Shady Side is a small, tight-knit community on the banks of the Chesapeake Bay in Anne Arundel County, Maryland. Nestled among its picturesque marinas, the rolling hills of South River are home to a vibrant community of boaters, fishermen, and birdwatchers. Whether taking advantage of the views from the beaches, fishing off its piers and docks, or experiencing the rich culture of its shops and restaurants, Shady Side offers a unique and special experience for visitors and locals alike.
1. Shady Side parks and places for a walk on a first date
One of Shady Side’s most attractive features is its many parks and trails. Baker’s Cove Park, with its grassy shoreline, offers wonderful views of the Chesapeake Bay. Take a walk along the pier and watch the boats go by, and then find a spot to sit and admire the view. A visit to Flag Pond Nature Park is perfect for a first date—explore the trails that meander through tall grasses and wetlands, and look out for wildlife like muskrats, great blue herons, and bald eagles. The park is also home to a large pond, home to much aquatic wildlife. For a nature walk on a first date, Sandy Point State Park is a great choice. The park has over 2 miles of trails taking visitors through forests and along the scenic Chesapeake Bay.
2. Places for a coffee date in Shady Side
If you’re looking for a cozy place to share a cup of coffee with your date, you’ll be spoilt for choice in Shady Side. One favorite is the Shady Side Coffee Co. a cozy café with an impressive selection of coffees and teas. If you’re feeling adventuresome, you can even try one of their homemade kombuchas or cold brews. Another popular spot is the Chesapeake Coffeehouse, located right on the bay. Enjoy a cup of their fair trade coffee or a delicious latte while watching the boats go by.
3. Shady Side galleries, museums and exhibitions to visit on a date
Shady Side has an impressive selection of galleries and exhibitions, making it the perfect spot to explore culture on a date. The Shady Side Museum houses a fascinating collection of artifacts from the town's past, from photographs and documents to pottery and tools. For art lovers, there’s the Shady Side Arts Center, which hosts a variety of exhibitions throughout the year. Browse the work of local artists and enjoy a chat about the latest art trends. If it’s a rainy day, the Shady Side History Museum is a great option, with a range of permanent and temporary exhibitions as well as interactive activities.
4. Live music and entertainment to invite your date to in Shady Side
Shady Side is bustling with live music, entertainment, and fun all year round. Pop into The Waterside for great music and drinks, or listen to some blues at the Shore & Shore Blues Club. During the summer months, you can take your date to the South River Concert Series, a series of free concerts held at the South River Amphitheater. As the sun goes down and the stars come out, the outdoor amphitheater is a romantic spot for a first date.
5. Shady Side pubs, bars or restaurants for a first date drink or food
If drinks and food are more your speed, Shady Side has no shortage of pubs, bars, and restaurants to explore. Stop into The Lighthouse for delicious seafood and a fine selection of beers, wines, and cocktails. The Crab Claw Restaurant is another popular spot, where you can sample the region’s famous blue crabs. For a romantic dinner, make a reservation at The Fisherman’s Inn. This family-run restaurant has an amazing view of the bay and an extensive menu of seafood specialties and creative takes on classic dishes.
6. Other date ideas to try in Shady Side
Aside from the typical first date activities, there are plenty of other fun and unique things to do in Shady Side. Take your date on a sailing adventure, or rent a kayak and explore the creeks and rivers of the area. You can also take a tour of the South River and the Chesapeake Bay by boat, or go for a morning or evening cruise. For a bit of mystery, try your hand at an escape room. Shady Side also has a few wineries, so you can sample some of the local wines
