64th annual Labor Day White Marlin Fishing Tournament
SEPT. 1-3, OCEAN CITY, MD
Registration from 6:30 to 8 p.m., Aug. 31. Fishing Days (2 of 3) Sept. 1-3, lines in 8 a.m., lines out 4:30 p.m. Weigh-ins on fishing days from 6 to 8 p.m.
Clear Space presents Final Bow
SEPT. 2, REHOBOTH BEACH
Clear Space Theatre will host a cabaret-style performance by its summer cast before they embark on their next adventure. The show starts at 10 p.m. on the Clear Space stage, 20 Baltimore Ave., Rehoboth Beach.
CAMP Rehoboth Sun Festival
SEPT. 2-3, REHOBOTH BEACH
A two-night event featuring headline entertainment, this annual fundraiser takes place at the Rehoboth Beach Convention Center, 229 Rehoboth Ave. On Saturday, Sept. 2, it’s a night of comedy, drag and a live auction. The evening features Dixie Longate and Randy Roberts. Sunday, Sept. 3, it’s a night of dance, featuring DJ Robbie Leslie and DJ Joe Gauthreaux.
Piping Out of Summer
SEPT. 4, REHOBOTH BEACH
Starts at 5:30 p.m. on the boardwalk at the Henlopen Hotel and proceeds to Bandstand. Revelers with musical instruments of any and all varieties are asked to gather on the Boardwalk and will proceed to Pipe Out down the Boardwalk to the Bandstand. The historical society provides kazoos for those without instruments.
Bethany Beach Jazz Funeral End of Summer Celebration
SEPT. 4, BETHANY BEACH
Starting at 5:30 p.m. at the north end of the Bethany Beach Boardwalk, the funeral proceeds to the Bandstand. Three New Orleans-style Dixieland Bands help Bethany bid a “Fond Farewell to Summer.” The Jazz Funeral features a gathering of mourners who will walk down the boardwalk carrying a casket representing summer.
RBFS presents “Fleabag”
SEPT. 7, LEWES
Rehoboth Beach Film Society will present a one-time showing of “Fleabag” at 4 p.m., Thursday, Sept. 7 at the Cinema Art Center on Dartmouth Drive, Lewes.
COST: $25 general admission, $20 members, $22 for seniors, $5 students
Clear Space Theatre: A Grand Night Gala
SEPT. 8, REHOBOTH BEACH
Clear Space Theatre will host a Grand Night Gala & After Glow Party beginning at 6 p.m., Sept. 8 at the Rehoboth Beach Country Club. The event includes a silent auction, wine pull and a preview of the 2024 season.
COST: $195 Gala tickets (add $25 for After Glow Party); $75 for After Glow Party only.
Cheer Fall Festival at Trap Pond State Park
SEPT. 8, TRAP POND STATE PARK, LAUREL
Seniors from all over Sussex County enjoy a day of hiking, dancing, games, raffles, and a picnic lunch. Games with prizes are enjoyed as well as the opportunity to meet with old friends.
Wine on the Beach
SEPT. 8-9, OCEAN CITY, MD
The event features a full complement of products from Maryland wineries and also includes craft vendors, artisans and on-stage entertainment. Park at 809 S. Atlantic Avenue.
COST: $30 online or $35 at the door
Youth Fishing Tournament
SEPT. 9, CAPE HENLOPEN STATE PARK, LEWES
Youth 15 and younger are invited to participate in the annual fishing tournament set for 8 to 11 a.m. at the Cape Henlopen State Park Fishing Pier. Prizes will be given for the largest fish caught, the most fish and the first and last fish caught. All entrants will receive a prize.
Town-wide Yard Sale
SEPT. 9, MILTON
Discover treasures and one-of-a-kind finds at this annual event. The town-wide yard sale will take place throughout the town of Milton beginning at 7 a.m., Saturday, Sept. 9.
Annual Chocolate Tasting
SEPT. 9, CAPE HENLOPEN STATE PARK, LEWES
This annual event, featuring homemade chocolates, is held from 1 to 4 p.m. at the Officer’s Club located in Cape Henlopen State Park.
COST: $8 for six tastings
45th Annual Bethany Boardwalk Arts Festival
SEPT. 9, BETHANY BEACH
This show runs from 10 a.m. to 5 p.m. and features paintings, woodwork, metal, clay, baskets, jewelry and porcelain from more than 100 artists as well as a silent auction and wine tasting. Rain date is Sept. 10.
COST: $30 for wine tasting
36th Annual Amish Country Bike Tour
SEPT. 9, DOVER
This event takes place from 7 a.m. to 5 p.m. Routes begin and end on Legislative Mall, 411 Legislative Ave, Dover. There are 16, 25, 50, 62, or 100-mile loops through peaceful, flat, low-traffic Amish countryside. To promote safety at the start and to ensure that rest stops are not overwhelmed, a staggered start is planned for this year. Up to five rest stops are included. Following the tour there will be music, vendors, food and awards.
Delaware Agricultural Museum and Village Fall Craft Show
SEPT. 9, DOVER
The Delaware Agricultural Museum and Village, Fall Craft Show, will take place at 866 N DuPont Hwy, Dover, from 10 a.m. to 3 p.m. This large outdoor event will be held in the museum’s 1890s village, and will feature local vendors selling home and garden goods, handmade crafts, health and beauty products, jewelry and more. Proceeds will benefit the museum.
COST: $5 general public; free to members
86 Hook & Ladder Brewfest
SEPT. 9, REHOBOTH BEACH
The first 86 Hook & Ladder Brewfest will be held from noon to 4 p.m., Sept. 9 at the Rehoboth Beach Convention Center, 229 Rehoboth Ave. Regional craft breweries will offer samples of their beer and patrons will enjoy great food, music, raffles and giveaways. All proceeds benefit the purchase of new equipment for the Rehoboth volunteer department.
COST: $45 for adult drinkers; $5 for adult non-drinkers
45th Annual Nanticoke Indian Powwow
SEPT. 9-10, MILTON
A Sussex County favorite, this festival is held from 10 a.m. to 7 p.m. both days at 30045 Eagles Crest Road. The gathering includes American Indian drummers and singers from the area as well as visiting tribes, and authentic Indian arts and crafts vendors. There’s also a kids corner with face painting and make-and-take crafts, a car show and more. Grand entry will be held at noon both days.
COST: $10 for adults; $5 for children, kids under 10 admitted free
Berlin Small Town Throwdown Concert
SEPT. 10, BERLIN, MD
The town of Berlin will feature a free country music concert from 1 to 6 p.m. featuring the music of Red Dirt Revolution. Beer and food will be available for purchase and shops will be open. Bring your own chair. Parking available at Stephen Decatur Park on Tripoli Street.
Hooper’s Island Watermen’s Rodeo Boat Docking Contest
SEPT. 10, FISHING CREEK, MD
This event takes place from 11 a.m. to 5 p.m. at P.L Jones Marina and Boatyard. Benefiting the Hoopers Island Volunteer Fire Company.
Bahia Marina Flounder Pounder Fishing Tournament
Sept. 10, OCEAN CITY, MD
Held out of Bahia Marina, 22nd Street and the Bay in Ocean City, the tournament is for all ages. Sign up 8 to 9:30 a.m.; captains meeting, 9:30 a.m.; fishing, 10 a.m. to 4:30 p.m. Prizes for first, second and third place.
Sept. 11 Memorial Sport Fishing Tournament
SEPT. 11, OCEAN CITY, MD
This annual tournament takes place at the Ocean City Fishing Center, 12940 Inlet Isle Ln, Ocean City, Md.
Ocean City Bikefest
SEPT. 12-17, OCEAN CITY, MD
The largest motorcycle rally on the East Coast, participants will gather at the Convention Center, 809 S. Atlantic Ave. Event is a family-friendly motorcycle rally with four days of concerts, food and drink vendors. Music lineup includes: Joan Jett and the Blackhearts, Lynyrd Skynyrd, and ZZ Top.
44th Annual OC Marlin Club Challenge Cup
SEPT 14-16, OCEAN CITY, MD
Two of three fishing days. This release tournament is a competition between Ocean City Marlin Club and the Cape May Marlin and Tuna Club.
Delmarva Folk Festival
SEPT. 15-16, HOUSTON
Presented by the nonprofit Delaware Friends of Folk, the festival hosts folk musicians from Delmarva and the Mid-Atlantic region and will include camping, craft and food venros, workshops and more. Taking place at G & R Campground, 4075 Gun & Rod Club Rd, Houston, DE.
Possum Point Players presents “Ragtime”
SEPT. 15-24, GEORGETOWN
Based on the novel by E.L. Doctorow, Ragtime is set in the turn of the century New York and features three interweaving stories. Shows are Friday, Saturday and Sundays at Possum Hall, 441 Old Laurel Road, Georgetown.
COST: $27, $25 for students and seniors
Indian River Marina Autumn Art Festival
SEPT. 16, DEWEY BEACH
This first annual event is a spin off from the Marina’s Seafood and Art Festival that began in 2009. Festivities will take place at the Indian River Marina, south of Dewey Beach, Delaware Seashore Park, from 10:00 a.m – 5:00 p.m. This festival will spotlight the local artist community, and provide a fun, family atmosphere with games, entertainment and music.
SEPT. 16, OXFORD, MD
The 4th annual Oxford Community Center Road Rally will begin at 8 a.m. with breakfast and coffee. Flag out will begin at 9 a.m. Enjoy navigating over 70 miles of scenic roads in your classic car with little traffic.
SEPT. 16, CAMBRIDGE, MD
A long-distance triathlon that is considered one of the most difficult one-day sporting events in the world. Triathletes compete to make it through 140.6 miles all in one day. A 2.4 mile swim in the Choptank River, a 112-mile bike ride around Dorchester County, and a 26.2-mile run in Cambridge. Spectators are welcome to cheer on participants along the course (where safe).
Dewey End of Season Beach Party
SEPT. 16, DEWEY BEACH
Join the Dewey Business Partnership for its annual end of season party on the beach at New Orleans Street.
Southern Delaware Wine, Food & Music Festival
SEPT. 16, LEWES
A celebration of life, laughter, friendship, and togetherness that pours each year’s proceeds into local nonprofits doing important work to strengthen our community. The event, held from noon to 3:30 p.m. at Nassau Valley Vineyards, features tastes, sounds, people and passions of coastal Delaware. Enjoy unique culinary experiences featuring food from local restaurants and award-winning chefs; wines, craft beers, and cocktails; a silent auction and more. Ticket includes all you can eat and drink.
COST: $125 to $250
Annual Native American Festival
SEPT. 16, VIENNA, MD
An event hosted by the Nause-Waiwash Band of Indians to preserve their history, enhance their traditional culture, and maintain their traditions through education, the 31st Annual Native American festival is set for 10 a.m. to 4 p.m., at 214 Middle St., Vienna, rain or shine. The festival features traditional dancers, singers, drumming, vendors, crafts, artists’ demonstrations, authentic Native food, bake tables, raffles, exhibits, a large silent auction and more.
COST: $7 for adults; ages 4 and under are free
Broad Creek Bike and Brew
SEPT. 16, LAUREL
Begins at Laurel Elementary School and ends at Janosik Park on Broad Creek, Laurel. There are 15, 25, 50, or 100 mile rides past historic attractions, beautiful waterways and more. Finish Party features local breweries, live music and chicken BBQ.
Fall Fling, Long Neck Methodist Church
SEPT. 16, MILLSBORO
The Fall Fling will be held from 9 a.m. to 1 p.m. and will feature a yard sale, food & dessert sale, homemade desserts, soups, salads, sandwiches and more.
Lewes Artists Studio Tour
SEPT. 16, LEWES
An annual art event from 10 a.m. to 4 p.m. that presents the unique opportunity to enter the working environments of regionally and nationally acclaimed local artists. Have the chance to enter the free raffle drawing for a unique piece of art that each artist will be offering as a thank you for your visit. The location of the studios covers an area in both the historic Lewes town center as well as in the newer residential areas within a couple of minutes from downtown Lewes. The tour promises a day filled with color and form and an inspired view of the Eastern Shore through the eyes of our artists.
Annual Milford Riverwalk Freedom Festival
SEPT. 17, MILFORD
Held in Bicentennial Park, this outdoor festival has activities for all ages. Craft vendors, kids corner, car show, food trucks, duck dash, beer garden and live music. The day ends with fireworks over the Mispillion River.
Festival Hispano Maxima Hispanic Fest
SEPT. 17, GEORGETOWN
This event will be held from 11 a.m. to 7 p.m. Celebrate the diversity of the Hispanic cultural heritage in Delaware, Maryland and Virginia. There will be music and dances performed by local, national and international groups, traditional arts and crafts, and traditional food with an emphasis on Latino cuisine.
Milton Garden Club Tour
SEPT. 17, MILTON
The tour will be held from 10 a.m. to 3 p.m. at seven diverse gardens. Advance tickets will be available at Peppers Nursery, The Mercantile, Bella Terra and Lewes Printing. In addition to the gardens, the day will feature artists and musicians in the gardens, vendors selling garden-related items, a plant sale and a bake sale. There is no rain date, but there is a hurricane/nor’easter date of Sept. 23.
COST: $20 in advance; $25 day of the tour
SEPT. 17, FRANKFORD
The annual Alpaca Festival will be held from 10 a.m. to 2 p.m., Sept. 17 at Four Acres farm in Frankford. A family day of fun and celebration featuring all things alpaca. Admission is one nonperishable food item.
Worcester County Plein Air
SEPT. 17-23, WORCESTER COUNTY AND BERLIN, MD
Artists capture the essence of Worcester County in their paintings during this annual event. The event culminates with the sale and open to the public exhibit from 5 to 7, Friday, Sept. 22 at the Berlin Library, and from 10 a.m. to 2 p.m., Saturday, Sept. 23.
Glitz & Glam Fashion Show
SEPT. 21, DEWEY BEACH
The Hyatt Place in Dewey Beach will host a Glitz & Glam Fashion Show and Luncheon, featuring a preview of 2023 Fall and Winter fashions by Crazy Ladyz. Event takes place from 11 a.m. to 2 p.m., Thursday, Sept. 21 to benefit the Harry K. Foundation, which works to defeat childhood hunger throughout Delaware. Individual tickets and Sponsor tickets for tables of ten attendees are available.
Save ’Em By The Sea Casino Night H.A.P. Anniversary Celebration
SEPT. 21, MILLSBORO
The second ever Save ‘Em By The Sea Casino Night in honor of Humane Animal Partners 150th anniversary will be held at Baywood Greens from 6 to 9:30 p.m. to celebrate the HAP and its accomplishments for the people and animals of Delaware.
COST: $125 per ticket, $200 for two
Sunfest Kite Festival
SEPT. 21-24, OCEAN CITY, MD
Hosted by The Kite Loft, the annual Sunfest Kite Festival in Ocean City is a kite flying extravaganza and funfest for kite fliers and spectators. You can expect to see kites in the air daily from 9 am till dark, wind and weather permitting. All events are free, including a giant kite candy drop for children.
Clear Space presents “The Cemetery Club”
SEPT. 21-OCT. 1, REHOBOTH BEACH
In this comedy, three Jewish widows meet for tea once a month before going to visit their husbands’ graves. They meet Sam the butcher, who is visiting his wife’s grave and things take a comedic turn.
COST: $20 to $34.50
OC Adventure Fest
SEPT. 22-24, OCEAN CITY, MD
This outdoor sports and gun show will be held at Roland E Powell Convention Center, 4001 Coastal Hwy, Ocean City, Md. The event includes something for everyone, from military and law enforcement to residents and families. Auction items will be on display in the convention center lobby throughout OC AdventureFest. Auction items will include: custom gun, custom surfboard and autographed guitars. Concerts include musicians, Dave Bray, Lee Greenwood and Don McLean.
Berlin Fiddler’s Convention
SEPT. 22-24, BERLIN, MD
Three days of live bluegrass music on Main Street in Berlin, Md. Features bluegrass, old-time, Celtic, Irish and Cajun musicians from all over the country. Local crafts, food, beer and wine vendors. Lineup includes: Songs for the Road Band, Rebecca Frazier, The High and Wides, and The Plate Scrapers.
Concours d’Elegance on Chesapeake Bay
SEPT. 22-24, CHESTER, MD
A judged exhibition of exceptional vintage and classic motor vehicles in a new location, the Kent Island Yacht Club. The event includes locally sourced cuisine, music and vendors.
COST: $55 in advance
Apple Cider Festival
SEPT. 23, LEWES
The festival celebrates all things fall and apple from 10 a.m. to 3 p.m. at the Lewes Fire Station 82 in Nassau. More than 50 local crafters and vendors will be in attendance.
Delaware Resorts Fall Home Expo
SEPT. 23-24, LEWES
Two days of exhibitors showing the latest in the resort area home market, home-related goods, and home-related services, held at Cape Henlopen High School. All the most successful local real estate developers, builders, mortgage, financial, home products and home service providers under one roof. Sept. 23 hours are 9 a.m. to 4 p.m., and Sept. 24 is 10 a.m. to 3 p.m.
25th Annual Delaware Seashore Fall Surf Fishing Classic
Sept. 23-24, REHOBOTH BEACH
Tournament headquarters is Old Inlet Bait and Tackle. Fishing areas are Delaware Seashore State Park and Fenwick Island State Park designated fishing areas. Fishing licenses are required. More than $15,000 in cash and prizes will be available.
COST: $40 for adults, $15 for kids under 14
Delaware Botanic Gardens Dinner Party
SEPT. 28, DAGSBORO
Held from 5 to 8 p.m. at Delaware Botanic Gardens, 30220 Piney Neck Road, patrons will enjoy an evening in a beautiful open-air setting, sipping wine while dining in view of the Piet Oudolf Meadow Garden. Coastal foods presented by SoDel Concepts, wine presented by Bin 66, and music provided by Vince Varrassi and 5th Avenue.
COST: Single, $150; members, $140
Mid-Atlantic Symphony Orchestra
SEPT. 28, EASTON, MD
The symphony presents a master works concert at 7:30 p.m., Easton Church of God, Easton, featuring Strum by Jesse Montgomery, Tchaikovsky’s Serenade for Strings and Beethoven’s Symphony No. 4.
Fall Yoga Camping Festival
SEPT. 28-OCT. 1, HOUSTON
All are welcome to enjoy a weekend of morning meditation, drum circles and cocktails by the campfire (included in ticket price). Event is held at G & R Campground in Houston.
Dewey Golden Jubiliee
SEPT. 29-OCT. 1, DEWEY BEACH
Goldens and their friends are invited to attend the Golden Jubilee weekend to recognize a great cause, Morris Foundation’s Golden Retriever Life Time Study. Events include a parade through Rehoboth Friday night, a romp on the beach and a beach bonfire.
History Book Festival
SEPT. 29-OCT. 1, LEWES
The festival will feature best-selling authors of historical fiction and nonfiction from all over the country who share insights, talk about their books and answer questions.
COST: $28 for closing address only
Oceans Calling Music Festival
SEPT. 29-OCT. 1, OCEAN CITY, MD
A three-day music festival in partnership with musicians O.A.R. featuring over 30 performances on 3 stages, all on the Ocean City Boardwalk. Lineup includes: Jack Johnson, John Mayer, The Lumineers, and more. Held at 809 S. Atlantic Ave.
Mid-Atlantic Symphony Orchestra
SEPT. 30, LEWES
The symphony presents a master works concert at 7:30 p.m., at Cape Henlopen High School, featuring Strum by Jesse Montgomery, Tchaikovsky’s Serenade for Strings and Beethoven’s Symphony No. 4.
Cape Artists Gallery Sidewalk and Tent Sale
SEPT. 30, LEWES
The Cape Artists Gallery will hold its Sidewalk and Tent Sale from 10 a.m. to 5 p.m. at 110 W. Third St., Lewes. Light refreshments will be available.
Shore Living Expo
SEPT. 30, SALISBURY, MD
Held from 10 a.m. to 4 p.m. at the Wicomico Youth & Civic Center, 500 Glen Ave, Salisbury, Md, the event celebrates health, wealth, and home on Delmarva. This family-friendly event celebrates health, wealth, home and all that makes Delmarva a great place to live.
Stars & Stripes Festival
SEPT. 30, MILLSBORO
Festival will be held at at Cupola Park from 6 p.m. – 9:30 p.m. An evening of great food, drinks, games, and a fireworks display at dusk.
Chesapeake Film Festival
SEPT. 30 – OCT. 1, EASTON, MD and VIRTUAL
Live showings Sept. 30 through Oct. 1 at the Avalon Theatre. Virtual showings Oct. 3 through Oct. 8. The Chesapeake Film Festival entertains, educates and inspires diverse audiences of all ages by presenting exceptional independent films and events.
COST: $125 for VIP tickets; $20 for most films; $30 for Virtual Festival
Mid-Atlantic Symphony Orchestra
OCT. 1, OCEAN PINES, MD
The symphony presents a master works concert at 7:30 p.m., at Community Church, Ocean Pines featuring Strum by Jesse Montgomery, Tchaikovsky’s Serenade for Strings and Beethoven’s Symphony No. 4.
UD Coast Day
OCT. 1, LEWES
Located at the University of Delaware’s Hugh R. Sharp Campus, 770 Pilottown Road, Lewes, this is a day of fun for families to learn about coastal, marine and environmental science. Events take place from 11 a.m. to 3 p.m.
Greyhounds Reach the Beach
OCT. 5-8 REHOBOTH BEACH
Event celebrates lovable greyhounds, creates awareness of the need for foster and adoptive homes, and raises needed funds to support greyhound adoption.
Annual Endless Summer Cruisin’ Hot Rod & Custom Car Show
OCT. 5-8, OCEAN CITY, MD
The Hot Rod & Custom Car Show will take place indoors at the OC Convention Center from Oct. 5-8. In addition, car shows and vendors will take place at the Convention Center Parking Lot and the Inlet Parking Lot, plus several more car shows will take place at various business locations in and around Ocean City. Vendors will be inside and outside of the Convention Center.
COST: $10 Thursday and Friday; $15 Saturday and Sunday. Children under 14 admitted free with an adult.
Wings and Wheels
OCT. 6-7, GEORGETOWN
Set for 10 a.m. to 4 p.m. at Delaware Coastal Airport, 21553 Rudder Lane, Georgetown, the festival features planes, car show, WWII re-enactors, food vendors, entertainment, craft vendors and more. There will also be a Friday dinner show from 6 to 10 p.m. Parking will be at the Marvel Museum, 510 Bedford St, Georgetown, with trams and buses available to shuttle to the airport.
Lewes Merchants’ Sidewalk Sale
OCT. 6-8, LEWES
The annual Lewes Merchants’ Fall Sidewalk Sale is a three-day event featuring discounts and sales at participating downtown businesses.
Rehoboth Beach Annual Fall Sidewalk Sale
OCT. 6-8, REHOBOTH AND DEWEY BEACH
The Rehoboth Beach-Dewey Beach Chamber of Commerce and Visitors Center announces its fall sidewalk sales. It’s a weekend for deals and fabulous finds. Downtown Rehoboth Beach, Dewey Beach, and Route 1 has never offered more merchandise at discount prices.
Mid-Atlantic Small Craft Festival
OCT. 6-8, ST. MICHAELS, MD
Held at the Chesapeake Bay Maritime Museum, 213 N Talbot St, St. Michaels, this is one of the nation’s largest gatherings of small boat enthusiasts and unique watercraft. Hundreds of amateur and professional boat builders and enthusiasts come from all over the region to display their one-of-a-kind kayaks, canoes and other traditional small craft. Small craft owners hailing from all over the country will also be available to share their knowledge. Hours are 10 a.m. to 5 p.m. all three days.
COST: $17 for adults; $14 for seniors and students; $6 for children 6 to 17.
Coastal Concerts – Michelle Cann
OCT. 7, LEWES
Coastal Concerts will host a concert featuring Michelle Cann on the piano at 2 p.m. at Cape Henlopen High School. Cann made her orchestral debut at age 14 and has since performed as a soloist with many prominent ensembles.
7th Annual Easton Beer Festival
OCT. 7, EASTON, MD
Held from noon to 4 p.m. at the Easton Volunteer Fire Department, 315 Leonard Rieck Drive, Easton, Md. Maryland’s largest under cover craft beer festival will feature 40+ breweries, wineries and distilleries which will be pouring 120+ craft beers, ciders, seltzers, wines and spirits and more from the Mid-Atlantic region and beyond. Live music by Black Dog Alley. Food, vendors, raffles and games of chance will be available. Event is indoor/outdoor. Attendees must be at least 21 with valid ID to enter.
Boast the Coast Maritime Festival
OCT. 7, LEWES
Boast the Coast was conceived in 1996 to showcase Lewes’ nautical heritage and to feature activities that complemented the already long-established University of Delaware’s annual Coast Day event. Maritime-themed events are presented from 11 a.m. to 2 p.m. at the 1812 Park and local businesses.
Boardwalk Buddy Walk
OCT. 7, REHOBOTH BEACH
This annual fundraiser takes place from 9 a.m. to 2 p.m. and unites participants in promoting acceptance and inclusion of people with Down syndrome.
Berlin Fall Cruisers Classic Car Show
OCT. 7, BERLIN, MD
10 a.m. to 2 p.m. Main Street, Berlin, Md. The Berlin Fall Cruisers Classic showcases roaring classic automobiles as they cruise into downtown Berlin. Music in the streets, boutiques, antiques, a wine bar, a brewery, galleries and vintage stores to browse and lots of delicious artisan and locally crafted food at nine amazing restaurants, this is the place to stroll around while enjoying hundreds of 50s, 60s and 70s classic cars of all types.
COST: $10 to register a car
The Big Draw Festival
OCT. 7, MILFORD
This local event is hosted by the Mispillion Art League and is part of the international celebration of drawing, the Big Draw Festival, which originated in the UK and now takes place in more than 25 countries. This year’s event will be held from 9 a.m. to 3 p.m., in the streets around the Mispillion Art League. There will be activities for all to enjoy – families, kids, artists and nonartists.
Ocean City Inshore Classic Fishing Tournament
OCT. 7-8, OCEAN CITY, MD
The Ocean City Inshore Classic is a 32-hour inshore fishing tournament with categories for rockfish, founder, tautog and open. 1st, 2nd and 3rd Place prizes will be paid in all four categories and calcuttas will be paid to the largest fish in each category.
10th Annual True Blue Jazz Festival
OCT. 11-15 LEWES-REHOBOTH BEACH
The 11th annual True Blue Jazz Festival is an independent jazz festival. The festival is focused on straight ahead or real jazz, featuring songs from the Great American Standards Songbook. From local & regional jazz musicians with legendary talent to national and internationally recognized jazz artists, masters and icons.
Rehoboth Beach Jazz Festival
OCT. 12-15 REHOBOTH BEACH
The Rehoboth Beach Jazz Festival is local and the artists are global. Since 1990, some of the greatest artists of smooth jazz and R&B have graced the stages of the RBJF. Main Stages include Rehoboth Beach Convention Center, Cape Henlopen Performing Arts Theater, Rusty Rudder and Epworth United Methodist Church. Shows are also in many restaurants and smaller venues throughout Sussex County. Tickets are sold online, by phone, or at the box office.
30th Annual Apple Scrapple Festival
OCT. 13-14, BRIDGEVILLE
A festival that is the hometown of T.S. Smith and Sons Farm and RAPA Scrapple. Opens at 4 p.m. Friday, Oct. 13 and at 9 a.m. Saturday, Oct. 14. A 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, an Invitational Scrapple Sling, health and safety fair, trade show and more.
Good Beer Festival
OCT. 13-14, SALISBURY, MD
Hours are Friday, 5 to 10 p.m. and Saturday, noon to 5 p.m. The Good Beer Festival in Pemberton Park, Salisbury offers festival-goers unlimited tastings of American craft brews. Friday offers the only nighttime beer festival on the Eastern Shore. In addition to great beer, the festival offers music, games, vendors and food.
Clear Space Theatre presents “Young Frankenstein”
OCT. 13-29, REHOBOTH BEACH
Clear Space Theatre presents the story of Frederick Frankenstein, grandson of Victor, who inherits his family’s estate in Transylvania. With the help of his sidekick Igor and a leggy lab assistant called Inga, Frederick finds himself in the mad scientist shoes of his ancestors.
COST: $20 to $34.50
Easton Airport Day
OCT. 14, EASTON, MD
This free event, held at 29137 Newnam Rd, Easton, Md., showcases rare and unique aircraft, military jets, airport equipment. Classic cars will also be on display during the event. Food and beverage vendors will be on site.
Berlin Oktoberfest and Sidewalk Sale
OCT. 14, BERLIN, MD
Featuring authentic Oktoberfest music from The Edelweiss Band and other performers, and including a Fall Sidewalk Sale. Event also includes brats, German chocolate cake, beer, mead and more.
Bark on the Boards
OCT. 14, REHOBOTH BEACH
Join the Brandywine Valley SPCA for its annual Bark on the Boards block party. From 11 a.m. to 2 p.m., guests will enjoy live music, dock diving dog competition, a pet costume contest, kids’ activities and more.
CAMP Rehoboth Block Party
OCT. 15, REHOBOTH BEACH
Held on the second block of Baltimore Ave. from 11 a.m. to 4 p.m., the annual Block Party is a day of celebration, performances, and vendors including local restaurants, caterers, businesses, nonprofits and more.
Mid-Atlantic Symphony Woodwind Quintet
OCT. 15, EASTON, MD
This concert takes place from 4 to 6 p.m. at Academy Art Museum, 106 South St., Easton. Doors open at 3 p.m.
Milford Community Parade
OCT. 18, MILFORD
Held annually the third Wednesday in October in Milford, the Milford Community Parade has delighted everyone for the last 30 years and provided support of businesses and families across Delmarva. The parade will step off at 6:30 p.m. This year’s theme is The Great Outdoors.
OCT. 19-22, OCEAN CITY, MD
This family-friendly event includes a Great Pumpkin Race, a pet parade, trunk or treat, the Halloween Maze and more. All events are weather-dependent.
OCT. 19-22, OCEAN CITY, MD
Attracting tens of thousands of attendees each year, this is one of Ocean City’s biggest and best festivals. Held Thursday through Saturday: 10 a.m. to 8 p.m.; Sunday: 10 a.m. to 6 p.m. Enjoy four fun-filled days of arts and crafts, food vendors, hayrides, kids’ activities and live music.
Mid-Atlantic Symphony Woodwind Quintet
OCT. 21, REHOBOTH BEACH
This concert takes place from 3 to 5 p.m. at Epworth United Methodist Church, Rehoboth Beach. Doors open at 2 p.m.
Wags & Whispers Fall Festival
OCT. 21, MILTON
Bring your furry companions and celebrate one of the most dog-friendly gatherings in the area from 10 a.m. to 4 p.m. at Hudson Fields, Milton, hosted by Yarn and Bone. The event will feature photo opportunities, games, vendors, food trucks and adoption opportunities.
Milton Theatre Zombie Fest
OCT. 21, MILTON
Zombies are back in Milton. Beginning at 4 p.m., the popular event draws thousands to downtown Milton to celebrate all things All Hallows Eve. Featuring food vendors, local merchants, street performers, entertainment inside and outside at the Milton Theatre, kids fest, costume contests and the Zombie Walk.
Beach Brunch to benefit Meals on Wheels
OCT. 22, REHOBOTH BEACH
Guests will enjoy a seated upscale brunch with cocktail parings from 10:30 a.m. to 1:30 p.m. at the Rehoboth Beach Country Club. Local chefs will prepare hors d’oeuvres and desserts.
Academy Art Museum Craft Show
OCT. 28-9 EASTON, MD
Held at the Academy Art Museum, 106 South St, Easton, Md. and The Waterfowl Festival Building, 40 S Harrison St, Easton, Md., the event includes a Friday preview event from 5:30 to 8:30 p.m. Show hours are Saturday: 10 a.m. to 5 p.m.; Sunday: 11 a.m. to 4 p.m. The event is an Indoor, juried craft show featuring over 60 artists from across the United States. For-sale collections encompass all craft mediums; basketry, ceramics, glass, fiber, jewelry, metal, mixed media, sculpture and wood.
Boos & Brews
OCT. 27, LEWES
Spend a memorable evening from 7 to 10 p.m. with spirits on the ghostly, historic campus of the Lewes Historical Society, 110 Shipcarpenter St. Partake in the flavors of the local eateries, breweries and vineyards. Evening includes food, drink, music and entertainment. Costumes are encouraged. 21+ to attend.
COST: $50 per person
32nd Annual Sea Witch Festival
OCT. 27-29, REHOBOTH BEACH
The signature annual event of the Rehoboth Beach-Dewey Beach Chamber of Commerce, the Sea Witch Festival will hauntingly delight thousands of locals and visitors with fun for all ages. Events include beach games, trick or treating at local businesses, scarecrow building, broom toss and more. The centerpiece of the weekend is the Costume Parade featuring vehicles, floats, individuals and groups on Rehoboth Avenue Saturday, Oct. 28. Don’t miss the Costumed Dog Parade Contest on the Boardwalk.
Mactoberfest Macaroni & Cheese Competition
OCT. 28, RIDGELY, MD
A competition hosted from 11 a.m. to 3 p.m. in downtown Ridgely, MD. Featuring mac and cheese tastings, vendors, games, a DJ, alpacas and more.
Shore Craft Beer’s Octoberfest
OCT. 28, OCEAN CITY, MD
All are welcome to attend the annual festival held from 1 to 5 p.m., Saturday, Oct. 28 in Sunset Park, 700 S Philadelphia Ave, Ocean City. A celebration of great, local beer, local food trucks. Children, nondrinkers, and dogs are welcome.
Wags, Witches & Warlocks
OCT. 28, BETHANY BEACH
A town-wide event from 9 a.m. to 1 p.m. featuring a parade, costume contest, Halloween crafts, storefront decorating contest, trick-or-treating and pet adoption. Costume contest categories include: most original, funniest, scariest, cutest, best pet, best with a pet and best family.
COST: $20 per individual/dog or $50 per family (suggested)
OCT. 28, ST. MICHAELS, MD
Get ready to sip, slurp, and savor at the Chesapeake Bay’s favorite fall festival. The event features live music on two stages, boat rides, retriever demonstrations, oysters and other local fare, an oyster stew competition and cooking demonstrations, along with children’s activities, oyster demonstrations, harvesting displays and Chesapeake-related documentary screenings.
NOV. 3, REHOBOTH BEACH • NOV. 4, OCEAN CITY, MD
The Cape Region’s only homegrown professional symphony orchestra will feature works by Elfrida Andree, Samuel Coleridge-Taylor and Felix Mendelssohn highlight this concert. On November 3, the event takes place at 7∶30 p.m. at Epworth United Methodist Church, Rehoboth Beach. Doors open at 6∶30 p.m. On November 4, the event takes place at 3 p.m. at the Performing Arts Center, Ocean City, Md. Doors open at 2 p.m.
Delaware Resorts 55+ Expo
NOV. 4, LEWES
The 55 + Expo presents a wide range of health, wellness, fitness, leisure-oriented organizations, and many home product and home service companies. Exhibitors include medical facilities and services, home health care agencies, physical therapy firms, lifestyle coaches, physical fitness programs, and 55+ residential communities. There will be free health screenings, flu shots and boosters, realtors, home builders and renovators, developers, insurance and financial firms.
Rehoboth Art League’s annual Holiday Fair and Fine Craft Show
NOV. 4-5, REHOBOTH BEACH
Held from 10 a.m. to 4 p.m. at the Rehoboth Art League Homestead & Garden, 12 Dodds Lane, Rehoboth Beach. New this year is a ticketed prevIew night on Friday, Nov. 3. Proceeds support Rehoboth Art League year-round exhibits and education programs. Featuring a variety of artisans exhibiting and selling their work, including jewelry, glasswork, ceramics, mixed media, and decorative and wearable fiber creations. Patrons can stroll the campus and find artists throughout the historic Peter Marsh Homestead, Chambers Studio, and the Corkran and Tubbs galleries to select the perfect gifts for family, friends and themselves. Food and beverage vendors on site.
COST: $5 per adult; children under 12 free
NOV. 5, WYE MILLS, MD
Works by Elfrida Andree, Samuel Coleridge-Taylor and Felix Mendelssohn highlight this concert set for 3 p.m. at the Todd Performing Arts Center, Wye Mills, Md. Doors open at 2 p.m.
Rehoboth Beach Independent Film Festival
NOV. 8-12, REHOBOTH BEACH
This event is held every November and offers a wide variety of American and international feature, documentary and short films. Film screenings will take place at Cinema Art Theater.
Autumn Home & Condo Show with Arts, Crafts and Critters
NOV. 10-12, OCEAN CITY, MD
The show takes place from 10:30 a.m. to 5 p.m., Friday and Saturday and from 10:30 a.m. to 3:30 p.m., Sunday and is held at the Ocean City Convention Center. Exhibitors will be on hand with merchandise, product demonstrations, and interior and exterior displays. With a combination of new products and advice from the pros, the Home Show inspires homeowners with ideas on enhancing their home’s comfort and functionality, as well as aesthetic appeal, and overall value. The Arts and Crafts Fair will offer a wide assortment of creative and unique gifts and accessories made by artists and quality crafts people from near and far.
COST: $6 for adults; free for children 13 and under
NOV. 10-12, EASTON, MD
The Waterfowl Festival is an award-winning event that is a celebration of Eastern Shore sporting tradition and conservation. Featuring the best of local wildlife, nature, art, heritage, food and fun.
Clear Space Theatre presents “Godspell”
NOV. 10-12, REHOBOTH BEACH
Presented by its Spotlight on Young Performers, this musical feature a parade of beloved songs, including the international hit, “Day by Day.” A small group of people help Jesus Christ tell parables by using games, storytelling and some excellent comedic timing.
RBFS presents “Best of Enemies”
NOV. 15 AND NOV. 18, LEWES
The Rehoboth Beach Film Society will host a screening of “Best of Enemies” at 1 p.m., Nov. 15 and 4 p.m., Nov. 18 at the Cinema Arts Center, Dartmouth Drive, Lewes. The film is part of the National Theatre Live Series.
COST: $25 general admission, $20 for members, $22 seniors, $5 students
Dogfish Head Analog A-Go-Go
Nov. 17-19, MILTON
Sip Dogfish Head fall inspired beer samples while strolling through the outdoor marketplace where unique finds will be available for purchase. The bazaar will feature independent merchants and artisans selling vintage and hand made goods, arts, crafts, apparel, jewelry, vinyl and more.
Christmas Boutique & Book Sale
NOV. 18, LEWES
Held from 9 a.m. to 3 p.m., at the Officers’ Club, Cape Henlopen State Park, this event features a Christmas boutique and book sale including handmade arts and crafts, Christmas decor and Friends of Cape Henlopen State Park branded merchandise. Donations welcomed. Drop off clean books and crafts on Friday Nov. 17 from 10 am to 1 pm at Officers Club at Cape Henlopen State Park.
Eastern Shore Sea Glass & Coastal Arts Festival
NOV. 18, ST. MICHAELS, MD
The Eastern Shore Sea Glass and Coastal Arts Festival brings artisans and craftspeople together for a holiday marketplace. Artisans and craftspeople exhibit and sell coastal and sea-glass related jewelry, home décor, art and more.
NOV. 18 – DEC. 31, REHOBOTH BEACH
A showplace of holiday delights taking place at Seaside Outlet Dr. (located behind the Tanger Outlets). Schellville Enchanted features decorated iconic miniature buildings and houses, a large Santa Claus house, a 100-by-200-foot roller rink, musical entertainment, train rides
to view decorations. Also featuring food and drink vendors, artisan vendors, a beer garden, sledding hill, tree houses, mini golf, arcade room, playground, snowball fights and more. A portion of proceeds will be donated to the Harry K foundation.
Millsboro Holiday Market
NOV. 18, MILLSBORO
Festival takes place Saturday from 9am – 4pm. Featuring exhibitors, music, food and more.
Clear Space Theatre presents “Estella Scrooge”
NOV. 24 – DEC. 10, REHOBOTH BEACH
Estella Scrooge is a modern retelling of “A Christmas Carol”.
COST: $20 to $34.50
Hospitality Night at the Zwaanendael
NOV. 30, LEWES
The Zwaanendael Museum will be decked out in holiday decorations by the Sussex Gardeners. The event will be held from 5 to 8 p.m. and includes refreshments.
Winter Wonder Party and Auction
DEC. 1, LEWES
Benefiting the Children’s Beach House, this party will be held from 6∶30 to 9∶30 p.m. and include dinner, drinks and an auction.
COST: $150 per person
Lewes Historical Society’s Holiday House Tour
DEC. 2, LEWES
The Lewes Historical Society’s 50th Annual Holiday Tour will take place from 10 a.m. to 4 p.m.