Holiday Wine Bottles for an East Coast Holiday

A Magical Eastern Shore Holiday Season

With the holiday season right around the corner, it’s the perfect time to plan a little R&R into your busy schedule for a mid-season pick-me-up for this year’s festivities. Great Oak Manor on the Chesapeake Bay is the perfect destination for a magical East Coast Holiday. Join us at our waterfront Chestertown, Maryland bed and … 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

View from an old, wooden sailing ship

Chestertown Tea Party Festival 2018

In the spring of 1774, when news of the port of Boston’s closing reached Chestertown, the citizens met to determine what actions should be taken in response. They forth a list of grievances, which became known as the Chestertown Resolves, which made it unlawful to buy, sell or drink tea that came from England. According … Read More

Why You Need to Visit Maryland’s Eastern Shore after the Holidays

The holidays are over. The past few weeks were spent decorating the tree, baking cookies, squinting at the computer screen as you searched Amazon or Wayfair for the perfect gifts, reminding your (grand)children that Santa is watching them, shopping for holiday food, gift wrap, and other supplies, and wrapping an endless pile of presents. The … Read More

Holiday Shopping in and around Chestertown

The holidays are here again… and you know what that means! Shopping! Don’t strain your eyes pouring over websites. Avoid the stress of the malls and shopping centers. Instead, support local vendors and give your friends and family unique, heartfelt gifts from Chestertown. Here are some of our favorite shops in and around Chestertown: Bloomin’ … Read More

Celebrate the 2017 Holidays at Great Oak Manor

Holidays can often be stressful affairs between the gift giving, cooking, and cleaning. Why not treat yourself to a break this season and spend Thanksgiving or Christmas on Maryland’s Eastern Shore. Imagine waking up in the morning knowing you don’t have to cook and enjoying all the holiday splendor the Chesapeake Bay has to offer. … Read More

Fun Facts about Labor Day

Did you know… Labor Day celebrates the contributions of the millions of men and women in the US workforce. The first US Labor Day was planned by the Central Labor Union and held September 5, 1882 in New York City. On this day, nearly 10,000 workers took unpaid leave and marched from City Hall and … Read More

Festivities & Fireworks to Ring in the 4th of July

There is no better place to spend 4th of July weekend than the beautiful Chesapeake Bay. Whether you’re looking to relax by the waterfront with a good book, explore the bay and shoreline in a kayak or canoe, or watch spectacular firework displays, your awesome adventure starts at Great Oak Manor.   This year, Kent County … Read More