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Wintry Mix of Notecards and Prints from the Eastern Shore of Maryland and VirginiaIf you’re anything like me, the batch of resolutions you make for each new year always includes getting out and about more often on the Eastern Shore and in Southern Delaware. So get your calendar out–here come 16 Delmarva Events to look out for in 2016

First, one bit of fair warning. Official 2016 dates have not been formally announced for some of these events. You will see how some of the links go to information on the 2015 dates. Please confirm all dates in this list before making plans written in stone.

(1) Feb. 26-27, The National Outdoor Show in Golden Hill

The National Outdoor Show in Golden Hill, on Maryland's Eastern ShoreThe 71st annual edition of this timeless Eastern Shore classic will feature, as always, a sweet small-town beauty pageant, the World Championship of Muskrat Skinning, and lots of other stuff dripping with remote South Dorchester-ness.

Championship bonus: The Ward World Championship of wildfowl carving weekend will be April 22-24 in Ocean City.

(2) April 23, The Milford Bug and Bud Festival

Get your ladybug gear together, as that is the preferred fashion touch for this annual welcome-to-spring affair in Milford, Del. Shoppers can expect to find more than 100 vendors.

16 Delmarva Events in 2016: Springfest in Ocean City on Maryland's Eastern Shore(3) May 5-8, Ocean City Springfest

Let beach season begin! This inlet spring fiesta features football-field-sized tents full of interesting vendors. There is sure to be some top notch old-school country star on the bill, too. And the Boardwalk favorites you missed this winter will be ready to welcome you back with open arms.

(4) May 6-8, Dover Days

Get your Colonial on at the 83rd annual edition of this capital classic in Delaware. They promise more than 300 vendors to go with a slew of concerts, kids stuff, and re-enactor types.

Colonial alternative: At the Tea Party on May 27-29, downtown Chestertown will be mobbed, and some bad-guy Brits will get tossed in the river.

16 Delmarva Events in 2016: The Firefly Festival in Dover, in Southern Delaware(5) June 16-19, the Firefly Festival in Dover

Early bird passes to one of the world’s premier rock & pop festivals are on sale now.

Country alternative: Now in its second year, the Big Barrel Festival is aiming to be a country Firefly. It will be June 24-26, also in Dover.

(6) June 18-19, The Ocean City Air Show

The Blue Angels headlined this show last year. It was the Thunderbirds in 2014. With that kind of history, you get to start selling tickets–they are available now–before even announcing a lineup.

Easton alternatives: The Great Chesapeake Balloon Festival features public rides and a photogenic mass ascension. It will be on July 30-31 if they copy last year’s scheduling. Easton Airport Day, with its famous rubber chicken drop, will be on Sept. 24–again, that’s if they follow last year’s scheduling.

16 Delmarva Events in 2016: Running of the Bulls in Dewey Beach, in Southern Delaware(7) July 9, Running of the Bulls in Dewey Beach

Take a look at the photo here. It depicts maybe one-one thousandth of the belly-laugh zaniness this event strives to deliver every year.

(8) July 27-28, The Pony Swim and Auction in Chincoteague

Most people associate this humongous annual event with the Misty of Chincoteague books, but the event actually dates clear back to 1835–and maybe earlier. I wrote about that history for you here.

16 Delmarva Events in 2016: Blessing of the Combines in Snow Hill, on Maryland's Eastern Shore(9) Aug. 6, the Blessing of the Combines in Snow Hill

This is the year. I can feel it. After many years of bad deadlines and summer colds and scheduling snafus, I am finally going to make it to Snow Hill for this classic Shore event in 2016. Fingers crossed!

(10) Sept. 2-5, the National Hard Crab Derby in Crisfield

The Shore’s ultimate crab feast will be marking its 69th birthday this year on Labor Day weekend. There will be crab picking, crab cooking, crab races, and lots more crabby fun.

And more food fests: More seafood bliss will await at the Chincoteague Seafood Festival (May 7); the Tilghman Island Seafood Festival (June 25); the Taste of Cambridge Crab Cook-off (July 9); and the Chesapeake Bay Maritime Museum Oyster Festival (Oct. 29).

(11) Oct. 8-9 Apple Scrapple Festival in Bridgeville

This is another Delmarva staple that I hope to see in person for the first time this year at long last. I plan to starve myself a few days in advance to make extra room for scrapple. And I find it hard to believe what I keep seeing in event notices–can there really be more than 500 vendors at this affair?

16 Delmarva Events in 2016: Uncle Nace Parade in Trappe, on Maryland's Eastern Shore(12) Oct. 9, Nace’s Day Parade in Trappe

When it comes to Maryland’s Eastern Shore, this might be the oldest small-town tradition of them all, a celebration of the emancipation of the slaves. You’ll see at the link that I wrote a piece for the website with background on “Uncle Nace” Hopkins and the parade held annually in his honor. It’s a cool story.

(13) Oct. 28-30, the Sea Witch Festival in Rehoboth Beach (and nearby towns)

Hoo boy, they love them some Halloween over in Rehoboth! Hundreds of different events and attractions are involved in this over-the-top affair.

(14) Oct. 31-Nov. 2, the Downrigging Festival in Chestertown

This farewell-to-sailing-season blowout is one of the biggest annual tall ship festivals not just on the Eastern Shore, but on the whole East Coast. It’s the event pictured up top here.

Alternate rendezvous: Some of the boats headed for Chestertown stop en route to take part in the smaller but charming Schooner Rendezvous in Cambridge the weekend before–this year’s dates should be Oct. 21-23.

(15) Nov. 11-13, the Waterfowl Festival in Easton

The 2016 edition of this Eastern Shore stalwart will be its 46th annual go-round come November. There will be lots of waterfowl art, along with calling contests, dock dogs, fishing demos, and more.

16 Delmarva Events in 2016: Christmas Parade in St. Michaels, on Maryland's Eastern Shore(16) Dec. 9-11, Christmas in St. Michaels

While I can’t say I’ve been to all of the two dozen or so holiday parades held annually on the Eastern Shore and in Southern Delaware, I can say that the one that happens here on the Saturday morning of this weekend-long event is the best of the ones I have seen.

There you have it–that’s my list of 16 Delmara Events for 2016. If you have a favorite Eastern Shore or Southern Delaware event you would like to plug, feel free to do so in the comments down below here. Include a link, if you can. And please chime in there, too, if you know for sure about some of these 2016 dates that haven’t been announced formally yet.

Happy getting out and about in the new year!

–Written by Jim Duffy




  • Diane Johnson says:

    How can an irganization get their event listed?

    • Hi Diane,
      There are a couple of things you can do. The best is to tell me about the best online calendar of events for your area so that I can have it in the bookmark rotation of things I always check. The other is to send event into to me by email ( or in a FB message ( Only word of caution is that there are a lot more events in front of me every month that I can possibly put in, so be patient with that.
      Thanks! Jim

  • Karl Wolfe says:

    Thanks for this list. You’ve covered all my favorites and more. Perhaps add sandcastle contests to the list? Rehoboth has a good one every year.

  • Connie says:

    Thanks for the info, some of these I didn’t know about and I have lived here for 65 years!

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