Written by on August 29, 2017

Happy Hour at Skipper’s Pier Restaurant and Dock Bar

Although the kids are heading back to school, there are still two beautiful months to extend that carefree summer feel on the water in South County. With all the waterfront restaurants in and around Annapolis, many choose to stay with the familiar and close to home. However, a ride into South County to Skipper’s Pier Restaurant and Dock Bar (6158 Drum Point Road, Deale, Maryland )is well worth the thirty-minute drive. The view is truly breathtaking.  Next to Skipper’s lies Rockhold Creek where you can watch a variety of work and pleasure boats pass by to one of the many marinas. Shift your gaze and there lies an expansive vista of the Chesapeake Bay.

Happy Hour at Skipper's Pier Restaurant and Dock Bar

Skipper’s is no secret to the South County and northern Calvert County crowd. A huge second parking lot is often packed, so you may want to go early.  On a recent Tuesday evening, I wasn’t expecting a crowd, but I didn’t realize it was Crab Night.  From 3:00 p.m. until close (or until the crabs run out) every Tuesday, crabs are $2.50 each. This popular night also offers $2.50 domestic bottled beers.

Happy Hour at Skipper's Pier Restaurant and Dock Bar

Upper Deck

Skippers has several different sections including an inside bar with tables and a large inside restaurant which opens in good weather onto a huge deck perfect for crab picking. My favorite area, however, is at the end of a long pier where there is another very open bar, a few tables on the end dock, and always a wonderful breeze off both the creek and Bay. If you really want a bird’s eye view of the surrounding waters, you can eat and drink on the deck above the pier bar. Blisssssss.

We found a high top table at the pier bar and took a moment to savor the view. It always feel as if I am on vacation when I am here. Skipper’s has an extensive drink menu and there were a number I wanted to try. The Crush menu even includes a “Skinny Crush” for those watching their waistlines, along with the more traditional orange and grapefruit crushes, as well as a coconut pineapple crush to try another time or attempt at home.

Happy Hour at Skipper's Pier Restaurant and Dock Bar

Bay Breeze Bucket

From the Blended Concoctions drink section, I was quite tempted to order the Chocolate Covered Dirty Banana made from dark rum, Kahlua coffee liquor and banana mix. – served in a chocolate swirled cup with whipped cream and chocolate toppings…Wow…dessert!  However, I knew that would ruin my appetite (and undo the benefits of my earlier work out), so I resisted. However, I always like to try specialties, so selected a “Bay Breeze Bucket” from the Signature Cocktails section. This generously-sized plastic bucket is filled with a combination of Coconut, Banana, Passion Fruit and Mango Malibu rums which are blended with fruit juices. Sweet, summery, and priced at $12.00, this reminded me of past vacations in the Caribbean Islands. Due to its size, I could not order another drink, but made note of one for a return visit, perhaps in the winter? How about this description from the Bloody Mary selections for “The Black Pearl”? “Tito’s gluten free vodka blended with George’s Bloody Mary Mix, topped with pearly Chesapeake Bay oysters, smoky bacon, jumbo olives and celery in a Chesapeake rimmed cup.”  They had me at bacon. Ummmm….that almost sounds like a meal in a glass.

Happy Hour at Skipper's Pier Restaurant and Dock Bar

Crab Cake

While tray after tray piled high with delicious smelling crabs passed us en route to other happy hour guests, we decided that time was not on our side for picking crabs this evening. My friend instead ordered a broiled crab cake sandwich, where all the work was done for her. This was a thick, crab heavy sandwich served with what I call “Boardwalk fries”. I have been on a fresh tomato kick this summer, so selected the tomato pie. This was very different from any tomato pie I have had. Instead of a crust, it is served in a cast iron skillet.  This signature dish composed of sliced tomatoes, stewed tomatoes, and melted cheese is topped with three huge, herbed, buttermilk biscuits.  I think my mistake was ordering this dish now instead of in the winter.  The biscuits were killer; however, while this hot dish would be great comfort food in cold weather, for me it was a bit too hot and heavy for such a warm summer day. What was I thinking? I should have fed my tomato craving with the Farmer’s Tomato and Avocado Stack which looked divine.

Happy Hour at Skipper's Pier Restaurant and Dock Bar

Tomato Pie

Most of the bar and appetizer choices are offered in The “For the Table” section of the menu.  Here, you’ll find a number of seafood selections including many favorite crab offerings: crab balls, crab crusted oysters, crab bruschetta and both Maryland and Cream of Crab soups. Clams and oysters on the half shell are also available.

Although Skippers doesn’t have a traditional Happy Hour, each weekday (except Mondays when it is closed) there is a special. As noted, Tuesdays are for $2.50 crabs and bottled beer. Wednesday’s special is a bottomless shrimp bucket with corn, potato, coleslaw and garlic bread for $19.99. On “Throw back Thursday,” the chef offers “your favorite comfort foods,” and Friday hosts the popular All You Can Eat Seafood Buffet from 5:00 until 8:30 for $26.99.

Happy Hour at Skipper's Pier Restaurant and Dock Bar

On Saturdays and Sundays there is live music from 3:00 to 7:00 on the deck. So, don’t lament that summer is coming to a close. Keep those shorts and flip flops handy and head down to Skipper’s to enjoy fabulous views, a summer drink, local seafood, beach tunes, or to catch a football game on one of the televisions at the inside or outside bars. You deserve it!

Natalie was teaching in Delaware in 1996 when a friend suggested meeting in Annapolis for lunch. Crossing the Severn River Bridge, Natalie knew she had found where she belonged. After five years as a weekend-only resident of Annapolis, Natalie transitioned to a full-time resident in 2005. In warm months, Natalie is found sailing from Back Creek to the Bay Bridge and, on the return, motor sailing into Annapolis Harbor. There she enjoys checking out boats on the moorings and the occasional mega-yachts. Her favorite Annapolis boating memories are watching the Blue Angels’ precision maneuvers above the Severn River during Commissioning week at the Naval Academy. She has sponsored midshipmen and is a fan at Navy Football home games. Natalie enjoys hiking and biking through the scenic parks and trails in Annapolis and Anne Arundel Co. with one of the areas many Meetup groups. With a fondness for craft beer, Natalie firmly supports the motto, “Friends don’t let friends drink light beer,” and, for those who do, she attempts to help them see the error of their ways by suggesting something with a bit more flavor. Natalie volunteers at festivals in the Annapolis area. She appreciates the opportunity to listen to great bands, make friends and contribute to the sponsoring organizations who donate the majority of festival proceeds to local charities. Natalie is a teacher in Anne Arundel County Public Schools. She can be reached at her personal blog: Naptownchowdown.com or at Natalieksc@gmail.com

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