The transition from summer to fall is equal parts bittersweet and rousing. While we loathe seeing summer go, we also welcome the break in the oppressive summer heat as well as the decline in the summertime masses. Fall also marks the return of some of our favorite things; pumpkin (everything), apple picking, leaves changing, football, holiday excitement, hoodies and boots. For our social calender, fall means events, and lots of them. While summer is jam packed with beach days, summer camps, BBQ’s and, for us locals, work, work and more work, fall affords visitors and locals alike with the opportunity to indulge in the fantastic line-up of fall festivals across the Eastern Shore. There truly is something for everyone. Giant trebuchets hurling pumpkins through the air? We’ve got it. Craft beer festivals? Yep. Scrapple-centric events? Ohhhhh yeah. Our calendar sure is filling up quickly…

Bridgeville Apple-Scrapple Festival – October 11 & 12

There are several foods that are indigenous to our area, blue crabs being the most notable, but chances are if you travel outside of the Delaware, Maryland, Pennsylvania or Virginia zip codes and order a side of scrapple, you’ll be met with a blank stare. If you aren’t familiar with scrapple, it really is one of those foods you have to try for yourself. Bridgeville is the scrapple capital; after all, RAPA Scrapple was incorporated there in 1926. For the past 22 years, Bridgeville has been celebrating what bests represents Sussex County – apples and scrapple. The Apple-Scrapple Festival is more than just apples and scrapple though, there’s an abundance of food including oyster sandwiches, BBQ, cheesesteaks and more. Entertainment includes a car show hosted by the Southern Delaware Street Rod Association, a carnival, the Little Miss Apple Scrapple Contest, crafts shows, trade shows, apple baking contests, children’s’ rides and games, and an entertainment stage with live music. You’ll be sure to see us there!

Octoberfest Berlin – October 19

Head to Berlin for the 3rd Annual Octoberfest, to be held Saturday, October 19 in historical downtown Berlin from noon to 6pm. What to expect? Polka music featuring the Continentals from Washington D.C., a beer garden overflowing with German-style beers from Burley Oak Brewery, and a delicious collection of German foods including pretzels, strudel, bratwurst and sauerkraut. Berlin events are always a great excuse to head to #mdscoolestsmalltown to enjoy the downtown vibes, the shops, local arts, and good eats.

OCtoberfest – October 19-20, 26-27

Not many towns get to boast of an Octoberfest celebration on the beach. The annual OCtoberfest on the Beach offers free Halloween events for the entire family. Located at the beach at North Division Street in Ocean City, events include a beach maze, pet parade and pumpkin race. The beach maze is open from 10am to 5pm and includes the likes of wicked witches, pirates of the sand, spooky scarecrows, ghouls in the graveyard, zombies and more. Pets will showcase their owners’ inventive costume creations on Saturday, October 19 at 2pm on the boardwalk for the Howl-O-Ween Pet Parade. Prizes and surprises will be awarded for the best-dressed pets. Entry in the parade is free with the donation of pet food or other pet-friendly items to the Humane Society. The Great Pumpkin Race is a wacky and zany side-by-side race featuring wild and tricked-out pumpkin race cars. The pumpkin race is to be held Saturday, October 26 at 2pm on North Division Street.

Sea Witch Halloween & Fiddler’s Festival – October 25-27

The Rehoboth Beach-Dewey Beach Chamber of Commerce & Visitors Center invites you to join them for the 24th Annual Sea Witch Halloween & Fiddlers’ Festival. Each year, thousands head to the annual festival that pays homage to all things Halloween. The list of activities and events is extensive…seriously, it’s several pages long. We’ll focus on the main events, starting with the Costume Parade, which kicks off on Saturday, October 26 at 11am. Judges award trophies for their favorite costumes at the bandstand after the parade ends. The Costume Dog Parade will be held Sunday, October 27, with canines parading their finest and most creative costumes. Other highlights include the Sea Witch 50/50 raffle, movies in the park, broom tossing contest, sea witch hunt and a cackle contest. There’s also the Fiddlers’ Festival to look forward to, to be held Saturday, October 26 at the Rehoboth Beach Convention Center. Adult and children’s competitions for best fiddle, blue grass and banjo playing will highlight the event.

Good Beer Festival – October 12 & 13

Brought to you by Tall Tales Brewery, the Good Beer Festival offers festival-goers unlimited tastings from over 125 different American Craft Brews. For local brews, check out the local beer garden to experience eight Eastern Shore breweries including Tall Tales, Evolution Craft Brewery, Third Wave, Burley Oak, 16 Mile, Dogfish Head, Fin City Brewing and Shorebilly. There’s also the Firkin garden this year, which allows tasters the opportunity to try the unique, one-of-a kind batches made exclusively for the event. There’s more than just beer, the festival also offers music, a Home Brew Competition, Hangover 5K Run, and a WBOC Sports Zone for all of your weekend sports updates. The Festival is located at Pemberton Historical Park, October 12 and 13 from 12:30 to 6:30 daily. All tickets include a tasting glass for sampling as many tastings as you can responsibly consume. Advanced tickets are $25, with at-the-gate tickets costing $35. Non-tasting tickets in advance and at the gate are $5 and $10 respectively.

Punkin Chunkin – November 1-3

Punkin Chunkin is a beloved Eastern Shore event that has grown to international notoriety, bringing thousands of spectators and participants from all over the world for the three-day spectacular. The event got its start in 1986, with some simple pumpkin tossing at what was then Salisbury State. The rest is pretty much history, with the event growing and evolving each year into what is now the grand festival that it is. Busloads of spectators will camp out or visit the chunk grounds the first weekend in November to watch the machinery and skill involved in chunking a pumpkin thousands of yards. It really is one of those bucket list events. Located in Bridgeville, Delaware, a large portion of the events’ proceeds are earmarked for charitable giving. We don’t just chunk on the Eastern Shore, we chunk for a cause!

Waterfowl Festival – November 8-10

Art galleries and exhibits, conservation exhibits, kid-friendly activities, sporting and hunting, and a wine and beer pavilion are just a few of the finer points of the Waterfowl Festival. The 43rd Annual Waterfowl Festival will take place in Easton, with the galleries and exhibits held in the historic buildings of Easton, while the events and demonstrations are held at the surrounding parks and scenic areas. Promotion of wildlife art, conservation and providing a showcase for the Eastern Shore are the foundation of the event, drawing between 18,000 and 20,000 people each year. There are a number of reasons to attend the festival, but as avid dog-lovers, we’re partial to the Retriever Demonstrations. The exceptionally skilled canines put their skills to the test as the leap into the pond to fetch the thrown or hidden dummy.

Rehoboth Beach Jazz Festival – October 17-20

Celebrating its 24th year, the Rehoboth Beach Jazz festival has blossomed from a small music gathering to a full-blown jazz extravaganza. This year’s show will be held on 5 stages, with many more local restaurants and bars in Lewes and Rehoboth offering great, live entertainment.  Dozens of performances are scheduled throughout the weekend, and if the weather stays as good as it has been lately, we can’t imagine a better way to spend a weekend then with a trip to Rehoboth to enjoy some truly incredible live performances.