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Deal Island is located on Maryland's "slower lower" eastern shore. Best described as scenic rural Chesapeake Bay country. It's true to say that how it looks today is pretty much how it has always looked...going back to the late 1700s. It's secret. The Deal Island Wildlife Management area weaves throughout it. No condo resort projects here!


How to (prepare) steam a Maryland Blue hard crab for consumption

Step 1

buy crabs directly from a Captain along Wenona Harbor (the Captains usually return to harbor after a day of harvesting crab on the Tangier Sound area of the Chesapeake Bay around 2:00 pm)

Step 2:

So when you buy crab directly from a Captain, they are very alive. You (steam) cook'em.

Please see below a great demonstration (with humor) link via Youtube


Community website


State of Maryland Department of Natural Resources fishing and crabbing reports


Deal Island Charter Fishing Boat Captains

These captains are generational waterman and represent hundreds of years of fishing experience! 

1. Stan Daniels capt's the "Little Art"/410-784-2693/"The Singing Fisherman" has the "Best Fishing on the Chesapeake Bay!"

2. Dickey Webster capt's the "Three K's"/410-784-2053/ up to 22 passengers

3  Larry Tawes capt's the "Tina Louise"/410-546-3968/ up to 24 passengers

4. Paul Benton capt's the "Madam X"/410-784-2343/ up to 6 passengers

5. Harry Nauman capt's the "JA Parks"/410-784-2690/ up to 6



Arby's Bar & Grill 

(Wenona Harbor, 410-784-ARBY!)

GOOD Food, COLD Beer, GREAT People!


(Princess Anne, Md, 410-651-1950)

Famous crab cakes and eastern shore style fried chicken

Beach to Bay Seafood

(Princess Anne, MD; 410-651-5400)

Everything local seafood, delicious



State of Maryland birding info    

Shore erosion project 

Annual Skipjack Bike Tour link below: 

Deal Island Annual Skipjack Race (every Labor Day weekend)




Fun to read blog. A great way to learn about fishing and hunting in Deal Island. Copy and paste 

2011 a new fishing pier and boat ramp have been added to the harbor located just a short walk from the Sunrise~Sunrise Cottage.

2012 Arbys store opened Shedders Restaurant and Bar. Captain David Whitelock



Captain David Whitelock

 Deal Island, MD 21821


Captain Whitelock offers 3-hour afternoon and sunset sails aboard the skipjack Hilda Willing (built 1905).  Tours depart from Deal Island and are $40 per person with steamed crabs available upon request.  Custom charters are available if guests are interested in different times and durations.  Trips run Monday through Saturday beginning April 1st and the season ends October 20th when Captain Whitelock begins the commercial oyster-dredging season.

Captain Whitelock has 25 years of experience as a commercial watermen and is certified by the US Coast Guard to carry up to 6 passengers.  He?d love to have you come sail with him on the beautiful Tangier Sound and forget about life for a while.  Give him a call at his home 410-784-2550 or catch him when he?s out on the water at 410-251-6980.




Enjoy going back in time to small island Chesapeake Bay life as it was from decades ago! 

I.  Deal Island beach: a white sandy ¼ mile beach featuring open water views of  the Chesapeake Bay. Relax, swim, fish? It?s located just past the Deal Island Bridge next to the harbor.

II. Fishing and crabbing: Ask Arby!  Arby Holland and his family (they run the General Store in Wenona) are the experts on the greater Deal Island area best fishing and crabbing areas.  That said; if you want to buy crabs or fish from the boat Captains let Arby know at least a day or more in advance Or   If you want to reserve a Charter boat directly from a Captain, see b 


III.  The State of Maryland Deal Island Wildlife Management Area can be found on both sides of Deal Island Road in and around greater Deal Island. It features scenic water vistas of the Chesapeake Bay and it?s tributaries. It is 13000 acres. It has over 9 miles of flat trails used by walkers, hikers, off road cyclist, crabbers and birdwatchers.  See the 3 access areas below:

Deal Island Wildlife Management Area

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Deal Island Wildlife Management Area protects 13,000 acres (53 km2) in western Somerset County near the community of Deal Island. As a wildlife management area, the area is managed by the State of Maryland's Wildlife and Heritage Service to conserve wildlife populations and their habitats, while providing public recreational use of wildlife resources.[1]

Features of the Deal Island WMA include over 9 miles (14 km) of flat trails] and a 2,800-acre man-made pond or "impoundment."[1]

Recreational activities include photography, fishing, small boating (canoe and kayak), birdwatching (waterfowl including uncommon duck species), hunting (geese and duck) and crabbing...

The nine mile trail is frequented by hiking and off-road cycling enthusiasts.

1. The Messick Road public boat ramp area in Dames Quarter features a ramp and fishing/crabbing pier. When facing the water, you are looking at the mouth of Dames Quarter Creek. From the ramp, small boat owners go to the right up in to the creek. Large boat owners head to the left where they quickly meet the waters of the Monie Bay/Wicomico River. The Tangier Sound open waters on the Chance, MD side of the Chesapeake Bay quickly follow. This ramp is used for fishing and recreational boating activity. The Messick Road pier and shoreline is a popular spot for fishing, crabbing and bird watching.

(Messick Road is approximately 10 miles in from Rte 13. From Deal Island Road turn on Messick Road and go approximately 1 mile. The public boat ramp area is at the end. )


2. The Riley Roberts Road public boat ramp area is in Dames Quarter. This is actually considered the main entrance to the WMA. It has two (2) ramps. The ramp on the left is used by small boater owners. It features the east side of the impoundment (lake) area of the Deal Island Wildlife Management Area. Primarily known for 2 things. Catching Maryland Chesapeake Blue crabs the old fashion way. IE by line/chicken neck/weight/net. And for its 9 miles of scenic water vista related trail. The ramp on the right is used by larger boat owners. It quickly feeds in to where the mouth of the Manokin River meets the Tangier Sound waters of the Little Deal Island side of the Chesapeake Bay. Mainly used for fishing, hunting and recreational boating activity.

( Riley Roberts Rd is approximately 12 miles in from Rte 13. From Deal Island Rd turn on Riley Roberts Road. Take it to the end. Riley Roberts Rd is approximately 3 miles long. Very rustic, very rural. A good halfway marker is the old Deal Island School property which is directly across from 10876 Riley Roberts Road ).


3. The Wenona public boat ramp is located at the southern most tip of Deal Island. Launch your kayak, canoe or other small boat for the 10 minute paddle to Little Deal Island. Little Deal Island is uninhabited. Walk it's beaches, explore it's creeks ("guts"), fish, crab, birdwatch... (Wenona Harbor is approximately 19 miles in from Rte 13. Take Deal Island Road to the end. Look for the harbor ramp and parking area on the left.


4.  Weekend Yard Sales:  along Deal Island Rd. enjoy meeting island residence and maybe finding a Chesapeake keepsake or 2

5.  Nature:  stargazing is supreme.  Enjoy seeing the milkyway and beyond by naked eye.  Bird watching is a guest favorite too.  Ospreys (fish hawk), Pelicans, Snowy Egrets, Herons? Site seeing.  Wenona has been around since the mid 1800s.  The terrain is flat. Enjoy walks and bike rides throughout old small town Bay charm.



* Princess Anne is a Historical small town with several small shops & eateries. 

* Salisbury has a small zoo that has won national awards


* There is also the Ward Wild Fowl Museum in Salisbury.* 

* Visit the beautiful vineyards winery & tasting facility of Bordeleau Vinyards in Eden Md.