Shady Side Fishing Charters

107 fishing charters

The best out of 107 charter fishing deals in Shady Side - enter dates to check availability

Loading...

Top Fishing Charters in Shady Side

Shady Side: 107 fishing charters available

Showing 1 - 10
Listing image
Loading...

32 ft

Up to 6 people

Tight Times Charters

4.8/5 (39 reviews)
Edgewater (19 min drive from Shady Side)
Tight Times Charters offers a variety of charters, including sport fishing, cruises, Blue Angels demonstrations, and parties. The professional captain and crew know all the hotspots to put you on the fish.

"We booked the 3-hour fishing tour with Tight Times for my son’s 11th birthday, and it was an unforgettable experience!" —⁠ Andrea,
Trips from
US $450
Trips from
US $450

Angler's choice

Listing image
Loading...

42 ft

Up to 6 people

Hallock's Grace Charters

4.8/5 (110 reviews)
Deale (10 min drive from Shady Side)
Hallock’s Grace Charters is a family owned and operated business. Trips depart from their private location in Shady Side, Maryland where you can bring your family aboard for a hands-on fishing or crabbing experience.

"Started the day fishing for stripers. They were not biting that day so we switched to fishing for bluefish." —⁠ Patrick,
Trips from
US $595
Trips from
US $595

Angler's choice

Listing image
Loading...

46 ft

Up to 6 people

Patent Pending Charters

4.9/5 (162 reviews)
Tracys Landing (12 min drive from Shady Side)
Chesapeake Bay may be a world-famous fishery, but there’s no better way to experience it than through the eyes of a local.

"Capt. John and First Mate Ronnie gave us the best day of fishing!" —⁠ Rich,
Trips from
US $795
Trips from
US $795
Listing image
Loading...

38 ft

Up to 6 people

Vickie Ann Charters

4.9/5 (137 reviews)
Deale (12 min drive from Shady Side)
Vickie Ann Charters is based in Deale, Maryland. The Captain and his crew fish the water of the Chesapeake Bay, specializing in catching Striped Bass, Bluefish, White Perch, Spanish Mackerel, and many other species.

"Captain and crewman were awesome for our groups fishing trip and definitely one to remember." —⁠ Isaac,
Trips from
US $450
Trips from
US $450
Listing image
Loading...

46 ft

Up to 20 people

Hot Pursuit Charter Fishing

4.9/5 (38 reviews)
Edgewater (20 min drive from Shady Side)
Whether you’re looking for a memory-making family vacation, a day with fishing buddies, or a business outing, Hot Pursuit Charter Fishing offers an exceptional angling experience for guests of all ages and skill levels.

"We had an absolutely amazing fishing trip! From start to finish, the crew made the experience smooth and enjoyable with excellent communication." —⁠ Sherry,
Trips from
US $600
Trips from
US $600
Listing image
Loading...

40 ft

Up to 10 people

Penny Sue Charters

4.9/5 (68 reviews)
Edgewater (20 min drive from Shady Side)
Penny Sue Charters invites you out for an unforgettable day of fishing the Chesapeake Bay. With over 25 years of experience, you can count on Captain Michael Smolek to get the job done.

"We had a great time on the Penny Sue!  The captain and mate were helpful, interesting, knowledgeable, and did a great job." —⁠ Meghan,
Trips from
US $700
Trips from
US $700
Listing image
Loading...

46 ft

Up to 17 people

Lucky Strike Charters

4.8/5 (236 reviews)
Deale (11 min drive from Shady Side)
“Lucky Strike Charters” welcomes all angling enthusiasts to experience the thrill of fishing the Chesapeake Bay and Potomac River! We launch out of a few different marinas through out the season depending where the best fishing locations are.

"We treated my husband to a Father’s Day fishing trip. Capt Shawn & Kenny made it fantastic." —⁠ Mary-Lacey,
Trips from
US $750
Trips from
US $750
Listing image
Loading...

51 ft

Up to 47 people

Loosen Up Charters

4.8/5 (25 reviews)
Deale (11 min drive from Shady Side)
If you’re after for great fishing on a spacious boat with an experienced captain, Loosen Up Charters is the place to be. Operating out of Deale, MD, these guys bring over 40 years of local experience to each trip they run.

"We recently booked Loosen Up for a company fishing trip with 14 people, and the experience was absolutely fantastic." —⁠ Luke,
Trips from
US $900
Trips from
US $900
Listing image
Loading...

36 ft

Up to 6 people

Good Stuff Charters

5.0/5 (5 reviews)
Shady Side
If you're ready to go fishing out of Shady Side, MD look no further than Good Stuff Charters. With Captain Jeremy at the helm, you'll have a knowledgeable and experienced guide.

"We originally had a trip set for a weekday evening, but storms rolled in causing a need for a change." —⁠ Christopher,
Trips from
US $450
Trips from
US $450
Listing image
Loading...

42 ft

Up to 6 people

JadeLady Charters

4.9/5 (130 reviews)
Stevensville (51 min drive from Shady Side)
Operating out of Stevensville, JadeLady Charters specialize in inshore fishing and crabbing. They are located on Maryland’s eastern coast, at Kentmorr marina, fishing the magnificent Chesapeake Bay, home of the Striped Bass and Maryland Blue Crab.

"Took my brother in law plus our sons & nephews for day on Chesapeake Bay." —⁠ Richard,
Trips from
US $625
Trips from
US $625

Top deep sea fishing trips in Shady Side

Loading...
Loading...
Loading...
Loading...
Loading...
Loading...
Loading...
Loading...

Top-rated family fishing trips in Shady Side

Loading...
Loading...
Loading...
Loading...
Loading...
Loading...
Loading...
Loading...

Half-day fishing trips in Shady Side

Loading...
Loading...
Loading...
Loading...
Loading...
Loading...
Loading...
Loading...

Top Targeted Species in Shady Side

Loading...Loading...Loading...Loading...Loading...Loading...

Top Types of Fishing in Shady Side

Loading...
Loading...
Loading...
Loading...
Loading...Loading...Loading...Loading...

Top Fishing Techniques in Shady Side

Loading...
Loading...
Loading...
Loading...
Loading...Loading...Loading...Loading...

Frequently Asked Questions about Fishing Charters in Shady Side

Loading
Loading

Frequently Asked Questions about Fishing Charters in Shady Side

Loading
Loading
Loading
Loading
Loading
Loading
Powered by AI

Fishing in Shady Side

Nestled on the Chesapeake Bay, Shady Side, Maryland, is a premier gateway to world-class fishing adventures. This charming waterfront community provides direct access to the abundant waters of the Chesapeake, renowned for thrilling catches of Striped Bass (Rockfish), Bluefish, White Perch, and Spanish Mackerel. Anglers flock to Shady Side for its prime location near productive fishing grounds like Eastern Bay, the Choptank River, and Kent Island, all within minutes of departure.

Shady Side fishing charters cater to all skill levels, from families seeking a memorable day on the water to seasoned anglers targeting trophy catches. Local captains employ proven Chesapeake Bay techniques including light-tackle jigging, trolling, and drift fishing, often adapting methods like chumming to maximize success. Many charters operate from private docks in Shady Side, offering personalized trips aboard well-equipped vessels designed for both comfort and functionality.

The area's rich maritime heritage is reflected in its family-owned charter operations, where generations of local expertise ensure an authentic Chesapeake experience. You'll find captains deeply knowledgeable about seasonal patterns and migratory routes, whether pursuing spring Rockfish or summer Bluefish. Conveniently located just 45 minutes from Baltimore and Washington DC, Shady Side provides an easily accessible yet immersive Chesapeake Bay fishing escape where the day's catch can often be cleaned and filleted right on board.

Shady Side

5/5
Based on 29,543 reviews by FishingBooker anglers

Shady Side Fishing Calendar

Loading

Featured photos from Shady Side

What anglers said about fishing in Shady Side

Loading...
Loading...
Loading...
Loading...
Loading...Loading...Loading...Loading...

How did anglers rate fishing charters in Shady Side?

Loading...Loading...Loading...Loading...

Nearby Fishing Destinations

Loading...
Loading...
Loading...
Loading...