Waterfront Wonders of Maryland’s Eastern Shore Itinerary

Days 1 & 2: Discover the historic and colonial town of Chestertown

Day 1: Explore the Heart of Chestertown

Morning:

• Historic District Stroll: Begin your day with a leisurely walk through Chestertown's well-preserved historic district. Admire the colonial-era buildings, pop into charming shops, and explore art galleries and local boutiques.

Lunch:

• The Kitchen at the Imperial Hotel: Savor a delightful lunch at this historic hotel, known for its fresh, locally sourced ingredients and inviting atmosphere.

Dinner:

• Chester River Packet Dinner Cruise: Embark on a scenic dinner cruise along the Chester River. Relax as you glide through the water, enjoying a delicious meal while taking in the serene views.

Evening:

• Garfield Theatre: Cap off your day with a live performance at the Garfield Theatre, a community-focused arts center. Whether it’s a play, concert, or special event, you're in for an unforgettable experience.

Stay:

• Brampton 1860

Brampton 1860

Day 2: Sip, Stroll, & Savor

Morning:

• Crow Vineyard: Start your day with a visit to Crow Vineyard, where you can sample a variety of wines. Learn about the winemaking process and enjoy the picturesque surroundings.

Afternoon:

• Waterfront Stroll: Take a peaceful walk along Chestertown’s waterfront. The serene views and gentle breezes make it the perfect spot for reflection or a casual stroll.

Late Afternoon:

• The Retriever: Head to The Retriever for drinks and a taste of local oysters. This spot offers a cozy atmosphere, making it a great place to unwind and enjoy local flavors.

Dinner:

• Watershed Alley: End your stay in Chestertown with dinner at Watershed Alley, a local favorite known for its creative menu and farm-to-table offerings.

Stay:

• Brampton 1860

Days 3 & 4: Explore the quaint coastal town of Rock Hall

Day 3: Nature & Seafood Delights

Morning:

• Eastern Neck Wildlife Refuge: Begin your day at this beautiful refuge, where you can hike trails, birdwatch, or fish. The diversity of wildlife and scenic views make it a nature lover's paradise.

Lunch:

• Waterman's Crab House or Harbor Shack: Savor fresh Maryland seafood at one of these local spots. Indulge in the state’s famous crabs while enjoying waterfront views.

Afternoon:

• Ferry Park Beach: Spend a relaxing afternoon at Ferry Park Beach. Whether you want to swim, have a picnic, or simply lounge on the sand, the views of Chesapeake Bay are sure to delight.

Stay:

• Inn at Huntingfield Creek

Inn at Huntingfield Creek

Day 4: Beachside Bliss & Farewell

Morning:

• Tolchester Marina: Enjoy your final morning with an iconic Maryland orange crush at Tolchester Marina’s beach bar. Sip your refreshing drink as you take in the stunning views of the Chesapeake Bay.