Shady Side, Maryland
A Memorable Weekend Getaway in Shady Side, Maryland
Welcome to Shady Side, a hidden gem on the Chesapeake Bay! This charming waterfront town is the perfect destination for a relaxing three-day weekend trip with friends. With its picturesque landscapes, rich history, and delectable seafood, you’ll surely fall in love with this tranquil oasis. Let’s dive into an exciting itinerary that will help you make the most of your visit to Shady Side!
Day 1: Exploring Shady Side’s Natural Beauty
Morning:
Start your day with a rejuvenating walk along Franklin Point State Park. This hidden paradise offers breathtaking views of the Chesapeake Bay and is home to diverse ecosystems. Explore the park’s pristine beaches, hike its nature trails, and keep an eye out for the abundant wildlife that calls this area home.
Afternoon:
For lunch, head to Pirates Cove Restaurant, a local favorite renowned for its fresh seafood and stunning waterfront views. Indulge in mouthwatering dishes like crab cakes, fried oysters, or their famous shrimp salad. The casual atmosphere and friendly service make it the perfect spot to relax and enjoy the coastal vibes.
Afterward, embark on a scenic kayak tour with South River Boat Rentals. Paddle through the serene waters of the South River, surrounded by lush greenery and picturesque landscapes. This guided tour allows you to immerse yourself in nature while learning about the area’s history and wildlife from knowledgeable locals.
Evening:
As the sun sets, make your way to the Captain Avery Museum. Housed in a beautifully restored historic home, this museum offers a fascinating glimpse into Shady Side’s maritime heritage. Explore the exhibits showcasing local artifacts and learn about the region’s fishing, oystering, and boatbuilding traditions. Don’t miss the panoramic views of the bay from the museum’s observation deck—it’s a perfect spot to capture memorable sunset photos.
For a delightful dinner experience, visit the famous Skipper’s Pier. This waterfront restaurant serves up an array of seafood options, from steamed crabs to lobster mac and cheese, all made with the freshest ingredients. Savor your meal while enjoying the gentle breeze and panoramic views of the Chesapeake Bay. Cap off the night with a leisurely stroll along the pier, taking in the beauty of the shimmering waterfront under the starry sky.
Day 2: History, Art, and Local Flavors
Morning:
Immerse yourself in Shady Side’s rich history by visiting the Captain Salem Avery House Museum. This 19th-century home-turned-museum offers a captivating look into the lives of local watermen and their families. Explore the meticulously restored rooms, filled with period furnishings and artifacts, and learn about the challenges and triumphs of those who shaped Shady Side’s past.
Afternoon:
For lunch, head to the charming Wooded Inn Bar & Grill. Known for its cozy atmosphere and friendly staff, this local eatery offers a range of delicious comfort food options. Treat yourself to their famous crab melt or juicy burger, accompanied by a cold craft beer or refreshing cocktail.
Afterward, venture to Galesville Heritage Museum to discover the region’s African American maritime history. This small but impactful museum showcases the contributions of African Americans to the local seafood industry, shipbuilding, and the overall community. Engage with interactive exhibits, personal stories, and historical photographs that shed light on this often overlooked aspect of Chesapeake Bay’s heritage.
Evening:
For an evening filled with art and entertainment, visit the West River Artists Gallery. This cooperative art gallery features stunning works by local artists, including paintings, pottery, sculptures, and more. Take your time to browse the diverse collection and appreciate the talent that thrives in Shady Side. If you’re lucky, you might even catch an artist at work or attend one of the gallery’s engaging events.
To satisfy your taste buds, dine at Christopher’s Fine Foods. This cozy restaurant offers a refined yet relaxed atmosphere, complemented by a menu featuring seasonal dishes crafted with locally sourced ingredients. Whether you opt for the mouthwatering grilled rockfish or the savory mushroom risotto, each bite is a celebration of Chesapeake Bay’s culinary excellence.
Day 3: Sun, Sand, and Seafood
Morning:
Spend your final day in Shady Side soaking up the sun at the serene Beverly Triton Nature Park. This hidden coastal gem boasts two miles of secluded beaches, perfect for a morning stroll or a picnic with friends. Take in the breathtaking views of the bay, search for seashells along the shore, or simply relax in the peaceful surroundings.
Afternoon:
For a delightful lunch, make your way to the cozy Umai Sushi House. This charming eatery surprises visitors with its exceptional sushi rolls and authentic Japanese cuisine. From classic favorites like the California roll to unique creations bursting with flavor, Umai Sushi House is a must-visit for sushi enthusiasts.
Afterward, head to the nearby Herrington Harbour South Marina to embark on a memorable sailing adventure. Choose from a variety of boat rentals or join a guided tour to explore the Chesapeake Bay’s tranquil waters. Feel the wind in your hair as you glide across the bay, taking in the beauty of the surrounding coastline and enjoying the company of your fellow adventurers.
Evening:
As your weekend trip comes to an end, relish a final dinner at the cozy and welcoming Pirates Cove Restaurant. With its rustic charm and unbeatable waterfront views, it’s the perfect place to reminisce about your Shady Side getaway. Indulge in their famous crab imperial or opt for their mouthwatering filet mignon—the perfect way to conclude your trip on a high note.
Shady Side offers a unique blend of natural beauty, rich history, and delectable seafood that will leave you yearning for more. With its tranquil atmosphere and warm community, this hidden oasis is the ideal destination for a memorable weekend getaway with friends. So pack your bags, embark on this adventure, and let Shady Side captivate your heart.