Middletown Holiday Events

Holiday events Happening Next in Middletown, DE

Holiday Soap-Making Workshop

MOT Social (Next to Toba) 13 Dec 2025
WORKSHOPS USD 61

Sweets with Santa (ticketed event)

1 Spring Hollow Dr, Middletown, DE 19709, United States 7 Dec 2025
PICTURES-WITH-SANTA

My Father’s Daughter @ Mulligans

631 bayview rd, Middletown, DE 10 Jan 2026
HOLIDAY

FSBC Trivia! Featured Round: Holiday Movies

First State Brewing Company (Middletown, DE) 4 Dec 2025
ENTERTAINMENT

Middletown’s Holiday Spectacular Parade

Main Street, Middletown, DE 6 Dec 2025
CHRISTMAS-PARADES

MOT 2025 Winter Fest

300 S Scott St, Middletown, DE, United States, Delaware 19709 6 Dec 2025
FESTIVALS

Brunch With Santa 🎅✨

316 Auto Park Dr., Middletown, DE 19709 7 Dec 2025
BRUNCH

7th Annual MHS Cavaliers Holiday Market

Middletown High School 13 Dec 2025
CHRISTMAS-MARKETS-AND-FAIRS

4th Annual Festivus Ugly Sweater Party

Volunteer Brewing Company 19 Dec 2025
UGLY-CHRISTMAS-SWEATER-DAY

Macrame Ornaments

gilbert w. perry, jr. center for the arts, West Main Street, Middletown, DE, USA 4 Dec 2025
WORKSHOPS USD 39

🎄 CIGAR SESSIONS HOLIDAY PARTY 🎄

17 Wood Street, Middletown, DE, United States, Delaware 19709 11 Dec 2025
HOLIDAY

The Art of Hand Lettering

gilbert w. perry, jr. center for the arts, West Main Street, Middletown, DE, USA 2 Dec 2025
ART USD 41