Greyhounds Reach the Beach
Greyhounds Reach the Beach is an event for greyhound and sight hound owners, held every Columbus Day weekend in the ocean communities of Dewey Beach and Rehoboth Beach, Delaware. The event creates awareness of the need for foster and adoptive homes for retired racing greyhounds, raises funds to support greyhound adoption and brings owners/adopters together to celebrate their hounds.
Convention Center | Rehoboth Beach
Oct 5th - 9th | times vary
Fall Sidewalk Sale
Shop our Sidewalks!! The Rehoboth Beach-Dewey Beach Chamber of Commerce & Visitors Center announces their annual spring and fall Sidewalk Sales! Sales run from 10:00 AM to 8:00 PM (store hours may vary). It is a weekend for deals and fabulous finds! Shopping in downtown Rehoboth Beach, Dewey Beach, and Route One has never offered more merchandise at discount prices!
Downtown | Rehoboth & Dewey Beach
Oct 7th - 9th | 10 a.m. - 8 p.m.
Delmarva Folk Festival
Delaware Friends of Folk presents their 31st Annual Folk Fest! Join us for a weekend of live music, camping, vendors and more!
G & R Campground | Houston
Oct 7th and 8th | 2 p.m. - 11 p.m.
Boardwalk Buddy Walk
Join us as we unite for a common cause and raise funds for the 2022 Boardwalk Buddy Walk®. Whether you have Down syndrome, know someone who does, or just want to show your support, take the first step and donate or register today! Help us spread the word; all are welcome for our day of celebration!
The Bandstand | Rehoboth Beach
Oct 8th | 9 a.m.
The Big Draw Festival
A celebration of Drawing and Art making with free, family friendly art activities for families and kids, artists and non-artists! Fun for everyone! Presented by Mispillion Art League for the 4th year.
Downtown | Milford
Oct 8th | 9 a.m. - 3 p.m.
Delaware City Day
Family, friends, and fun! Join us for music, food, vendors, children’s activities (1 p.m. - 7 p.m. at the library), a parade at 1 p.m. and, fireworks at dusk!
Battery Park | Delaware City
Oct 8th | 10 a.m. - Dark
Dewey Goes Pink
SOLD OUT! The 'Gugie' Run on October 8th!
The Starboard | Dewey Beach
Oct 8th | 11 a.m.
OktDoverFest
The biggest block party in Downtown Dover featuring the best local music, beer, wine, spirits, food, and entertainment!
Downtown | Dover
Oct 8th | 2 p.m.
Ohmfest
Ohmfest is a grassroots, yoga, art and music festival in Dover! Our vision is to bring together healers, artists, and musicians to raise the vibration of our community & create an unforgettable festival that inspires our community to practice yoga, create art and play music.
Abridge Scout Reservation | Dover
Oct 8th and 9th | 9:30 a.m.
The Fast and the Furriest 5K
Join us on for a morning of fitness, furry friends, and raising funds to support our lifesaving animal services. The Fast & the Furriest 5K welcomes all different types of involvement, whether you choose to participate by running or walking, supporting us with a corporate sponsorship or individual donation, setting up a vendor table at the event, or simply setting up a chair in the park to cheer for our runners! This year participants will also enjoy an interactive photobooth, vendor village, food trucks, and more.
Rockford Park | Wilmington
Oct 9th | 8 a.m. - 11:30 a.m.
Beach Brunch
Guests will enjoy a seated brunch at Grain on the Rocks with each course prepared by a guest chef plus a cocktail reception with hors d’oeuvres and dessert stations. Guest chefs will each prepare a brunch-themed dish paired with brunch cocktails. Best of all, you will support Meals On Wheels programs in your local community and across Delaware which delivered 6,600 nutritious meals to homebound seniors last year. There may be limited tickets available, please call Regina Dodds at (302)656-6451.
Grain on the Rocks | Lewes
Oct 9th | 10:30 a.m. - 1:30 p.m.
Overfalls Rock the Boat Gala
Overfalls Annual Gala and 50th Anniversary Kick-Off Party. To be held at Baywood Country Club in Longneck. Live auction, dinner, dancing and live music. Tickets now on sale!
Baywood Country Club | Longneck
Oct 9th | 6 p.m. - 9 p.m.
Rehoboth Beach Jazz Festival
The Rehoboth Beach Jazz Festival is THE annual, 4-day fall music event held in multiple locations in Sussex County. Bringing great music to the area since 1990, we've had the greatest Artists of Smooth Jazz and R&B grace our stages. We take pride in being part of the exciting Fall season that occurs every year here at the beach. Come for the food, come for the tax free shopping, come for the beauty of the beach in the fall air.....but most of all, come for the MUSIC!
Locations Vary | Sussex County
Oct 13th - 16th | time vary
Little Show of Horrors Opening Night
The deviously delicious Broadway and Hollywood sci-fi smash musical has devoured the hearts of theatre-goers for over 30 years. The meek floral assistant Seymour Krelborn stumbles across a new breed of plant he names "Audrey II" - after his coworker crush. This foul-mouthed, R&B-singing carnivore promises unending fame and fortune to the down and out Krelborn as long as he keeps feeding it, blood. Over time, though, Seymour discovers Audrey II's out of this world origins and intent towards global domination! We implore you: Don’t feed the plants!
Clear Space Theatre | Rehoboth Beach
Oct 14th | 7 p.m.
Apple-Scrapple Festival
Come celebrate this unique Delaware event celebrating food and fun! The Apple-Scrapple Festival features a food court, car show, live entertainment, a home decorating contest, apple orchard tours, wagon rides, and more!
Downtown | Bridgeville
Oct 15th | 9 a.m. - 4 p.m.
Blackbird Creek Fall Festival
Join us for the 14th Annual Blackbird Creek Fall Festival to celebrate everything the Delaware Bay has to offer. There will be fun and games for all ages and best of all - it is FREE to attend!
Blackbird Creek Reserve | Townsend
Oct 15th | 10 a.m. - 4 p.m.
Bark on the Boards
Join the Brandywine Valley SPCA for the 5th annual Bark on the Boards block party! Live music, dock diving dog competition, a drag show, yoga with puppies, kids fun zone, and more!
The Bandstand | Rehoboth Beach
Oct 15th | 11 a.m. - 2 p.m.
Zombie Fest
The zombies are BACK! Complete with zombie make-up stations, Kids Fest, costume contests, and of course, the traditional Zombie Walk at 8pm! Join the Milton Theatre as we try to survive an evening of haunting entertainment of epic proportions!
Downtown | Milton
Oct 15th | 4 p.m. - 9 p.m.
Designer Bag Bingo
Gather your friends, family, and luckiest crew for a fun evening out at Designer Bag Bingo! This is our first major fundraising event in Sussex County since 2019, and we promise an exciting evening full of fun and fabulous prizes.
Convention Center | Rehoboth Beach
Oct 19th | 5:45 p.m. - 9 p.m.
Milford Community Parade
Held annually the third Wednesday in October, the Milford Community Parade has delighted all ages for the last 30 years. More than 10 marching bands are scheduled to appear. The parade will step off at 6:30 p.m. The theme is “Splish Splash!”
Downtown | Milford
Oct 19th | 6:30 p.m.
Ice Cream Social
We invite you to our downtown station on Rehoboth Avenue on Thursday, October 20th, for an ice cream social event! Come and enjoy a variety of ice creams and toppings and learn more about fire safety. Sparky the Safety Dog will be in attendance, teaching us all about fire safety: smoke alarms, escape plans, stop drop roll, and more! All welcome! Park behind the station at the city hall parking for easy access.
Volunteer Fire Company | Rehoboth Beach
Oct 20th | 4:30 p.m. - 6:30 p.m.
Station #2 Open House
FREE EVENT! Live fire and vehicle extrication demos, equipment display, children's activities, smoke house and MORE! Revelation Beer Truck serving Craft Beer and Sposato Wines. At Station #2, next to the Nassau Bridge!
Station #2 Lewes Fire Department (next to the Nassau Bridge) | Lewes
Oct 20th | 4:30 p.m. - 8 p.m.
The Ultimate Tailgate
Get a taste of New Castle County’s best creative tailgate bites at the Ultimate Tailgate! Grab your friends and family and wear your team’s colors to this fun-filled community event. This laidback event features craft beer tastings curated by Two Stones as well as wine, cocktails, live music and the Brew Masters’ Beer Auction. All while supporting the incredible mission of Meals On Wheels Delaware – Together we can end senior hunger!
The Grove at Delaware Park | Wilmington
Oct 20th | 6 p.m. - 9 p.m.
Fall Craft Fair
Come on out and support our first annual craft fair. Over 100 vendors!
Volunteer Hose Company | Middletown
Oct 22nd | 8:30 a.m. - 3 p.m.
Fall Craft Fair
The public is invited to celebrate the work of talented artisans and enjoy live music, and delectable treats. There is an admission fee of $5 for adults, and children 12 and under are free. Plan to spend the day and enjoy the festive atmosphere of our main campus where our historic buildings will be open to the public. The complex is filled with shade trees and gardens, providing a beautiful setting for your visit.
Historical Society | Lewes
Oct 22nd & 23rd | 9 a.m. - 4 p.m.
Fall Sidewalk Sale
The annual Lewes Merchants’ Fall Sidewalk Sale is a three-day event featuring discounts and sales at participating downtown businesses. For more information visit the Lewes Chamber website!
Downtown | Lewes
Oct 22nd & 23rd | 10 a.m. - 5 p.m.
Boos & Brews
Beware our ghostly affair and attend if you dare! When the spirits awaken and witches take flight, we'll gather in Lewes in the dark of night! Spend a memorable evening with the living (and the not-so-living) on the ghostly and historic Shipcarpenter Street Campus of the Lewes Historical Society. While you mingle amongst the supernatural, partake in the flavors of the local eateries, breweries, and vineyards. Small bites will be provided by caterers and vampires alike. Complimentary witches brew will be available for you!
Historical Society | Lewes
Oct 28th | 7 p.m.
Wicked Weekend
Join us for trick-or-treating, pumpkin painting, a haunted train ride, and other family-friendly Halloween activities on Saturday, October 29th in downtown Milton! This is a FREE event!
Memorial Park | Milton
Oct 29th | 5 p.m. - 8 p.m.
Sea Witch Festival
Three solid days of spook-tacular fun await! In addition to the annual parade down Rehoboth Avenue Saturday morning, the Sea Witch Festival features entertainment, vendors, trick-or-treating, games, hayrides, a dog parade, 5K, and more throughout the city.
Downtown | Rehoboth Beach
Oct 28th - Oct 30th | time vary
Flannels & Fizz
A fun day of fall and fizz! Come out and shop over 70 local vendors in our fall market, bring the kids for inflatables and pumpkin bowling and enjoy a large selection of wines, ciders, beer and alcohol!! Fall treats including cider, hot chocolate and more! Bring the whole family for a day of fall fun! Best of all…..a Grass Roots adoption event!! Proceeds will be donated to this amazing organization! Stop and visit Grass Roots and take home a new family member!
Hudson Fields | Milton
Oct 30th | 10 a.m. - 3 p.m.
“Finding Their Voices”: Lewes Walking Tour
The Lewes Historical Society will address, recognize and celebrate the lives and accomplishments of the African American community in Lewes in the past and present. On your visit to the historic Shipcarpenter Street Campus and surrounding areas you will learn about surviving landmarks and discover the discover the preserved stories of this diverse community. For more information and to purchase tickets, visit www.historiclewes.org