Chestertown Taste of the Town

Chestertown’s Taste of the Town Coming In May Chestertown Taste of the Town will be back for its 11th year on Sunday, May 7, 2017. It’s a cornucopia of earthly restaurant delights, and you don’t want to miss it! Restaurants from Kent County’s finest dining establishments feature a sampling of their signature dishes. From classic … Read More

Celebrating Art and Conservation in Chestertown

With Spring as the advent, April is the month of renewal and re-birth. So it’s fitting that April is the time Chestertown’s RiverArts celebrates each April by hosting the The Art of Stewardship Exhibition. Artists and poets are invited to submit work that was inspired by nature through inspiration or reflection with the theme “Convergence … Read More

Winter Events at Great Oak Manor

Winter is upon us, and you may be feeling all of your daylight hours are wasting away in the office.  While it can be tempting to spend those chilly weekends huddled up at home watching Netflix (hey, we’ve all been there), why not do something different with your precious weekend time? Studies show that vacations, … Read More

The Holidays in Chestertown

Chestertown is a picturesque microcosm of all the Eastern Shore has to offer.  Historical, cultural, and quaintly distinct all year, Chestertown is beyond festive during the Holiday season.  Whether you already made plans to visit us during the next month, or you are scoping out a place to head off to this weekend, here are a … Read More

Give the Gift of a Great Oak Manor Gift Certificate

The gift giving season is incredible.  It’s a time to reconnect with friends and family, showering them with heartfelt, thoughtful, and personal tokens.  But, let’s face it; the gift giving season can also be incredibly stressful.  What do you get your in-laws?  Or your boss?  What about the friend who has everything and wants nothing?  … Read More

A Very Veggie Vacation: Vegetarian Cuisine in Chestertown, MD

Did you know that Great Oak Manor accommodates a number of dietary restrictions? Let us know if you’re dairy-free, gluten-free, meat-free, or all of the above, and we’ll prepare a tasty meal free that suits your palate and your lifestyle. Furthermore, there are a number of local eateries who also cater to the meat-free, so … Read More

3 Aspects of a Day in the Life of a Great Oak Guest

With the holiday season upon, this may be your last chance to enjoy a 2016 vacation before the seasonal chaos sets in! You may be wondering a bit about the Great Oak Manor experience and what you’ll see and do here in Chestertown, Maryland. We decided to break it down into 3 important aspects that … Read More

Fall Fun in Chestertown, Maryland

Revised 8/17 – Fall will be here soon, which is beautiful on the Eastern Shore of Maryland. If you’re planning a trip to Great Oak Manor in the coming weeks, then you may enjoy immersing yourself in these fun fall activities, including everything from “spooktacular” historic ghost walks to fall foliage photography opportunities along local … Read More