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48 Hours on Maryland’s Eastern Shore

The Eastern Shore of Maryland is synonymous with two things: shoreline and crabs. Shoreline comes in many flavors here and you can spend your day on the ocean, on the marshes backing barrier islands like Assateague Island, on the Chesapeake Bay, or one of the many rivers flowing into it. Crabs come in one flavor—crab—but you can find them everywhere. Pack your paddle and your pfd, grab some sunscreen and bug spray, then read on to find how to spend 48 hours on the shore that you won’t soon forget.

Day 1:

If you’re headed to the shore, then head to the shore and make your way to Assateague Island. This 41,000-acre National Seashore extends from Ocean City to the Virginia border and two herds of wild ponies—about 100 in all—call the island home. If you want to see them you can take your chances and hope to spot them on your own or you can join a boat tour with Assateague Adventure Day Tours departing out of Ocean City. South Ocean Beach, on Assateague, was ranked as one of the best beaches in the nation, and one look at the sand and the surf and you’ll know why. Slather on the sunscreen, spread out your towel, and relax a little.

Two herds of wild ponies—about 100 in all—call Assateague Island home.

The fishing is fine along Assateague (crabbing too, but that’s on the back side of the island), and if you want to do a little surfcasting, go for it (with a valid fishing license, of course). You can catch flounder, fluke, drum, striped bass, even dogfish from the shore. If you want to get out on the water, there are plenty of ocean-going and bayside charters.

You can’t go to Maryland without eating some crabs, and Phillips Seafood is the place to do it. This Ocean City staple has been serving crab since 1956 and their game is on point. Order from their regular menu or go all out with the all-you-can-eat option.

Harris crab beer_wide
You can’t go to Maryland without eating some crabs, and Phillips Seafood is the place to do it.

Day 2:

On the Chesapeake Bay, Blackwater National Wildlife Refuge is a must stop. Here, the Blackwater River makes it way to the Chesapeake Bay and a 25,000-acre site consisting of forest, marsh, and open water, has been set aside for recreation and preservation.

It’s a stop along the Atlantic Flyway for migrating ducks, geese, and swans, and more than 200 other bird species call this home full time or seasonally, making for a good reason to bring your binoculars. A trio of paddle trails ranging from 3 to 18 miles round trip will carry you through the waters here and allow you to get up close with many of the birds or even put you into areas where the fishing is fine and hard to reach by powerboat. Potomac Paddlesports provides tours of the Refuge and Blackwater Paddle & Pedal will rent you equipment to tour on your owner.

Kayakers Janes Island 03_0
Paddling is big here, and it’s no wonder when you consider the 1,700-miles of shoreline in and around the Refuge.

Paddling is big here, and it’s no wonder when you consider the 1,700-miles of shoreline in and around the Refuge, but that also makes for great fishing. Hoopers Island Expeditions caters to anglers itching to get into those little creeks and marshes (he also runs charters for birders and photographers too); he’s on the water year-round and knows what’s biting where and when. Tide Runner Fishing Charter goes for deeper waters around the mouths of the rivers and out into the Chesapeake Bay, reeling in rockfish, speckled trout, red drum, and other hard fighters.


Sneaky Pete’s, perched at the end of a dock over Assawoman Bay (really) in Ocean City, serves some wicked crab dishes: steamed claws, soft-shells, broiled crabs and steamer buckets full of fresh shellfish.If you want to eat some Maryland Blue Crab until you can’t eat no more Assateague Crab Shack can deliver. This spot has a bit of that locals-only vibe, but they’ll serve you a bucket of fresh steamed and seasoned blue crab with all the accouterments.

Hooper’s Crab House is the place to go for fresh seafood and other Eastern Shore favorites.

Libations & Nightlife

Fin City Brewing Company is the oldest brewery in Ocean City and their brews—IPAs and ales, mostly—go great with seafood, which is fitting because they’re located at Hooper’s Crab House, same as Sneaky Pete’s.

Fin City Brewing Company is the oldest brewery in Ocean City.

The Bar at the Inlet is right on the boardwalk in Ocean City and it’s thick with loyal patrons. Some call it a dive, some call it blue collar, but whatever it is, it’s among the last of its kind. Don’t expect anything too fancy, just cold beer and stiff drinks.

The Best of the Rest

Bartlett Pear Inn

Offering up sumptuous feasts of locally sourced foods and artisanal cocktails that will wow the most discerning pallet, chef Jordan Lloyd’s Bartlett Pear Inn was named one of the 100 Very Best Restaurants by Washingtonian magazine. Consider combining dinner with a stay at adjoining boutique hotels.

RAR Brewing

A Chesapeake Bay brewery located in an 80-year old former pool hall & bowling alley with a goal of producing well-balanced American and Belgian inspired brews 10 barrels at a time.

Ocean Odyssey

Starting in 1947 as a small crab factory located directly on the waterfront in Crocheron, Md., Bradye P Todd & Son Inc. opened its doors to produce some of the Eastern Shore’s finest Maryland Blue Crab meat and crab products.

Crabcake Factory USA

Crabcake Factory is known for several things. World Famous Crabcakes, Over the Top Breakfast, and outrageous bloody marys. The Beach locations are both open year round with the Fenwick location open from 9 a.m. till 9 p.m. Daily.

Courtney’s Restaurant & Seafood

A small mom and pop seafood joint offering the freshest of locally caught seafood.

More 48 Hours…

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