Essential Chestertown and Environs

DAY ONE

Morning

Sleep late and enjoy a famously fabulous breakfast in the dining room or if you prefer and weather permitting on the front porch.

If you are golfers you may use our membership at the Chester River Yacht and Country Club and play a round of golf. Our golf package is very reasonable and you won't need a tee time!

If golf is not your thing check out the eclectic shops, galleries and antique shops on Cross and High Street in Chestertown.

Don’t miss Twigs and Teacups.

Afternoon

Get a delicious lunch from Herb's on your way to town and take it to the end of High Street, sit on a bench and enjoy the view of The Chester River.

After lunch, enjoy the Chestertown Architectural Tour with over 65 points of interest. Our favorite building is Whidehall at the foot of High Street.

Break up the walk by relaxing in Fountain Park or grab a cup of coffee at our best java shop, the funky Play it Again Sam.

Head back to the Inn for a Cheese and Fruit Platter on the spectacular Brampton front porch or by the wood-burning fire depending on the season.

Enjoy classic Eastern Shore Cuisine, featuring fresh local ingredients at Brooks Tavern. Enjoy an after dinner stroll by the Chester River and watch the moon rise.

DAY TWO

Morning

After breakfast, ask Danielle or Michael for a quick architectural tour of Brampton, including a peek at the belvedere, with views all around. Learn about the amazing transformation and restoration of this property.

Pick up your Brampton Picnic lunch (please order 24 hours in advance) from the Innkeeper. Borrow a pair of binoculars from the inn and head out towards Rock Hall. On your way, drive through Chesapeake Farms. After you reach Rock Hall, go out to Eastern Neck Wildlife Refuge. Take the driving tour and spend some time on the trails looking for Osprey, Bald Eagles and unusual varieties of ducks.

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Enjoy an invigorating outing on the Chesapeake Bay in one of the Brampton kayaks docked at Rock Hall Yacht Club.

Afternoon

Enjoy the picnic lunch on the water. Drive back to Rock Hall and get a taste of Ice Cream at Durding’s. It’s sooooooooooo gooooooooooooood.

Visit St. Paul’s Chapel and cemetery on the way back from Rock Hall and pay respects to the film legend, Tallulah Bankhead. Yes, dahlings!

If it happens to be the First Friday of the month return to Chestertown after your visit to Rock Hall, check out the gallery openings and music in Chestertown.

Enjoy a romantic dinner at Blue Heron Cafe in downtown Chestertown. Danielle's favorite recommendation is the Oyster Fritters as an appetizer and Crab Cakes as an entree. Awesome.

DAY THREE

Morning

If it’s Wednesday and the sun is shining rise a bit earlier and head out to Crumpton after breakfast. Dixon's Auction in Crumpton is the best-kept secret for Antique Dealers, Treasure Hunters and Discriminating Yard Sale Experts alike. Think of all the beautiful stuff with great potential awaiting your expert eyes........!!!

For sustenance consider lunch at the Amish Restaurant before continuing your quest for that perfect treasure.

Head back to the inn to prop your feet up and enjoy a nice cool glass of iced tea or lemonade and cookies on the front porch.

Afternoon

Cool off at the pool of the Chester River Yacht and Country Club. For dinner consider the very casual Fish Whistle located on the Chester River in Chestertown.