Date Guide – Charlestown

There’s no better place to spend a summer afternoon in Boston than in Charlestown. With sweeping views of the city skyline and a number of great restaurants it’s an ideal date spot. Let us help you plan the ideal afternoon in one of the most historic neighborhoods of Boston.

Brewer’s Fork

Brick oven pizza, one of Boston’s best tap lists and a patio. These are the makings of a killer afternoon. The pizza at Brewer’s Fork is some of our favorite in the city. The toppings are unique and high quality and the dough is thin and light. If you are a fan of Neapolitan style then this is your spot. All of their pizzas sound good to us, and luckily since they are so light, you can try a few different kinds with a group and not leave absolutely stuffed. The Killa B has hot honey on it, which gives it an addictingly sweet and spicy finish. If you are looking for something with that umami flavor, the Forager has a cream sauce base covered in mushrooms.

The tap list at Brewer’s Fork is always changing and you never know what treats they will have at the bar. They are one of the few spots that gets Vitamin Sea and Trillium on tap. Plus, with a full bar there are plenty of options for everyone.

The Anchor

The Anchor is the perfect spot to let your pizza digest while you soak in some of the best views Boston has to offer (all while enjoying live music). Open from April all the way through the summer, The Anchor is always hosting fun events and great artists. Located in an old brick structure in Charlestown’s navy yard, you can swing in chairs hanging from the ceiling, play some cornhole, or just take in the beautiful views of downtown Boston. Being a wine and beer garden, they have a wide variety or local brews and a robust wine list. This is the type of place you can spend a few hours and work on your tan while catching a buzz. 

Pier 6

Pier 6 is the ideal way to end a romantic day. If you thought the views at Anchor were great, just down the way, Pier 6’s rooftop takes it up another level (if you are lucky enough to get a seat up there). Specializing in all New England foods you can get your seafood fix and so much more. You are definitely paying extra for the food here, but it is well worth it. We always judge a seafood spot by its calamari, and Pier 6 is as good as they come. It’s crispy and crunchy, served with an aioli that has a nice kick to it.  

We Hope You Enjoyed Our Charlestown Food and Drink Guide!

There are so many other hidden gems in Charlestown, and this is just the tip of the iceberg. Don’t sleep on one of the most underrated neighborhoods of Boston!