Discover Stevensville, Maryland

Founded & Early Settlement (1600s–1800s)
Stevensville traces its roots to Kent Island, first settled in 1631 by English colonists under William Claiborne, making it one of the earliest English settlements in Maryland. The town itself was formally established in 1850 and named after Philip Stevens, son of Maryland Governor Philip Francis Thomas. Its location along the Chesapeake Bay positioned it as an early center for agriculture, trade, and maritime activity.

Steamboat Era & Regional Gateway (1800s–Early 1900s)
During the 19th century, Stevensville grew as a busy steamboat port, linking the Eastern Shore to Annapolis and Baltimore. Farmers and watermen used the harbor to transport oysters, crabs, and crops, while travelers relied on ferry and steamboat routes that made the town a key transportation hub across the bay.

Transportation Shifts & Bridge Era (1930s–1960s)
The rise of automobile travel and the opening of the Chesapeake Bay Bridge in 1952 dramatically changed Stevensville’s role. No longer dependent on ferries, the town evolved from a maritime transfer point into a gateway community connecting Maryland’s Western and Eastern Shores.

Suburban Growth & Preservation (1970s–2000s)
As Kent Island developed, Stevensville experienced residential and commercial growth while preserving its historic character. Efforts to protect the Stevensville Historic District helped maintain landmarks like the old train station, post office, and early churches that reflect the town’s colonial and maritime heritage.

Modern Era & Coastal Community (2000s–Present)
Today, Stevensville blends historic charm with modern coastal living. Its proximity to Annapolis and the Chesapeake Bay Bridge has made it a desirable commuter town while retaining its small-town feel, waterfront culture, and ties to Maryland’s Eastern Shore traditions.

Today
Modern Stevensville offers a mix of preserved colonial-era landmarks, marinas, and local shops, maintaining its identity as Kent Island’s historic heart and a welcoming gateway to Maryland’s Eastern Shore.

1. Walk the Stevensville Historic District – The heart of town with preserved colonial buildings, charming streets, and local shops reflecting Kent Island’s heritage.

2. Visit Terrapin Nature Park – Scenic waterfront park with walking trails, sandy shoreline, and some of the best Chesapeake Bay Bridge views.

3. Relax at Matapeake Beach – A peaceful bayfront spot for swimming, picnicking, and watching stunning sunsets over the water.

4. Explore the Chesapeake Heritage & Visitor Center – Learn about Kent Island’s maritime history, ecology, and local culture through exhibits and events.

5. Bike or Walk the Cross Island Trail – A paved multi-use trail stretching across Kent Island, perfect for biking, jogging, and enjoying coastal scenery.

6. Dine at Kent Narrows Waterfront – Just minutes away, this area offers top seafood restaurants, marinas, and lively waterfront views.

7. Go Boating or Charter Fishing – Stevensville’s marinas make it a prime launch point for fishing charters, crabbing, and Chesapeake Bay cruising.

8. Visit Matapeake Clubhouse & Beach Area – Historic clubhouse grounds with picnic areas, dog beach access, and panoramic bay views.

9. Enjoy Local Wineries & Breweries – Nearby vineyards and craft breweries provide relaxed tastings with a laid-back Eastern Shore vibe.

10. Drive the Chesapeake Bay Bridge Scenic Route – A must-do experience offering dramatic views of the bay while connecting Kent Island to Annapolis and the Western Shore.

Chesapeake Bay Bridge

1. Libbey’s Coastal Kitchen & Cocktails – Upscale coastal dining with craft cocktails, fresh seafood, and a stylish waterfront vibe.
Located at 357 Pier 1 Rd, Stevensville, MD 21666.

2. Knoxie’s Table – Hidden inside the Inn at Chesapeake Bay Beach Club, serving refined American fare and elevated cocktails.
Located at 180 Pier One Rd, Stevensville, MD 21666.

3. Cult Classic Brewing – Local favorite brewery with creative small plates, live music, and a laid-back bar atmosphere.
Located at 1169 Shopping Center Rd, Stevensville, MD 21666.

4. The Kentmorr Restaurant & Crab House – Classic Eastern Shore crab house with bay views, steamed crabs, and casual bar seating.
Located at 910 Kentmorr Rd, Stevensville, MD 21666.

5. The Narrows Restaurant – Longtime waterfront staple known for seafood platters, raw bar options, and sunset views over Kent Narrows.
Located at 3023 Kent Narrow Way S, Grasonville, MD 21638.

6. Harris Crab House – Local go-to for steamed crabs, cold beer, and authentic Chesapeake Bay seafood experience.
Located at 433 Kent Narrow Way N, Grasonville, MD 21638.

7. Fisherman’s Crab Deck – Relaxed open-air deck with crabs, crushes, and unbeatable marina views, especially in summer.
Located at 3032 Kent Narrow Way S, Grasonville, MD 21638.

8. The Jetty – Waterfront tiki-style bar and restaurant popular for live music, frozen drinks, and casual seafood bites.
Located at 201 Wells Cove Rd, Grasonville, MD 21638.

9. Bridges Restaurant – Hidden gem fine dining spot overlooking the marina, offering seafood, steaks, and craft cocktails.
Located at 321 Wells Cove Rd, Grasonville, MD 21638.

10. Big Owl Tiki Bar – Seasonal tiki bar with a fun island vibe, rum drinks, and live entertainment right on the water.
Located at 216 Wells Cove Rd, Grasonville, MD 21638.

Libby's Coastal Kitchen

Cult Classic Brewing