Enjoy the perfect blend of luxury and comfort at The Oaks, your home away from home. Featuring 7 suites, chef-inspired breakfast, and wine and charcuterie upon arrival, this is the perfect stay for families, professionals, or a romantic getaway.

Our family-owned winery began with a simple love for wine and the land it grows from. Today, nestled in Cooksville, Maryland, we continue that journey—growing grapes with care, crafting wines with character, and sharing them with people like you!

Lodging, Event Venue

Adventure Smith Island at 3 Knots Marine of Smith Island offers charters, boat and kayak tours, and rentals for anyone wishing to explore our amazing Smith Island, MD. We also offer transient slip spaces with a bath house for visiting mariners.

A local history organization dedicated to Kent County with a museum, shop, research library and archive located in the heart of historic Chestertown.

Looking for a Maryland Getaway? Discover Fleur De Montagna in Deep Creek, MD. This beautiful appointed property is the perfect blend of architecture and nature - more than a stay; its an experience!

A seafood restaurant serving locally sourced seafood. We are located in a quaint fishing village that was once the school house for the island children.

The Oxford Museum preserves and celebrates the town of Oxford’s rich history and its continuing role in the life of the region. By documenting and sharing what makes the community such a unique place to live, work or visit.

Simpatico specializes in exclusively Made in Italy wines, foods, ceramics, gifts, and more: you will feel like you're in Italy. We also offer take out meals from our Trattoria, wine and food events, and cooking classes. Free wine tasting every day.