Here at ShoreBread, we embrace the month of September wholeheartedly. We are always sad to see another summer come to an end, but the dawn of September means chillier mornings, less crowded beaches, pumpkin-flavored everything and the start of the off-season. For locals in the resort towns, we look forward to the change of the seasons because it brings a little less traffic and a chance to enjoy our little towns again without all of the hustle and bustle (and Rt. 50 backups). Despite a decline in tourist activity, September is still also one of the busiest months for Ocean City and the surrounding Eastern Shore towns, with events across Delmarva each weekend of the month. With festivals every weekend; we can guarantee that you can’t pass up at least one of them.

So happy (almost) September to all of you! As sad as we are to wrap up August, the fall brings with it new beginnings, cooler weather and a whole lot of fun!

Brews on the Beach

September 6th

Brews on the Beach is Hooper’s annual (and highly anticipated) craft beer festival. This event has become a fast favorite amongst locals as they offer a serious sampling from our favorite local breweries, along with live music, great food and usually (fingers crossed) amazing weather. The event is held outside in the parking lot at Hooper’s Crab House. Expect to see some local favorites being poured, including: 3rd Wave Brewing Co, 16 Mile, Fin City Brewing Co, Burley Oak, Evolution, De Lazy Lizard, OC Brewing Co, Tall Tales, Backshore Brewing, Dogfish Head and Assawoman Bay Brewing. The event is held from noon until 5PM and your $35.00 ticket includes unlimited samples and great live entertainment. This is one of the hottest events of the fall and something you don’t want to miss…we sure won’t!


September 6th

If you’re looking for a fun way to spend your Saturday… look no further than Pocomoketoberfest. The Pocomoke festival is celebrating its 3rd anniversary this year, which means more fun and of course, new beer and wines to sample. The annual beer and wine festival is located in Cypress Park in Pocomoke from 12PM to 6PM, and if you’ve never spent the day in Pocomoke, this is a great excuse to check out the adorable town and the scenic surroundings.  Local breweries slated to attend the event are Evolution, Burley Oak, 3rd Wave Brewing Co, 16 Mile Brewery and Dogfish Head. Local wineries are: St Michaels Winery, Great Shoals, Layton’s Chance and Fenwick Wine Cellars. In addition to beer and wine for purchase, live entertainment will be set up.

Pocomoke Plein Air

September 5th & 6th

If we haven’t made it clear enough to you, you need to experience a plein art festival. They’re abundant across the Eastern Shore and quite frankly, we love it. Watching artists at work in their natural surroundings is awe-inspiring and made even better by the fact that those same pieces of art are then displayed and put up for sale. Pocomoke celebrates their annual plein art event starting Friday, September 5th in Downtown Pocomoke and Saturday, September 6th on the Pocomoke River. The best part about this is how close it is to Pocomoketoberfest – we suggest making a day out of it starting at the Plein Art Fest and then ending your Saturday at the Pocomoketoberfest with a cold brew and some great food!

7th Annual Salisbury River Run Boat Dockin’ Contest

September 6th

Starting on Saturday at 1PM at the Dock Bar at Brew River, the 7th Annual Boat Dockin’ Contest will take place. Doors open at 11AM. Each year, hundreds of spectators come to check out the area’s most talented watermen as they compete to see who can dock their boats the fastest. There are two classes- small and large boats – and the crowd gets to cheer on their favorite’s right from the docks. In addition to the title of “fastest boat docker” there are cash prizes available. This is an event that supports our local watermen so what are you waiting for?! Did we mention Brew River has delicious food and a wide selection of beverages to enjoy while you cheer on the contestants?! Yep, it’s pretty much the perfect Saturday afternoon in Salisbury.

36th Annual Bethany Beach Boardwalk Arts Festival

September 6th

Hosted by the Bethany-Fenwick Area Chamber of Commerce, the Bethany Beach Boardwalk Arts Festival is an event all locals look forward to. Held in Downtown Bethany Beach from 10AM-5PM on Saturday, September 6, the event promises an eclectic array of vendors and activities. This year there are over 100 artists featuring paintings, metal, clay, jewelry, baskets, porcelain and more. In addition to the arts festival, there will be a farmer’s market, a wine tasting, and a place for kids to have fun.

Brown Box Theater Performance of Macbeth

Various Dates

Brown Box Theater returns this September and as Shakespeare enthusiasts, we couldn’t be more excited for another chance at Shakespeare in the park! The Boston-based group embarks on a five-week tour each year that brings them to dozens of locations across Delmarva including Berlin, Ocean  Pines, Snow Hill, Ocean City, Princess Anne, Easton, Lewes, Salisbury, Rehoboth, Pocomoke and Stevensville. The performances are free to the public and will begin promptly at 7:30PM and last until 9:30PM.  Bring your own chair or blanket and enjoy the welcome splash of culture and arts here on the Eastern Shore. For more information on dates and locations, click

OC Bike Fest

September 11th– 14th

Each year, Ocean City and the surrounding areas welcome thousands upon thousands of motorcycle riders. Because of the beautiful weather, fun activities and breathtaking scenery, this event is very popular and seems to grow more and more each year. OC Bike Fest is an off-shoot of Delmarva Bike Week and takes place at the Ocean City Convention Center, Ocean City Inlet and other various supporting businesses around town. The pricing is $35.00 for the event pass and includes tons of concert admissions, stunt arenas and exhibitors.  Even if you aren’t riding a motorcycle into town, the Bike Week crowd is always friendly and fun and the events are to be enjoyed by all.

Annual West Wicomico Heritage Ride

September 13th

Wicomico County is known as ‘cycling country’ because of their wide and flat roads. This bike tour’s main goal is to focus on appreciating our Eastern Shore heritage. It takes riders across 300 years of Maryland history, starting at Pemberton Historical Park- which is a plantation home built in 1741. From there you explore towns such as Whitehaven, Hebron and Quantico. During the ride, you can choose from a 32, 50 or 62 mile ride. Each ride includes rest areas and a celebration when you make it back to Pemberton Historical Park for an outdoor picnic, beer and live music. The ride starts at 7:00AM and goes until 2:30PM. (Participation costs $40.00 per rider.)


September 18th– 21st

Sunfest is hailed as the unofficial end of the summer season for Ocean City and marked as  one of our favorite fall events. When the weather works in our favor, Sunfest can bring just as many people as a busy summer weekend in July. In addition to massive white tents selling any craft you can imagine and stellar concert performances, Sunfest offers some of our favorite fair-style foods (ahem, fried goodies galore!). You can’t beat the atmosphere, especially with a view of the Atlantic Ocean in your background. To top off the fun, Sunfest also includes an annual Kite Festival, located on the beach between 2nd and 6th Streets courtesy of the Kite Loft. Thousands of spectators will enjoy kite making workshops, kite battles, demonstrations, aerial displays and more.

Berlin Fiddler’s Convention

September 19th– 21st

This beloved event is a serious favorite of locals all across Delmarva. The Berlin Fiddler’s Convention has taken place on Berlin’s Main Street for almost 22 years. Bluegrass musicians from across the country descend upon Downtown Berlin to battle it out for prizes in a variety of competitions. The event is free and officially kicks off at 7PM Friday night with a live performance from last year’s winners, The Wood Pickers.  In addition to the amazing music, there will be food vendors, Hotel Atlantic’s famous orange crushes and much fun to be had!

St. Michaels Oyster Crawl

September 25th

Fordham Brewing Company and the Chesapeake Bay Maritime Museum are presenting the first ever St. Michaels Oyster Crawl on Thursday, September 25th for a limited number of people. The event takes place from 4-7PM and features a history lesson at the Museum followed by a walking tour of St. Michael’s historical district for oyster stout and oysters at four amazing waterfront restaurants. During the brief history lesson, the museum will offer local Choptank oysters and a 12-ounce tasting glass of the new oyster brew, Rosie Parks Oyster Stout. For all of you oyster lovers, that’s not all…you’ll also get to enjoy oysters a variety of ways including oyster Rockefeller, oysters casino and raw on the half shell. The cost for the crawl is $65 per person with limited registration. Make sure to register before September 22nd!

Wine on the Beach

September 26th– 27th

This is the 19th year for the annual Wine on the Beach Festival in Ocean City so it’s safe to say they’re doing something right. Located near the inlet, the festival features wines from all over the region. In addition to wineries, the event includes micro-brewed beers, Delmarva Cuisine, arts and crafts and live music. Admission is $30.00 at the gate with photo ID. Some of the wineries included are: Boordy Vineyards, Dove Valley Vineyards, Knob Hall Winery, Legends Vineyard, St. Michaels Winery, Solomans Island Winery, Fenwick Cellars, Horton Vineyard and more. Breweries: Fat Tire and St. Michaels Ale.

Seagull Century

September 27th

The most popular cycling competition in the area takes place on Saturday, September 27th. Seagull Century welcomes cyclists from across the country to participate in the 100 mile race through the picturesque Eastern Shore. It’s a weekend full of exercise, along with celebrating the City of Salisbury, Salisbury University and the surrounding areas on the Eastern Shore.

So there you have it! Enjoy September on the Eastern Shore for all it’s worth and attend some (or all) of these events. And stay tuned for ShoreBread’s coverage of all your favorite events this fall, from interviews to photos to weekly updates!

Looking for a place to stay? We’ve got that covered too – click here for more!