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The 411: Cape Cod + The Islands

Updated: Jan 14, 2020

Backwoods Good's round-up of some of the very best food + drink spots to hit in Upper Cape and Islands to get the Cape Cod experience.

If you're fond of sand dunes and salty air Quaint little villages here and there (You're sure)You're sure to fall in love with old Cape Cod (Cape Cod, that old Cape Cod)

-Patti Page

Yes, I did sing that as I typed it out. No, it did not sound like Patti Page- but the emotions were there! Ahh- the Cape. A favorite spot of mine, filled of the best memories with the best of friends.

You can't beat this man-made island, especially in the Summer time. We've rounded up some of our favorite, must-hit spots on Cape Cod and the Islands.

First stop: Bourne

There are two ways to get on the Cape- the Bourne Bridge and the Sagamore Bridge. For reasons that can only be explained in the main photo of this blog post- I prefer the Bourne Bridge. There's nothing better than crossing the Cape Cod Canal onto the Cape and seeing the Rotary (or round-a-bout depending on where you're from) that gives you a warm welcome with, well, bushes.

The Bourne Bridge brings you directly into, well, Bourne. Which is where I think we should begin. Made up of several small villages- I have two absolute FAVORITES here: Chart Room and Lobster Trap.

Chart Room

1 Shipyard Ln, Cataumet, MA 02534

Located at Kingman's Marina- the Chart Room is a must for anyone who loves beautiful views, great atmosphere, great food and a killer mudslide.

Comprised of both indoor and outdoor seating, you can stop in for "drinks on the shells" (refer to picture to the right)- or head inside to the bar or grab a table with covered outdoor seating for some of the best seafood you can get.

The outside is personally my favorite. You can order a drink (get the mudslide) at the outdoor bar-window and head over to snag a picnic chair and admire the boats on the water and people watch your heart out.

This is where I have some of my favorite memories. These mudslides are no joke. They are seriously so delicious and believe me when I tell you- they're poured with a heavy hand.

Bonus tip:

If you ask the bartender for goldfish- they pour you a plastic cup full...for free!

Believe it or not, there's more to the Chart Room than their amazing 'slides and gorgeous views. They have amazing seafood. Everything is fresh and everything is very mouthwatering.

Here's some of our favorites.

Mussels Steamed with White Wine and Garlic (left) and Lobster Salad Stuffed Tomato (right).

Scallops Baked in a Casserole with Butter, Sherry Wine and Seasoned Breadcrumbs (left) and Broiled Swordfish with Seasoned Breadcrumbs Topped with Anchovy Butter (right).

And last but not least...

Baked Stuffed Lobster (drooling).

Stuffed with Fresh Lobster Meat and our Seasoned Breadcrumbs, Served with Drawn Butter and Lemon.

This bad boy is caught fresh. stuffed well. and baked to perfection.

Believe me when I tell you, this is oh-so-delicious and oh-so-filling. But it's worth it, and they're famous for it.

Lobster Trap

290 Shore Rd, Bourne, MA 02532

You know that saying "a picture is worth a thousand words"? Well that's gonna be the case with this next spot.

Located not too far from Chart Room in the Bourne Village Monument Beach, is the Lobster Trap. What was once a BYOB joint with cafeteria style ordering and only open in the Summers- is now a year-round spot with a full bar and sit down dining for locals and tourists who love to drink and eat damn good seafood.

The menu is comprised of 90% seafood. And when we say it's fresh- we mean it. is. fresh. Before the Lobster Trap is what it is today, they started out as a neighborhood fish market in 1969 and now distribute and cater world-wide- on top of the restaurant side.

Next Up: Falmouth

Just one town over is Falmouth- another favorite of mine where I have many fond memories. Just like Bourne- there are lots of different parts, all with their own personalities. Falmouth is our next stop.

Deans Market

580 North Falmouth Highway, North Falmouth, MA 02556

What may look like a simple local convenient store- is much much more. This post will be simple and straight forward. One word- subs.

A staple to any beach day, or rainy day, or any day really- a Dean's Sub (which clearly we buy in bulk, cause we're smart). Getting a Dean's Sub became a ritual for anytime I came to the Cape. They are by far one of my favorite sandwiches and I highly suggest- no demand- you grab one next time you're in the area. My favorite? Their Italian.

Tip: Get it on their "crusty bread". I know, the word "crusty" isn't one we particularly water in the mouth over. But trust us- this is only way to get it.


188 Main St, Falmouth, MA 02540

Probably one of the best Mexican spots on the Cape. Located on Falmouth Main Street (a must when you visit Falmouth) is Anejo. Surrounded by local shops, cafes and restaurants- this spot is fantastic for people watching!

They have fabulous margaritas with lots of choices to choose from- my favorite is the "Anejo"- with is Camarena añejo, Torres Orange, organic sugar cane, squeezed lime and orange.

We know guac is extra- and we'll take two. Made table-side, their guac is to die for. Customize it however your taste-buds desire and indulge. There's nothing like watching your food be prepared in front of you- seeing your ingredients and watching your dish get created right before your eyes really gets Backwoods Goods goin'!

While honestly everything on this menu is fantastic- we of course do have a few favorites we strongly encourage you try below.

(From left to right)

Langosta Taquitos: local lobster lightly fried in a flour tortilla with chipotle crema, guacamole, sour cream

Pescado Encornflecado: corn flake encrusted local cod, fire roasted corn, cilantro-lime rice, house verde sauce, cotija cheese-- (our favorite)

Chipotle Beef Chimichanga fried flour tortilla, chipotle braised beef, rajas, Oaxaca-jack cheese, fire roasted potatoes, black bea:ns, pico de gallo, sour cream, cotija cheese, chipotle negra mole

The Flying Bridge

220 Scranton Avenue, Falmouth MA 02540

Serving great seafood with a great view for over 30 years, The Flying Bridge is a great place to enjoy dinner on the water. Looking over Falmouth Marina, enjoy cocktails on their multi-level outdoor deck and watch the boats and Falmouth Ferry come and go. This place is also a hot spot for weddings and other events.

(Photos provided by Flying Bridge)

Shuckers World Famous Raw Bar

91 Water St A, Woods Hole, MA 02543

Located in the extreme southwest Falmouth is the village of Wood's Hole. This quaint village is the home to some of the best waterfront restaurants as well as the Steamship Authority- the largest ferry service to the Islands of Martha’s Vineyard and Nantucket from Cape Cod.

Wood's Hole is also the home to Shuckers- a true Cape Cod experience. With freshly squeezed cocktails, lobster rolls, and oysters hand-shucked by the wait staff (hence the name)- this place is an experience.

Landfall Restaurant

9 Luscombe Avenue, Woods Hole, MA 02543

Just a stones throw away from Shuckers, you'll find Landfall Restaurant. This place has views for days and a classic Cape Cod feel.

Originally built in 1946- Landfall is constructed of wood taken from ship wrecks and boards from old local buildings and serves local fresh seafood cuisine giving you a truly authentic Cape Cod experience.

(Photos provided by Landfall Restaurant)

Third Stop: Martha's Vineyard

After lunch and drinks in Woods Hole- walk over to the Steam Ship and take the ferry from Wood's Hole to the Vineyard. Our two favorite towns are Oak Bluffs and Edgartown- both very different from each other but each with their own eclectic flare.

Since the steamship does not run to Edgartown- let's start our Vineyard round-up in Oak Bluffs, the more "party" area of the vineyard.

Nancy's Restaurant and Snack Bar and Donovan's Reef

29 Lake Ave, Oak Bluffs, Massachusetts 02557

When I think Oaks Bluff- first thing I think of the world-famous Dirty Banana's from Donovan's Reef and beautiful views at Nancy's.

First thing you must do when you arrive in Oak Bluffs is head towards Nancy's and stop at Donovans Reef at Nancy's is located on the ground floor of Nancy's- next to Nancy's Snack Shack. Named after the Vineyard's favorite bar tenders who gifts us with the desert-like frozen drink, "Dirty Bananas"- this place is infamous if you've ever been to the Vineyard.

What's in a dirty banana? While the recipe for the famous dirty banana is a highly guarded kept-secret, the gist of this tasty concoction is part mudslide, part banana liquor...

But believe me- there's something Donovan's doing that keeps this recipe a secret- because its AMAZING.

Next, head just to the left of Donovans for some casual dining and drinking at Nancy's Snack Bar. The more casual version of Nancy's offers cafeteria style ordering of delicious food, snacks, and drinks.

Order and take your food to relax under shaded umbrellas at picnic tables right on the harbor. You can't beat some of New England's best quality seafood (and much, much more) all while taking in the iconic Island view at this original waterfront restaurant. Plus- you're right next to Donovan's should that Dirty Banana start running low.

On the other hand- if you're looking for more of a sit-down spot, head just upstairs to Nancy's Restaurant with beautiful views of Oak Bluff's harbor from all angles.

Lookout Tavern

8 Sea View Avenue Ext, Oak Bluffs, Massachusetts 02557

photo card: Lookout Tavern

The name says it all. This spot looks out over the ocean with prime seating (if you're lucky enough to snag a stool) lined up across the outside railings. Great beer, great vibes, great views and great food that varies from sushi to tacos to sandwiches and ribs.


2 Main Street, Edgartown MA 02539

Image provided by Atlantic

Now we head over to Edgartown- a charming, quaint area on Martha's Vineyard and the home to fabulous shops and restaurants. One that we highly suggest you stop at is Atlantic Fish & Chop House- "a destination within a destination".

What sets this place apart you ask? Well besides the spectacular views, elegant dining and 5-star cuisine- they also offer this:

Complimentary Basket of Bacon Strips.

This ain't no typical bread basket to pick on while you review the menu. Nope. Atlantic gets you started with straight up bacon- and all is officially right in the world.

Despite the high-end food they offer on their menu, the complimentary bacon gives you a more laid back feel as you sit at the bar contemplating between Osso Bucco, Lobster Ravioli or the Crackling Pork Shank.

While we have your mouth-buds going crazy over the basket of bacon- let's also take a moment to drool over some of their main dishes.

(images provided by Atlantic)


There are so many more fabulous spots on the Cape + Islands! Stay tuned for our next Cape Roundup!

Have a spot in mind you think we should feature? Email us at

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