Living Like a Local on MDs Eastern Shore

You've found the perfect house, now let us help you plan your perfect vacation!  From fabulous food to experiencing bay breezes out on the water, biking and kayaking, shopping or history, there is something for everyone. There are so many different ways to enjoy the Eastern Shore, tell us what you like to do on vacation and we can point you in the right direction!

Boat, Bike, Kayak and Paddle Board Rentals

A visit to MD`s Eastern Shore would not be complete without getting out on the water. Rent a boat, or book one of our popular local charters to experience our more than 600 miles of shoreline. No sea legs? No problem! There are many places to rent bicycles for meandering along our top rated scenic bike trails.

Grocery Stores

Of course, 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, or, with advance notice, ESVR will deliver. Arrive to your vacation home with kitchen stocked and ready to go! $50 delivery fee ($75 for Cambridge, Chestertown and Tilghman) for first $100, then 25% over $100. Seven day advance notice required for arriving guests, 24 hour notice for in property guests. Contact us for more information at [email protected]

Kid Friendly Fun

Got kids? There are lots of family friendly activities to entertain kids of all ages!


It`s all about the food! Here are some of our suggestions to soak up some unique local flavor.

You, the Artist

Discover why artists come from all over the world to showcase their art and be inspired to create. Whether taking in a gallery or museum, shopping for local artisan jewelry and other handmade items, or enjoying a show at our classic Avalon Theatre, there`s plenty to nurture your creative side!

You, The Sportsman

The Eastern Shore of Maryland has a longstanding tradition of outdoor sporting. Whether you are interested in hunting, fishing or crabbing, we can help you find the resources you need to enjoy the wild side of the Eastern Shore!

You, on the Water

Spend an afternoon taking in our area`s most popular water attractions from our seasoned tour guides.

You, and your Dog

The Eastern Shore is very pet friendly! Here are some fun things to do with your best friend while staying in the area.

Farmer`s Markets

From April to October, you will want to be sure and check out our Farmer`s Markets in Easton, St. Michaels and Oxford, or stop by one of many local fruit and vegetable stands.

Wine, Beer and Spirits

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

Fresh Local Seafood

You may want to try your hand at crabbing while visiting, but for a quick and easy crab feast, here are some local vendors to pick up a hot bushel of #1`s!

Coffee, Ice Cream and 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!

Golf Anyone?

Maryland`s Eastern Shore is home to several excellent public courses, ranging from nationally top rated to scenic waterfront courses to satisfy any golf enthusiast.


Our area is rich in history and tradition. Be sure to spend some time at our museums to learn about Eastern Shore Heritage.

Local Parks and Playgrounds

While the Eastern Shore does offer plenty of room to roam and stretch out, little ones will love our local playgrounds, many with nautical themes and interactive educational experiences.