Escape Guide // Cape Cod, MA

Escape Guide // Cape Cod, MA

While Cape Cod has long been known as a playground for Kennedy style wealth, the small fishing villages, roadside seafood shacks and unspoiled beaches attract people from all walks of life. While the year round population of the cape is a manageable 220k, this number swells by 3x each summer across the cape’s 15 towns, so one of our first tips in this guide is trying to time your trip for September when you get the warmest water (relatively speaking) and the most elbow room. So join us on a journey “down cape” (that’s up the arm of Cape Cod for you New Yorkers) as we explore the best of the cape from a locals point of view.


The Squire


You’ll be seeing a lot of this name on here as The Squire is the quintessential New England beach bar. The type of place with license plates on the walls, house made clam chowder on the menu and bumper stickers announcing that Chatham is a “drinking village with a fishing problem.”



The “Comba” as it’s known to locals sits atop the sandy bluffs of the National Seashore in Wellfleet and has easily the best view anywhere on the cape. In addition to the outdoor area, there is a live band just about every night and plenty of beers to go around. Insiders tip- get there early to avoid lines and lack of parking.

Local’s Tip

Wequassett Hotel


While some locals get uppity about this upscale hotel in Chatham, there’s not a better low key spot to grab a drink in our opinion. Grab some beers from one of the bayside bars and post up in front of the outdoor fire pits overlooking Pleasant Bay for a decidedly laid back evening.


Corner Store


This low key roadside shop sells some of the best sandwiches and burritos on the Cape. Do yourself a favor and grab one of their homemade whoopie pies from the fridge by the door as well. During the busy season, try calling your order in and picking up, though be forewarned that they stop picking up the phone during busy times.

Fish Pier


You’re not going to find fresher seafood anywhere in the country as the commercial fishing boats literally unload and process their catch 50 feet away from the retail shop. If you’re staying at a friend’s house or an Airbnb, swing by the fish pier to pick up everything you need for a seafood grilling session. Be sure to order some of the clam chowder and lobster bisque as a starter.


The Squire


Not only good for drinking, the Squire is serving up some of the best pub food you’re going to find on the cape. Definitely grab a clam chowder for starters and try the fried clam plate for the full experience. After dinner stick around to avoid the line and kick back some suds → see above

Rock Harbor Grill


While only their fourth year in operation, locals know this is the spot to hit, so expect a crowd any weekend all year round. It starts with the warm pretzel bread and honey butter you’re served as a bread plate and gets downright ridiculous when you order the wood fired wings and the wild boar sliders to share. For mains try the house burger or any of the wood fired pizzas. This might be our favorite restaurant on the cape.


Liams Nauset Beach


The definition of a beachside seafood shack, Liam’s lets you grab some fried clam strips and onion rings all while keeping your toes in the sand. Expect long lines, but they move you through quick.

The Raw Bar Ocean Street


All of the seafood is great at the Raw Bar, but it’s their overflowing lobster rolls that have the people wanting more. Get there during off hours to enjoy the outdoor patio and harbor view.


Chatham Cookware


Cookware has all the coffee and sandwiches you’ll need to kick start your day, but be sure to also grab a linguica, egg and cheese on a portuguese roll. Linguica is a slightly spicy portuguese sausage and the rolls are basically softer, larger english muffins. All around worth a trip to plug in or settle the stomach after a night at the Squire.


Downtown Provincetown

You probably will only want to make the drive to Provincetown once during your stay- after all, aren’t you heading to the beach to avoid “downtowns”? It’s worth a drive however to check out the dunes, grab some food and drinks, and walk around downtown for a bit of shopping.

Yankee Ingenuity


Birthday coming up for that special someone? Yankee Ingenuity is the perfect spot to grab some off the beaten path and original one of a kind gifts while on vacation. It’s also a hop skip and a jump down from the Squire, are you seeing a pattern here yet?

Mahi Gold


The home of everything preppy, you’ll be well rewarded spending some time walking around Mahi Gold’s flagship store. The brand started with only their own apparel, but are now selling everything you’ll need to blend in with the pastel masses on the cape.

Yellow Umbrella Books


Family owned, old school book store that has the perfect beach read whether you’re 2 or 92.



Chatham Bars Inn


Beach, pool, boats, views, it’s tough to find something wrong with CBI. Rooms can get pricey- rental homes even more so- but you won’t regret the experience. Cross the street to the private pool and beach side for one of their weekly clam bakes or just to watch the fishing boats cruise through the harbor on their way to the fish pier. Trips to the outer beach in their private boat are included in the stay.



The best way to experience the cape is in a private home. Do yourself a favor and rent a house to truly experience the cape like a local.

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