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Sussex Holiday GuidebyLocal Loop

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Holiday Events

Parades, markets, lights and family outings in Sussex County and nearby Delmarva towns.

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Showing 204 events

Local Loop lists events as a free community guide. We are not the organizers. Dates, times and locations are subject to change by the organizers, so please check with the venue or host before you go.

Lights

Ocean City Winterfest of Lights

Thu, Nov 19 – Sat, Jan 2, 2027
Nightly 5:30–9:30 PM, Nov 19–Jan 2 (subject to weather closure). Carriage-only Enchanted Evenings, reservations required: Nov 30; Dec 1, 7, 8, 14, 15, 21, 22

Northside Park · Ocean City, MD

Nearby Delmarva · outside Sussex County

$6 plus fees ages 12+; ages 11 and under free

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Community

YMCA Turkey Trot 5K (Salisbury)

Thu, Nov 26, 2026
8:30 AM ET

Richard A. Henson Family YMCA · Salisbury, MD

Nearby Delmarva · outside Sussex County

Adults $43.40 Oct 1-31; $48.70 Nov 1-22; $50.82 Nov 25-27; ages 7-17 $24.32-$27.50; 6 & under $6.30

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Lights

Gift of Lights at Dover Motor Speedway

Thu, Nov 26 – Sun, Jan 3, 2027
Nov 26–Jan 3 · Sun–Thu 5–9 PM · Fri–Sat 5–10 PM

Dover Motor Speedway · Dover, DE

Nearby Delmarva · outside Sussex County

$35 per car; $60 bus/limo/RV (one price per carload)

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Lights

Talbot Hospice 41st Annual Festival of Trees

Fri, Nov 27 – Tue, Dec 1, 2026
Preview Gala Fri Nov 27, 6:00–8:00 PM; Sat Nov 28 & Mon Nov 30, 10:00 AM–8:00 PM; Sun Nov 29, 11:00 AM–8:00 PM; Tue Dec 1, 10:00 AM–6:00 PM

Gold Room, The Tidewater Inn · Easton, MD

Nearby Delmarva · outside Sussex County

$10; children 6-12 $5; under 5 free

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Lights

Seaford Museum Holiday Trains

Sat, Nov 28 – Sun, Jan 3, 2027
1:00–4:00 PM on Nov 28; Dec 3–6, 10, 11, 15–19, 22, 23, 29, 30; Jan 2, 3 (closed Dec 25)

Seaford Museum (Webb Room) · Seaford

$3 adults; kids free (with paid adult); $7 full museum incl. trains

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Parade

Berlin Christmas Parade

Thu, Dec 3, 2026
7:00 PM ET

Main Street, Berlin (Welcome Center to Berlin Fire Company) · Berlin, MD

Nearby Delmarva · outside Sussex County

Admission details: see organizer

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Community

Christmas at the Creamery 2026

Fri, Dec 4 – Sat, Dec 19, 2026
Fridays & Saturdays only: Dec 4, 5, 11, 12, 18 & 19. Hours: see organizer

Evans Farms & The Frozen Farmer · Bridgeville

Admission details: see organizer

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Entertainment

The Nutcracker - Eastern Shore Ballet Theatre

Fri, Dec 4 – Sun, Dec 6, 2026
Opens Fri Dec 4, 7:30 PM; runs through Sun Dec 6 (see esbt.org for the full schedule). Sensory-friendly Act II performance Fri Dec 4, 1:30 PM

Wicomico High School Auditorium · Salisbury, MD

Nearby Delmarva · outside Sussex County

Ticket info not yet posted; see organizer

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Entertainment

Rehoboth Beach Santa Bar Crawl

Sat, Dec 5, 2026
End time not posted

Starts on the boardwalk at Wilmington Ave, then participating bars · Rehoboth Beach

No ticket; bring a new unwrapped toy for Toys for Tots and donate $5+ to the Tunnel to Towers Foundation

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Parade

Seaford Christmas Parade

Sat, Dec 5, 2026
Starts 7:00 PM sharp; end time not posted; no rain date

Nylon Blvd to Market St (ends near Seaford Middle School) · Seaford

Admission details: see organizer

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Entertainment

Christmas by Candlelight - The Collingsworth Family

Mon, Dec 7, 2026
7:00 PM (doors 6:00 PM)

Lighthouse Christian Center · Milford, DE

Nearby Delmarva · outside Sussex County

$28.75 general admission; $51.75 Gold Circle; $74.75 Artist Circle (fees included); kids 14 and under free with an adult ticket (not Artist Circle)

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Market

Milton Holly Festival

Sat, Dec 12, 2026
9:00 AM–3:00 PM ET

Multiple venues around Milton (Milton Fire Dept., H.O. Brittingham Elementary, Milton Public Library) · Milton

Free

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Entertainment

Chorus of Dorchester Christmas Concerts

Sat, Dec 12 – Tue, Dec 15, 2026
Sat Dec 12, 4:00 PM and Sun Dec 13, 4:00 PM

Christ Episcopal Church (Dec 12); Immanuel UCC (Dec 13); Dorchester Center for the Arts (Dec 15) · Cambridge, MD

Nearby Delmarva · outside Sussex County

Free

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Community

Dewey Crush Drop

Thu, Dec 31 – Fri, Jan 1, 2027
Starts 11:30 PM; end time not posted

Route 1 & New Orleans Avenue · Dewey Beach

Admission details: see organizer

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