Travel Itinerary: Winterfest Weekend - A Holiday Lights & Festivities Itinerary

Check In For Your Stay

When you arrive in Ocean City, head to your accommodations to check in, drop off your bags, and relax for a few minutes before heading back out! Whether you’re staying Downtown, Midtown, or Uptown, you’re sure to be surrounded by great activity and food options. Explore all of our accommodation recommendations!

Afternoon

After you’ve settled, head downtown to soak in the salty air as you stroll the iconic Ocean City boardwalk. If any of the businesses are open, be sure to stop inside to find some treasures!

Evening

If you’re in town on Friday, December 12th, your evening may look extra exciting! On this night, Ocean City is celebrating with the 150th Anniversary Gala. The black tie event will take place at the Ocean City Convention Center and will feature music, historical touches, food, drinks, dinner in the Grand Ballroom, and dancing!

But, if you’re in town for a different weekend, close out your day with a nice meal. All throughout town, restaurants are ready to provide a cozy ambience and appetizing menu. Try Liberatore’s, Longboard Cafe, or Blue Fish for something savory and delicious!

Morning

Rise and shine and start your Saturday morning with breakfast at Ocean 13 or Bayside Skillet, followed with a brisk walk along the ocean! A fall and winter beach walk in the crisp air is always the best medicine and perfect for clearing your head while you get some steps in.

Midday

After your walk, your Saturday morning recommendations will depend on which weekend you’re in town! Throughout the holiday season, there are a bunch of different holiday happenings going on.

If you’re in town during the weekend of November 28-30th, head to the Convention Center for the 43rd Holiday Shoppers Fair! This annual event kicks off the holiday shopping season with over 120 exhibitors offering merchandise like gourmet items, nautical crafts, candles, photography, florals, jewelry, ceramics, and more. There will be children' s activities as well!

On November 29th, treat kiddos to an experience they won’t forget with the Holiday Character Breakfast. This fun event allows kids to enjoy a meal in pajamas and meet their favorite characters like Mickey & Minnie Mouse, Stitch, Bluey, and more!

Saturday, December 6th offers a chance to get into the festive spirit with the Ocean City Christmas Parade! This marks the 42nd year of the holiday tradition, which will run from Old Landing Road to 120th Street.

Afternoon

Chill out with a spa appointment at Creative Day Spa! Nothing is more relaxing than spending the day enjoying Christmas activities followed by a massage or manicure.

Evening

Finally, it’s time for another evening of delicious food and even more holiday cheer! Start the evening with a nice dinner at Fager’s Island, Captain’s Table, or Oyster & Scales.

After dinner, head to Winterfest of Lights for the perfect and most magical way to end your evening and celebrate the season! At Northside Park, thousands of lights illuminate the night sky and offer a breathtaking holiday experience. In addition to the lights, the experience offers bonfires, rides, hot chocolate, a giftshop, and more!

New this year at Winterfest are four Enchanted Evenings! If you’re in town on December 1st, 8th, 9th, or 15th, consider enjoying the lights in a new way with a horse and carriage ride!

Morning

Sunday morning is a wonderful time to check out the many parks throughout Ocean City! Whether you’d like to go for a jog, play some pickleball, skateboard, or just spend a moment in nature, there’s a park for you. There’s even a park for the pups!

Afterward, refuel with breakfast at one of the many spots throughout town. Bai-Tee Bakery and Crawl Street Tavern are great options!

Midmorning

Post-breakfast is the perfect time to browse local small businesses and work on your holiday shopping! Check out stores all around town like Malibu’s Surf Shop, Kite Loft, Monkees of Ocean City, and Innerbloom to find the perfect treasures for your family and friends. You’re guaranteed to find something special!

Looking for treats to take back home? Fisher’s Popcorn, Dolle’s Candyland, and Candy Kitchen are your go-tos!

Evening

If you stick around into the evening the weekend of December 7th, head to the Convention Center for a very special event: The Mid Atlantic Symphony’s performance of Holiday Joy! Enjoy this memorable evening as the orchestra plays “a festive selection of music celebrating the spirit of the season!”

Enjoy the full itinerary list below:

Friday

• Check in to your accommodations.
• Afternoon: Stroll the boardwalk.
• Evening: Enjoy dinner at Liberatore’s, Longboard Cafe, or Blue Fish.
  • December 12th: Spend the evening at the 150th Anniversary Gala!

Saturday

• Morning: Enjoy breakfast at Ocean 13 or Bayside Skillet, followed by a walk along the ocean.
• Midday:
  • November 28th-30th: Enjoy the Holiday Shoppers Fair!
  • November 29th: Treat kiddos to some fun at the Holiday Character Breakfast.
  • December 6th: Enjoy the exciting Ocean City Christmas Parade!
• Afternoon: Chill out and enjoy a relaxing afternoon at Creative Day Spa.
• Evening: Have a nice meal at Fager’s Island, Captain’s Table, or Oyster & Scales.
• Night: Experience the magic of Winterfest of Lights!
  • December 1st, 8th, 9th, 15th: Create memories with Enchanted Evenings.

Sunday

• Morning: Enjoy one of Ocean City’s many parks!
• Midmorning: Grab a bite at Bai-Tee Bakery or Crawl Street Tavern, then sneak in some holiday shopping at Malibu’s Surf Shop, Kite Loft, Monkees of Ocean City, and Innerbloom! Grab treats at Fisher’s Popcorn, Dolle’s Candyland, and Candy Kitchen.
• Evening: Stick around for the Mid Atlantic Symphony’s performance of Holiday Joy!
• Head home & start planning your next trip to OC!