2025 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 Boutique and Book Sale, Lewes•Nov 15th

2025 Millville Holiday Marketplace, Millville•Nov 15th

19th Annual Holiday Auction & Tastes of Milford, Milford•Nov 20th

Christmas Tree Lighting, Rehoboth Beach•Nov 28th

MUSEUM HOLIDAY TRAINS, Seaford•Nov 28^th – Jan 10^th  

Santa's House on the Boardwalk, Rehoboth Beach•Nov 28^th, 29^th, 30^th, Dec 6^th, 7^th, 13^th,14^th, 20^th, 21^st, 22^nd, 23^rd

Rehoboth Beach Holiday Tree Lighting, Rehoboth Beach•Nov 28th

Shop Local Extravaganza 2025, Fenwick Island•Nov 29^th,  6^th, 13^th

Bethany Beach Trolley Tour 2025, Bethany Beach•Nov 29^th, Dec 6^th, 13^th, 20^th

Old Town Holiday Market & Tree Lighting, Ocean View•Nov 29th

Santa at his Home on Second Street in Lewes, Lewes•Nov 29th – Dec 4^th, 6^th, 11^th, 13^th, 18^th, 20^th, 23^rd

Dewey Beach Tree Lighting, Dewey Beach•Nov 29^th

Milford’s Annual Tree Lighting Ceremony!, Milford•Nov 29th

Santa's House, Milford•Nov 30th – Dec 5^th, 6^th, 7^th, 12^th, 13^th, 14^th, 19^th, 20^th, 21^st

December ☃️

RBVFC Hometown Christmas Parade, Rehoboth Beach•Dec 1st

Town of Millville Tree Lighting, Millville•Dec 4th

Christmas Parade & Caroling on the Circle, Georgetown•Dec 4th

Holiday Village & Market, Lewes•Dec 5th

2025 Holiday Stroll & Christmas Market, Milford•Dec 6th

Lewes Old Fashioned Christmas Parade, Lewes•Dec 6th

2025 Weekend Wonderland in Bethany Beach, Bethany Beach•Dec 6^th, 13^th, 20^th

Holiday Village & Market, Lewes•Dec 6th

South Bethany 4th Annual Holiday Tree Lighting Ceremony, South Bethany•Dec 6th

Holiday Happenings, Bethany Beach•Dec 6th

Fenwick Island Winter Holiday Tree Lighting Ceremony, Fenwick Island•Dec 6th

Holiday Village & Market, Lewes•Dec 6th

Dagsboro Christmas Parade, Dagsboro•Dec 9th

Sonshine Equine Live Nativity, Millsboro•Dec 12^th-13^th

Milton’s Annual Holly Festival, Milton•Dec 13th

Christmas at the Cottages, Bethany Beach•Dec 13th

Cartoon Christmas Trio, Milton•Dec 17th

Sinatra’s Christmas with Tony Sands, Milton•Dec 20th

Chesapeake Silver Cornet Brass Band Holiday Concert, Milton•Dec 21st

Milton’s Merry Melodies: A Hometown Holiday Cabaret – EVENING, Milton•Dec 22nd

Looking for more Holiday fun around Delaware? Check out Delaware's Hidden Holiday Gems Trail!