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Labor Day Weekend Adventures

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Anna Osgoodby Life + Design : Labor Day Weekend Adventures

This Labor Day weekend I hopped on a bus and headed north to New England for a little exploring with two of my favorite people! First stop? The lovely, Boston!

Let me start by saying I LOVE this city! I visited a couple of years ago but somehow hadn’t made it back until this weekend. It’s about a 4 and a half bus ride from the city, so it’s a little way, but totally doable for a weekend trip. 

There’s just something about this city that just gives off good vibes. The city is gorgeous, clean, full of colonial charm and the people come across as very friendly! It didn’t hurt that the weather was beautiful when I hopped off the bus either! 

My bus ended up getting caught up in some traffic on the way up, but it actually ended up getting me into our hotel only a few minutes before the Hardersen, which worked out perfectly!

Kathy booked us a totally fabulous hotel for the evening in the Back Bay of Boston. The very nice man at the concierge desk explained to us that back in the day the area was very industrial, but in the last several years it had gotten a complete facelift and become a hub for new developments. I’m totally obsessed with the design and decor of our hotel too!

Industrial, yet super modern. Sliding metal doors, exposed pipes and beams, aw interior design heaven! Love the look! The area reminded me a lot of the Pearl District in Portland too. 

For the evening we took a walk across the water and went to a dueling piano bar called Howl at the Moon! I’d never been to a piano bar before and this location was a great place to be my first! How much FUN! It was remarkable to hear some of the piano versions of songs as well as a few surprises.. “Baby Got Back” and… “The Circle of Life”? Yep, that happened!

On our walk back to the hotel we ran into a fireworks show too! The perfect way to end the night! 

We started out the morning with an awesome breakfast at the hotel (please admire my first waffle I’ve made!) and then we headed to the North End with one place on our agenda…dun, dun, dun. Mike’s Pastry!

If you go to one place and one place only in Boston. Go to Mikes. Their cannolis are out of this world! The hype is real and delicious!

Once we had our cannolis in tow it was time to head to Route 3A towards Cape Cod! 

Along our way we came across Plymouth, the city where the pilgrims landed. Talk about going back to your colonial roots, right!? So that was pretty cool, we got to see Plymouth Rock too which, spoiler alert, was kind of underwhelming.

It was still cool to see though.. even if it probably wasn’t really what the pilgrims saw when they arrived. Did you know they didn’t talk about Plymouth Rock until over 100 years after they landed? Sounds a little fishy to me!

Either way, Plymouth was cute and we got to see a recreation of the Mayflower too. Let’s just saw, I’m glad I live in modern days and wasn’t traveling thousands of miles across the ocean in that boat. Can you imagine!??

Along our drive to Cape Cod we got to see some really adorable architecture. I’m totally a fan of the old colonial homes and the cape cod shake style homes. SO cute! We also got to go through some fun little towns like Sandwich! Yes, there’s a town named Sandwich!

The weather had clouded up a bit by the time we made it to our destination but we still got in plenty of adventure time! 

We definitely hit a couple of firsts for me on this trip! Another being trying a lobster roll from the Summer Shanty. I have to say, I’m not sure if I’ve even had lobster prior to that roll, but man was it tasty! Their chowder was seriously on point too! Cape Cod, you’re serious about that seafood thing ;-)

The next morning we did a little more sightseeing and stopped at this cute little beach style coffee house in Brewster. I really liked the town of Brewster, it was seriously cute! there were several Inns, antique shops, and art galleries.

The Cape definitely has a very laid back vibe. There’s some cute little shops to check out and some restaurants, but for the most part you can tell that people really go there to head to the beach and just relax with family and friends. Oh, and play mini golf, if you want to open a mini golf business, that is the place to do it!

To wrap up my time in the Cape we headed further up the peninsula to Provincetown so that I could catch an express ferry back to Boston to catch my bus back home, I didn’t spend much time in Provincetown but it looked like a colorful and hopping little city! Would love to explore a little more if I make it back one day!

And that’s a wrap! What a wonderful weekend with two amazing people! So thankful I was able to tag along their trip and check out a new part of the country!