We have an amazing array of restaurants, from casual local specialties to world-class fine dining.

Enjoy fresh local seafood, fruits, and vegetables in the summer as well as our famous ice cream (voted one of the Best in the Country!), or plan a winter destination to enjoy a cozy gourmet meal. Whatever the time of year, you will not leave disappointed or hungry!


Grocery stores

Of course, the first order of business for your vacation home will be to gather your provisions! Here is a list of local grocers. Be sure to plan ahead! Some areas, such as Tilghman, Oxford, and parts of Cambridge are not close to a major grocer, so you may want to plan to stop prior to heading to the property.

The area`s newest grocery store, Harris Teeter, offers online ordering for pick up.

Acme (Easton)

200 Marlboro Avenue, Easton

(410) 822-7073

Acme (Chestertown)

711 Washington Avenue, Chestertown

(410) 778-5641

The Village Shoppe
(St. Michaels)

501 S. Talbot Street, St. Michaels

(410) 745-9300

Chestertown Natural Foods

303 Cannon Street, Chestertown

(410) 778-1677

Harris Teeter

28528 Marlboro Ave, Easton Marketplace, Easton

(410) 690-7203

The area's newest grocery store offers online ordering for pick up on your way to your vacation home or during your stay. Convenient to homes in Easton, Oxford, St. Michaels, and Tilghman Island, or stop on way to Cambridge.


Whether you are looking for local seafood specialties, gourmet pizzas or high-end fine dining, we have an amazing variety of restaurants for you to experience during your stay!

Where you decide to eat during a vacation can make or break your day. Luckily, we already sorted through the possibilities and picked out the best options for you to enjoy. Whether you are planning a romantic dinner on the waterfront or a casual night out with the family, we have got you covered. Discover the best restaurants on the Eastern Shore of MD and get one step closer to a full stomach. You can even plan the ultimate foodie getaway by booking one of our beautiful vacation rentals near your favorite eateries!

Interactive Restaurant Guide

Whether you are looking for local seafood specialties, gourmet pizzas or high-end fine dining, we have an amazing variety of restaurants for you to experience during your stay!

If you are not sure where to start or have not chosen your ideal destination yet, we invite you to check out our interactive guide. It provides a complete, convenient overview of all the best Eastern Shore restaurants. You can view a map, find addresses, look at reviews, and even get a sneak preview of what each restaurant looks like. Or, feel free to scroll down for more detailed recommendations on the top spots for each community.

View the Guide

St. Michaels Restaurants

St. Michaels is home to gorgeous scenery, beautiful homes, and historic streets, making it one of the most sought-after destinations for peaceful retreats.


Easton Restaurants

There are also several restaurants in Easton, MD, awaiting you a little further inland. From cozy cafes to elegant dining areas, there is something for everyone here.

Cambridge Restaurants

Cambridge, Maryland, is a destination in itself. So, of course, it has several fantastic places to eat!

Oxford Restaurants

This small town is perfect for low-key, relaxing getaways.

Tighman Island Restaurants

Tilghman Island is a quiet stretch of land known for fishing, boating, and a wealth of unspoiled natural beauty. We highly recommend trying the seafood here.

Chestertown Restaurants

You may have heard of the quaint, charming atmosphere in Chestertown, but do you know about all the great restaurants it has in store for you? This area is home to local farms and vineyards, making it perfect for businesses to implement farm-to-table practices. Best of all, you get to taste all the fresh flavors and seasonal ingredients for yourself! It does not get much better than that.

Wine, Beer & Spirits

We are proud to have our very own wineries, brewery, and distillery! Stop by for a tour or tasting.

Eastern Shore Brewing

605 S Talbot St, St Michaels

(410) 745-8010

Lyon Distilling Company

605 S Talbot St #6, St Michaels

(443) 333-9181

St. Michaels Winery

609 S Talbot St, St Michaels

(410) 745-0808

Layton's Chance Winery

4225 New Bridge Rd., Vienna

(410) 228-1205

RAR Brewery

504-506 Poplar Street, Cambridge, MD 21613

(443) 225-5664

Triple Creek Winery

11138 Three Bridges Branch Road, Cordova, MD 21625

(410) 924-4190

Restaurants & Seafood Markets

With a variety of choices, you can find something for everyone in your group.

Awful Arthur's

402 South Talbot Street St. Michaels

(410) 745-3474

Chesapeake Landing Restaurant

23713 St. Michaels Road St. Michaels

(410) 745-9600

Foxy's Harbor Grille

125 Mulberry Street St. Michaels

(410) 745-4340

Gay's Seafood

896 Port Street Easton

(410) 822-5019

St. Michaels Crab and Steak House

305 Mulberry Street St. Michaels

(410) 745-3737

The Crab Claw Restaurant

304 Burns Street St. Michaels

(410) 745-2900

Doc's Sunset Grille

104 West Pier Street Oxford

(410) 226-5550

Fish Whistle

98 Cannon St, Chestertown

(410) 778-3566

Farmers Markets

From April to October, you will want to be sure and check out our local Farmer's Markets or stop by one of many local fruit and vegetable stands.Take full advantage of our plentiful fresh produce, seafood and other local specialties at these locations.

Days, times and hours vary seasonally. Please check for hours of operation.

The Oxford Market

203 N Morris St, Oxford

(410) 226-0015

Easton Market Square

100 Block of N. Harrison Street Parking Lot, Easton

(410) 822-7778

Cambridge Farmers Market

Long Wharf Park, Cambridge

Chestertown Farmers and Artisans Market

High and Cross Streets, Fountain Park, Chestertown

Coffee, Ice Cream & Dessert

A day of sightseeing or shopping calls for a break for a treat! Here are some local places to check out that are worth breaking your diet!

Blue Crab Coffee Company

102 Freemont Street, St Michaels

(410) 745-4155

Justine's Ice Cream

106 N Talbot St, St Michaels

(410) 745-0404

Rise Up Coffee

618 Dover Rd, Easton

(410) 822-1353

Bay Country Bakery

2951 Ocean Gateway, Cambridge

(410) 228-9111

Gina's Sweet Shoppe

531 Poplar St., Cambridge

(410) 228-4884

Jojo's Cupcakes and Cream

218 N. Washington Street, Easton

(410) 763-4930

Food Tours

An incredible opportunity to go behind the scenes of some of the areas top restaurants and learn more about why talented chefs from all over the world are making the Eastern Shore their home.

Eastern Shore Food Tours

(410) 635-4130

Select your destination to explore. Eating ST. MICHAELS, Eating CAMBRIDGE & Eating EASTON all offer a different variety of cuisines to sample.

Each location has a three-hour tour that features:

  • A bite and sip at minimum of FOUR amazing local restaurants
  • Behind-the-scenes access to local food culture
  • Specialty alcoholic or non-alcoholic pairings
  • A visit to a distinctive culinary shop
  • An educational and delectable experience

Reservations strongly recommended! Contact us for more information.