Another October weekend is here, and Coastal Delaware has plenty going on!
From two major jazz festivals and zombie-themed celebrations to fall festivities, live music, and community fundraisers, there's something for just about everyone.
True Blue Jazz Festival at The Boardwalk Plaza Hotel
The 14th Annual True Blue Jazz Festival is bringing five days of incredible music to downtown Rehoboth Beach!
Founded by Eddie Sherman and Peggy Raley, this independent festival celebrates traditional and mainstream jazz, with performances inspired by the Great American Songbook.
This weekend's lineup includes Monty Alexander's "Jamaica to Jazz" on Friday, the Smokin' Hot Firehouse BIG BAND Jazz Marathon and Pat Bianchi Organ Trio on Saturday, and Two Gals Swingin' featuring Peggy Raley and Jackie Johnson on Sunday.
Expect a mix of local talent and internationally recognized jazz musicians throughout the celebration.
- Date: October 14-18
- Hours: Various times
- Location: 2 Olive Avenue & Boardwalk, Rehoboth Beach
Rehoboth Beach Jazz Festival
Jazz lovers have another reason to be excited this weekend!
The Rehoboth Beach Jazz Festival returns with performances by nationally and internationally recognized artists, including Grammy Award winners.
Established in 1989, the festival takes place across several venues, including the Cambria Hotel, Rusty Rudder, and Cape Henlopen Performing Arts Theater.
Beyond the music, the event supports the Beebe Medical Foundation and Tunnell Cancer Center, helping fund cancer care, research, and medical equipment.
Some performances are already sold out, but tickets remain available for others, including a few free shows.
- Date: October 15-18
- Hours: Various times
- Location: Various venues throughout Coastal Delaware
Image: Visit Rehoboth
Jazzfest Weekend at Bluecoast Rehoboth
Keep the jazz celebration going with three days of live music on the patio at Bluecoast Rehoboth.
The restaurant is hosting a special Jazzfest Weekend lineup, starting with Joe Baione on Friday. Holly Lane & Shore Jazz take the stage Saturday, followed by Tin Pan Alley on Sunday.
It's a great excuse to enjoy some good food and drinks while listening to live jazz throughout the weekend.
- Date: October 16-18
- Hours: Friday 4 PM to 7 PM, Saturday 3 PM to 6 PM, Sunday 1 PM to 4 PM
- Location: 30115 Veterans Way, Rehoboth Beach
Shanty Night at Sussex Tavern
Travel back in time at the Sussex Tavern in Lewes during its monthly Shanty Night.
Held every third Friday, this lively gathering recreates the spirit of British sailors through traditional maritime singing, cheering, and plenty of spirited participation.
Whether you're familiar with sea shanties or just curious about the experience, everyone is welcome to join in.
Admission is free, with drinks available for purchase.
- Date: Friday, October 16
- Hours: 6 PM to 8 PM
- Location: 110 Shipcarpenter Street, Lewes
First Annual Pink Out Party at Big Chill Surf Cantina
Put on your favorite pink outfit and head to Big Chill Surf Cantina for its first Pink Out Party benefiting the Delaware Breast Cancer Coalition.
The evening features live music from OFF 24, special guest bartenders, a 50/50 raffle, and a creative Bra Decorating Contest where guests can bring their own decorated entries for a chance to win.
Even better, 20% of event sales and 100% of guest bartender tips will be donated directly to the coalition, making it a fun night out that also supports an important cause.
- Date: Friday, October 16
- Hours: 6 PM to 10 PM
- Location: 19406 Coastal Highway, Rehoboth Beach
Old Crow Manor: Extreme Haunt Night (18+)
If you're looking for a Halloween experience that goes well beyond the usual haunted house, Old Crow Manor in Georgetown is hosting two Extreme Haunt Nights this weekend!
This adults-only attraction features live scare actors, dark corridors, psychological scares, and intense interactive encounters.
Unlike a traditional haunt, participants may be separated from their groups, experience sensory challenges, or encounter direct physical contact from performers.
It's designed for serious horror fans who want a more immersive and unpredictable experience, so make sure you know what you're signing up for!
- Date: October 16 & 17
- Hours: 7 PM to 10 PM
- Location: 22518 Lewes Georgetown Highway, Georgetown
Rehoboth Beach Zombie Bar Crawl
The first annual Zombie Bar Crawl invites adults 21 and older to dress up in their creepiest costumes and spend the afternoon visiting six participating spots: Purple Parrot Grill, Nalu, Above The Dunes, Aqua Bar & Grill, Zogg's Raw Bar & Grill, and Tiki Jac's Street Eats & Brews.
The fun kicks off with a group zombie photo on the Boardwalk at noon before everyone heads out for drinks, music, and Halloween festivities.
No ticket is required, but attendees are encouraged to bring diapers, cereal, peanut butter, canned goods, or grocery store gift cards to support the Community Resource Center, which helps local individuals and families in need.
- Date: Saturday, October 17
- Hours: 12 PM to 4 PM
- Location: Downtown Rehoboth Beach, various participating locations
Bark on the Boards With Delmarva DockDogs
Get ready to watch some seriously talented dogs take to the air at Bark on the Boards.
Delmarva DockDogs is bringing a full day of canine competitions to the Rehoboth Beach Boardwalk, featuring dogs showing off their jumping distance and retrieving skills.
The action begins with registration and practice, followed by four Big Air waves throughout the morning and early afternoon.
Speed Retrieve finals and Big Air finals begin in the afternoon.
Whether you're a dog owner or simply love watching these athletic pups in action, this should be a fun event to catch!
- Date: Saturday, October 17
- Hours: Starts at 7:30 AM
- Location: 1 Rehoboth Avenue, Rehoboth Beach
Zombie Fest: Undead Disco at Hudson Fields
Halloween meets disco at this year's Zombie Fest: Undead Disco, happening at Hudson Fields in Milton.
This themed celebration brings together live music, food trucks, local vendors, freak shows, fireworks, and costume contests for an afternoon filled with spooky entertainment.
Families can also check out KidsFest, featuring games and activities for younger visitors, while zombie makeup stations help everyone get into character.
With its new, larger location and a fun disco twist on the traditional zombie theme, there's plenty to explore.
Free parking is available!
- Date: Saturday, October 17
- Hours: 2 PM to 7 PM
- Location: 30045 Eagle Crest Road, Milton
10th Ashley Furio 5K Run/Walk at Crooked Hammock Brewery
Lace up your sneakers for a great cause at the 10th Annual Ashley Furio 5K Run/Walk.
Starting and finishing at Crooked Hammock Brewery in Lewes, this flat residential course is followed by a celebration featuring music, food, brews, and family activities.
The event supports the Ashley Nicole Furio Endowment Fund, benefiting the Margaret H. Rollins Child Development Center at the Children's Beach House.
Not interested in running? You can register for the Crooked Crawl, which lets participants skip the full course and head straight to the celebration.
- Date: Saturday, October 17
- Hours: Starts at 9 AM
- Location: 36707 Crooked Hammock Way, Lewes
Image: Fish On
French Farm to Glass Wine Dinner at Fish On
Spend Saturday evening exploring French wines and a carefully crafted five-course dinner at Fish On in Lewes.
Chef Ian has created a special menu featuring smoked trout mousse, delicata squash with crispy prosciutto and figs, spiced pork belly, roasted chicken breast au jus, and pumpkin cake with apple cinnamon cream cheese and salted caramel.
Each course is paired with a French wine selected from Bowler Wines, with National Sales Director Jessica Gualano guiding guests through the pairings and sharing more about each selection.
- Date: Saturday, October 17
- Hours: 6 PM to 8:30 PM
- Location: 17300 North Village Main Boulevard, Lewes
SDTR's 10th Annual Barn Dance
Get ready for an evening of country music, dancing, and giving back at Southern Delaware Therapeutic Riding's 10th Annual Barn Dance.
The fundraiser features live music from the Mason Dixon Band, line dancing, a barbecue dinner catered by Whole Roast Barbeque Services, bourbon tasting, and a live auction.
Every ticket and sponsorship helps support SDTR's therapeutic riding programs, scholarships for participants in need, and the daily care of the organization's horses.
It's a chance to enjoy a fun Saturday night while supporting a program that makes a difference in the local community.
- Date: Saturday, October 17
- Hours: 6 PM to 10 PM
- Location: 17170 Harbeson Road, Milton
Schellville Fall Harvest Fest
Schellville is getting into the fall spirit with its annual Fall Harvest Fest, bringing two evenings of seasonal fun to Rehoboth Beach!
Families can enjoy pumpkin decorating, a spooky zone, character appearances, balloon making, bounce houses, an obstacle course, and rides on the Schellville Express.
The skating rink, sled hill, and snow zone are also part of the festivities, with food trucks, snack shacks, and bars available throughout the event.
Tickets are required for guests over age 2, while younger children enter free.
Some activities have additional fees, including $5 for face painting and $5 for skating. Proceeds help support Schellville's free Christmas season celebration.
- Date: October 17 & 18
- Hours: 5 PM to 8 PM
- Location: 36470 Seaside Outlet Drive, Rehoboth Beach
Open Space, Open Strings: Bluegrass By The Bay
Enjoy an afternoon of bluegrass music with beautiful waterfront views at the Lewes Ferry Grounds.
Presented by the Sussex County Land Trust and produced by Rocking The Docks, Bluegrass By The Bay features live performances from Old Town Flood and Wood Flower.
The family-friendly outdoor event also offers food trucks, craft beverages, and plenty of space to enjoy the music by the water.
Guests are welcome to bring blankets and low-back chairs for designated seating areas, and free parking is available on-site.
- Date: Sunday, October 18
- Hours: Doors open at 12 PM
- Location: 43 Cape Henlopen Drive, Lewes
Image: Browseabout Books
Deborra M. Torres Book Signing at Browseabout Books
Browseabout Books is welcoming author Deborra M. Torres for a signing of her book “A Funny Thing Happened on the Way to the Nurse's Station.”
Drawing from her experiences as a patient, nursing student, and healthcare professional, Torres shares humorous stories about embarrassing moments, medical terminology mix-ups, and the unexpected situations that come with working in healthcare.
Whether you're a nurse, medical professional, student, or simply enjoy a funny look behind the scenes of the medical world, stop by to meet the author and learn more about her book.
- Date: Sunday, October 18
- Hours: 11 AM to 1 PM
- Location: 133 Rehoboth Avenue, Rehoboth Beach
For more weekend events, local news, and things to do around Coastal Delaware, keep following our blog!
Have any questions about our blog(s), the Coastal Delaware real estate market, or local life in our beautiful beach towns? Do you think there is something we should write about? Did you see an event coming up that we should know about? Shoot us an email at [email protected] or give us a call at (302) 212-0074. We would love to hear from you!
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