This time of year is always a bit of a paradox for us. While we hate bidding farewell to the month of August and the glory of summer, we also welcome September with very open arms. We love September for SO many reasons here on Delmarva (especially in Ocean City), but mostly for the fantastic line-up of events that come with it. Our event calendar is teeming with options at the moment, leaving us struggling to figure out how we are possibly going to fit it all in! The month starts off strong with free Shakespeare performances across Delmarva, as well as the National Hard Crab Derby in Crisfield. Mid-month, we’ve got our eyes on Delmarva Bike Week, Oktoberfest in Lewes, and the Berlin Fiddler’s Convention. The last weekend of the month is chocked full with festivals, including Kite Fest, Sunfest, Layton’s Chance Harvest Festival, and Pocomoketoberfest. And that’s not all! Take a look at what’s happening in September on Delmarva…

Brown Box Theatre Presents: The Taming of the Shrew

When: Various Times

Where: Delmarva

What: Our friends at Brown Box Theatre return to the Eastern Shore this month for another fantastic year of FREE, outdoor Shakespeare performances! This year, the talented theatre group will perform The Taming of the Shrew, with performances in Berlin, Snow Hill, Ocean City, Salisbury, Pocomoke City, St. Michaels, Lewes, Rehoboth and Princess Anne throughout the entire month. Click here for the full schedule.

National Hard Crab Derby

When: Labor Day Weekend (Sept. 3-6)

Where: Somers Cover Marina, Crisfield

What: We love any excuse to make the drive to Crisfield, especially when Maryland blue crabs are involved! The National Hard Crab Derby is a weekend-long event, featuring crab races, crab cooking and picking contests, carnival rides, arts and crafts, vendors, live entertainment, beauty pageants, a parade, fireworks and more! This is definitely one of our summer bucket list items!

Wings and Wheels Expo

When: Saturday, September 5, 10am-2pm

Where: Ocean City Airport

What: Bring the whole family out for the annual Wings and Wheels Expo in West Ocean City. Private aircraft, custom cars, and antique military vehicles will be on display, along with their owners who will be available to answer questions. Admission is $5 per person, children under 12 are free.

Paddle for a Purpose

When: Saturday, September 5

Where: Ayers Creek Adventures Paddle for a Purpose

What: Ayers Creek Adventures is dedicating an entire day to giving back to the local community by donating all tour and rental proceeds from September 5 to the following charities: Maryland Coastal Bays Program, Lower Shore Land Trust, Worcester Youth and Family Counseling Services, Habitat for Humanity Worcester County, and Women Supporting Women Worcester County. Rentals are available from 8:30am until 5pm, with two tours available as well, one at 9am and the other at 1pm. Reservations are required for the tours.

Cars & Coffee

When: Sunday, September 6, 8:30am-10:30am

Where: Rosenfeld’s Jewish Delicatessen

What: Cars & Coffee returns to the Rosenfeld’s and Dead Freddie’s parking lots this Sunday, as car enthusiasts line up for the free event. Enjoy classic and custom cars and motorcycles before or after you grab breakfast and coffee at Rosenfeld’s.

9/11 Parade of Brothers

When: Friday, September 11, 8:30am-1pm

Where: Boardwalk, Ocean City, MD

What: The annual Parade of Brothers event takes place along the Boardwalk in OCMD, with a motorcycle ride and memorial service to commemorate 9.11.2001. It’s a great opportunity to enjoy the beach and boardwalk while paying tribute to 9/11. Look for our pics if you can’t make it!

Food Truck Friday in Rehoboth

When: Friday, September 11

Where: Epworth United Methodist Church

What: Two of our favorite things, Fridays and food trucks, combine forces for a fundraiser for Epworth’s Food and Love Soup Kitchen and Epworth Skate Park. Ten vendors will be on the scene, dishing out a diverse selection of menu items. Participating vendors will include The Sea Hogg, Maxie’s Grill, Jakarta’s, Sherri’s Crab Cakes, Mojo Loco – eclectic street food, Mr. BBQ, Hot Dogs at the Beach, Mama Mia, Sno Yo, and Vanderwende’s Farm Fresh Ice Cream.

Cambridge Summer Send-Off: Blues, Brews & BBQ

When: Saturday, September 12, 5-10pm

Where: Downtown Cambridge

What: This signature Cambridge event is one of our favorites, with plenty of blues, brews and BBQ to enjoy as the crowds collectively bid farewell to summer. The festival is free, and boasts fun for the kids, live local music, and the ‘wacky Main Street mile relay race.’ Food vendors will also be on the scene, along with craft brews and cocktails.

Brews on the Beach

When: Saturday, September 12, noon-5pm

Where: Hooper’s Crab House

What: Craft beer lovers, this one is for you! Live music, great food, and local beer are the featured headliners for this annual Ocean City event, which includes a massive selection of local craft beer like 3rd Wave, Evolution, Burley Oak, Fin City, Tall Tales, Backshore, and more! Tickets are $25 in advance or $30 at the door ($10 for designated drivers).

37th Annual Bethany Boardwalk Arts Festival

When: Saturday, September 12, 10am-5pm

Where: Downtown Bethany

What: The popular one-day show returns to downtown Bethany Beach, with jewelry, glass, pottery, watercolor and oil painting, photography, basketry, woodworking, and much, much more! Expect to see over 100 juried artists as well, as they display their works of art along the bandstand and boardwalk. Don’t forget to stock up on goodies at the Farmer’s Market, located in the PNC Parking lot (10am-2pm).

River City Arts Jam

When: Saturday, September 12, 10am-7pm

Where: Downtown Riverwalk, Salisbury

What: The Salisbury Fall Festival of the Arts aims to support downtown revitalization, local arts, and tourism with a full day of arts, entertainment, food and more! Held along the Riverwalk in downtown Salisbury, the event will also feature art sales, demonstrations, and vendors along with plenty of kid’s activities. Support downtown Salisbury while enjoying a fun-filled afternoon in Salisbury with the whole family.

8th Annual Boat Docking Contest at Brew River

When: Saturday, September 12, 1pm

Where: Brew River, Salisbury

What: The highly-anticipated boat docking contest returns to Brew River for its 8th year, with what will undoubtedly be another afternoon of fun along the river in Salisbury. Admission is $10 for adults and $5 for children and includes some truly unique Eastern Shore entertainment.

Doggie Swim Fundraiser for WCHS

When: Saturday, September 12, 10am-2pm

Where: Mumford’s Landing Pool, Ocean Pines Yacht Club

What: It’s Doggie Swim Saturday! The Worcester County Humane Society presents this unique fundraising event at Mumford’s Pool Landing just before the pool closes for the season. Cost is $6 per dog, with two hours of swim and playtime in the pool. Dogs under 20-pounds will swim from 10-12, with all others jumping in from 12-2. All proceeds will benefit the WCHS.

2015 Historic Georgetown Art Crawl & Annual Farmer and Foodie Festival

When: Sunday, September 13, 10am-4pm

Where: Downtown Georgetown

What: This dual event will feature artists, area art leagues, and a juried art show in conjunction with the annual Foodie & Farmer Festival, which celebrates our local farmers by creating awareness for their farm fresh foods, food products, and culinary talents. This rain or shine event is fun for all ages and FREE.

Lewes Dragon Boat Festival

When: Sunday, September 13, 10am

Where: Canalfront Park, Lewes

What: The Sussex Academy Foundation presents the 3rd Annual Dragon Boat Festival, a capital campaign for the Sussex Academy, which is a local public charter school serving students in grades 6-11 in Sussex County. Teams will pile into their dragon boats for a morning of competitive fun for a great cause. Head to the scenic Canalfront Park and enjoy what will undoubtedly be a beautiful September day in Lewes.

Lewes’ 4th Oktoberfest Celebration

When: Friday, September 18, 4-6:30pm

Where: Historic Lewes (Market Street, between Front Street and Second Street)

What: The Lewes Chamber of Commerce’s Historic Lewes Business Committee proudly presents their fourth Oktoberfest celebration this month with all the typical Oktoberfest fun – good beer and German food! Dogfish Head Brewery will sponsor the event again this year, so look for their commemorative glass beer steins, available for $7 each starting September 17 at the Chamber’s visitor center and at the festival. Bring your stein to participating restaurants for a discount on Dogfish beer too! And don’t forget to check out the Bavarian-style dancers and 10-piece German Oompah band performing in the streets.

23rd Annual Berlin Fiddler’s Convention

When: Friday, September 18 & Saturday, September 19

Where: Main Street, Berlin

What: It’s no secret that the annual Berlin Fiddler’s Convention is one of our favorite events of the year, and with two days of free, family-friendly entertainment in Downtown Berlin, who can blame us! Bob Perilla and Big Hillbilly Bluegrass will hit the concert stage Friday night, along with last year’s band competition victors, Such Fools. Saturday, enjoy a full day of entertainment as Main Street shuts down for the annual Fiddler’s Convention and Competition. More to come!

Paint Berlin

When: September 17-19

Where: Berlin

What: Artists will gather in and around Berlin for the 6th Annual Paint Berlin Plein Air event. Artists are tasked with painting outdoors over the three day event, which will culminate with the Wet Paint Sale & Exhibit on Saturday, September 19 from 1-4pm at the Worcester County Arts Council Gallery.

Delmarva Bike Week/OC Bikefest

When: September 17-20

Where: Various Locations

What: Bike Week is coming up on its 15th year on Delmarva, with OC Bikefest celebrating its 5th year. This year, expect plenty of live music, vendors, participating local businesses, and of course, bikes! Thousands of motorcycles will head to Delmarva and Ocean City for the event, which is heralded as one of the biggest events of the ‘shoulder season’ for Ocean City.

36th Annual Sunfest Kite Festival

When: September 24-27

Where: The Kite Loft, Ocean City

What: The entire family will enjoy the annual Kite Festival in OCMD, which includes five full days of kite competitions, games, relays, mass ascensions, workshops and fun. Visit for the full schedule and stay tuned for our full article as the event nears.


When: September 24-27

Where: Inlet Parking Lot, Ocean City

What: Sunfest marks the official end of summer for us in OCMD, with a summer sendoff featuring food, crafts, hayrides, kid’s activities, and musical entertainment. This year’s headlining acts are Tony Orlando (Thursday), Wynonna Judd & the Big Noise (Friday) and the Gin Blossoms & The Spin Doctors (Saturday).


When: Saturday, September 26, 2-8pm

Where: Cypress Park, Pocomoke City

What: The annual beer and wine festival features a wide array of Eastern Shore beers and wines, along with free tastings, a commemorative glass, great food and live music. Advanced tickets are $15 and $25 at the door. There are also non-drinking passes for $5. For more information, contact the Pocomoke Chamber at 410-957-1919 or

BLOC Party – Berlin Library, Our Community

When: Saturday, September 26, 2-6pm

Where: Harrison Avenue (behind the library, next to the Waystead Inn), Belin

What: The Berlin branch of the Worcester County library invites you to join them as they kick off their fundraising campaign for a new branch library! Pony rides, face painting, raffles, games, and a moon bounce are just a few of the kid’s events on tap, along with music by the WWIIunes.

6th Annual Layton’s Chance Harvest Festival

When: Saturday, September 26, 11am-5pm

Where: Layton’s Chance Vineyard, Vienna, MD

What: Grape stomping, hay rides, a fishing derby, tours, live music, vendors and plenty of wine await you for the 6th Annual Harvest Festival at Layton’s Chance! Tickets are $5 per person.