First Trip to Boston: 5 Days on the East Coast

For my first* trip to the the East Coast, Matt and I ventured to Boston, MA where most of his family lives. We did a lot of exploring and I got to meet the last of his relatives I’ve had yet to meet! We chose mid-October and were blessed with incredible weather and beautiful foliage. After such a long hot muggy summer in San Diego, I was so happy to wear jeans…and a sweater…and SCARVES!! It seriously felt like forever since the last time I was completely dry and clean for an entire day (everyone in SoCal knows what I’m talking about) and this trip was full of those perfect crisp fall days.

I was really glad we chose to spend 5 days on the East Coast, giving us enough time to explore as tourists, check out the foliage in Maine, and cruise around like locals by the last day. Below are some of the stops we made, some photos I took, and my favorite parts. I didn’t bring my Pentax, so all photos are from my iPhone.

*Back in June, I went to NYC for work for 24 hours…so I don’t exactly count it, although I did walk over 100 blocks in 4 hours to see as much as I could.

Night 1: Harvard Square

Beat Brasserie. This little gem was probably my favorite bar that we went to. Located in Harvard Square, it was very cool inside…plus there’s wine on tap!

The Long Fellow House. George Washington ran the Revolutionary War from this home in Harvard Square and we happened to be staying right around the corner from it, which was pretty sweet.

Day 2: Boston History Tours

I knew that a lot of our trip would consist of learning about New England’s history because Matt loves war history, which Boston is full of. And by love, I mean he’s a little obsessed. To give you a better picture, every time Matt goes to Boston, he takes a tour of the Freedom Trail and takes a Duck Tour through the city by himself. Only now do I realize how cute it is that he likes these historical tours enough to have trek throughout downtown Boston on his own.

Although I’m not a huge fan of tours, the Freedom Trail was awesome since we could guide ourselves, which to us means lots of stops, historical facts from Matt, pictures, and most importantly, cruising at our own pace. First stop…Boston Common, as shown below.

Granary Burying Grounds. Home of Sam Adams, John Hancock, and Robert Paine.

Union Oyster House. The Chowda..I mean Chowder here was BOMB. Plus, it’s a historic landmark, so it was a fun pit stop on our Freedom Trail venture.

Dunkin’ Donuts. I’ve never understood the hype until visiting Boston. After multiple flatbreads, a few chai lattes, an apple cider, a green tea, numerous pumpkin munchkins, and eight stops in 5 days, I can say that I become a little obsessed. And it doesn’t help that there are two stores just about every block.

Duck Tour. I’m going to be honest and say that I had no idea we were going in the water, but of course it makes sense with the whole “duck” aspect. I would recommend this as a great way to see a lot of the city and it’s really fun!

Beacon Hill. I was told to check out this neighborhood for the amazing architecture, but unfortunately we only had time to drive through on the Duck Tour. Next time, I’d love to do some walking in this area.  

Quincy Market. I have a love hate relationship with this place. It was cute, there were lots of shops, and I found my souvenir ornament. On the other hand, it’s crowded, very touristy, and my wallet disappeared here. On the bright side, it only had my credit card and driver’s license in it. Thanks to FedEx and Matt’s wonderful colleague, I got my passport over-nighted and didn’t get stuck in Boston for the rest of my life as I initially (and dramatically) thought might happen.

We’ll never know what happened to my favorite little wallet, but I like to think that some young blonde girl is enjoying tasty beverages at the cool bars of Boston…because I sure couldn’t get in anywhere between Thursday and Saturday.

Harvard University. I took this from the top of the Hertz rental car building. I don’t think I’ve seen such a beautiful view from the top of such a non-beautiful building.

Day 3: Maine

In Maine, we stayed at Anchorage By the Sea in Ogunquit. This tiny town was incredibly cute and perfect for a non-city night. Since I couldn’t get in to the bars without my ID, we took advantage of our cozy hotel room and spent the night in watching Jackass 2. I am no longer allowed to watch TV in a bed with white sheets while drinking wine.

Apple Crisp from Rose Cove Restaurant…they’re not famous for nothin’!

Day 4: Exploring the Streets of Maine

This was definitely my favorite part of the trip. We got to Maine at the perfect time and I was absolutely amazed by all of the colors. I loved the small town feel of Maine and driving down random streets to check out the cute houses and all of the foliage.

Day 5: Harvard Square

Having seen a good amount of the city, by day 5, we decided to have a very mellow day and walk around nearby. This turned out to be the perfect decision, since the Head of the Charles was just around the corner from our hotel for our last night, The Charles.

Head of the Charles Regatta. Apparently we chose one of the busiest weekends in Boston to come. While our first night in Harvard Square was just another night, by Saturday thousands of people were bustling around. Armed with our Dunkin’ cups, we headed off to the Head of the Charles Regatta on Sunday afternoon.

All in all, we had a fantastic time and I loved seeing a new part of the country. Next up, Europe! Until next time, Boston!


Do you have any favorite spots in Boston? Comment below!


One thought on “First Trip to Boston: 5 Days on the East Coast

  1. t.s. Linzey says:

    I really enjoyed spying all of the photographic evidence and descriptions of your splendid adventure. You look beyond happy and energized and that makes me happy. Hell, your chronicling here has piqued my interest so much that I may have to visit the East Coast soon. Here’s to a wonderful blog and your continued adventures through travel!

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