Close
1902
The Oaks Waterfront Hotel
Easton, Maryland
The Oaks Waterfront Hotel
25876 Royal Oak Rd, Easton, Maryland 21601 Original Property Opened in 1902 Historic Hotels of America member since 2025The Oaks Waterfront Hotel's property is steeped in American history, with the land initially being granted by Lord Baltimore. This history has included service as a spacious farm, a setting for a Hollywood film, and a successful resort. Guests can enjoy time on the water, trips to local nature preserves, and calmer moments by the hotel's pool. They can relax in our luxury hotel in Easton, MD, dine in the elegant Oak Room and stage beautiful, memorable events.
Discover
- Uncover the hotel's role as a setting for one of the last films in Hollywood's Silent Era. In 1928, the estate hosted Gary Cooper and King Kong star Faye Wren while they shot The First Kiss.
- Take in the manor's Neoclassical architecture, including Greco-Roman influences like the columned façade topped with ornate capitals.
- Explore the hotel's history as a family estate and homestead dating back to colonial times. The initial land grant was signed by Lord Baltimore and the manor grew to include many working farm buildings before becoming a resort retreat.
Explore
- Learn more about Chesapeake Bay history through visits to the Chesapeake Bay Maritime Museum and Hooper Strait Lighthouse, which was constructed in 1879. Guests can expect interactive exhibits and historical artifacts.
- Visit local galleries and museums, including the Academy Art Museum, and appreciate local art, past and present, and enjoy unique events including concerts and lectures.
- Enjoy the unique flora and fauna of the Eastern Shore at Pickering Creek Audubon Center. This preserve features trails with dramatic views of a variety of habitats and interpretative exhibits. Also, the area hosts an annual waterfowl festival to further celebrate its conservation efforts and culture.
Experience
- Enjoy time spent on the water of Chesapeake Bay, one of America's most storied waterways. Guests can charter Grateful Miles, the hotel's private, 40-foot Hinckley picnic boat, or rent kayaks and paddleboards, all departing from a private dock.
- Relax around the hotel, enjoy dips in the saltwater pool, evenings enjoying bay views from the firepit, or touring the area on complimentary bikes.
- Shop or dine in the local resort communities of Easton and St. Michaels, some of the most welcoming retreats in the Mid-Atlantic. Complimentary shuttles are available and can be arranged at the front desk.
Taste
- Savor elegant dishes and an extensive wine list in the Oak Room, the hotel's chic bar and lounge. Diners can enjoy gourmet takes on favorite local ingredients in a bright room with welcoming accents.
- Dine out at delicious local restaurants on the Eastern Shore. Tastes range from classically prepared fine dining at nearby Bistro St. Michaels to trendy bars, pizzerias, and trademark Maryland crab shacks.
- Sample local wines, rums and brews at nearby vineyards and distilleries. Hotel staff can help guests arrange tours and tastings throughout the area.
