Shady Side, United States offers 5 beaches perfect for sunbathing, surfing, swimming, and more. Shady Side, Maryland, United States, is known for the Captain Avery Museum and its scenic Chesapeake Bay waterfront. The best time to travel to Shady Side, United States, is in late spring (May), when the average air temperature is around 70°F (21°C) and the water temperature is approximately 65°F (18°C). Sandee provides detailed maps, photos, and reviews from fellow beachgoers to help you Choose Your Beach™ and plan your perfect beach vacation!