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Eastern Shore Fun

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50 October/November Fundays 2026 Good Times & Fun Events

50 October/November Fundays 2026

Oyster Festivals! Tis the sason! Chincoteague, Saxis, Easton, Exmore, Rock Hall, Tilghman, Machipongo, Snow Hill ... Here is where to go for the low down on more than a dozen oyster roasts and seafood parties on the horizon. TL/DR: October Classics What five October events (not counting the oyster fests) get the most clicks in this newsletter year in and year out? • The Apple…
September 1, 2026
50 September Fundays Good Times & Fun Events

50 September Fundays

Skipjack Triple Crown! • The Deal Island (Md). Skipjack Festival and Races happen Sun Sept 6 and Labor Day Mon Sept 7. Races on Monday morning. • The Annapolis race on Sun, Sept 13 is part of the Maryland Seafood Festival (Sept 11-13) at Sandy Point State Park. • The Choptank Heritage race in Cambridge, Md. is Sat Sept 26. • Isn't the photo here…
September 1, 2026
By In The Newsroom

Delmarva Storyteller Jim Duffy in Bethany Beach, Del. on Tue., Nov 10

Delmarva storyteller Jim Duffy from Secrets of the Eastern Shore and WBOC-TV's "DelmarvaLife" will spin fun and fascinating true-life tales…
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Christmas Poem McKinsey 1919 Featured Photo SIZED
Delmarva Storyteller Jim Duffy in Pocomoke City, Md. on Thu., Oct 1 The Newsroom

Delmarva Storyteller Jim Duffy in Pocomoke City, Md. on Thu., Oct 1

Delmarva storyteller Jim Duffy from Secrets of the Eastern Shore and WBOC-TV's "DelmarvaLife" will spin fun and fascinating true-life tales from Delmarva days gone by on Thu., Oct. 1, 2026 at the Delmarva Discovery Museum in Pocomoke City, Md. The show starts at 6:30pm. Jim Duffy Duffy has written six books about the Delmarva Peninsula, including two collections of Eastern Shore Road Trips. His latest…
September 1, 2026
Oyster Roasts Delmarva Eastern Shore 2022 Featured Photo
Delmarva Oyster Roasts: Fall and Winter 2026/’27 Good Times & Fun Events

Delmarva Oyster Roasts: Fall and Winter 2026/’27

In other parts of the world, the first chilly nights of autumn bring an end to outdoor festival season. But when cold winds start blowing here on Delmarva, it’s time to break out an extra layer or two and head out to slurp down bivalves and beer. There are dozens of oyster festivals between October and March--some outdoors, some indoors. Here are a few of…
August 24, 2026
Labor Day Events on the Delmarva Peninsula
The Labor Day Classics, 2026 Good Times & Fun Events

The Labor Day Classics, 2026

Labor Day weekend means classic Delmarva events. Think skipjack festival, crab derby, jazz funeral, and kazoo parade. If you subscribe to the Fundays newsletter, you already got this info in your email inbox. If you don’t subscribe, here ya’ go: The 79th (!) annual edition of the Hard Crab Derby in Crisfield, Md. runs Thu-Sun Sept 3-6. The Deal Island (Md). Skipjack Festival and Races…
August 22, 2026
Photo of Ocean City Boardwalk for Labor Day Riot Featured Photo
In 1960, the ‘Labor Day Riot’ Had a Mob of 2,500 Angry Teens Marching the Streets of Ocean City, Md. Way Back Machine

In 1960, the ‘Labor Day Riot’ Had a Mob of 2,500 Angry Teens Marching the Streets of Ocean City, Md.

This is one of the 44 “Strange and Wondrous Delmarva Tales” in my book titled You Wouldn’t Believe! More info on the book here. The incident that set off the Labor Day Riot in Ocean City, Md. began as a trifling affair. On the Saturday evening of Sept. 4, 1960, the owner of a boardwalk arcade got into a little spat with a young man…
August 4, 2026
By In Way Back Machine

News Flash, 1930s: The Fox Trot Sails into Controversy on Smith Island

In April 1938, concerned citizens of Smith Island, Maryland sent a delegation to the mainland. The cause was urgent, a…
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Peach Festivals Delmarva Featured Photo
The 2026 Delmarva Peach Festival Season Is Here … Good Times & Fun Events

The 2026 Delmarva Peach Festival Season Is Here …

This is the link where you can go straight to info on seven different Delmarva peach festivals coming up in late July and August of 2026. But wait ... why peach festivals? Here is how I answer that question in my book, Shore Fun! The Delmarva Wanderer's Guide. It has easy-as-pie, snapshot info on 150+ annual events and 125+ fun destination on the Eastern Shore…
June 28, 2026
Fundays Summer Happy Dog Featured Photo
Summer of Fundays! 75+ Hot Events & Happenings on Delmarva in July & August Good Times & Fun EventsMonth of Fundays Newsletter

Summer of Fundays! 75+ Hot Events & Happenings on Delmarva in July & August

Best summer ever! The 2026 Summer of Fundays newsletter will help you make it happen with 75+ hot events and happenings and shows and exhibits and festivals and more. Here is the link. • County fairs & fire company carnivals! • Hot air balloon fest in Dover! • Easton's big art show! • The Chincoteague Pony Swim! • The Blessing of the Combines street party!…
June 21, 2026