

Excited to announce that I will be giving away a one-night stay to Hotel Commonwealth along with their Bedtime in Benton package (a sleepover package that includes the slumber party tents & Terry the Bear stuffed animal + books) Head to my IG for more info!  (CLOSED)


Our Boston Memorial Day weekend broadened our summer kick-off routine beyond the pool parties and drives out to the beach.


**original post June 3rd 2019 

For more Memorial Day Weekend plans, visit here!

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22 thoughts on “Boston Memorial Day Weekend”

  1. I’m dying to go to Boston!!! That field of flags is truly striking. Was it only there because of Memorial day? Very cool tribute!

  2. We have never been to Boston but will definitely want to stay at The Hotel Commonwealth when we visit. Those pop-up tents would have my girls super excited! The bad part would be getting them to leave the room to go see the sights, LOL!

  3. Amy Desrosiers

    Looks like you had a blast in my neck of the woods. I was in Boston this weekend too and took the T.

  4. That looks like so much fun. I’ve always wanted to go to Boston. I definitely still want to go after seeing all these photos.

  5. I really love the tents in the hotel room. I am going on a trip next weekend with my family and I am dreading all of us smashed into one room.

  6. What an amazing trip! This looks like such a fun Memorial Day trip. Thanks for sharing and taking us on your adventure!

  7. i loved that they incorporated McCord Chocolates in your basket. Shows the quality of the place. The tents were so cute and I bet the girls loved them. The Boston Women’s memorial is what I would like to see.


    We have never been to Boston, but it has been on my bucket list for years! It looks like you guys had a blast!

  9. Boston is one of the best states anyone can visit. Looks like you and you’re family had an amazing time there. The photos are so lovely.

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