Young Couple Biking in the sunshine

Adventures by Land and Water in Maryland

Our magnificent country estate on Maryland’s Eastern Shore offers stunning views of the Chesapeake Bay and is located minutes away from Chestertown. Be as active as you’d like, or simply relax – the options are plentiful. If you’d like a little adventure, read on to learn about some of our favorite outdoor activities – on land … Read More

Romantic couple about to kiss by the water at sunset

Romance on the Eastern Shore

The Perfect 3 Days Away Whether you’re celebrating a honeymoon, anniversary, birthday, or simply being in love, Chesapeake Bay is an ideal destination for romance, and Great Oak Manor is the perfect setting for your special occasion. Want to get away with your one and only? All you have to do is select your favorite … Read More

Blue crab in the sand

Tastiest Catch – Crabbing on the Eastern Shore

The Chesapeake Bay is the largest estuary in the United States, with over 3,600 species of plants and animals. Although it is home to many creatures, the Bay’s signature crustacean is the blue crab – the pride and joy of the Chesapeake coastline. Its scientific name is Callinectes sapidus, which means “savory, beautiful swimmer,” but … Read More

Ocean sunset

Summer Festivals on the Chesapeake Bay

  Summers on Maryland’s Eastern Shore offer plenty of fun for everyone. Kent County, in particular, has planned a variety of events this summer that will delight the young and old. Here’s a list of what’s coming up soon: Music in the Park June 23, July 7 & 21, and August 4 & 18 Grab … Read More

Fireworks on the 4th of July

Fourth of July Festivities on the Eastern Shore

It’s not often that Independence Day celebrations last all week, but that’s the case this year in Kent County, Maryland! Spend an entire week at Great Oak Manor on the Chesapeake Bay to enjoy THREE nights of fireworks and other fun festivities throughout the County. Start your week in Rock Hall on July 1 to … Read More

Person in a chair on the beach with a kayak

Summertime Fun at Great Oak Manor

Great Oak Manor is gearing up for summer 2018 and we know it’s going to be the best summer yet! Here are some of our favorite fun summertime activities for kids of all ages! Go fishing. Fishing on the Eastern Shore is permitted from banks and certain public landings. There are also fishing charters that … Read More

Mother's Day gift and flowers

Mother’s Day on the Bay

Mom does it all for us – from packing lunches to homework to help to watching our own babies when we need a night out. Mother’s Day is the perfect opportunity to show mom just how much you care for her and appreciate all she does for you. This year, let her escape to Maryland’s … Read More

Couple and their dog watching the sunset over the water

A Letter from the Innkeepers – April 2018

  Spring is here – well, almost here. This time last year we were just settling in and rushing around to make spring happen. This year we are super excited about some wonderful changes that are taking place around here. Richard has been working all winter on the inside of the Manor, painting and sprucing … Read More