Some people start to think of bonfires, pumpkin spice lattes and apple picking once the month of September rolls around, but on Delmarva, we’re still enjoying wonderful beach weather and less traffic.  We’re soaking up the last bits of summer, and looking forward to these amazing September Events.

Ocean City Hotel Week

When: August 28 – September 11

Where: Participating Ocean City Hotels, Ocean City, MD

What: Ocean City hotels offer wonderful deals for this annual event.  

National Hard Crab Derby

When: September 2 – 4

Where: Somers Cove Marina, Crisfield, MD

What: The Crab Capital of the World celebrates the end of summer with a carnival, parade, crab races and more!

Free Shakespeare Performance: Cymbeline

When: September 2 – 18

Where: Various Locations on Delmarva

What: Brown Box Theatre brings free Shakespeare performances to Delmarva every September.  This year, they will be performing Cymbeline. Performances are often outside around sunset.

Wings and Wheels Expo

When: September 3

Where: Ocean City Municipal Airport, Ocean City, MD

What: The Ocean City Municipal Airport welcomes a showing of private aircraft, cars and antique military vehicles.

Route 13 Speedway Fair

When: September 9 – 18

Where: Delaware International Speedway, Delmar, DE

What: Enjoy rides, live entertainment, fireworks and food at the Speedway in Delmar!

West Wicomico Heritage Day

When: September 10

Where: Pemberton Historical Park

What: A celebration of the quiet towns on the West side of Wicomico County.  Enjoy a bike tour, scavenger hunt to multiple historical sites, and guided tours at Pemberton Hall.

Brews on the Beach Craft Beer Festival

When: September 10

Where: Hooper’s Crab House, Ocean City, MD

What: A celebration of craft beer with live music and great food.

Cruzan the Bay

When: September 13

Where: Fish Tales, Ocean City, MD

What: Teams will walk and kayak to clean up the bay areas.

Delmarva Bike Week

When: September 15 – 18

Where: Winterplace Park and the Shorebirds Stadium, Salisbury, MD and Rommel Harley Davidson, Seaford, DE

What: Motorcycle enthusiasts will love this event, featuring live entertainment, vendors, demos and more!

OC Bikefest

When: September 15 – 18

Where: Ocean City Inlet, Convention Center and Boardwalk, Ocean City, MD

What: Live entertainment, stunt shows, vendors and artisan bike show.

Sand Castle Home Tour

When: September 22 – 23

Where: Designated Homes, Ocean City, MD

What: Take a self-guided tour through 10 gorgeous Ocean City homes.


When: September 22 – 25

Where: Ocean City Inlet, Ocean City, MD

What: An amazing display of arts and crafts, delicious food and live entertainment by the ocean.

Sunfest Kite Festival

When: September 22 – 25

Where: The Beach from 2nd – 6th Street, Ocean City, MD

What: Enjoy an incredible display of kites along the boardwalk and see master kite flyers from around the world.

Dewey Beach Music Conference

When: September 22 – 25

Where: Various Venues, Dewey Beach, DE

What: Enjoy great performances, connect with music industry professionals and attent mentoring sessions.

Berlin Fiddlers Convention

When: September 23 – 25

Where: Main Street, Berlin, MD

What: A street festival celebrating friendly fiddling and bluegrass competition.


When: September 24

Where: Main Street, Cambridge, MD

What: Eastern Shore and German fare come together for this fun event featuring carnival games, live entertainment and dancing.

Bluegrass on the Bay

When: September 29 – October 2

Where: Castaways RV Resort and Campground, Ocean City, MD

What: Bluegrass lovers gather for some of the best bands in the genre!

Taste of Chincoteague

When: September 30

Where: Chincoteague Center, Chincoteague, VA

What: Enjoy food samplings from local eaters, live entertainment and local and regional artwork.

Wine on the Beach

When: September 30 – October 1

Where: Ocean City Inlet, Ocean City, MD

What: Sample wines from across the Mid-Atlantic area, receive a complimentary wine glass and enjoy a selection of vendors.

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