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Best of October: 15+ Delaware Beach Events for This Month 

October 1, 2021

Lauren Cosca


Check out more Delaware Beach Area Events on our full Calendar!

Kristen & The Noise will take the stage this year at The Starboard Halloween Party in Dewey Beach! 


Summer is over, but that doesn’t mean the fun has to stop down at the Delaware beaches! The Fall season on the Eastern Shore means tons of action-packed, entertaining events for the whole family to enjoy! Trade in your floatie and bathing suit for fangs and candy when you attend any number of the Halloween and Fall themed events this October. Keep reading below for information on dates, locations, and tickets!

1. Lewes Craft Fair

When: Saturday, October 2 | 10 a.m. to 4 p.m. | Sunday, October 3 | 10 a.m. to 3 p.m.

Where: The Historic Campus, located at Second & Shipcarpenter Streets in downtown Lewes

The Lewes Fall Craft Fair is well known for the exceptional quality of the craftspeople, including new and returning artists from across Delmarva and the Eastern Shore. The Historic Complex consists of numerous historic buildings that will be open to the public for the fair. Enjoy festive live music and delicious food when you attend this yearly event. Admission to the festival is $5 per person to be paid at the gate; children under 12 are free.

2. Wings and Wheels

When: Saturday, October 2 | All Day

Where: 21553 Rudder Lane, Georgetown, DE 19947

Celebrating their 13th anniversary, this popular Sussex County event on Saturday features a “fly in” of WWII-era, military and other vintage aircrafts, a huge classic car show, and various craft and food vendors. The festival also includes WWII encampments and re-enactors, and the show stopping Pilot’s Flour Bombing competition.


3. Annual Beach Brunch

When: Sunday, October 3 | 10:30 a.m. to 1:30 p.m.

Where: The Rusty Rudder | 113 Dickinson Ave, Dewey Beach, DE 19971

Guest are invited to enjoy a seated brunch prepared by local guest chefs at the Rusty Rudder. This fundraiser event highlights brunch-themed dishes paired with brunch cocktails, and includes an auction and entertainment by the Hot Sauce Band. This event benefits Meals on Wheels Delaware.


4. Apple Scrapple Festival

When: Friday, October 8 |Open at 4 p.m. | Saturday October 9 | Open at 9 a.m.

Where: Apple Scrapple &, S Laws St & Delaware Ave, Bridgeville, DE

Apple Scrapple has become a major fundraiser for local community organizations and helps elevate awareness of the agricultural profession in lower Delaware. Festivities begin at 4:00 pm on Friday

evening with the carnival, food court and street dance. Things start up again on Saturday morning with carnival rides, kids’ games, live entertainment, car show, trade show, two craft shows and delicious food vendors, including apple dumplings, scrapple sandwiches, oyster sandwiches, and more. There is something for all ages and all appetites at this exciting event.


5. Multiple October Events Happening at The Starboard


Dewey Goes Pink

When: Saturday, October 9th | 4 to 7 p.m.

Where: Starboard | 2009 DE-1, Dewey Beach, DE 19971

This yearly event brings patrons from near and far to remember, honor, or enjoy being with family and loved one’s on a day that thousands do the same in their own way. Pre-registration packet pick up is Friday, October 8 at The Starboard, and day-of registration is Saturday Oct 9 at 9 a.m. The race kicks off promptly at 11 a.m. that day, with a delicious spread served by Bethany Blues BBQ following the race, live music, plenty of refreshing cold beer, seltzers and pink grapefruit Crushes!

Starboard Halloween Party

When: Saturday, October 30 | 9 p.m.

Where: The Starboard | 2009 Costal Highway, Dewey Beach DE 19970

Spend your Saturday at the Starboard in Dewey Beach at their annual Halloween party.  Jam out to Kristen and the Noise, and participate in the costume contest! 


6. Rehoboth Jazz Festival

When: October 14 to October 17

Where: Rehoboth Beach Convention Center and the Rusty Rudder

The Rehoboth Beach Jazz Festival is produced by the Delaware Celebration of Jazz. The festival will feature live music during the first weekend at Rehoboth Beach Convention Center and the Rusty Rudder. Organizers will also bring back The Taste of Rehoboth event, during which 10 restaurants will make a signature dish for attendees to sample and vote on prior to the evening's concert.

7. True Blue Jazz Festival

When: October 13 to October 17

Where: Live Events all over Rehoboth Beach

The 9th Annual True Blue Jazz Festival returns to Downtown Rehoboth Beach Delaware….& you don’t want to miss a single show! From October 13th – 17th…to catch the best Live & Streaming Live Straight Ahead Jazz Acts…True Blue Jazz is THE only place to catch the best LIVE Straight Ahead Jazz Acts in Rehoboth Beach, Delaware! We’ve got’em!!!


8. Multiple October Events Happening at The Pines Rehoboth


Broadway Jordan and Michelle’s Haunted Cabernet

When: Thursday, October 28 | 6:30 p.m. to 8:30 p.m.

Where: The Pines | 56 Baltimore Ave, Rehoboth Beach, DE 19971

The Pines in Rehoboth has an entire weekend of ghostly events lined up to make this Halloween an unforgettable one! Stop in to enjoy all your favorite Halloween tunes as Michelle and Jordan kick off this SPOOKTACULAR Halloween Weekend!


Rocky Horror Interactive Showing

When: Friday, October 29 | 9:00 p.m.

Where: The Pines | 56 Baltimore Ave, Rehoboth Beach, DE 19971

This month The Pines is having an interactive showing of The Rocky Horror Picture Show. Hosted by the incredible House Entertainer Kristina Kelly, this show has all the supplies, provided to audience members at the beginning of the movie, so you'll have everything you need to enjoy this classic. Tickets are $25 per person with a minimum of four for a table.


Spooky Drag Brunch

When: Sunday, October 31 | 11:30 a.m. to 2 p.m.

Where: The Pines | 56 Baltimore Ave, Rehoboth Beach, DE 19971

Get started early on Halloween day with this spooky drag brunch at the pines! This brunch offers Halloween themed food and entertainment, and plenty of drinks!

Wizard of Oz Halloween Event with Aqua Bar & Grill

When: Sunday, October 31 | 7:30 p.m.

Where: The Pines | 56 Baltimore Ave, Rehoboth Beach, DE 19971

These two popular restaurants are joining together to bring you The Wizard of Oz themed Halloween 2021 Party. Explore the Enchanted Forest at Aqua and then venture over to the Emerald City within The Pines. The theme is not required, so feel free to dress up in any style of costumes and enter the cash -prize Costume Contest. Themed food and cocktails will be served!

9. Boo’s and Brew’s

When: Friday, October 29 | 9 p.m.

Where: Lewes Historical Society | 110 Shipcarpenter St Lewes, DE 19958

Spend a memorable evening with the living and the dead on the ghostly, historic campus of the Lewes Historical Society. Wander the grounds and encounter historic figures of the past and hear their tales of lamentations. Join the Lewes Historical Society at this Halloween sensation complete with food, drink, music, entertainment, and a costume party!


10. Sea Witch Festival

When: Saturday, October 30 | 8:00 a.m. to Nightfall

Where: Rehoboth Avenue

Every year, in late October, hundreds of witches, monsters, zombies, and other characters gather on Rehoboth Beach for the Sea Witch Halloween & Fiddlers Festival. The fun-filled two-day festival includes a costume parade and a dog parade, contests for the best costume, magic shows, monster art, pony rides, broom tossing contest, and more. Different activities of the Sea Witch Festival begin at 8 a.m. and last until dark.


11. Wags, Witches, and Warlocks

When: Saturday, October 30 | 10 a.m. to 1 p.m.

Where: Downtown Bethany Beach

The Annual Halloween Festival of Bethany Beach, Wags, Witches & Warlocks features a parade, costume contest, crafts, pet adoptions and more throughout downtown Bethany Beach! This event is family friendly, and all are welcome to partake in the fun!


12. Fifers Fall Fun

When: September 25 to October 30 | Mondays through Saturdays 10 a.m. to 5 p.m.

Where: Fifers Orchard | 1919 Allabands Mill Rd, Camden Wyoming, DE 19934

Explore the massive 6-acre Corn Maze, spend the day at the Fun Park, or do both! The fun park includes Super Straw Slides, Giant Corn Crib, Pumpkin Pad, Pedal Tractors, Rubber Ducky Races, Farmer Foosball, Roller Bowlers, Farm Volleyball, Octo-ball, Hula Cows, Funnel Ball, Wall Ball & more games U-Pick Pumpkin Patch. Some Saturdays may feature live music. Don't forget to visit the Farm Store for fresh fruits & veggies, apple pies, pumpkin rolls, kettle corn, apple cider donuts and other local foods.


13. Multiple October Events Happening at The Milton Theatre


Monster Mash Murders Dinner

When: Friday, October 8 | 6:30 p.m.

Where: The Milton Theater | 110 Union St, Milton, DE 19968

An annual Halloween meeting of ghouls turns "deadly" - all the little monsters come out, along with the princesses and super heroes of the more modern world. A villain, named 'X', is on the loose and wants to take over the world. Suspects abound with monsters to the left, mortals to the right, and detectives stuck in the middle with BOO in this audience-interactive thriller.

Milton Zombie Fest 2021 “Homecoming”

When: Saturday, October 16 | 4 p.m.

Where: The Milton Theatre | 110 Union St, Milton, DE 19968

Complete with zombie make-up stations, Kids Fest, costume contests, and of course, the traditional Zombie Walk at 8pm! Guests will enjoy plenty of food from the Milton Theatre food stalls, shopping from local merchants, spooky drink specials, and a little bit of horror from street performers! Makeup stations will be provided by the Delaware Learning Institute of Cosmetology for zombie transformations.

Quayside @ Nite Halloween Kid's Cabaret

When: Thursday, October 28 | 7 p.m.

Where: The Milton Theatre

An evening of music from some of the most talented kids in Delaware. Fun Halloween event for all ages. Come in costume. Free trick-or-treat bag for kids under 13. 


Oh, the Horrors! Film Trailer Challenge

When: Every Tuesday | 9 to 11 p.m.

Where: The Milton Theatre | 110 Union St, Milton, DE 19968

Get ready horror hounds and fear fiends! The Revival House is bringing back The Horror Trailer Challenge, with a chance to bring home a portion of the $1,500 cash up for grabs. This is your chance to take part in a fun film challenge and have your project seen on the big screen in front of a crowd at the Milton Theatre.

14. Hocus Pocus Drive-In Showing at Lefty's

When: Friday, October 29 | 7 p.m.

Where: Lefty's | 36450 Plaza Blvd, Lewes, DE 19958

Catch a fun family-friendly Halloween flick at Lefty's drive-in for only $25 per vehicle. Window-side delivery is available for food & drinks. Gates open at 7 and show starts at 7:30pm. 

15. RBDBCC Scarecrow Trail & Show

When: All month long

Where: Entire resort area - Dewey Beach, downtown Rehoboth Beach & Route 1.

Travel the Scarecrow Show & Trail during September and October, pick your favorite scarecrow and vote!

Dozens of numbered scarecrows will be located at various businesses throughout the Resort Area including Dewey Beach, Downtown Rehoboth & Route One.  Maps will be available at the Chamber’s Administration Building at 306 Rehoboth Avenue, Rehoboth Beach or at  Electronic and paper voting will be available and winners will be announced in November!

Check out more Delaware Beach Area Events on our Calendar!

For more things to See & Do at the Delaware Beaches! Visit our See & Do section!


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