Hero banner

Shady Side Fishing Charters

Compare 105 captains, read reviews, and book in minutes

The best out of 105 charter fishing deals in Shady Side - enter dates to check availability

Trip date
Loading...

Top Fishing Charters in Shady Side

Shady Side: 105 fishing charters available

Showing 1 - 9
 Show on map
  • Angler's Choice

    Hallock's Grace Charters

    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.

    "What an incredible day aboard the Grace. We really can't say enough good about it!" —⁠ Sean,

    Trips from:
    US $750
    • Tyler's first Rockfish

    Patent Pending Charters

    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.

    "We had a great time with Patent Pending Charters! The trip was a belated birthday celebration for my 15-year-old son and four of his friends, and Captain John and first mate Ronnie made it a fantastic experience." —⁠ Pete,

    Trips from:
    US $795
    • NEW 51 WEAVER

    Loosen Up Charters

    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.

    "Awesome fishing trip! The captain took us to some great spots, and we caught our limit of fish." —⁠ Juan,

    Trips from:
    US $950
  • Angler's Choice

    Lucky Strike Charters

    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 had such a great time on the Lucky Strike! Captain Shawn worked hard to find the fish for us." —⁠ Arnold,

    Trips from:
    US $750

    Miss Ashleigh

    Deale: 11 min drive from Shady Side

    Loosen Up Charters is located in Deale and offers to show you a memorable time in these waters. Capt. Frank will do his best to make sure you have a fun day full of fishing.

    "We had such an amazing time, they were so enthusiastic and knowledgeable with everything we needed to know." —⁠ Abigail,

    Trips from:
    US $900
    • New look for 2021!

    U.S. Blues Chesapeake Charters offers exciting fishing trips in Chesapeake Bay, Maryland. Captain Robert Flynn and his first mate welcome anglers of all skill levels.

    "We had a fantastic time with Captain Matt and Taylor! These guys know where to find the rockfish and we limited out." —⁠ Tom,

    Trips from:
    US $695
  • Angler's Choice

    Vickie Ann Charters

    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.

    "My husband and son both have milestone birthdays this year so we decided to go charter fishing as a family to celebrate together." —⁠ Crystal,

    Trips from:
    US $460

    Bay Hunter II

    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.

    "We went out on a morning trip. We caught plenty of Rockfish." —⁠ Anthony,

    Trips from:
    US $750
  • Angler's Choice

    JadeLady Charters

    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.

    "it was a great experience we love it I recommend this trip , we catch rockfish and it was fun we was waiting for this moment , the captain and crew was really nice this trip was one of the best because we had fun and we also like it , and of course we going back with othes guests , for future guests I personally I recommend it thanks to the captain and his crew !" —⁠ Wilfredo,

    Trips from:
    US $675
View all fishing charters
See all 105 fishing charters in Shady Side

Top deep sea fishing trips in Shady Side

  • Loading...
  • Loading...
  • Loading...
  • Loading...

Top-rated family fishing trips in Shady Side

  • Loading...
  • Loading...
  • Loading...
  • Loading...

Half-day fishing trips in Shady Side

  • Loading...
  • Loading...
  • Loading...
  • Loading...
Loading
Loading

Real catches shared by our community in Shady Side

  • Loading...
  • Loading...
  • Loading...
  • Loading...

Top Types of Fishing in Shady Side

  • Loading...
  • Loading...
  • Loading...
  • Loading...

Top Fishing Techniques in Shady Side

  • Loading...
  • Loading...
  • Loading...
  • Loading...
Powered by AI

Frequently Asked Questions about Fishing Charters in Shady Side

Loading...
Loading...
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

5.0
/5
Based on 31,726 reviews by FishingBooker anglers

What anglers said about fishing in Shady Side

  • Loading...
  • Loading...
  • Loading...
  • Loading...

How did anglers rate fishing charters in Shady Side?

  • Loading...
  • Loading...
  • Loading...
  • Loading...

Nearby Fishing Destinations

  • Loading...
  • Loading...
  • Loading...
  • Loading...