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50 Fun Things to do in Delaware in October!

Posted by Team Awesome on Oct 11, 2019 6:45:00 PM
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artilce by: AMY WHITE

The Vendemmia da Vinci Wine and Food Festival returns to Wilmington on Oct. 13./Photo courtesy of the Greater Wilmington Convention and Visitors Bureau, by Moonloop Photography.

From Bridgeville's annual Apple-Scrapple Festival to the Vendemmia Italian Wine and Food Festival in Wilmington, here's what's going on this month.


Week of Oct. 1-7

Brandywine Baroque
10/4 • Wilmington
This event is full of big noise this fall. The season kicks off Oct. 4 with a selection of cantatas and sonatas from 18th Century London, with Laura Heimes, soprano; and Tony Boutté, tenor. Hear it in Wilmington.

Pink Martini Featuring Meow Meow
10/4 • Wilmington
If the idea of a Latin, jazz, cabaret and cinema score mash up with strong 1940s vibe sound right up your alley, may we suggest spending an evening with little orchestra Pink Martini? How do you describe their sound? You’ll know it when you hear it, baby. You’ll hear popular favorites from the band’s latest release, “Je dis oui!,” which will take you on a musical trip from France to Iran, Armenia to South Africa and then some.

Delaware Auto Show
10/4-10/6 • Wilmington
Is it your jam to know about the next big thing before it goes to the masses? Step up right up and get behind the wheel of the newest, coolest cars on the planet when they park it for the weekend at the Chase Center.

Rehoboth Fall Sidewalk Sale
10/4-10/6 • Rehoboth Beach
Calling all bargainistas—the 43rd annual event is a weekend full of deals and fabulous finds in downtown Rehoboth Beach.

 Wings & Wheels Fall Festival
10/4-10/19 • Georgetown
Up, up and away! Check out the exciting fly-in of vintage airplanes, a huge car show, WWII re-enactors and encampments, food and craft vendors, entertainment all day and much more at the Delaware Coastal Airport in Georgetown. Get your boarding pass for Friday night and be there for Katie Martin’s tribute to the Woodstock Generation. It’s BYO, so grab a bottle, some friends, and your vintage 70s threads.

"Art with Purpose"
10/4-10/25 • Wilmington
Photographer Leah Beach’s solo show “Art with Purpose” is about inspiring social change through the power of creative vision. The artist will exhibit the large-scale prints she took in Haiti in partnership with a local hospital and a U.S- based community health organization, and her “Flora and Fauna” paintings. 

Dewey Goes Pink
10/5 • Dewey Beach
Now you finally have a rational excuse to let loose at The Starboard—lace up those sneakers and enjoy a run through Dewey Beach as you paint the town pink with the Delaware Breast Cancer Coalition.

Dover Heart Walk
10/5 • Dover
Stride with pride when your two feet put in the work to benefit the American Heart Association at the Del Tech’s Terry Campus.

"The Wizard of Oz"
10/5-10/27 • Wilmington
You know the story: Yellow brick roads, red ruby slippers, Emerald City—somewhere over the rainbow, all these colors lead to an epic, enduring and heartwarming adventure.

Celebrity Chefs’ Beach Brunch
10/6 • Dewey Beach
The Rusty Rudder in Dewey Beach plays host to a celebrity chef throw down, beach-brunch style. In-demand area chefs come together for a good cause—the profits benefit Meals on Wheels and the goods profit your palette. Save us a mimosa and we’ll see you there.

UD’s Coast Day
10/7 • Lewes
The university’s scientists, staff and students will be on hand at the Lewes campus to drop knowledge on ocean environments. The day-long family spectacular boasts educational programs, children’s activities, food and learning. There will be a crab-cake cookoff and a Seafood Chowder Challenge, and the kiddos can get up-close-and-personal with horseshoe crabs and dogfish sharks at the touch tanks. The fun starts at 11 and goes till 5.

Arts and Appetizers
10/8 • Wilmington
Enjoy a unique blend of unpredictable sketches, interactive games and a bit of bawdiness for the fun-loving folks of Wilmington and beyond at the University and Whist Club.

Week of Oct. 8-14​

Symphony Orchestra
10/9 • Newark
The University of Delaware music department invites you to an evening of tremendous sound at the CFA Puglisi Orchestra Hall.

Greyhounds Reach the Beach
10/10-10/13 • Dewey Beach
It’s a not-so-ruff life for the greyhound gang when their owners throw their annual get-together in Dewey Beach.

Shakespeare, Poe & Friends
10/10-10/13 • Wilmington and beyond
If you think you and your crew are squad goals, you have another thing coming—when the masters of macabre get together, it’s an all-time hang. Check out “Shakespeare, Poe & Friends” for a night (or two) of readings from the dark side. The venues include Wilmington’s Old Town Hall, the New Castle Court House Museum, the Historic Odessa Stone Stable and Dover’s Old State House.

10/11 • Wilmington
Spring your imagination to great heights with this theatrical combination of dance, story-telling and sculpture. Founded in 2009, Catapult rose to fame on Season 8 of “America’s Got Talent”, going all the way to the finals of the NBC hit show. Catapult is about the human body and its ability to transform: you won’t believe your eyes as you watch these incredible dancers become a mountain, an elephant, a helicopter, even a house, all via innovative behind-the-scene silhouette work. You’ll never look at your own shadow the same way again. See it in Wilmington at 8 p.m. 

Opera Jukebox
10/11, 10/13 • Wilmington
What better way to make opera accessible than firing up the request line from the casual environment of OperaDelaware’s riverfront studios? Opera Jukebox features OperaDelaware’s favorite singers—and Aurelien Eulert tickling the ivories—bringing your favorite tunes, up close and personal. You can order up your favorites, no pocket change required.

Apple-Scrapple Fest
10/11-10/12 • Bridgeville
Looking for a festival that makes you feel sad for all the unlucky folks who don’t live in the First State? Try this one—it has “scrapple” in the name, for crying out loud! The fest kicks off in Bridgeville with more food and fun than you can shake a frying pan at. Watch out for flying iron skillets (that’s not a joke). Bring the kids—see how far they can toss an apple.

"The Hobbit"
10/11-10/13 • Milford
Milford’s Second Street players puts on the journey of all journeys, to the sometimes dark, sometimes charming, always compelling world of Middle Earth. Bilbo Baggins is a little man with a big love for rousing adventure stories. Real adventures, though? Not his jam. So, when Gandalf the wizard knocks on his door with a contract for an adventure to recover the lost treasure of Lonely Mountain, Bilbo could not be less into it—at first. What happens next? Find out in Milford.

Boardwalk Buddy Walk
10/12 • Rehoboth Beach 
Hit the boards in Rehoboth and enjoy festivities to benefit the National Down Syndrome Society.

Hayrides at Hagley
10/12-10/27 • Wilmington 
It’s fall, y’all, and the proof is in the haystack. Check out beautiful fall foliage at its best when you hop a hayride along the Brandywine Creek.

Vendemmia da Vinci Wine and Food Festival
10/13 • Wilmington
Little Italy comes to the Wilmington Riverfront this month during the Vendemmia da Vinci Wine and Food Festival. Spend your Sunday savoring tasty Italian food, wines and beers. Plus, see who takes home the blue ribbon in the gravy-making, homemade wine and limoncello contests. The event also features a Dogfish Head beer garden and an appearance by the company’s founder, Sam Calagione. Entertainment includes classic Italian music from crooner Steve Silicato, as well as other live performances. The festival takes place Sunday, Oct. 13, from 2 p.m. to 6 p.m. at the Tubman Garrett Riverfront Park. General admission tickets are $60.

Plein Air Brandywine Valley
10/13-10/19 • Wilmington
This annual painting and photography competition culminates in a reception, show and sale at Winterthur.

Week of Oct. 15-21

The Great Pumpkin Carve
10/17-10/19 • Chadds Ford, Pa.
They’ll start out as pumpkins, but once the 60 talented carvers get a hold of ’em, who knows what’ll happen. Fun fall festivities continue all three nights—pop in on Thursday to see the artists in action; the fruits of their labor will be the talk of the town Friday and Saturday. The event isn’t just for grown up gourds—they’re hayrides, a kid-friendly haunted house, fall treats and live music. Free admission for the 6-and-under crowd. (We suggest getting there early to avoid the 9 p.m. exit scramble.) Gates open at 4 p.m. Thursday and Friday; 3 p.m. on Saturday.

Rehoboth Beach Jazz Festival
10/17-10/20 • Rehoboth Beach
All the cool cats will be in Rehoboth this weekend taking in sultry acts like Boney James, Gerald Albright and Will Downing, among others. (Our fave: the Nina Simone tribute show on Saturday.) Venues around town include Dogfish Head Brewery, Rusty Rudder, Chesapeake & Maine and the Lewes Farmers Market.

10/18-10/27 • Rehoboth Beach
See the play that put pottery-making on the pop culture map — cry your eyes out all over again with “Ghost” to usher in October. Sam and Molly have a good thing going, until Sam dies. Desperate to connect with Molly and certain she’s in danger, he uses a storefront psychic as his own personal Instagram direct message to communicate with his beloved.

Bram Stoker’s Dracula
10/18-10/20 • Wilmington
You’ll really want to sink your teeth into the ballet when Transylvania meets tutus in the dramatic staging of Bram Stoker’s beloved (hey, it is!) original entry into the vampire canon. This world premiere production features award-winning choreographer Viktor Plotnikov. It’ll be a gothic good time.

Alzheimer’s Walks
10/19 • Wilmington
The Alzheimer’s Association’s walk steps off at Frawley Stadium in Wilmington.

Brasil Guitar Duo
10/19 • Lewes
Brazil Guitar Duo’s innovative sound features a seamless blend of traditional and Brazilian works, resulting in a full global touring schedule and a growing catalogue of critically acclaimed recordings. The Duo has appeared internationally on major concert series and at festivals in Cuba, Germany, England, Canada, South Korea, Colombia, Brazil, Austria, Panama, Poland, and Bermuda—and now they come to do their thing at Lewes’ Bethel United Methodist Church Hall.

The Great Delaware Pumpkin Carve
10/19 • Harrington
Last year’s The Great Delaware Pumpkin Carve at the Delaware State Fairgrounds, with all its fall essentials—hayrides, bonfires, seasonal brews and perfectly Instagram-able barns—was such a treat that the Biggs Museum of American Art has no choice but to do the whole shebang again. This Biggs Museum fall-tastic family extravaganza takes place on the Delaware State Fairgrounds in Harrington.

Monster Mile for a Cause
10/19 • Dover
Start your engines. Ever wanted to walk the Monster Mile at the Dover International Speedway? The Delaware Breast Cancer Coalition invites you and your pit crew to join in this untimed lap around the Mile, which raises funds for DBCC programs that increased breast cancer awareness. You don’t have to step on the gas, but wear pink or your best Halloween look for the costume contest.

Paws for People Wag-N-Walk & 5K
10/19 • Glasgow
Wag-n-Walk returns to its original home of Glasgow Park. People of all ages get pledges from their family, friends, and neighbors and come together to run or walk in the 5K and/or walk in the 1-Mile Doggie Walk. Create a team and participate as an individual.

Hagley Craft Fair
10/19-10/20 • Wilmington
It’s fall decorating season, y’all. Hit this two-day Hagley Craft Fair, which boasts Mid-Atlantic artisans selling all kinds of goodies—wood works, pottery, gourmet candies and foods, jewelry, metals, clothes.  If you want it on Etsy, come find it here in real life. If nothing else, come for the gorgeous historic grounds.

"Posing Beauty in African American Culture"
10/19-1/26 • Wilmington
If the intersection of gender and race is your thing—and it really should be—you’d be remiss not to check out “Posing Beauty in African American Culture,” Curated by Deborah Willis, the exhibition explores the contested ways that African American beauty has been historically represented.

Week of Oct. 22-28

Chamber Series Concert 1
10/22 • Wilmington
The Hotel duPont’s opulent gold room hosts a little ditty of Piazzola and Tchaikovsky.

The World Famous Glenn Miller Orchestra
10/23 • Dover
Dance the night away to the big sound of the Glen Miller Orchestra playing “Moonlight Serenade,” “A String of Pearls,” Tuxedo Junction,” “Danny Boy” and more. After, why don’t you take a spin on the casino floor? It might be your lucky night.

"Romeo and Juliet"
10/23-11/15 • Wilmington and beyond
Art should be accessible to all—this principle guides the Delaware Shakespeare Festival’s community tour, which began in 2016 with stagings at community centers, homeless shelters, detention facilities and other nontraditional theatre locations across the state. This year, the theatre company is pleased to hit 18 venues on its quest to bring the arts to the underserved. “Romeo and Juliet” hits the (unconventional) road Oct. 23 through Nov. 15. The tour comes home to OperaDelaware studios Nov. 16 and 17 for two nights of Montague and Capulet drama—the tea will be spilled.

"One November Yankee"
10/23-11/10 • Wilmington
“One November Yankee” brings stars Harry Hamlin of L.A. Law and Stefanie Powers of Hart to Hart to our Wilmington stage. The play, which the L.A. Times says “unfolds like theatrical origami,” explores human connections in the aftermath of a tragic plane crash. Poetic and haunting, this one won’t be easy to shake off once the house lights come up.

Ultimate Tailgate
10/24 • Dover
Football is back, and the same old, same old won’t work this season when it comes to your game day eats. Take your tailgate spread next level with a little inspiration by the local restaurants that compete in this game of gridiron gluttony. This sophisticated, yet casual event will also feature wine, spirits and a Two Stones Pub-curated craft beer trail. The Stone Shakers will be in the house with live music. Dover Downs hosts.

Sea Witch Festival
10/25-10/27 • Rehoboth and Dewey Beach
Haven’t made it down to the Sea Witch Festival yet? Well, what’s taking so long—you’ve only had 30 years to do so. Stop down to the beach for this 30th Anniversary spectacular. Costume parade, dog parade, beach games, trick or treat, a 5k, live bandstand entertainment and much, much more will entertain you and your little ones all weekend long.

Halloween Express
10/27 • Wilmington
The Wilmington & Western Railroad celebrates Halloween with three departures throughout the day. You’ll meet a friendly witch or two. Don’t forget to wear your costumes—that means you, too, mom and dad.

Ending this month

"August: Osage County"
​Thru. 10/13 • Newark
Want to be a voyeur at the family reunion from hell? Then the UD Resident Ensemble Players has you covered with “August: Osage County.” When family patriarch Beverly Watson slips away into a muggy summer night and doesn’t come back, his sister-in-law and three daughters head to the family estate to stabilize the family’s pill-popping, manipulative matriarch, Violet. Wine will be poured. Insults will fly. And decades-old wounds will reopen in this rich, brilliant, Pulitzer-Prize winning black comedy about family, trauma and going home again.

Rehoboth Dreaming
Thru. 10/20 • Rehoboth Beach
Catch this homage to our dreamy little beach town at the Rehoboth Beach Municipal Building.

Read Aloud
Thursdays Thru. 10/24 • Chadds Ford, Pa.
Thursday mornings at the Brandywine River Museum are all about story-telling, crafts, art and giggles.

Pennsylvania Renaissance Faire
Thru. 10/27 • Manheim, Pa.
Get a taste of Elizabethan life—a dino-sized turkey leg on a stick oughta do it—on weekends and on Labor Day at Mount Hope Estate and Winery.

"Dark Shadows"
Thru. 10/30 • Ocean View
The artists at Gallery One in Ocean View interpret this month’s spooky, seasonal theme.

The 2019 Big Draw Festival
Thru. 10/31 • Milford
The Mispillion Art League has your October covered with The Big Draw, which features arts programming every Saturday this month. It kicks off on Oct. 5 with “Farmer’s Market Saturday.” The whole family can paint pumpkins, add a stroke or two to the Community Canvas painting activity and write an inspiring postcard to a stranger with the Postcard Connection. Oct. 12, Park Avenue is closed for Street Feet Painting (really!), a giant Chalk Walk and Sand Castle Building. Oct. 19, the genre is scribble—sketch outside in the gorgeous fall air. To end an outstanding month of art, Oct. 25 boasts origami, self-portraiture, creative lettering and Halloween mask making. If you say there’s nothing going on in Milford this month, you’re not paying attention. All events are free and start between 9 a.m. and 10 a.m.

Milford Farmers Market Saturday
Thru. 10/31 • Milford
It’s the last month of the season to head to the Riverwalk to see what’s in store.

Pumpkin Playground
​Thru. 10/31 • Kennett Square, Pa.
Have you ever wanted to see what a 550-pound pumpkin looks like? Yes? Well, orange you glad you asked, because we’ve got just the answer—the Pumpkin Playground at Longwood Gardens, otherwise known as the best spot to get those must-have fall photos. Check out the Children’s Corner and let the littles see, touch and play with in the patch. And don’t forget the grand gourd of them all.

Throughout the month

"Sound the Deep Waters"
10/5-4/12 •​ Wilmington
Arist Angela Fraleigh’s “Sound The Deep Waters” brings majestic, opulent, glimmering oil paintings that look rich and deep enough to sink your fingers into. The showcase is all about depicting women freed from the social constructs of their time—we can get behind that.

"Reality Reassembled"
Thru. 11/3 • Chadds Ford, Pa.
Add some (calorie-free!) culture to your trick or treat bag this year with a visit to the Brandywine River Museum of Art when it hosts “Reality Reassembled: The Halloween Paintings of Peter Paone.” Paone, a longtime Philadelphia artist, has a thing for Halloween, which he likens to a “day of denial.” Utilizing jewel tones and textured surfaces, Paone’s paintings bring unsettling concepts to bootiful, thought-provoking fruition.

Blooms & Bamboo
Thru. 11/17 • Kennett Square, Pa.
Masterworks of Ikebana—the time-honored Japanese art of flower arrangement—along with masterfully grown chrysanthemums take center stage at Longwood Gardens this fall. Enjoy headmaster Sogetsu Iemoto Akane Teshigahara’s exquisite, towering curations of bamboo and natural elements exclusively designed for Longwood’s conservancy. While you’re there, don’t forget the Children’s Corner is open—the Pumpkin Playground will keep ‘em busy.

Beijing Booster Paintings
Thru. 2/26 • Wilmington
This fall will be nothing short of visionary at The Delaware Contemporary. Their first get of the season? Oh, no big deal, just critic’s darling Peter Wayne Lewis, the internationally coveted Jamaican-born painter who has spent the past 10 years making his abstract art out of a studio in Beijing’s renowned artists’ district. The large-scale abstractions that color “Beijing Booster Paintings” are a cultural revolution: see influences of African American expressionists, Japanese sumi ink paintings, Chinese calligraphy and traditional American painting. This one will transport you across the globe.

Costuming the Crown
Thru. 2020 • Wilmington
Catch Costuming The Crown, which features more than 40 iconic costumes from the Emmy-Award winning Netflix series. With season three of the acclaimed drama anticipated to drop in November, binge all the costumes from season one and two at Winterthur, which is literally the only place on planet Earth where you can do so. Getting up close and personal with the crystal beading on the incandescent wedding gown Claire Foy wore as the queen bee is worth the price of admission alone.



Topics: Wilmington, Delaware, Appetizers, breweries, parents, Event, Food trucks, gluten-free, Local, Local businesses, Locally Grown, WHYFLY, WhyFly Wilmington, Work Life Balance, Family Friendly, Delaware Today

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