2023 Holiday Happenings in Southern Delaware

2023 Holiday Happenings in Southern Delaware

There's no shortage of holiday cheer to be had in Southern Delaware! Check out our up-to-date list of holiday events below.

For further info on certain event details and dates, please visit our calendar

November 🦃

HOLIDAY FAIR - Preview Night, Rehoboth Beach•Nov 3rd

39th Annual Holiday Fair, Rehoboth Beach•Nov 4th-5th

Happy Holly Days at Delaware Botanic Gardens & Woodlands Discovery Trail, Dagsboro•Nov 9th

Members' Holiday Sales Gallery, Rehoboth Beach•Nov 10th-Dec 31st

17th Annual Holiday Auction & Tastes of Milford, Milford•Nov 16th

The Yule Market at Brimminghorn Meadery, Milton•Nov 16th

Inaugural Holiday Microgala, Milford•Nov 17th

Schellville 2023 Enchanted Winter Celebration, Rehoboth Beach•Nov 18th-Nov 30th

Merry Millsboro Holiday Market, Millsboro•Nov 18th

Holiday Craft Fair, Millsboro•Nov 18th

Holiday Train Display at Train Museum, Seaford•Nov 24th-30th

SSP Presents: A Christmas Carol The Musical, Milford•Nov 24th-Nov 30th

ESTELLA SCROOGE, Rehoboth Beach•Nov 24th-Nov 30th

Dewey Sip & Shop, Dewey Beach•Nov 24th- 26th

Tree Lighting and Sing-Along, Rehoboth Beach•Nov 24th

Santa's HouseRehoboth Beach•Nov 24th-26th

Tree Lighting, Dewey Beach•Nov 25th

Shop Local Extravaganza 2023, Bethany Beach•Nov 25th

2nd Annual Coastal Christmas showdownBethany Beach•Nov 25th

Annual City Hall Tree Lighting, Milford•Nov 25th

Ocean View Holiday Market, Ocean View•Nov 25th


Shop Small Saturday and Santa's Arrival, Milford•Nov 25th

Visit Santa, Milford•Nov 25th-26th

Pancakes with Santa, Frankford•Nov 25th

Ocean View Holiday Market, Ocean View•Nov 25th

Caroling in the Park and Tree Lighting, Seaford•Nov 27th

December ☃️

Candlelight Concert, Rehoboth Beach•Dec 1st-2nd

Visit Santa, Milford•Dec 1st-23rd

Nutcracker BalletMilford•Dec 1st-2nd 

Lewes Lights, Lewes•Dec 1st-30th

Santa's HouseRehoboth Beach•Dec 1st-23rd (weekends only)

ESTELLA SCROOGE, Rehoboth Beach•Dec 1st-Dec 10th

Holiday Train Display at Train Museum, Seaford•Dec 1st-31st

Schellville 2023 Enchanted Winter Celebration, Rehoboth Beach•Dec 1st-Dec 31st

The Life and Adventures of Santa Claus, Georgetown•Dec 1st-10th

SSP Presents: A Christmas Carol The Musical, Milford•Dec 1st-Dec 3rd

A Holiday Tour of Lewes, Lewes•Dec 1st-2nd

Winter Wonder Party, Lewes•Dec 1st

Spirit of the Season — a Holiday Cabaret, Selbyville•Dec 1st

62nd Annual Selbyville Christmas Parade, Selbyville•Dec 1st

Second annual Rehoboth Beach Bar Crawl, Rehoboth Beach•Dec 1st

A Holiday House Tour of Lewes, Lewes•Dec 2nd

Holiday Village & Market, Lewes•Dec 2nd

Shop Local Extravaganza 2023, Bethany Beach•Dec 2nd,9th,16th

Breakfast with Santa at Camp Arrowhead, Lewes•Dec 2nd-3rd

Yuletide Festival & Tree Lighting, Millville•Dec 2nd

Holiday Happening at Bethany Beach, Bethany Beach

47th annual Christmas in Bridgeville Craft Show, Bridgeville•Dec 2nd

50th Annual Christmas Tour of Lewes, Lewes•Dec 2nd

2023 Weekend Wonderland, Bethany Beach•Dec 2nd,9th




Christmas Parade, Rehoboth Beach•Dec 4th

Milton Christmas Parade Festivities @ Quayside, Milton•Dec 6th

Victorian Christmas Tea, Seaford•Dec 7th

Georgetown Caroling & Christmas Parade, Georgetown•Dec 7th

2nd Annual Christmas Open House, Millsboro•Dec 8th

Greenwood Christmas Parade, Greenwood•Dec 8th

Annual Milton Holly Festival, Milton•Dec 9th

Holiday House Tour, Milton•Dec 9th

Victorian Christmas Children's Day, Seaford•Dec 9th

14th annual Holiday Open House, Rehoboth Beach•Dec 9th

Town of Bridgeville's Annual Christmas Parade, Bridgeville•Dec 9th

Winter craft and vendor fair, Lewes•Dec 10th

Victorian Christmas Concert - The Capital Ringers, Seaford•Dec 10th

Candlelight Tour Ross Mansion, Seaford•Dec 10th

10th Annual Town of Dagsboro Christmas ParadeI'm Interested Share, Dagsboro•Dec 12th

High Tea with Santa at Camp Arrowhead, Lewes•Dec 13th

Santa's Workshop, Seaford•Dec 15th

Polar Express Pajama Party! & Film Screening, Milton•Dec 16th

Jingle Laughs: Holiday Stand-Up Comedy Spectacular!, Milton•Dec 16th

Southern Delaware Orchestra Holiday Concert, Rehoboth Beach•Dec 16th

Holiday Peace, Lewes•Dec 17th

It's A Wonderful Life (1946): Film Screening, Milton•Dec 18th

Duke Ellington's The Nutcracker Suite by Delmarva Big Band, Milton•Dec 20th

A Merry Manilow Christmas - The Music of Barry Manilow, Milton•Dec 21st

Christmas with the Rat Pack...Together Again, Milton•Dec 22nd

“Weather or Not” Lewes Craft Beer Christmas Party, Lewes•Dec 22nd

Holiday Cabaret, Milton•Dec 23rd

A Carole King Christmas with Michelle Foster, Milton•Dec 29th

Dewey Ball Drop, Dewey Beach•Dec 31st

New Years Eve Anchor Drop in Lewes, LewesDec 31st

January 🎉

Fenwick Freeze, Fenwick Island• Jan 1st

2024 Annual Hair of the Dog Walk/Run/Plunge, Bethany Beach•Jan 1st