My Photography & Travel Guide to Saint Michael’s, Maryland

Welcome to Saint Michael’s, Maryland, a picturesque gem tucked away on the Eastern Shore of Chesapeake Bay. Known as the “Town That Fooled the British” during the War of 1812, this charming waterfront destination boasts a rich maritime heritage, quaint streets lined with historic buildings, and stunning waterfront views. Whether you’re a history enthusiast, a seafood lover, or a photographer looking for your next breathtaking shot, Saint Michael’s has something for everyone.

If you live in the Washington DC area, Saint Michael’s is a perfect weekend getaway.

Where to Stay

The heart of Saint Michael’s—and the best area to stay—is the historic downtown and waterfront district. Here are some top-notch accommodations to suit your travel style:

Using My Drone

Luxury Options:

1. Inn at Perry Cabin – A luxurious retreat with waterfront views, lush gardens, and an onsite spa. Perfect for those seeking a serene escape.

2. The Wildset – Boutique charm meets modern elegance at this stylish inn, steps away from the harbor.

3. St. Michaels Harbour Inn, Marina & Spa – Enjoy waterside accommodations, a full-service spa, and an easy walk to local attractions.

Mid-Level Options:

1. George Brooks House B&B – A charming bed and breakfast with a pool and peaceful gardens.

2. Parsonage Inn – A cozy, historic inn offering comfortable rooms and homemade breakfast.

3. St. Michaels Inn – Affordable and friendly, with modern amenities and a convenient location.

How Long to Stay and Best Time to Visit

Plan to spend 2-3 days in Saint Michael’s to fully immerse yourself in its charm. The best time to visit is spring (April to June) and fall (September to November) when the weather is pleasant, and the town’s beauty is at its peak. Summer is ideal for boating and seafood festivals, while winter offers a cozy, quiet retreat.

Getting Around

Saint Michael’s is a walkable town, but bikes are also a fantastic option for exploring the area. Many hotels provide complimentary bike rentals. For longer distances, Uber and Lyft are available, though availability may vary. Having a car is recommended if you plan to explore nearby attractions like Tilghman Island or Easton.

Where to Eat

Saint Michael’s is a culinary delight, especially for seafood enthusiasts. What blew us away when we stayed at the Inn at Perry Cabin was the Canine Menu that they gave us for our sweet Labrador.

Here are some must-visit spots:

1. The Crab Claw – Famous for its steamed Maryland blue crabs and waterfront dining.

2. Bistro St. Michaels – A cozy spot offering farm-to-table cuisine with a creative twist.

3. Foxy’s Harbor Grille – Casual waterside dining with fresh seafood and lively vibes.

4. Limoncello Italian Restaurant & Wine Bar – Delicious Italian dishes with a welcoming atmosphere.

5. Rise Up Coffee Roasters – Start your day with a locally roasted coffee and a pastry.

6. Blue Heron Coffee – A charming coffee shop perfect for a mid-day pick-me-up.

Photography Gear to Bring

1. Camera Body: A versatile camera like the Canon EOS R6 or Sony A7 III.

2. Lenses:

   • Wide-angle lens (16-35mm) for capturing waterfront landscapes and historic streets.

   • Standard zoom lens (24-70mm) for everyday scenes and portraits.

   • Telephoto lens (100-500mm) for wildlife and distant boat shots.

3. Accessories: A sturdy tripod for sunrise and sunset shots, ND filters for long exposure photography, and plenty of memory cards.

Best Photography Locations

1. Chesapeake Bay Maritime Museum (Link) – Capture the iconic Hooper Strait Lighthouse and historic boats.

2. Harborfront – Perfect for golden hour shots with boats silhouetted against the sky.

3. St. Michael’s Nature Trail – A serene path for wildlife and landscape photography.

4. Ava’s Pizzeria & Wine Bar Exterior (Link) – Its colorful facade makes for a charming shot.

5. Tilghman Island (Link) – A short drive away, offering rustic maritime scenes and dramatic sunsets.

6. Saint Michael’s Marina (Link) – A lively spot for vibrant dockside photos.

Special Events and Festivals

• St. Michael’s WineFest (April): A celebration of fine wines and local cuisine.

• St. Michael’s Maritime Day (May): Perfect for capturing traditional boat parades and maritime traditions.

• Watermen’s Appreciation Day (August): A lively event with a crab feast and boat docking contests.

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