6 Stellar Places to Eat and Drink in Chatham & Orleans, MA

There’s always something good cooking in Chatham and Orleans, Massachusetts. Likewise, it’s easy to find an adult beverage to enjoy over good food and even better company. From daily caught seafood to authentic Caribbean cuisine to island-inspired drinks, you’ll find a wide selection of spots to make your trip to the Cape a memorable one.

Read on to discover some of the best places to eat and drink in Chatham and Orleans.

Get Your Seafood On

Your visit to Chatham and Orleans wouldn’t be complete without a luscious meal comprised of the freshest daily-caught seafood the waters of Cape Cod have to offer. To feast on these treasures of the sea, look no further than Mac’s Chatham Fish & Lobster. Choose from irresistible fish like salmon, flounder, halibut, swordfish, and more. Or lose yourself in the ecstasy of a lobster BLT, seared local sea scallops, or a few top-notch fish tacos.

This family-friendly joint is an easy choice with mouthwatering desserts and a kid’s menu loaded with non-seafood items.

Did Someone Say Whoopie Pie?

For a quick and convenient bite, duck into the quaint and cozy Corner Store with convenient locations in Chatham and Orleans. Serving the Cape Cod community since 2005, the Corner Store offers up savory burritos and burrito bowls, remarkably fresh salads, and more. Don’t forget to grab a made from scratch whoopie pie or rice krispie treat. With eats this tasty, you’ll probably stop in a few times during your visit.

Caribbean Style, Please

A mere mile from the ocean in the center of Chatham, sit down at Branches Grill and Café for unrivaled Caribbean-American cuisine. This local, family-owned gem will exceed your expectations with out-of-this-world jerk chicken, steamed fish, phenomenal paninis, and so much more. When it comes to freshness and flavors that’ll make your tastebuds dance, it’s hard to beat this authentic Caribbean-inspired restaurant. Did we mention the full bar?

Satisfying Drinks and Lively Nightlife

There’s something special about experiencing the local nightlife after a long day of vacationing. Sure Chatham Squire has excellent pub food, but there’s also a rockin’ tavern chock full of character (and characters!) with live music, DJs, and dancing. Make an evening of it to experience some real, local flavor. Open since 1968, you know they’re doing something right!

For a top-shelf seafood menu and island-inspired drinks, hit up The Blue Coral. Take advantage of the fresh air on the patio while you laugh the night away over frozen daiquiris, tiki rum drinks, margaritas, or beer.

Or, head straight to the Jailhouse Tavern in Orleans for fantastic drinks and food in a cool speakeasy-style setting. Formerly the old home of the town constable during Prohibition, the front room used to serve as a Saturday night lockup. Now the location serves up a great time in an energetic, jailhouse/speakeasy-themed atmosphere. Don’t miss the lush green patio with live music and fun games like cornhole.