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Good Times & Fun Events

50 October/November Fundays 2026

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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 Scrapple Festival in Bridgeville, Del.  Fri/Sat Oct 9/10.
• The Amish School Auction Sat Oct 17 in the countryside west of Dover.
Sunfest weekend at the Inlet in Ocean City, Md. Oct 22-25.
• The Seawitch Festival in Rehoboth Beach, Del. Oct 23-25
Downrigging weekend in Chestertown, Md. Oct 30-Nov 1
* Hey, that’s a sweet downrigging photo!

Twilight at Downrigging 1200 Chestertown Maryland

Festivals & Parties!

• Pumpkins galore: Fall Kick Off Weekend Easton, Md. Sat/Sun Oct 2/3.
• The Eastern Shore of Virginia Agricultural Fair Sat Oct 3 in Machipongo, Va.
• The Boast the Coast Maritime Festival Sat Oct 3 in Lewes, Del.
• Prohibition days come alive at the BB Speakeasy Thu Oct 8 in Stevensville, Md. J. Coursey Willis will tell bootleggin’ tales.
• A revolutionary evening with Patrick Henry Fri Oct 9 in Onancock, Va.
• The Apple Scrapple Festival in Bridgeville, Del. is a Delmarva classic. If you haven’t been, get Fri/Sat Oct 9/10 on your calendar.
• Adkins Arboretum near Ridgely, Md. has a kid-friendly Fairyfest Sat Oct 10.
The Richardson Maritime Museum in Cambridge, Md. is throwing a Boatyard Bash on Sat Oct 10. I’ll be telling some stories there.
Harbor Day at the Docks is back in West Ocean City, Md. Sat Oct 10.
• Little Sudlersville, Md. is throwing a Community Picnic Sat Oct 10–there will be some Old Fashioned Baseball going on as well.
• Thick-with-history Crisfield (Md.) has a Heritage Festival Sat Oct 10.
• Church Hill, Md. has a Fall Fest Sat Oct 10.
• Rackliffe House’s Colonial Harvest Festival Sun Oct 11 near Berlin, Md.
• Bowers Beach, Del. has stories to tell, too. That Heritage Day is Sun Oct 11
• The Amish School Auction Sat Oct 17 on a farm west of Dover, Del. is for bargain hunters and browsers and people watchers alike.
• Seafood and boat docking and Bird Dog and Road Kings and more at Tilghman Island (Md.) Day Sat Oct 17
• Thick-with-history Eastville, Va. has a Heritage Festival Sat Oct 17.
• Schellville’s Fall Festival is  Sat/Sun Oct 17/18 in Rehoboth Beach, Del..
Fall Into St. Michaels (Md.) Sat/Sun Oct 17/18.
Blackbird Creek Fall Festival in Townsend, Del. is Sat Oct 17
• The famous Milford (Del.) Community Parade is Wed Oct 21.
• The big Sunfest party at the Inlet in Ocean City, Md. is Oct 22-25.
• Celebrate Centreville (Md.) Day Sat Oct 24.
• Tall ships galore at Downrigging weekend in Chestertown, Md. Oct 30-Nov 1. You will need to reserve spots on public sails well in advance.
Delaware Renaissance Faire, Sat Oct 31 to Sun Nov 15 in Townsend, Del.
• Head to Georgetown, Del. on election day–Thu Nov 5–to experience one of Delmarva’s oldest and grandest traditions, Return Day.
• Meet, greet, and shop with local authors galore (including yours truly) at the Holiday Book Festival Sat Nov 7 at Cult Classic in Stevensville, Md.
• At the Delaware Heritage Festival in Dover Sat Nov 7 you’ll step back in time to shop an 18th century marketplace, meet brave suffragists, and more.
Fungi Fest Sat Nov 7 at Pocomoke River State Park near Snow Hill, Md.
• The humongous Waterfowl Festival in Easton, Md. Nov 13-15 is a town-wide festival with art and dock dogs and street musicians and lots more.

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Music & Theater

• The Country Calling festival in Ocean City, Md. Oct. 2-3 has Lainey Wilson, Rascal Flatts, Chris Stapleton, Miranda Lambert, and more.
• Enjoy Jazz on the Waterfront in Crisfield, Md. Sat Oct 3
• This year’s edition of Rockin the Porch in Centreville, Md. has Sweet Leda, J. Coursey Willis, Mama’s Black Sheep, and more, Sun Oct 4.
• Enjoy Great American Songbook selections by The Jazzmen during a “Jazz in the Afternoon” concert in Rehoboth Beach, Del. Sun Oct 4.
• A Mid-Atlantic Symphony horn/piano ensemble, three shows Oct 9-11–Ocean Pines, Md.; Rehoboth Beach, Del.; Easton, Md.
• The traditionalist True Blue Jazz Festival in Rehoboth Beach, Del., Oct 14-18. One highlight: The four-group Big-Band Jazz Marathon.
• The Rehoboth Jazz Festival in the same town on the same weekend (Oct 15-18) has violinist Damien Escobar, pianist Walter Beasley, and many more.
• The touring rendition of the Broadway classic The Music Man is coming to Ocean City Sun Oct 18.
Pianist ​Awadagin Pratt–Coastal Concerts show Sat Oct 24 in Lewes, Del.
• Musical comedy take on Mrs. Doubtfire Thu Oct 29 in Ocean City, Md.
• Discover Armenian folk music with Naghash Ensemble Wed Nov 4 at Salisbury (Md.) University.
• Dogfish Head’s Analog a Go Go party is Sat Nov 7 in Milton, Del. Live music in addition to voluminous vinyl.
• Look up more theater shows here by checking the schedules of troupes based in various Delmarva towns.
• Look up more music shows here by checking on the schedules at your favorite concert venues.

Speakeasy!

• Jill and I are ready to travel back in time for the BB Speakeasy Thu Nov 8 at Cult Classic in Stevensville, Md. The great J. Coursey Willis will be tellin’ bootlegging tales. Specialty cocktails. Book signings with regional authors, including me. Photo backdrops. Costume contest. More.

• The party is put on by Brackish Books–have you been to their new store in Centreville, Md.?

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Scary Stuff!

• This is the biggest month of the year for Chesapeake Ghost Tours, so you might want to reserve a walking (or sailing) tour in advance. Ten or so towns on Maryland’s Eastern Shore.

• Super talented regional writers are going to tell original Scary Stories Thu Oct 15 at Cult Classic in Stevensville, Md. The event sold out last year, so don’t dawdle over buying tickets. Oh, and they let me in the lineup too.

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Art Attack! 

• Head to Stevensville, Md. to help the creative souls there celebrate Artoberfest Sat Oct 3
• Hang with literary artists in a 1920s gin mill environment at the BB Speakeasy party Thu Oct 8 in Stevensville, Md.
• This year’s edition of the Chesapeake Film Festival is Oct 8-10 in Easton, Md.
Fall Into the Arts on beautiful Chincoteague Island, Va. on Sat Oct 17.
• This year’s edition of the Upper Shore Decoy Show is Sat Oct 17 in Perryville, Md.
• The Rehoboth Film Festival in Rehoboth Beach, Del. runs Nov 1-8.
• The Plein Air painters will be working (and competing) at gorgeous Adkins Arboretum on Sat Nov 7–yes, works will be for sale.
• The Furnacetown Historic Site near Snow Hill, Md. is throwing a Fiber Festival on Sat Nov 7.
• The Rehoboth Beach Art League’s annual Holiday Fair Fine Craft Show is Sat/Sun Nov 7/8.

Food & Drink!

• The 86 Hook and Ladder Coastal Brew Fest happens at the Rehoboth Beach (Del.) Convention Center Sat Oct 3.
• The Blues & Brews party in Lewes, Del. Sun Oct 4 in part of the Rockin’ the Docks concert series.
• The Good Beer Festival returns to pretty Pemberton Park in Salisbury, Md. isFri/Sat Oct 9/10.
Dogfish Head is throwing a Pumpkin Ale Fest Sat Oct 10 in Milton, Del.
• Salted Vines winery in Frankford, Del. is celebrating Grapetoberfest Sat/Sun Oct 10/11.
• The big Oktoberfest party in Cape Charles, Va. is put on by St. Charles Borromeo Catholic Church. Sun Oct 11. Auctions, food, music, bounce house, etc.
• The Oktoberfest block party in Berlin, Md. Sat Oct 17. Two music stages, German food, big sidewalk sales, jugglers, petting zoo …
• Sip wine while looking out at Tangier Sound during Crisfield (Md.) Uncorked Sat Oct 17.
• Patriot Acres brewery is throwing a Beef and Brew party Sat Oct 17,  Sudlersville, Md.
• The Wine on the Beach party in Ocean City, Md. is now part of Sunfest weekend, a ticketed wristband option for Sunfest attendees. Fri/Sat Oct 23/24.
• Hot dog! RAR Brewery’s annual Glizzy Fest block party in downtown Cambridge is Sat Oct 24.
• Schellville is putting on its annual big Brew Bash Sat Oct 24 in Rehoboth Beach, Del.
• Who’s the king (or queen) of mac n cheese? Find out at Mactoberfest in Denton, Md. Sat Oct 24. Yes, there are tastings.
• A dozen chefs will contribute to The South You Never Ate” dinner in Chatham, Va. Sat Oct 24. Event honors the late, great foodie and historian Bernard Hermann and his lifetime of work documenting the culinary traditions of Virginia’s Eastern Shore.

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Cartoberfests!

• This year’s Wings and Wheels show in Georgetown, Del is Fri/Sat Oct 2/3.
• The Easton (Md.) Fire Dept. has a Hot Rods & Hose show Sat Oct 3.
• The Endless Summer Cruisin’ car extravaganza is on the long weekend of Oct 8-11 in Ocean City, Md.
• That same weekend–Sat Oct 10–is the
Berlin (Md.) Fall Cruisers show, a short drive from OC. 

The Monks!

Every couple of years monks from the famed Drepung Loseling Institute in Tibet visit Salisbury (Md.) University to do a residency that includes the creation of a sand mandala as well as various public ceremonies, lectures, and other associated events. This years dates are Oct 13-17. New this time: A Walk for Peace on Thu Oct 15. Scroll to date here for details.

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Halloween!

Rocky Horror at Clear Space Theatre in Rehoboth Beach, Del. Oct 9-31.
• The fun and ridiculous Zombie Fest put on by the Milton Theatre returns to Hudson Fields near Lewes, Del. Sat Oct 17.
Furnacetown Historic Site near Snow Hill, Md. will be celebrating Halloween in the Forest Sat Oct 17.
• The Witches of Rock Hall will gather for a weekend of camaraderie, partying, and, uh, paddleboarding Fri/Sat Oct 23/24.
• The weekend long Seawitch Festival in Rehoboth Beach, Del. encompasses dozens of different events and attractions, all highlighted by a big Saturday morning parade. Oct 23-25.
Wicked Brew Bash Sat Oct 24 at Schellville in Rehoboth Beach, Del.
• On Sun Oct 25 Schellville has its annual Spooktacular Kids Zone.
• The Pumpkin Palooza Parade in Denton, Md. is Fri Oct 30.
• Who remembers the Morbid Manor haunted house from days gone by in Ocean City, Md. Even if you don’t, the memories on this page are great fun.

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This spooky marshland image is by Jill Jasuta Photography. Want to see what she had to say about this shot? Want to see more of her work?

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