Guidebook for Shady Side

Theresa
Guidebook for Shady Side

Arts & Culture

One of the few public spots within walking distance to view our gorgeous Chesapeake Bay. On Wednesday evenings, it’s perfect to watch the sailboat races that start and end at Pirates Cove.
8 locals recommend
Captain Salem Avery Museum
1418 E West Shady Side Rd
8 locals recommend
One of the few public spots within walking distance to view our gorgeous Chesapeake Bay. On Wednesday evenings, it’s perfect to watch the sailboat races that start and end at Pirates Cove.

Essentials

Our closest grocery store for anything you forgot to bring with you. Roadside stands are also great for all produce that’s in season. So fresh!
30 locals recommend
Christopher's Fine Foods
5570 Shady Side Rd
30 locals recommend
Our closest grocery store for anything you forgot to bring with you. Roadside stands are also great for all produce that’s in season. So fresh!
We only buy liquor here. Check "use by" dates on any food you may buy.
6 locals recommend
Renno's Quality Food Market
6179 Shady Side Rd
6 locals recommend
We only buy liquor here. Check "use by" dates on any food you may buy.

Food Scene

We love to watch the charter fishing boats come in with their catch of the day, and they cut it up right there where you can watch. Naturally, all the birds in the area flock to that feast, and it’s just neat to see.
25 locals recommend
Dockside Restaurant & Sports Bar
421 Deale Rd
25 locals recommend
We love to watch the charter fishing boats come in with their catch of the day, and they cut it up right there where you can watch. Naturally, all the birds in the area flock to that feast, and it’s just neat to see.
Best soft serve around! Try their Peanut Butter Bomb! So goooood! Seasonally open; April thru October-ish Laundromat is right next door, and also a car wash.
Shadyside Soft Serve Ice Cream
6179 Shady Side Rd
Best soft serve around! Try their Peanut Butter Bomb! So goooood! Seasonally open; April thru October-ish Laundromat is right next door, and also a car wash.
Closest coffee shop; has great pastries and breakfast and lunch too
30 locals recommend
South County Cafe
5960 Deale Churchton Rd
30 locals recommend
Closest coffee shop; has great pastries and breakfast and lunch too
Just a few miles away, you'll find the famous "Driftwood skillet" breakfast that will satisfy all your breakfast cravings! It's so big that I always get the "half skillet" and still have to take that big biscuit home with me! I'm not kidding! :P
8 locals recommend
Drift Wood Diner
1468 Snug Harbor Rd
8 locals recommend
Just a few miles away, you'll find the famous "Driftwood skillet" breakfast that will satisfy all your breakfast cravings! It's so big that I always get the "half skillet" and still have to take that big biscuit home with me! I'm not kidding! :P

Getting Around

19 locals recommend
Largo Town Center station
9000 Lottsford Rd
19 locals recommend

Drinks & Nightlife

We like to catch the sunset from their rooftop bar :)
48 locals recommend
Skipper's Pier Restaurant & Dock Bar
6158 Drum Point Rd
48 locals recommend
We like to catch the sunset from their rooftop bar :)
New outside bar venue with occasional live music; great views of sunsets at Rockhold Creek; great food truck too! Try a grapefruit crush and the cauliflower bites. Yummy! They do an early "last call" at around 8:30 pm, so make this your first stop!
10 locals recommend
The Boathouse
604 Cabana Blvd
10 locals recommend
New outside bar venue with occasional live music; great views of sunsets at Rockhold Creek; great food truck too! Try a grapefruit crush and the cauliflower bites. Yummy! They do an early "last call" at around 8:30 pm, so make this your first stop!
They have darts and pool and karaoke too. Sometimes live music, sometimes DJ. The local hangout, for sure!
Corner Grille
1406 Cedarhurst Rd
They have darts and pool and karaoke too. Sometimes live music, sometimes DJ. The local hangout, for sure!

Parks & Nature

Trail goes by the water, is very pretty. Lots of bugs around, so spray heavily before going on trail. Otherwise, lots of other areas to walk that are not so buggy.
23 locals recommend
Smithsonian Environmental Research Center
647 Contees Wharf Road
23 locals recommend
Trail goes by the water, is very pretty. Lots of bugs around, so spray heavily before going on trail. Otherwise, lots of other areas to walk that are not so buggy.

Shopping

great selection of nautical souvenirs; friendly staff; great bargains.
18 locals recommend
Second Wind Consignments
661 Deale Rd
18 locals recommend
great selection of nautical souvenirs; friendly staff; great bargains.