Fall festivals are among some of the most beloved annual autumntime traditions, right along with pumpkin farm visits and apple-picking. Sometimes the latter activities are even incorporated into a compilation lineup of festival follies at a given location. Just the same, folks look forward to attending annual fall festivals as a last hurrah, of sorts—one final chance to spend time outdoors in milder weather conditions before the holiday season rolls in.
Maryland and Delaware coasts are more popular for their beach-culture connotations and reputations as summer getaway vacation destinations. Yet, they also play host to some of the most favored fall festivals on the Eastern Shore. I could list dozens of awesome autumnal happenings in these parts, but to keep things short and simple, here are my top seven suggestions for fall festivals to check out in the area this season.
Apple Scrapple Festival
Held October 13 and 14, the annual Apple Scrapple Festival in Bridgeville, Delaware is a beloved Sussex County tradition dating back more than three decades. The Festival kicks off Friday afternoon with an official 4 p.m. start time and will continue a full day run all of Saturday, October 14. Live entertainment, hundreds of crafters and other vendors, and of course delicious food are all part of the package deal. Highlights to take note of include their renowned RAPA Scrapple Cooking Demonstration, the Ladies Skillet Toss, a Little Miss Apple Scrapple Pageant, Car Show, and so much more.
The Apple Scrapple Festival will be held at 307 S. Laws Street, Bridgeville, DE 19933. Visit their website to learn more.
Berlin Oktoberfest & Sidewalk Sale
To clarify, this authentic Oktoberfest happening is taking place in historic Berlin, Maryland on October 14—NOT Berlin, Germany. Although, I can’t say for certain there aren’t also such happenings occurring at that location on this date as well. In fact, I’m certain there are!
Held in the heart of historic Main Street, local businesses will be presenting sidewalk sales during the event, joining the many other guest vendors who will be setting up shop for the day. Beer and other libations are of course the anchoring headlines, but do take note of all the other goodies too, including brats/knockwurst, pretzels, German chocolate cake, and more.
As this is a family-friendly event, there will be plenty of other onsite activities and enjoyments for all ages and interests, including a Scales n Tales Animal Show and Cascading Carlos juggling shows. Live musical performances by the Edelweiss Band and the locally acclaimed Dunehounds (sponsored by the Sterling Tavern) are sure to keep the hops hopping and folks enthralled throughout the day.
The festival’s official address location is 10 William Street, Berlin, MD 21811 (Downtown Berlin). Attendees are encouraged to park at Berlin Intermediate School and take the free shuttle service (sponsored by Ocean Downs Casino) to the event. These shuttles will operate throughout the day between 10:30 a.m. and 4:30 p.m. Click here to learn more about this year’s event.
Dogfish Head Punkin Ale Fest
Here’s another great “spirited” event on October 14, to help you get into pumpkin season. Taking place onsite at Dogfish Head Craft Brewery in Milton, Delaware, make no mistake that this is an entirely family-friendly free event. In fact, there are plenty of great hands-on activities and interests to suit visitors of any age throughout the day, including arts and crafts vendors, live music, karaoke, and more.
It’s not only the kiddos who are welcome to join in, as this event truly is for the dogs. That’s because the Festival benefits the Brandywine Valley SPCA as part of Dogfish’s Beer & Benevolence initiative. So go ahead and bring your furry friend out for a blast. There will even be a pet photo booth setup from 1 p.m. to 2 p.m. Oh, and if you don’t have a furry friend to bring, you have the option to meet new ones onsite, as several adoptable canine companions will be in attendance looking for a forever home.
This year’s Dogfish Head Punkin Ale Fest will take place between 11 a.m. and 4 p.m. on October 14, at the brewery at 6 Cannery Village Center Milton, DE 19968. Visit the website to learn more.
Sunfest and O.C. Toberfest
Because both these Ocean City Boardwalk traditions are happening concurrently, when you come out to attend one, you’re in for a twice as nice, two-in-one fall folly full of fun. First, there’s Sunfest—a beloved annual tradition going on 48 years. Spanning four days, Sunfest kicks off Thursday, October 19, and runs through Sunday, October 22. Setup is primarily around the famed Ocean City Boardwalk’s Inlet where more than 200 artists, crafters, and other vendors from all over the country come out to participate every year. Additionally, you will find ongoing live entertainment, delicious food, and plenty of slated activities and special event happenings lined up throughout the duration of the event. This remains one of the largest outdoor festivals in the region, drawing in tens of thousands of attendees annually.
O.C. Toberfest is a little younger—a just over a decade, to be exact. Yet it’s emerged as a free family-friendly happening on Ocean City, Maryland’s Boardwalk scene every autumn, presenting a host of Halloween-themed activities and participatory events. These include the Great Pumpkin Race, a Howl-O-Ween Pet Parade, Drive-in-Disguise event, and getting lost in the Halloween Beach Maze. Click here to learn more about Ocean City, Maryland’s Sunfest and here for more information about O.C. Toberfest.
Hagley Craft Fair
Consider heading north up to Wilmington, Delaware during the weekend of October 21 and 22 for the annual Hagley Craft Fair. Hosted onsite of the historic Hagley Museum and Library, this premier festival event brings together crafters, artisans, food vendors/trucks, and Mid-Atlantic business owners of many trades in an impressive setup you won’t want to miss. The Fair is set up along the vast stretches of Hagley’s immaculate scenic property as well as inside the Soda House building.
Do note that the Hagley Craft Fair is a ticketed event that charges admission, which includes access to the DuPont Family Home and Gardens. The Hagley Museum and Library is located at 200 Hagley Road, in Wilmington, Delaware 19807. Visit the website to learn more.
Schellville Fall Harvest Fest
The Schellville Brothers, known home builders in Delaware, are no strangers to leading family-friendly holiday events on location of their impressive Schellville Village in Rehoboth. And now they’re premiering their first-ever fall festival October 21, 2023. Running from 3 p.m. and 8 p.m., this awesome autumnal celebration will feature a host of wonderful activities, events, and amusements taking place onsite. The lineup includes local artisans and food trucks, pumpkin and face painting, balloon animals, bounce houses, hayrides, skating, photos with Disney Princesses, and more.
This is a ticketed event, taking place at 36470 Seaside Outlet Drive Rehoboth Beach, DE 19971. The following week of Friday, October 27, will be the free 2023 Schellville Spooktacular Kids Zone. Then on October 28 comes the Wicked Brew Bash. Click here to learn more about these and future Schellville events.
Sea Witch Festival
This all-out Rehoboth-based family fall festival returns for year 33 on Friday, October 27, concluding its run Sunday, October 29. Drawing in thousands of visitors annually, this premier event packs in nonstop entertainment, activities, and onsite attractions galore. From crafts vendors and artisans to delicious food and activities, there’s plenty to enjoy throughout these jam-packed three days. The now-famous Sea Witch Festival parade is one of their most hallmark events of all, taking place at 11 a.m. on Saturday. But there are many other onsite highlights to take in during the festivities as well.
The Sea Witch Festival will occur in Downtown Rehoboth, within the surrounding Boardwalk area. Owing to the popularity of the event, parking in the direct vicinity is not recommended. Fortunately, Jolly Trolley shuttles will be operating throughout the weekend, picking up and delivering attendees from various parking locations. Click here to learn more about the event.
This is just a sampling of the many awesome autumn happenings around the Eastern Shore. Additionally, I highly encourage you to go out on your own and start exploring the plentiful other possibilities that may just appeal to you personally.