Joan’s guidebook
Food scene
Jesse Jay's is a local favorite (and ours!). Make a reservation to avoid a long wait or you can order on their website, pick up, and bring back to the house. It's only about a 5-minute drive.
16 locals recommend
JesseJay's Latin Inspired Kitchen
5471 Muddy Creek RdJesse Jay's is a local favorite (and ours!). Make a reservation to avoid a long wait or you can order on their website, pick up, and bring back to the house. It's only about a 5-minute drive.
Skipper's is great to catch an evening sunset from the outdoor seating area. The food is great and they have a dock bar for those 21 & over with a rooftop area. There is an overflow parking lot if it's crowded that is a short walk away.
48 locals recommend
Skipper's Pier Restaurant & Dock Bar
6158 Drum Point RdSkipper's is great to catch an evening sunset from the outdoor seating area. The food is great and they have a dock bar for those 21 & over with a rooftop area. There is an overflow parking lot if it's crowded that is a short walk away.
Petie's is a local favorite. It's small, but the food is some of the best in the local area. It's not on the water so we enjoy it most during the colder months when we aren't seeking a place on the water.
13 locals recommend
Petie Greens
6103 Drum Point RdPetie's is a local favorite. It's small, but the food is some of the best in the local area. It's not on the water so we enjoy it most during the colder months when we aren't seeking a place on the water.
Pirates Cove is a fun place for all tastes. There is an outside patio/bar area that may have a small band or solo performer. There are several indoor and other outdoor spaces depending on your mood. You can arrive by boat or jet ski as well.
44 locals recommend
Pirates Cove Restaurant and Dock Bar
4817 Riverside DrPirates Cove is a fun place for all tastes. There is an outside patio/bar area that may have a small band or solo performer. There are several indoor and other outdoor spaces depending on your mood. You can arrive by boat or jet ski as well.
Stan & Joes is your typical local dockside restaurant with great views and food. It's usually packed with boaters stopping in for food and drink. There may also be a solo performer playing music on the dock bar.
20 locals recommend
Stan and Joes Riverside
4851 Riverside DrStan & Joes is your typical local dockside restaurant with great views and food. It's usually packed with boaters stopping in for food and drink. There may also be a solo performer playing music on the dock bar.
A true local breakfast favorite. Only about a mile from the house. It's popular so recommend getting there early.
8 locals recommend
Drift Wood Diner
1468 Snug Harbor RdA true local breakfast favorite. Only about a mile from the house. It's popular so recommend getting there early.
If you enjoy fresh, hot, made to order donuts then this is a must visit. Currently only open Fri-Sun 7am-1pm. Try the Surfer Dude - my favorite!
Sandy Pony Donuts Deale
620 e Bay Front RdIf you enjoy fresh, hot, made to order donuts then this is a must visit. Currently only open Fri-Sun 7am-1pm. Try the Surfer Dude - my favorite!
City/town information
Only about 30 minutes away, downtown Annapolis and Ego Alley, along with Eastport across the bridge, are a must visit if you are new to the area. Check out the historic Capitol building and then walk down Main Street to Ego Alley where you normally see some impressive boats docked. There are water taxis to take you over to Eastport or just walk across the bridge. The Boathouse is a great restaurant or try Davis's Pub nearby for a delicious crab stuffed pretzel!
80 locals recommend
Annapolis
Only about 30 minutes away, downtown Annapolis and Ego Alley, along with Eastport across the bridge, are a must visit if you are new to the area. Check out the historic Capitol building and then walk down Main Street to Ego Alley where you normally see some impressive boats docked. There are water taxis to take you over to Eastport or just walk across the bridge. The Boathouse is a great restaurant or try Davis's Pub nearby for a delicious crab stuffed pretzel!
City advice
Getting around
Don't expect to be able to Uber everywhere
Shady Side is far enough away from a major town (like Annapolis) that ordering an Uber ride to town is not easy or even available. Plan to drive your car or even bike to some of the closer spots.
What to pack
Bring a kayak or SUP or rent one
If you want to take advantage of the West River in your backyard we recommend bringing your kayak or SUP with you. Or you may wish to rent one from Chesapeake Paddle Sports in Deale, MD, only about 10 minutes from the house. https://chesapeakepaddlesports.com
Book before you go
Boat charter for fishing or sightseeing
There are several local charter services in Deale, MD. Or you can find several in Annapolis if you want to enjoy a sailing cruise. Best advice is to Google "fishing or sailing charters" near Shady Side, MD / Annapolis.