Event Highlights

Boat Docking

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The Boat Docking Competition is a favorite for event goers and its a chance for the captains to show off their skills!

This year the Boat Docking event will be kicked up … Chesapeake Cowboys will be here.  Our local working boats will have a separate competition immediately following the Cowboys!  http://www.chesapeakecowboysboatdocking.com/

We are looking for sponsors to cover the prizes and fees for the boat captains.  If you can help, contact any Lion.

The fun starts at 2 p.m.

Check out this awesome video on YouTube …  David Horseman of Chance gets to fire the starter’s horn for the Workboat Docking Contest.



Live Entertainment



The Islandfest Concert is held on Saturday night starting at 4:00 pm.  Featuring  The Island Boys, the Sons of Thunder, Reunion Quartet,  and The Deal Island Communities Choir. The concert is held outdoors at Deal Island Harbor, and there is some seating, but bring your lawn chair. Food vendors will be set up and open for the concert.  The concert is FREE — Love Offering

FUN for the kids!

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Lots of FUN for the kids! This year we are providing a Kids Bounce House, Giant Slide, and Free Skipjack Tattoos (don’t worry Mom the’re the temporary kind),  But wait, there’s more!  See the famous Django the Monkey perform on Monday from 10:30 till 2:30.


Fort McHenry Re-enactors

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Tentative ….

PHRF race

The PHRF race is a race between several racing sailing boats.  Deke Sheller is the lead official of this race, which is held at 9 AM. This is a handicapped race, with points handled by Deke Sheller , and the Racing association. it is Preferred Race Handicap Factor

Silent Auction

We accept memorabilia, speakers, radios, Photos, framed, pen and ink or painted pictures, handmade dolls, and almost anything. Starting Sunday Noon people can come and get a bidding number. Noone gets the name of the bidder if we can help it. You enter your bid and number on the sheet by the article, and we close bidding 5PM Monday afternoon.  High bidders are announced in the closing ceremonies, and I arrange to get the items to folks who are not present at that time.

Food vendors

We have soft shell crab sandwiches, hot dogs, sausage sandwiches, Ice Cream, drinks, some foreign food(maybe Thai)  While there is as much variety as we can get, we limit entrée offerings so there are not a group of folks selling the same thing, except for soda, coffee, or iced tea.

Food Vendors and Commercial Vendors can contact billsailer@verizon.net for more information and pricing.

Crafts Show and Vendors
The Show is on Sunday and Monday and there are usually 25 vendors.  Items are priced from $5 or less to moderately priced work.
Vendors are encouraged to have a complete scope of their work.
There are always jewelry, metal work, wood work, fabric art.,clay work, leather work, and authors.
There are  small prints, postcards, note cards with water themes.
Some vendors offer decorated furniture, watercolors, photography, wind chimes, dolls and doll clothes, soaps  and surprises.

Folks interested in becoming an Arts and Craft Vendor at the Skipjack Festival should contact Joanna Peak at 410 784 2799, or email skipjacknow@gmail.com

General Information: (Arts and Crafts)

  • Booth Fee – if coming for both days – $35
  • Booth Fee – if coming for one day only – $40 (either Sunday or Monday)
  • Booth is 12 x 12 – vendors supply their own equipment
  • Larger space is available for an additional fee
  • All items must be hand crafted – NO COMMERCIAL MATERIAL IS ALLOWED
  • Set up time is 8 am – vendors may leave at any time
For more information skipjacknow@gmail.com

Food Vendors can contact billsailer@verizon.net for more information and pricing by email or by phone at 410 784 2785.

Car & Motorcycle Show

Sunday, Day before Labor Day … 10 – 3:30 PM
(Rain Date – on Monday, Labor Day)

Antiques, Classics, Street Rods Welcome
Dash Plaques to the First 75 Registered, 25 Participant’s Choice Plaques

Registration at Harbor- 10 until 2:30 p.m.
Voting until 2:00 p.m. Awards: 3:15 p.m.
$10 Registration Fee (Lowered)

All Car Show Vehicles are invited to join in the Parade. (Bring Candy to pitch to kids.) Line up and register for Parade at Deal Island School by 12:30 p.m. At the end of the parade proceed into the harbor area for the Car Show. Three Parade Trophies will be awarded. For Car Show information call: 410-202-9271.


Entries are now being taken for the

Annual Skipjack Festival Parade!

Contact Kim East at 443-235-2056