St. Michaels Holidays

Explore maritime heritage at this waterfront museum featuring the historic Hooper Strait Lighthouse and indigenous Chesapeake Bay watercraft. Watch shipwrights craft vessels while enjoying Miles River views.

Explore the waterfront in St. Michaels with a trip to St. Michaels Marina.

This historic waterfront town showcases Maryland's maritime heritage through preserved colonial architecture. Explore the Maritime Museum or enjoy fresh seafood while watching sailboats glide across the harbour.

Sample the Eastern Shore's finest wines in this historic Old Mill District winery. Enjoy guided tastings of 18 handcrafted varieties while learning about Maryland's unique terroir.

This 9.5-acre community space offers well-maintained sports fields and a playground for active recreation. Enjoy a peaceful picnic in the pavilion or join a local baseball game in this serene St. Michaels gathering spot.

This rare screwpile lighthouse, relocated from Chesapeake Bay, offers a glimpse into 19th-century maritime life. Climb the spiral staircase to the lantern room for sweeping bay views and authentic keeper's quarters.

Step into three restored 19th-century buildings that reveal the rich history of this Chesapeake Bay town. Explore exhibits on Frederick Douglass's local connections through walking tours of historic St. Michaels.

Located in the St. Michaels Historic District, this town hall adds charm to the area's preserved 19th-century architecture. Explore the surrounding brick pavements while discovering the town's rich maritime heritage.