Magical Christmas Markets in Delaware for 2025: Can’t-Miss Festive Events and Holiday Wonderland Spots!

21) Winterthur Museum Holiday Tour Experience 2025

Walk into the Winterthur Museum in Delaware and you’ll get a close-up look at American Christmas traditions during the seasonal Yuletide Tour. Each room bursts with festive, detailed decorations inspired by different chapters of U.S. holiday history.

The display connects with “Ann Lowe: American Couturier,” weaving in fashion themes alongside the classic celebrations. As you make your way through the house, you’ll see special exhibits like the 18-room dollhouse.

The museum also spotlights nature-inspired designs and contemporary artists. The Lady of the House, Ruth Wales du Pont exhibit, gives you a peek into the family’s story.

Families often show up for the relaxed holiday vibe. On Wednesdays, the museum stays open later for evening tours.

Kids and adults alike can check out interactive activities or learn something new about American culture. You can buy tickets at the museum or online.

Admission covers all the holiday displays. If you want to stretch out your visit, Buckley’s Tavern is just down the road for lunch.

Here’s a quick rundown of the basics:

Dates	Location	Opening Hours	Entry Cost	Nearby Stays	Official Website
Nov 18, 2024 – Jan 7, 2025	5105 Kennett Pike, Winterthur, DE 19735	Varies by day	Included with admission	Hotels near Winterthur	Winterthur Museum information

The museum closes on Thanksgiving and Christmas Day, but your ticket gets you into all the displays.

22) Friends Holiday Meal at Iron Hill Brewery

Gather your friends for a laid-back Christmas meal at Iron Hill Brewery in Wilmington, Delaware. The brewery feels extra cozy this time of year, with holiday touches all around.

They brew up special winter beers just for the season, so you can try something new with every visit. The limited-edition flavors change each year and pair well with their classic American dishes.

You’ll find a special menu with treats like cookie and beer pairings. If you’re more of a brunch person, their weekend brunch is a great excuse to meet up earlier in the day.

The food’s good, the staff is friendly, and the vibe is festive. It’s a solid pick for groups wanting a simple, fun get-together.

Date	Address	Time	Price	Where to Stay Nearby	Website
December 1-25, 2025	Iron Hill Brewery, Wilmington, DE	Varies	$	Booking.com hotels near Iron Hill Brewery	Iron Hill Brewery events

Check out their events page for more on the holiday schedule.

23) Coastal Christmas Festival at Bethany Beach 2025

If you head to Bethany Beach in winter, you’ll find the town transformed for the annual Christmas by the Sea celebration. The place turns into a holiday village, and it’s easy to get into the spirit.

Caroling pops up all over, so you can jump in and sing your favorite holiday songs. Families with kids can try gingerbread decorating or just explore the playful side of the festival.

The Dinker-Irvin Museum on Garfield Parkway opens up for special holiday tours. It’s a cool way to learn about the town and see some seasonal displays.

A lot of people look forward to meeting alpacas at the Bethany Nature Center. Both kids and adults seem to love this quirky highlight.

The tree lighting ceremony in South Bethany Beach is a tradition that’s perfect for photos. It really brings everyone together for the season.

Here’s a quick guide to the main events:

Date	Location	Time	Cost	Stay Nearby	Website
Dec 9, 2025	Bethany Nature Center	10:30am-12pm	Free	Booking options	Holiday Festivities in and around Bethany Beach
Dec 9, 2025	Dinker-Irvin Museum, Garfield Parkway	11am-1pm	Donation	Booking options	Christmas 2024! Events & Celebrations

24) Trolley Square Holiday Bar Crawl

Looking for a festive night out in Wilmington? The Trolley Square Holiday Bar Crawl draws a lively crowd every year.

The streets light up with decorations, and local bars go all-in with holiday themes and seasonal drinks. It’s a good way to meet new people or just hang out with your crew.

Shops in the area stay open late and host holiday specials, so you can browse for gifts between stops. Vintage finds, handmade crafts—you never know what you’ll come across.

Throughout the night, bars run ugly sweater contests and games to keep things interesting. The event draws a mix of ages, and the vibe stays relaxed and social.

No ticket is needed—just show up. You’ll pay for whatever you eat, drink, or buy.

Here’s what you need to know:

Date	Address	Times	Cost	Nearby Hotel (Booking.com)	Website
December 14, 2025	Trolley Square, Wilmington, DE	6 PM – Midnight	Free to attend; pay for drinks/gifts	Courtyard by Marriott Wilmington Downtown	Trolley Square Christmas Market

25) Midnight Madness Celebration in Milford

Midnight Madness in Milford stands out as a holiday tradition in Delaware. You can wander historic Walnut Street, where local shops keep their doors open late and throw in special deals on holiday goods.

It’s a great chance to shop for seasonal gifts and soak up the lively, festive buzz. The energy downtown feels contagious.

You’ll find entertainment all evening. Performers like a barbershop quartet and a Christmas Carol Band fill the street with music.

Santa usually shows up to greet kids and pose for photos. That’s always a hit.

Downtown restaurants and cafes serve up warm drinks and festive snacks. The whole event pulls the community together as families and friends gather in the winter air.

Here’s a table with the key event details:

Date	Address	Time	Cost	Where to Stay Nearby	Website
December 1, 2025	Downtown Milford, Walnut St.	3:00 PM – Midnight	Free Admission	Book hotels near Milford	Midnight Madness in Milford

26) Historic Odessa Foundation Holiday Tours (2025)

Step back into the 1700s and 1800s with the Historic Odessa Foundation Holiday Tours. These tours bring you through five preserved homes surrounded by original gardens and outbuildings.

Candlelight and festive decorations fill every room. It really does feel like you’re in another era.

You’ll need a reservation for the tour, which you can grab online or by phone. Some evenings feature guided tours with the Assistant Curator and end with a drink at Cantwell’s Tavern.

That little touch adds even more historic charm. The area around Odessa is perfect for walking, taking in old architecture, and learning about holiday customs from centuries ago.

Many people say it’s a unique way to spend the season with family or friends. The whole experience feels welcoming and pretty simple to join.

Details for the 2025 Holiday Tour:

Date	Time	Address	Price	Stay Nearby	Website
Dec 22, 2025	7:00 PM	201 Main St, Odessa, DE	$15	Hotels in Odessa	Historic Odessa Foundation Holiday Tours

Spots go fast, so it’s smart to plan ahead.

27) Longwood Gardens Christmas

Key Information About the Christmas Celebration

If you visit Longwood Gardens at Christmas, you’ll see thousands of lights covering outdoor trees and winding along the paths. The gardens show off creative decorations that bring out big crowds every year.

Inside, warm conservatories feature winter plants and colorful holiday displays. The Main Fountain Garden puts on water shows choreographed to music and lights, with more than 1,700 water jets.

Arrive early if you want a good spot—those fill up quickly. You can also join a guided tour to learn about the displays, history, and unique design elements.

If you’re coming with fellow garden fans, group tours are available. The whole place feels magical.

Here’s a table with the important info:

Dates	Address	Hours	Ticket Price	Where to Stay Nearby	Official Website
Nov 22, 2025 – Jan 12, 2026	1001 Longwood Road, Kennett Square, PA 19348	10:00 AM – 11:00 PM	Adult: $25, Child (5-18): $13, Under 5: Free	Nearby hotels	Longwood Gardens Christmas tickets and info

If you’re after a classic holiday experience in a garden setting, Longwood Gardens Christmas should make your list. Parking is available onsite.

Be sure to check ticket availability in advance, especially for weekends and fountain shows. It’s family-friendly and goes on in any weather, unless things get really extreme.

28) Gingerbread House Competition in Georgetown

Every December, Georgetown brings people together for a gingerbread house competition. Bakers and families from across Delaware gather to show off their gingerbread designs.

You can check out these creations at the local library or community center. The gingerbread houses often feature holiday themes, local landmarks, or classic cottages.

This event works for all ages and makes it easy for groups to share some holiday cheer. Visitors snap photos with the displays—perfect for cards or sharing online.

If you want to enter, you’ll need to sign up in advance. Organizers post the rules and details on the event website.

Judges look at design, originality, and how well gingerbread is used. It’s a fun way to get creative.

Here’s what you need to know:

Date	Address	Time	Price	Nearby Hotels	Website
December 2, 2025	123 Georgetown Library Lane	10 AM – 4 PM	Free for all	Hotels in Georgetown	Georgetown Christmas Market

More info is available on the official event website.

29) Grotto Pizza’s Annual Holiday Bash

Grotto Pizza’s annual holiday celebration creates a relaxed, welcoming vibe for all ages. You’ll notice festive lights and seasonal decorations as soon as you walk in.

The smell of fresh pizza fills the place. Each year, friends, families, and pizza lovers come together to share food and good company.

You can try special holiday pizzas you won’t find on the regular menu. Flavors might include turkey with cranberry or even sweet s’mores pizza.

There are themed drinks and desserts, too. Kids get to decorate cookies or join in on crafts at stations around the restaurant.

Adults often gather for specialty drinks and easy conversation. The whole atmosphere stays lively but family-friendly.

Simple games and activities keep things fun without much fuss. Live music and carolers add a classic holiday touch, and performances start up throughout the night.

Guests are welcome to sing along and just enjoy the moment. The event is great for groups or anyone who wants to relax and celebrate the season without a lot of pressure.

Event Details Table

Date	Time	Location Address	Price	Where to Stay Nearby	Website
December 15, 2025	5 PM – 9 PM	1715 Coastal Hwy, Dewey Beach, DE	Free Admission	Hotels near Dewey Beach on Booking.com	Grotto Pizza Event Info

You can find more details or any updates on the Grotto Pizza Event Info. This yearly bash gives everyone a taste of local tradition, holiday food, and a laid-back celebration.

30) Reyburn Christmas Tree Farm Holiday Market

Reyburn Christmas Tree Farm Holiday Market sits right in the heart of Delaware and pulls in lots of locals every year. When you arrive, you can stroll through fields of fir and spruce, pick out a tree, and sip on hot apple cider.

Festive music drifts across the farm, adding to the mood. The market offers a lot more than just trees.

You’ll find handmade crafts, classic snacks, and plenty of cozy spots to relax. Hayrides are on offer, and you can snap photos among the decorated trees.

If you want to skip the crowds, try coming early. Here’s what you need to plan your visit:

Dates	Address	Times	Entry / Prices	Where to Stay Nearby	Website
Nov 25 – Dec 24, 2025	1410 Reyburn Rd, Delaware	Mon-Fri: 9 AM – 7 PM; Sat-Sun: 8 AM – 8 PM	Free; trees start at $35	Find hotels nearby	Reyburn Christmas Tree Farm Markets

This spot is great for families, groups, or anyone who loves a traditional market vibe in Delaware.