Sometimes, the best travel experiences stem from a mistake. For this post, I was supposed to go to World’s End, another great hidden gem that I will be featuring later. My dad loves taking walks there, so on a nice day we drove out to photograph it. But as we were halfway into our trip, I looked on the website and discovered that you needed to book tickets in advance because of Covid restrictions. Fantastic.
So with that plan ruined, I did what I do best—improvise. We were already just a few miles outside of Boston, so I decided to go to another one of my favorite spots that was just a few miles away. Even though we didn’t follow our original plan, we ended up someplace just as great.
Chickatawbut Overlook is one of the many great sites in the Blue Hills. This hidden gem is a great place to see a view of Boston’s iconic skyline while going on a short hike.
When you arrive at Chickatawbut, you’re able to see some great views of Boston right away, even from the parking lot that’s just across the road from the trail head. But the best views are further up along the trail. And don’t worry—parking is completely free.
If you head up the stairs across the road you’ll be able to see one of the most iconic landmarks of the overlook—Chickatawbut Observation Tower. The Tower was built by the Civilian Conservation Corps (CCC), a program created by FDR in order to provide jobs in the 30s during the Great Depression. The remains of an old CCC camp are just a two mile hike away. Even though the tower hasn’t been open to the public for decades, it still is a great spot to visit before heading further down the trail.
I will warn you not to make the same mistake that I did. When we went, it was just after Christmastime and the trail was still pretty icy. Because the path is so rocky, it was really hard to navigate through without slipping a little. Even though the trail was nice to hike in the winter, just make sure that there isn’t a ton of snow or ice on the ground before you go, or make sure to bring your hiking boots.
The best trail to hike is the Chickatawbut Yellow Dot Loop. If you follow the yellow dots scattered across trees and rocks, it will take you up to Nahanton Hill. The yellow dot loop will only take you about ¾ of an hour round trip.
Even though the trail is short, only half a mile, it does get pretty steep at points. Nahanton Hill itself is almost 500 ft tall. I wouldn’t say you have to be an advanced hiker to do this trail, (I’m definitely not!) but I would make sure to wear a good pair of sneakers or hiking shoes because you will have to be going up a sharp incline.
If you’re a photographer, make sure to bring a telephoto lens to grab some great shots of the Boston skyline. Even if you don’t know a Nikon from a Canon, it’s easy to grab a great shot of the city. It's nice to see the city from the highway or the top of a building, and it's an entirely different experience to see it from the Blue Hills. There’s a strange sensation of being surrounded by untouched nature but having an amazing man-made skyline towering over the horizon just a few miles away.
The Blue Hills are completely outside and are large enough that guests are easily able to social distance. Everyone over the age of five must wear a mask when in the Blue Hills due to COVID restrictions. But overall, the overlook is extremely safe in regards to coronavirus.
Overall, the climb up to the overlook is completely worth it if you want a truly unique view of Boston while still getting time in nature.
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