The Ultimate Eastern Shore Weekend: A 3-Day Itinerary

When you stay at The River, you are perfectly positioned to experience the best of Maryland’s historic waterfront, gourmet dining, and coastal nature. We’ve designed this curated weekend itinerary to help you make the absolute most of your luxurious home base.

Day 1: Arrival & Historic Downtown Vibe

Afternoon: Settle Into Luxury

Arrive at The River and take a moment to unpack and explore your 1,796 sq. ft. coastal retreat. Pour a refreshing drink, step out onto one of our three private outdoor living areas, and let the crisp Choptank waterfront breeze officially signal the start of your vacation.

Evening: A Stroll Down High Street & Local Brews

Charming Historic Walks: Walk right out your front door and take a late afternoon stroll down Cambridge’s historic High Street. Marvel at the beautifully preserved 18th and 19th-century architecture that leads straight to Long Wharf Park.

RAR Brewing 4.6

Opens 11:00 AM

Dinner & Drinks at: For a relaxed, incredibly vibrant first night, walk over to the popular local mainstay, RAR Brewing. Reviewers frequently rave about their creative, rotating craft beers on tap and excellent, high-quality pub fare. It’s the perfect way to soak in the local Cambridge flavor.

Day 2: Wildlife Trails & Coastal Day-Tripping

Morning: Fuel Up & Explore the Wild

Black Water Bakery + Eats

4.5

Closes 3:00 PM

Breakfast: Start your day with a short walk to Black Water Bakery + Eats. Visitors consistently praise this bustling spot for its market-fresh breakfast options, scratch-made pastries, and specialty coffees.

Blackwater National Wildlife Refuge

5.0

Wildlife refuge

Discover: Drive just a few minutes south to explore this stunning, expansive wildlife sanctuary. Known as a haven for bald eagles and migratory waterfowl, you can experience it comfortably via the scenic Wildlife Drive or by walking the peaceful marsh trails.

Afternoon: A Picturesque Escape to St. Michaels

Scenic Coastal Drive: Take a beautiful 35-minute drive northwest through the Eastern Shore countryside to the historic maritime town of St. Michaels.

Bistro St. Michaels

4.7

Bistro

An Unforgettable Lunch: Book a table at Bistro. This highly regarded New American establishment offers a market-fresh menu in an incredibly romantic, upscale setting. Guests highly recommend their sophisticated dishes and boutique wine list for an indulgent afternoon meal.

Boutique Shopping: Spend the rest of the afternoon wandering the charming shops, antique galleries, and scenic docks along Talbot Street before heading back to Cambridge.

Evening: Golden Hour at The River

Return to the property to host your own sunset happy hour. Utilize the fully stocked chef’s kitchen to put together a gourmet charcuterie board, open a bottle of wine, and watch the boats head in for the evening from your private deck.

Day 3: Lazy Mornings & Waterfront Fare

Morning: Coffee on the Deck

Sleep in and enjoy the morning sun filtering through the expansive windows. Take your time brewing a fresh pot of coffee and relaxing on the outdoor furniture, soaking in the peace and quiet of your luxury home away from home.

Afternoon: Maritime History & Departure

Before checking out, walk down to Long Wharf Park to snap some photos of the iconic Choptank River Lighthouse. Grab a casual waterfront lunch at a local crab shack, pick up a few unique souvenirs from the downtown boutiques, and begin planning your return trip to The River.