Ocean City Maryland holiday events dominate the season from November through January 2025, transforming this coastal destination into a winter wonderland. Whether you’re seeking festive family celebrations, holiday shopping adventures, exciting New Year traditions, or simply a peaceful coastal escape, Ocean City Maryland events offer unforgettable experiences that make it the perfect holiday destination.

The best part? All of these incredible Ocean City Maryland events are just steps away from comfortable, fully-equipped vacation rentals where you can retreat, relax, and recharge between adventures. Let’s explore what Ocean City has in store for you this season.

November: Ocean City Maryland Holiday Events Season Kicks Off

Winterfest of Lights Opens (November 20 – December 31)

Ocean City Maryland’s most iconic holiday tradition, Winterfest of Lights, celebrates its spectacular 33rd year in 2025. This premier among Ocean City Maryland holiday events runs from November 20 through December 31, transforming Northside Park into a glittering winter wonderland across 58 acres of twinkling magic.

Opening Hours:

• November 20 (Opening Night): FREE admission—get a preview of the magic before ticketing begins

• November 21 – December 21: Open Wednesday–Sunday, 5:30 PM – 9:30 PM

• December 22–31: Open daily, 5:30 PM – 9:30 PM

What You’ll Experience at This Ocean City Holiday Event:

A stunning 50-foot Christmas tree serves as the centerpiece, surrounded by over one million twinkling lights and elaborate animated displays. Lighted walking trails wind through the park, creating an enchanting journey through the holiday season. It’s the perfect backdrop for holiday photos and creating lasting memories with family and friends.

Admission:

• $6 for guests 12 years and older

• FREE for children 11 and under

New Experiences This Year:

Winterfest of Lights remains the crown jewel of Ocean City Maryland holiday events, with exciting additions that make 2025 truly special:

Horse-Drawn Carriage Rides: Experience the magic like never before aboard a festive horse-drawn carriage. Choose from private 2- or 6-person carriages, or reserve individual seats on the 12-person carriage. These special carriage-only evenings feature exclusive access to the park and a more intimate experience. Available dates: December 1st, 8th, 9th, and 15th. Reservations are required—call ahead to secure your spot!

Fire & Ice Nights: Fridays and Saturdays throughout Ocean City Maryland holiday events feature “Fire & Ice” experiences. Walk through the sparkling snow arch, snap a photo on the ice throne, warm up by a cozy bonfire, and grab delicious food from food trucks. Live entertainment plays under the tent, creating a festive atmosphere that feels like a miniature holiday village.

Winterfest Train Garden: New for 2025! Step inside the Winterfest tent and explore delightful Train displays featuring intricate holiday scenes. Admission is included with your Winterfest ticket. Experience the magic of the trains from 6:00–8:30 PM, Wednesday through Sunday (closed Thanksgiving, Christmas Eve, and Christmas).

Photo Opportunities with Santa: Visit Santa throughout Winterfest for professional photos and shared wishes with the big guy himself—the perfect way to capture holiday magic.

Pet-Friendly Evenings: Furry family members are welcome on Wednesday evenings, so your entire household can enjoy Ocean City Maryland holiday events together!

Accessibility & Convenience:

• Mobility devices available for rent on-site ($10 for two hours)

• Standard wheelchairs also available

• Weather closure possible—call 410-289-2800 for updates

Holiday Shoppers Fair (November 28–30)

The 43rd Annual Holiday Shoppers Fair brings artisan excellence and unique gift-giving to Ocean City Maryland events. Featuring over 120 exhibitors offering one-of-a-kind merchandise, this fair is your destination for gifts that matter and stands among the most beloved Ocean City Maryland holiday events.

What You’ll Find:

• Gourmet specialty items

• Nautical and coastal crafts

• Hand-poured candles

• Fine art photography

• Fresh florals

• Handcrafted jewelry

• Beautiful ceramics and pottery

• And so much more

Details:

• Dates: November 28–30, 2025

• Admission: $5 for the weekend

• Features: Door prizes throughout the event

• Perfect for: Unique holiday shopping without the mall experience

Trimper Rides Black Friday Sale (November 28–29)

Kick off your holiday season with the Trimper Rides Christmas Carnival & Black Friday Sale, a beloved Ocean City amusement park that opens special holiday hours with discounted admission and entertainment for the whole family, making it a must-see among November Ocean City Maryland events.

December: Ocean City Maryland Holiday Events in Full Swing

Ocean City Christmas Parade (December 6)

The beloved Ocean City Christmas Parade celebrates 42 years of holiday tradition. On Saturday, December 6, 2025, Main Street comes alive with festive energy as holiday floats, marching bands, local organizations, and Santa himself parade through downtown. This iconic Ocean City Maryland holiday event draws families year after year.

Details:

• Date: Saturday, December 6, 2025

• What to Expect: Elaborate holiday floats, live marching bands, community organizations, and a special appearance by Santa Claus

• Pro Tip: Arrive early, bring blankets and lawn chairs, and claim your spot along the parade route for the best viewing experience. Bring hot cocoa and treats for a cozy family tradition!

SantaCon Ocean City (December 12–13)

SantaCon transforms Ocean City’s boardwalk into a festive adult celebration where hundreds of creative Santas and holiday elves bar-hop in ugly Christmas sweaters and imaginative costumes. Now in its 15th year, this lighthearted SantaCon Ocean City Maryland event has become an anticipated tradition among young professionals and groups seeking festive Ocean City Maryland holiday events.

Details:

• Dates: Friday, December 12 – Saturday, December 13, 2025

• Locations: Purple Moose Saloon, Cabanas Beach Bar & Grille, and participating restaurants and bars throughout downtown and on the boardwalk

• Schedule: Bars open with “choose your own adventure” hours—arrive whenever and visit bars as you wish

• Main Events:

  • Friday Kickoff: Pre-SantaCon Happy Hour at Mother’s Cantina (5:00–7:00 PM), followed by Ugly Christmas Sweater Party at Pickles Pub (8:00 PM onward)

  • Saturday: Breakfast with Santa at Crawl Street Tavern (8:00 AM), then visit any of the participating establishments all day

Why Locals Love It: SantaCon has evolved from an organized bar crawl into a “choose your own adventure” celebration, making it flexible and fun for everyone who wants to participate in this unique Ocean City Maryland event.

Ocean City’s 150th Anniversary Gala (December 12)

As Ocean City celebrates its 150th year, this special Sesquicentennial Gala commemorates a century and a half of memories, community, and coastal heritage. This prestigious Ocean City Maryland holiday event marks a historic milestone for the town.

Details:

• Date: Friday, December 12, 2025

• Time: 6:00–10:30 PM

• Location: Roland E. Powell Convention Center, 4001 Coastal Highway

• Dress Code: Black Tie Optional

• Special Features: Valet parking available

This elegant celebration is perfect for those seeking a more formal way to ring in the season while honoring Ocean City’s rich history.

Holiday Joy Concert (December 13)

For a more intimate holiday experience, enjoy Holiday Joy, a festive musical performance featuring soprano Kresley Figueroa and baritone Jonathan Patton. This celebration of the holiday spirit through classic and contemporary music creates a warm, joyful atmosphere—the perfect evening for couples or small groups seeking meaningful Ocean City Maryland events during the holiday season.

Santa’s Pizza Night (December 13)

Perfect for families with young children, Santa’s Pizza Night combines holiday magic with kid-friendly fun. Enjoy pizza, festive crafts, cookie decorating, and a special visit with Santa complete with photos and shared wishes. The evening continues with a magical trip to Winterfest of Lights, creating a comprehensive holiday experience among family-friendly Ocean City Maryland events.

Seacrets Holiday Bazaar & Bubbly (December 12)

For a sophisticated holiday shopping and celebration experience, Seacrets Holiday Bazaar & Bubbly offers an elegant Friday evening among upscale Ocean City Maryland holiday events.

Details:

• Date: Friday, December 12, 2025

• Time: 6:00–9:00 PM

• Admission: $15 at the door

• Includes: Local artisan shopping, hors d’oeuvres, champagne toast, and live music

Ringing in the New Year: Ocean City Maryland Events Continue

First Night Ocean City (December 31 – January 1)

As the year comes to a close, Ocean City Maryland’s First Night Ocean City celebration creates a family-friendly, alcohol-free New Year’s Eve experience—a tradition since 1992. This iconic Ocean City Maryland event welcomes thousands of visitors seeking meaningful ways to celebrate the New Year.

First Night Details (December 31, 2025):

• Hours: 4:00 PM – Midnight

• Admission: Button purchase ($20–$25, inclusive of service fee) grants access to all 70+ entertainment programs at 20 venues

• Features: Ice skating rink, live music, comedy, magic shows, dance parties, karaoke, and much more

• Kickoff: Ocean City Music Pier ribbon-cutting at 3:45 PM

• Finale: Midnight fireworks display

• Parking: All municipal parking and metered spots FREE for button holders

• Transportation: Free jitneys transport visitors between venues throughout Ocean City Maryland events venues

First Day Celebration (January 1, 2026):

• First Day 5K Boardwalk Run: 1:00 PM start (pre-register or day-of registration available)

• First Plunge/Penguin Swim: 2:00 PM – The famous (and chilly!) polar plunge in the Atlantic Ocean supporting local charities

Planning Your Perfect Ocean City Maryland Holiday Vacation

With so many incredible Ocean City Maryland holiday events happening throughout November and December, having a comfortable vacation rental as your home base transforms a single holiday trip into a comprehensive, memorable experience that extends beyond typical tourist attractions. According to Visit Maryland’s comprehensive travel guide, over 500,000 visitors experience Ocean City’s seasonal attractions annually.

Why Choose a Vacation Rental for Ocean City Maryland Holiday Events?

Flexibility: Skip between Ocean City Maryland events at your own pace. Enjoy Winterfest one evening, rest and relax the next. No hotel checkout time stress allows you to experience more Ocean City Maryland holiday events during your stay.

Full kitchen: Prepare meals, save money, and enjoy intimate holiday dining with your family rather than dining out every night while enjoying Ocean City Maryland events. Studies show vacation rental guests save an average of 30% on dining costs compared to hotel stays.

Space and privacy: Gather your loved ones in an entire property rather than cramped hotel rooms. Create genuine family bonding moments while attending Ocean City Maryland holiday events.

Multiple guests: Whether you’re traveling with three people or a multi-generational family of ten, vacation rentals offer options for every group size interested in Ocean City Maryland events.

Authentic local living: Experience Ocean City like a resident, not just a tourist. Explore neighborhood restaurants, local shops, and hidden gems away from the tourist corridor while enjoying Ocean City Maryland holiday events. Discover local Ocean City dining options through the official tourism board.

Sustainable choice: Extended vacation rental stays during holiday season are often more environmentally friendly than traditional hotel experiences while maximizing your participation in Ocean City Maryland events, according to sustainable tourism practices.

Book Your Ocean City Maryland Vacation Rental Today

At Sonny Stays, we specialize in thoughtfully managed properties in Ocean City that are perfectly positioned for exploring all the holiday events the town has to offer. Our properties feature:

• Prime locations near Winterfest of Lights, the Christmas Parade route, and Ocean City Maryland event venues

• Fully equipped kitchens for cooking meals and preparing holiday treats

• Comfortable bedrooms ensuring restful sleep between adventures and Ocean City Maryland holiday events

• Reliable Wi-Fi and entertainment for relaxing evenings

• Hot tubs and pools available at select properties for added luxury

• Pet-friendly options so your furry family members can join the Ocean City Maryland events celebration

• Direct booking benefits: No platform fees, personalized service, and the genuine hospitality of a team that truly cares

Whether you’re planning a romantic winter escape for two, a multi-generational family celebration, or a friends’ getaway, Sonny Stays has the perfect Ocean City property for your holiday experience during these amazing Ocean City Maryland holiday events.

Explore Our Available Ocean City Properties and reserve your home away from home for this magical season. With Ocean City Maryland events running from November through January, you can choose the perfect timing for your escape. The question isn’t whether Ocean City will have something special—it’s which incredible Ocean City Maryland holiday events you want to experience first.

Make your 2025 holiday season unforgettable. Book your Ocean City property with Sonny Stays today and discover why Ocean City has become the holiday destination where families return to year after year to celebrate and create lasting memories at these beloved Ocean City Maryland events.