Restaurants & Entertainment - Mears Great Oak Landing

Restaurants & Entertainment

There are several entertainment venues on the Mears Great Oak Landing property and nearby by land or sea.

On-Site Attractions

Red Eye’s

Red Eye’s Dock Bar offers a full menu from appetizers, burgers, seafood and entrees. Daily drink specials and live entertainment Thursday-Sunday evenings make it a great place to end a long boating day. With 27 TVs and the NFL Sunday ticket, you can catch every game playing while enjoying a meal on the water.


The View

The View Restaurant provides a bird’s eye view of the Kent Narrows and the excitement of Red Eye’s Dock Bar. Offering great food, cold drinks and fantastic sports on 16 HDTVs, there isn’t a bad seat in the house.



Annie’s Paramount Steak and Seafood is a long-standing upscale restaurant offering steak and seafood with views of the Kent Narrows. The restaurant also features a sports bar with billiards. Annie’s is open for lunch and dinner daily, offering large beer and wine lists. Annie’s Sunday brunch features the most delicious parts of breakfast combined with the best lunch has to offer. With a half dozen entrees and dozens of sides, you will not have trouble filling your stomach.


Captain’s Cabana

The Captains Cabana at the Mears Point Marina pool is a bar & refreshment stand with ice cream, light fare menu and drinks.

The surrounding areas feature an array of eateries and bars that offer guests and slipholders a variety of dining options. From steamed crabs, casual burgers or pizza to contemporary beef and seafood entrees, there are varied menus and price ranges to accommodate everyone.Many are within an easy walk from Mears Point Marina.

Off-Site Attractions

Chesapeake Heritage and Visitor Center

The Chesapeake Heritage and Visitor Center features collections from local artists with an emphasis on the Eastern Shore. More exhibits are dedicated to the culture, history and heritage of the Chesapeake Bay. A visit to the Center is great opportunity to teach children the importance of the bay’s ecosystemto future generations.


Kent Island Cross Island Trail

Whether you’re an athletic enthusiast or enjoy a good walk with the family through nature, the Kent Island Cross Island Trail is a great path. Beginning right next to Mears Point Marina and stretching across Kent Island, ending roughly 6 miles away at Terrapin Nature Park, the path is well maintained and protected, exposing you to local wildlife, waterways and plant life.


Oyster Recovery Partnership (ORP)

The Oyster Recovery Partnership is a non-profit organization dedicated to restoring the shellfish life of the Chesapeake Bay. Over the past 20 years they have planted over 6.6 billion baby oysters (spat) in the Bay. There was once a time in history when there were enough oysters in the Chesapeake Bay to filter the entire bay in under three minutes. Located next to the marina at Harris’ Seafood packaging house, stop by and see the oyster restoration in progress.


Maryland Waterman’s Memorial

Located in front of Fisherman’s Restaurant, the memorial features a 7,000 pound bronze statue designed by local artist and boat Captain TilghmanHemsley.


Fisherman’s Seafood Market

Fresh local seafood is within walking distance. Entrées feature local blue crabs, fish, live lobster, shrimp, scallops and much more. Shore Tackle All your local fishing supplies can be found in one place, from fresh bait to custom built rods. Located in front of the Crab Deck.


Shore Tackle

All your local fishing supplies can be found in one place, from fresh bait to custom built rods. Located in front of the Crab Deck.

Restaurants and Night Life

Harris’ Crab House

Traditional and regional seafood in a no-frills waterfront location with outdoor seating and private dockage. Right next door is a seasonal ice cream shop.


Fisherman’s Restaurant

Dine in spacious dining rooms with panoramic views of the water. Enjoy a drink at the Nauti Mermaid Bar or go on a sunset cruise aboard Fisherman’s 46 foot charter boat.


The Crab Deck

Full service bar and restaurant, enjoy inside or outside waterfront dinning. The Crab Deck is known for their happy hour and locally caught steamed crabs.


Bridge’s Restaurant

Waterfront American restaurant known for seafood, small plates, pizza and an extravagant wine list.


The Narrows

A menu with a blend of local favorites and creative culinary offerings. Fine dining in a casual atmosphere with waterfront views.


Big Owl Tiki Bar

Live music on the weekends compliments the atmosphere at this dock bar and grill offering pub fare and seafood on the Narrows.


The Jetty

Looking for nightlife and live music?The Jetty hosts several bands. Also offering light pub fare and seafood with a full bar.



Don’t have a boat large enough to sleep on but still want to enjoy the marina? No problem! There are three hotels within walking distance of the marina: Holiday Inn Express, The Best Western and Hilton Garden Inn. Don’t feel like walking? We’ve got that covered too! Our staff will gladly give you a ride on one of our street tagged golf carts.


Holiday Inn Express


Best Western


Hilton Garden Inn

Attractions on the water and distances

St. Michaels- 17 NM Annapolis- 13 NM Chestertown- 17 NM Rock Hall- 10 NM Great Oak Landing and Jellyfish Joel’s- 17 NM Baltimore – 27 NW

Seasonal Events

Rock the Dock(May)

– Hosted by Red Eye’s Dock Bar


Kent Island Days(May)


Rock fishing Tournaments (CCA) (June) Bay Days(September) 4th of July fireworks are launched directly across from the marina on the Narrows.


Kent Island Volunteer Fire Department Carnival(July)


Pirates and Winches Fantasy Weekend (August)


Thunder on the Narrows(August)


Kent Island Fall Festival(October)


Chesapeake Bay Wine Festival(October)


Taste of the Narrows(October)


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