Shady Side Fishing Charters

106 fishing charters

The best out of 106 charter fishing deals in Shady Side - enter dates to check availability

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Top Fishing Charters in Shady Side

Shady Side: 106 fishing charters available

Showing 1 - 10
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32 ft

Up to 6 people

Tight Times Charters

5.0/5 (21 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.

"Things got off to a great start. Captain went over a few things, asked us what we wanted and expected for the day." —⁠ Ray,
Trips from
US $450
Trips from
US $450
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46 ft

Up to 6 people

Patent Pending Charters

4.9/5 (155 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
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40 ft

Up to 10 people

Penny Sue Charters

4.9/5 (67 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.
Trips from
US $700
Trips from
US $700

Angler's choice

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38 ft

Up to 6 people

Vickie Ann Charters

4.9/5 (125 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.

"The captain and mate were excellent!  Great personality, great conversation, baited every hook, and pulled every caught fish off." —⁠ BRENDA,
Trips from
US $450
Trips from
US $450
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42 ft

Up to 6 people

Hallock's Grace Charters

4.8/5 (105 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
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46 ft

Up to 17 people

Lucky Strike Charters

4.8/5 (230 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.

"Lucky Strike fishing charter gave us a great day on the Chesapeake." —⁠ Steve,
Trips from
US $750
Trips from
US $750
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51 ft

Up to 47 people

Loosen Up Charters

4.8/5 (23 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
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46 ft

Up to 6 people

Biff Fishing Charters

5.0/5 (116 reviews)
Stevensville (52 min drive from Shady Side)
Located on Kent Island, Biff Fishing Charters offers trips fishing for Striped Bass and Bluefish in the Chesapeake Bay. Captain Justin Kaufman has been fishing these waters for more than a decade and knows the area like the back of his hand.

"Perfect fishing Day on the Bay. Captain Justin is a fantastic and friendly charter captain who is very enthusiastic wants everyone to catch fish." —⁠ Stew,
Trips from
US $720
Trips from
US $720
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45 ft

Up to 38 people

Bay Hunter II

5.0/5 (4 reviews)
Deale (12 min drive from Shady Side)
Looking to catch some fish in Edgewater? That’s what Bay Hunter II is here for! Having logged many hours on these tides, Captain Mason can tell you all about the local fishery.

"I recently had the pleasure of going on a fishing trip with Captain mason, and I can’t recommend him highly enough!" —⁠ Sean,
Trips from
US $750
Trips from
US $750
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46 ft

Up to 20 people

Hot Pursuit Charter Fishing

4.9/5 (32 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.

"I was very impressed immediately with the communication of the captain." —⁠ Joseph,
Trips from
US $600
Trips from
US $600

Top deep sea fishing trips in Shady Side

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Top-rated family fishing trips in Shady Side

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Half-day fishing trips in Shady Side

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Top Targeted Species in Shady Side

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Top Types of Fishing in Shady Side

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Top Fishing Techniques in Shady Side

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Frequently Asked Questions about Fishing Charters in Shady Side

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Frequently Asked Questions about Fishing Charters in Shady Side

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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 29,155 reviews by FishingBooker anglers

Shady Side Fishing Calendar

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Featured photos from Shady Side

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What anglers said about fishing in Shady Side

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How did anglers rate fishing charters in Shady Side?

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Nearby Fishing Destinations

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