Saturday, December 20, 2025
5:00–8:00 p.m.
📍 Vienna, MD — just off Route 50
More info: https://viennamd.org
Tickets: https://shorecraftbeer.ticketspice.com/44th-annual-luminaria-in-vienna-md

If you are driving to Ocean City on Saturday, December 20th or you are in the area and want something really unique and fun to do, then head to Vienna, MD, just off of Route 50 for the 44th Annual Luminaria.  This event is the Eastern Shore’s most breathtaking holiday tradition—you get to tour historic homes decorated for the holidays and partake of the generosity of the Town and some of the homeowners who will be serving treats on your tour.

Governor Thomas Holliday Hicks

Governor Thomas Holliday Hick’s home will be open and you will see some treasured artifacts on loan from the Dorchester County Historical Society (including this portrait!).  Governor Hicks served from January 13,1858-January 8, 1862,  He has been credited with keeping Maryland in the Union.  President Abraham Lincoln attended his funeral in the U.S. Senate Chamber.

You will be greeted by a historic reenactor who will regale you with stories and history of Maryland’s 31st Governor.  

More than 1,500 luminarias illuminate Vienna’s streets, casting a warm glow over historic homes along the Nanticoke River. Visitors can explore:

•  Historic Christmas home tours
• A free town tram ride to get you around
• Holiday treats and beverages
• A quiet, magical small-town Christmas atmosphere

This is the holiday experience you’ll never forget.

📅 Nightly December 12–31, 2025
🕒 5:30–9:30 p.m.
📍 Northside Park, 200 125th St, Ocean City, MD
Event info: https://www.oceancity.com/winterfest/

Walk through millions of sparkling lights, animated tunnels, themed holiday displays, and the iconic Winterfest Christmas tree. Warm up with hot chocolate, enjoy the weekend food trucks, or visit Santa on select nights.

A must-do for anyone visiting Ocean City in December.

Sunday, December 14, 2025
Festivities typically begin midday
Multiple locations in Downtown Ocean City
Event info: https://santaconocmd.com

Get ready for the jolliest pub crawl of the year! SantaCon OCMD invites adults to dress up as Santa, elves, candy canes, or any festive attire and parade through Ocean City’s bars and restaurants—raising money for local charities while spreading cheer.

Expect:
Hundreds of Santas – and their elves!
Drink specials at participating bars
Costume contests
Music & festivities throughout downtown

This is one of OC’s biggest and most spirited December events for adults.

Monday, December 22, 2025
5:30–8:30 p.m.
📍 Northside Park, Ocean City, MD

Enjoy a special Winterfest night featuring Bryan Scar & The Barn Owls (Duo). Bring your family or date, sip hot cocoa, and enjoy the concert surrounded by glowing holiday displays at Northside Park.

Step inside the Winterfest tent and explore the delightful Winterfest of Trains displays, proudly housed in sheds provided by Woodland Sheds of Selbyville!

The Ocean City Beach Patrol is thrilled to once again welcome the Delaware Seaside Railroad Club, returning this year with two interactive model train displays for all to enjoy.

Admission is included with your Winterfest ticket. Cash and Venmo donations are gladly accepted and deeply appreciated!

Come experience the magic of the trains from 6:00–8:30 p.m., Wednesday through Sunday on Winterfest nights (closed Thanksgiving, Christmas Eve, and Christmas).

A special thank-you to Stephen of Continental Cycles for sharing his Treasured Antique Toys, now featured as part of the display! 

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Winter Night at the Gallery, Kids Event

Friday, December 12
5:00–8:00 p.m.

COST: $25.00 members $30.00 future members
📍 The Art League of Ocean City

Let it Snow, Let it Snow, Let it Snow for Kids!

Kids ages 6-13 are invited to a fun Winter Night at the Gallery! Parents may drop-off children for a fun-filled evening at the Art League of Ocean City.

Our evening will begin with a light dinner and then the fun begins!

Events for the Evening:

• Snow Globe – Each child will create a one-of-a kind snow globE.
• Paper Snow Flakes – Children will learn how to fold and cut snow flakes and then decorate so they sparkle like snow!
• Snow Making – Children will create snow in a science experiment and create snow. Children will then use the snow to create a snowman!
• Cookie Decorating – Children will finish the evening decorating and enjoying cookies.

Click here to register: https://canvas.artleagueofoceancity.org/classes/2638

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Miracle On 34th Street

Saturday, December 13, 7 pm – 9 pm

Art League of Ocean City

 

Visit Website

Step into the magic of the holiday season with Miracle on 34th Street, performed live by the Lower Shore Performing Arts Company at the Art League of Ocean City. This beloved Christmas classic tells the heartwarming story of belief, wonder, and the true spirit of the holidays — brought to life on stage by a talented local cast.

Enjoy an evening of festive cheer, moving performances, and timeless holiday charm in the gallery’s intimate setting.

Tickets: $25
Seating is limited — reserve your spot early!

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Berlin Holiday Weekends, Merry Marketplace & Santa at Kringle Kottage

December 13–14 & December 20–21, 2025
Santa: 10:00 a.m.–1:00 p.m.
Carriage Rides (FREE): 11:00 a.m.–3:00 p.m.
Downtown Berlin, MD

Berlin becomes a Hallmark-style Christmas village each December.  Make sure to download the Berlin Trail to filled with money-saving coupons, trivia, check-ins and more to add value and fun to your day in Berlin!

Santa at Kringle Kottage

Located on Artisans Green (behind the main parking lot, beside Honey Water Candles & HOUSE, behind Sterling Tavern).
Appearances:

• Dec 13–14 | 10 a.m.–1 p.m.

• Dec 20–21 | 10 a.m.–1 p.m.

FREE Horse & Carriage Rides

• Dec 14, 20, 21 | 11 a.m.–3 p.m.
  ❗ No carriage rides on Dec 13.

Merry Marketplace

Artisans, bakers, craftspeople, and holiday vendors fill downtown with:

• Local makers & gifts

• Outdoor stalls

• Christmas treats

• Small-town lights & charm

Berlin is a perfect afternoon stop before heading back for Winterfest or dinner in OC.

Wednesday, December 17, 2025
6:00–7:00 p.m.
$35 per person (plus tax)

Indulge in a curated holiday cookie + wine pairing experience. Each holiday cookie is matched with a wine that enhances its flavors—creating a festive sensory celebration.

Winery Winter Hours

• Mon–Tues: Closed

• Wed–Sun: 12–8:30 p.m.

Igloos Available

• Wed: 12–6:30

• Thurs (“Locals Night”): 12–6:30 — $25 for a 5-person igloo

• Fri–Sun: 12–6:30

Perfect for a cozy December date or friends’ night out.

December 12–31, 2025
Igloos available 12:00–6:30 p.m.

Step inside the softly lit glow of a heated winter igloo for one of the most unique dining experiences on the Eastern Shore.

Expect:
✨ Warm, private, beautifully illuminated igloos
✨ A chef-crafted Winter Igloo Dining Menu
✨ Fantastic wine selections
✨ Serene views and holiday ambiance

This experience books quickly—reserve early for weekends.

📍 Tanger Outlets. 📍 Dogfish Head Brewing & Eats

Finish your holiday shopping in style—then celebrate the season with a craft beer toast.

Tanger Outlets Rehoboth (3 locations)

A shopper’s paradise with:

Nike, Columbia, Coach, Kate Spade, North Face, J. Crew, Polo Outlet
…and many others.

Tanger Outlets Ocean City

Right off Route 50 — perfect for OC visitors. Stores include:

Coach, Sephora, Carter’s, Crocs, Chico’s, Under Armour and more!

After Shopping: Dogfish Head Brewing & Eats

Head to Rehoboth for a festive visit to Dogfish Head Brewing & Eats, where you can enjoy:

• Seasonal and signature Dogfish beers

• Wood-fired pizzas

• Holiday music & atmosphere

A perfect Christmas Eve tradition for couples or friend groups.

December 12–31, 2025
📍 Salisbury, MD

Start with a stroll through the Salisbury City Park Winter Wonderland, where Christmas displays reflect off the lake, creating a peaceful and festive evening setting.

Then warm up nearby at Burnish Beer Co., Salisbury’s award-winning craft brewery.

🍺 At Burnish Beer Co.

Expect:

• Innovative small-batch craft beers

• A full scratch-made kitchen

• Stylish holiday ambiance

• Great spot for a winter nightcap after seeing the lights

This pairing makes Salisbury one of the best off-OC day trips of December.

There is so much to do to get your Christmas vibe going.  We decided to put together an itineration built from our suggested activities – with a few enhancements – to help you execute the perfect lead up to Christmas in Ocean City.  Here’s what we recommend starting on December 20!

SATURDAY, DECEMBER 20 (Vienna, Salisbury and Ocean City, MD)

• Start your holiday journey with a stop at 5 pm in Vienna, MD for the 44th Annual Luminaria.  Tickets are only $5 or $20 for your entire family!  Learn a little about the history of one of the Eastern Shore’s coolest little towns, tour the homes and snack.
• Make your way to Salisbury for holiday lights and dinner at Burnish (see above) after the Luminaria.
• Drive the last 30 minutes to Ocean City.  You are at the BEACH for Christmas!!!
• Check in at https://hotels.oceancity.com

• Catch a late night holiday drink and something more to eat at Longboard Cafe at 67th Street.  

SUNDAY, DECEMBER 21 (Berlin)

• Wake up and have a leisurely breakfast.

• Download the Town of Berlin Trail to save some money as you shop until you drop!  Use the coupons and check into the listed businesses for a chance to win prizes!

• Head to Berlin, MD for some holiday cheer, a free carriage ride, great boutique shopping, and something yummy to eat or drink.  

• Visit Santa & holiday shopping (see above)

• Dinner in a Winter Igloo Village (see above)

• Back to Ocean City for a nightcap

MONDAY, DECEMBER 22 (Rehoboth, DE & North Ocean City)

Take another leisurely morning to check out the decorations along the Ocean City Boardwalk and find a fun place to grab breakfast.  You can start at the Ocean City Lifesaving Museum and walk north to see the sites!

Then, head to the Tanger Outlet Malls (You can check out the Seaside, Surfside and Bayside sections for all the shopping you could want – AND NO SALES TAX!) for some last minute shopping followed by a late lunch and a beer at Dogfish Head Brewing & Eats

Head back to your hotel for a nap and then head out to find something to eat and drink.  OceanCity.com’s dining guide should help you find what you are looking for.  If you want to check out the “Best of Ocean City” winners or try some $5 orange crushes or $5 local craft beers, download your favorite trails here.

Head over to Northside Park for Bryan Scar’s free holiday concert. Followed by dinner and some ice skating at the Carousel Hotel’s many options and their indoor skating rink!

Since you already have your Winterfest tickets (which you bought when you went to Bryan’s concert), you can head back to stroll around all the lights until it’s time to head back to your hotel, exhausted, but thoroughly ready for Christmas!