Your Guide to the Best Golf Courses on the Eastern Shore of Maryland

Those who are familiar with the Eastern Shore of Maryland know that there are countless reasons to pay a visit. The food is spectacular, the people are friendly, and there are plenty of charming historic sites. Our little corner of the Mid-Atlantic is even home to some pretty remarkable golfing spots! If you’d like a little tee time during your getaway, we recommend checking out one of these fantastic golf courses on the Eastern Shore of Maryland

3 of the Best Golf Courses on the Eastern Shore of Maryland

The Chester River Yacht and Country Club

Should you belong to a country club in your hometown use your reciprocal membership to play a round at this private course, then, if the weather is warm, go for a swim in the pool! The fairways here are tight and the greens small, albeit with great views. However you choose to use your time at The Chester River Yacht and Country Club, you’ll enjoy a relaxing experience.

Queenstown Harbor

You’ll discover a beautiful and fun place to play golf at Queenstown Harbor, just 30 minutes southwest of Brampton Inn. There are two public courses available at Queenstown—the moderately difficult Lakes Course and the more approachable River Course. The Lakes Course at Queenstown Harbor has even been ranked several times as one of the best courses for women! The waterfront River Course isn’t excluded from accolades, though. It has consistently been named one of the best places for golf in the Maryland and D.C. areas!

Great Oak Club and Golf Course

The course at Great Oak Club in Chestertown is another fantastic option for a round or two! The 9-hole, 60-par Great Oak Landing Marina course offers a challenging 3,244 yards of golf with exceptional marina views. Both beginners and advanced golfers alike will love this course’s well-groomed fairways and greens! The friendly staff may even provide their best tips and tricks for playing your best round.

Stay Near the Best Golf Courses on the Eastern Shore of Maryland!Mulberry Cottage Living Room

After bringing your A-game at one of Eastern Maryland’s best golf courses, you’ll need a comfortable and welcoming place to stay. In the heart of the countryside but less than two miles away from historic Chestertown, Maryland, you’ll find Brampton Inn. Our family-owned inn offers an incredible experience that begins the moment you arrive! As a member of Select Registry, our inn features unique amenities like wood-burning fireplaces, a grand front porch, and 20 acres of pastoral beauty. Our large and elegant Manor House is also listed on the National Register of Historic Places, so a visit to Brampton is a step back in time. Each of our bright and airy suites and cottages is appointed with guest comfort in mind. Isn’t it time you experienced Brampton Inn for yourself?

For a getaway (and round of golf) you’ll never forget, check our availability today! We can’t wait to welcome you to historic Chestertown and beautiful Brampton Inn.

Dine in Style! 

If you are looking for a unique dining experience, we have two amazing dining-series this season!

Check out Dining Under the Stars with Chef Kurt Peter starting May 2!


Gourmet Diner Club with chef Jordan Lloyd starting May 23!

Dining and entertainment experiences to remember! See our Specials page.

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