Our Goodbye to Boston 30-Mile Walk

Our Goodbye to Boston 30-Mile Walk

As Boston is truly a walking city, Bry and I figured the best way to get closure with this city that has seen us mature from college kids to married adults was with a 30 mile walk to each of its distinctive neighborhoods (including Cambridge, Somerville, and Arlington).

Not only did we walk 30 miles, but we kept a pretty good pace, finishing the walk in 8.5 hours – and that includes stopping for some much-needed snacks and beverages. If you’ve never been to Boston and are looking for key places to see while you’re here I can safely say that we hit most of them. Over the past 8 years Bry and I have had countless wonderful memories, both together and apart. And just as relationships need closure, it truly felt so cleansing to feel like we truly got to say goodbye to each corner of this city that has meant so much to us. So without further ado: A 30 Mile Walk Around Boston (and Arlington, Cambridge, Somerville).

To start we woke up at 7am, grabbed a protein bar and coffee and set out walking. Stop 1: Spy Pond in Arlington. Living on the boarder of Cambridge and Arlington, we walk the Spy Pond loop almost every weekend – not a bad way to start the day 😉

From Spy Pond, we headed down the Minuteman Bikeway, which was Bry’s old bike commute to work in Lexington. If you live in the Boston area or are visiting and looking for something active to do, I highly recommend renting bikes and biking along the gorgeous tree-lined path.

Next, we cut through Davis Square, probably our favorite neighborhood of the greater Boston area. Unlike Boston and Cambridge, Davis Square has a more laid back vibe with some awesome restaurants.

Mile 6: Our first true stop was at my all-time favorite breakfast spot in Cambridge/Somerville: Three Little Figs. This small coffee shop whips out the most amazing, thick homemade Greek yogurt, which you can pair with a slightly sweet cinnamon granola and fresh fruit – it’s like having a fruit crisp for breakfast, but a very filling, healthy fruit crisp. Bry the savory route with a turkey, brie, and apple sandwich. Usually we get coffee there too, but due to the heat and many miles ahead of us, we stuck with water to keep hydrated.

The next stretch was probably the ugliest, as we cut around the back of Somerville and Cambridge to get to the North End. But along the way we came across this billboard that I couldn’t help but take a picture of. Probably won’t see one like it anywhere else 😉

Finally, we were crossing over the river into Boston, with time to stop and take a picture of the duck boats near Science Park.

Surprisingly (at least to us) the most emotional part of the walk was when we reached the North End (aka Little Italy). While there are many unique neighborhoods in Boston, the North End just has this magical, only-in-Boston-quality to it that really made it hit home that we will be leaving here in 3 weeks. A trip to Boston is incomplete without walking around this historic neighborhood and grabbing some authentic Italian food while you’re at it.

As it was 10am, it was a little early for pasta, but definitely not too early for a cannoli (after all we had just walked 10 miles). There are two main places to get a cannoli in the North End: Mike’s and Modern. Always go with Modern. Yes, the line outside of Mike’s may make you think that you’re missing out, but unlike Mike’s, Modern Pastry fills your cannoli fresh when you order it. Trust me it makes a difference. We both went with the classic cannoli shell and sweet ricotta filling (thank goodness they had a mini option as I was still full from my Greek yogurt parfait).

From Modern, we made our way down Hanover Street and over to Quincy Market. From there, down along the harbor to the Seaport district. While neither of us spent a whole lot of time here, it’s one of the few places in the heart of Boston that actually feels like you’re near the ocean.

If you’re ever near the Seaport, take a stroll along the Harbor walk for a beautiful view of the city. In the background of this picture you can see the Boston Harbor Hotel where Bry’s mom and step-dad would usually stay when they came up to visit. Lots of fun memories at the spa and bar there 😉

Next, we made our way from the Seaport up to the Boston Common then over to the Boston Gardens.

After taking a brief rest while watching the swan boats, we headed down Boylston Street to the Boston Public Library, where I nerdily spent many afternoons studying during college.

From there we headed down to Huntington Ave and over to a walking path that cuts down through the South End and into North Eastern’s campus. While a pretty walk, the main reason for taking this path was that it was where Bry and I walked on our first date after finishing brunch at Trident Café. Here we hit mile 16.

After some reminiscing, we hiked it through the back of North Eastern’s campus, visiting Bry’s old dorm then up to Mission Hill where he lived with some of our closest college friends.

From the hill, we headed down to Green T, a funky coffee shop at the base of Mission Hill where Bry, his roommates, and I would often get coffee and breakfast sandwiches on the weekends. (Hint: it’s called Green T as it’s located along the Green Line). While we weren’t quite hungry enough for breakfast sandwiches, we did snack on a delicious spinach and feta pastry, as well as quenched our thirst with cold-brew coffee for Bry and Green T’s signature lemon ginger iced tea for me.

From Mission Hill, we cut down through Longwood – the route we would always take between Bry’s house and my apartment in college. Before heading into the Fenway area, we made an important stop at the bench where we first said “I love you” and where four years later Bryan proposed. 

Of course a tour of Boston wouldn’t be complete without stopping by The Green Monster. Going to BU, Fenway was always in my backyard, with two of my apartments being so close that all I had to do was open a window and I could hear all the games and concerts going on.

We then crossed through Kenmore Square, down to my freshman year dorm, then up over the bridge to the Esplanade.

While I was feeling sore while looking back at the BU boathouse at mile 22, it was mile 24 that I nearly had a meltdown. Every part of my body from the hips down was in so much pain, I was hungry, and the thought of having 6 more miles to go was overwhelming. But thanks to some cheerleading from Bry, I made it back across river and down to Tatte Bakery in Kendall Square (the home of M.I.T).

Mile 26: I have never been so excited to see a chair. For the first time all day, Bry and I treated ourselves to a rest longer than 5 minutes. We also got our bodies some much needed fuel in the form of a fresh mozzarella, tomato, and pesto sandwich (the mozzarella just melted in your mouth) and a short rib and beet grilled cheese.

With food in my belly, I got in a yoga-like zen and made it through the next two miles. It’s amazing how motivating a pitcher of Sangria can be.

Mile 28: Sangria! Our first apartment together was a 400sq ft box in the heart of Porter Square, and just across the street from Christopher’s. During the massive snow storm of 2015, Bry and I would escape cabin fever by crossing the road to Christopher’s for a pitcher of their red sangria. While it tasted good then, it tasted even better after walking 28 miles. But out of fear of our legs getting stiff if we sat too long, we gulped down the Sangria and made the final 2 miles home.

As I mentioned at the beginning of the post, this walk was so special for both of us as it mentally got us ready to say goodbye to one city and say hello to the next chapter of our life together. It also taught me that proper socks are just as important as proper shoes in preventing blisters. No joke, my feet were covered in water blisters and I literally crawled into bed that night. But with some stretching and foam rolling, we are both fully recovered. However, I think it will be a while before we want to do another 30 mile walk 😉

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  • sandra vitiello Avatarsandra vitiello3 years ago

    Great commentary and pictures. Thanks to you and Bryan for sharing this experience.

  • Kelly Jones AvatarKelly Jones3 years ago

    This is such a fun way for a foodie to bid farewell! Great post and best of luck for the next stop on your journey 🙂

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