Major holidays can serve as the perfect excuse to enjoy a rejuvenating getaway, and Thanksgiving is no different! There’s no better way to spend Turkey Day than surrounded by loved ones in historic Chestertown, Maryland. Though gratitude and family festivities are both important parts of this autumn holiday, we can’t pretend that food doesn’t play a pretty big role. We’ve listed a few of the ways to eat your way through an Eastern Shore Thanksgiving this year. For more of our handpicked food and seasonal event recommendations, be sure to request access to our free Eastern Shore Travel Guide!
Where to Enjoy an Eastern Shore Thanksgiving Dinner
If an elegant and special Thanksgiving dinner is what you seek, the waterfront restaurant at Osprey Point is a good place to host your afternoon festivities. Located in Rock Hall (12 miles southwest of Brampton Inn), this restaurant near Chestertown serves a turkey-centric meal supplemented by plenty of sides.
The Kitty Knight House
A great Eastern Shore Thanksgiving dinner spot is The Kitty Knight House. This historic restaurant, bar, and inn is located 12 miles northeast of Brampton Inn and historically serves a Thanksgiving buffet. During your holiday feast here, expect traditional turkey, prime rib, ham, and salmon.
Imagine retiring to a comfortable room. There, a crackling fireplace is waiting just for you. Cooking, cleaning, and hosting can wear you down, and the holiday season is all about enjoying each another’s company. Let go of your stress and book a stay where you and yours can sit back, relax, and enjoy premium amenities found nowhere else. The only thing you’ll need to worry about it choosing between our bright, airy guest rooms and spacious, comfortable cottages!