An Insiders Guide to Chatham, MA
- Liza Daniels
- Jul 30, 2020
- 6 min read
Updated: Oct 23, 2020
Ever since I was an idea inside the imagination of my parents, my family has been going on vacation to Cape Cod each summer. We specifically would spend a week or two in the tiny oasis of Chatham. What started off as a family vacation spot has now become one of the few places that I feel truly at home. While the feelings of comfort that I get from being in Chatham may not be because of its wonderful food, it certainly helps. In this guide, I will share with you the most amazing restaurants, some of which, me and my family have been going back to for over twenty years. If you're from the Northeast and live within driving distance of the Cape, I would highly recommend checking it out for a weekend.
Okay, now onto the guide.
Breakfast/Lunch:

Hangar B Eatery: One of my favorite things about Hangar B is that it is located at a biplane airport so you can sit outside, eat your DELICIOUS breakfast, and also watch tiny little one person planes take off the whole time. Free entertainment. Who doesn't love that! If the free entertainment wasn't enough to get you to go, the food is absolutely amazing. They make homemade donuts, amazing breakfast burritos: the steak & eggs one is great, and while I've never tried it, they also have one that has truffle arancini inside of it (fried risotto balls).
Chatham Bars Inn Breakfast Buffet: ok, so I will admit. This one is a definite splurge. That being said, the breakfast buffet is quite honestly amazing. They have everything from fresh made donuts & other pastries, to eggs, hash browns, an omelette station and lox. You name it, they have it. You can order from the menu too, if you prefer something lighter. It used to be tradition for my grandparents to take me and all my cousins there to stuff our faces when we were younger. I like to carry on the tradition myself. I should definitely note that you do not need to be staying at the hotel to enjoy their lavish breakfast buffet (or any other meal for that matter).

Jo-Mama's: Jo Mama's has breakfast and lunch sandwiches, all of which are to die for. However, they specialize in bagels. Yum. For breakfast, a simple Bacon, Egg and Cheese is the way to go. For lunch, my personal favorite is the Fire Bird because of its spicy chipotle mayo sauce. Alternatively, I also love making up my own sandwich creations.
Chatham Cookware: Chatham Cookware is a small coffee shop on Main Street that has delicious pastries and breakfast sandwiches. Not to mention their lunch is also amazing. For breakfast, if you're in the mood for something sweet, you have to get either the French breakfast muffin, which is basically just a muffin doused in cinnamon sugar or the Kouign Amann (which means cake of butter), and kind of reminds me of a croissant but with pockets of crisp sugar. If you're in the mood for savory, get their egg and cheese sandwich with linguica. It is a Portuguese sausage that tastes kind of like chorizo and is so delicious. For lunch, they have all kinds of wonderful sandwiches, but my favorites are the Quirky Mermaid and the Spinnaker.
Lunch/Dinner:

Chatham Bars Inn: As I said above, about their breakfast buffet, CBI is a little pricey, but most of the time it is totally worth it. Go have lunch down at the Beach House Grill and order the Lobster Nachos & Rose Sangria. If you're looking for a delicious dinner, then head to the Sacred Cod Tavern & see if you can sit outside on the veranda. It's always nice to go sit outside and have a drink at the Gazebo bar as well before you begin dinner. They have comfortable chairs, adorable string lights overhead and amazing drinks.

Mac's: Mac's is relatively new to Chatham, but not to Cape Cod at large. They have locations all over the Cape and are known for having fresh seafood. In my opinion, Mac's is one of the best additions to Chatham ever. They have everything from a raw bar: including oysters and an entire menu of the freshest sushi, fish sandwiches (think: lobster roll, blackened swordfish sandwich, etc.), to full on entrees like gnocchi or gilled salmon. Mac's is perfect for a nice lunch or a casual dinner. You can eat there or get takeout. Personally, for dinner, I prefer to get takeout and bring it to the beach.

Bluefins Sushi & Sake Bar: If you're in the mood for Asian food, this is a definite go to. Bluefins has great sushi, but also delicious other entrees. Specifically, their Lobster Pad Thai is to die for, and something that you won't find anywhere else. Definitely make sure to call ahead if you are hoping to go here as it gets really busy at peak times in the summer!
Impudent Oyster: The Impudent Oyster is a definite Chatham classic. It has a less beachy and more cozy feel inside. My favorite thing here is the Mussels. Specifically, the Moules Na Cataplana. The Mussels come sautéed in a spicy tomato sauce with pieces of chorizo. They bring this dish with their freshly baked warm bread that you can use to soak up all of the sauce. Warning: the entree portions here are very large.

Delmar: Delmar is located slightly past the main town of Chatham. They have wonderful food and sometimes even have live music playing. This is a great option if you have a large group. We have often gone with my entire family (12 people). I love all of their food, but their pizzas are especially delicious if you're craving a break from seafood.
Pisces: Pisces is a little out of the actual town of Chatham, but is one of my favorites. It is a small restaurant, so I would definitely recommend making a reservation in advance. One of my favorites is the cornmeal crusted fresh fish that comes with a side of toasted orzo pasta. They also have a delicious Almond Joy inspired ice cream sundae that is amazing. Warning: their portions are also huge.

The Chatham Fish Pier: Go here. Get the Blackened Swordfish sandwich. Tell yourself you wont eat all of the battered fries they serve you with your sandwich. Do it anyways. If you aren't going here for the blackened Swordfish sandwich, I would recommend the Lobster Roll or Shrimp Roll. The fish pier also has the freshest fish to pick up and cook yourself at home. My family always used to have a lobster bake and get our lobster from here to dip in drawn butter. Delicious.
The Squire: The squire is probably the most quintessential restaurant in all of Chatham. It is a local favorite. While the food there isn't going to change your life, the atmosphere just might. In the bar area, there are license plates from all over lining the walls. With the current pandemic, they have also set up picnic tables and an adorable "Squire-Mobile" van that serves as a bar behind the restaurant. They have recently changed owners and the food has definitely improved. I would recommend coming here for drinks and some simple bar food, like fried shrimp or French fries.
Dessert:

Emack & Bolio's: I am certain that people will debate me on this, but Emack's is by far my favorite ice cream on the Cape. Maybe it's because I've been going there since I was tiny, or because of all the memories that I have attached to it, but either way, it's delicious. My personal favorite is Grasshopper pie which is basically Mint Oreo. It is located in the town of Chatham and is a perfect place for an afternoon snack while walking around town or a post-dinner dessert.
Buffy's: Also located on Main Street in Chatham, Buffy's is a town favorite. If you're craving soft-serve, definitely go here, because Emack & Bolio's does not have it. Buffy's also has more flavors, and I will say, the ice cream is still delicious.
Chatham Candy Manor: Candy Manor is my GO TO chocolate store in town. they have homemade fudge, turtles, caramels and more. As I kid, I remember my grandpa used to give me and my cousins some money after dinner to run free in the candy store. It was always one of my favorite memories. My personal recommendation is to get the milk chocolate pecan turtles. Oh, and take way too many fudge samples.

Marions: Marion's pie shop may just be my most favorite place on this list. It is a tiny little bakery with the most amazing pastries. We always get a pie or two for our family barbecues. However, my favorite things from here are the apple turnovers, cinnamon rolls and Parker house rolls. If you go early enough in the morning, they will be warm. Plus, you'll be sure that they haven't run out of anything that you might want yet!