Unwrap the Magic of Maryland’s Coast This Holiday Season: 100 Ways to Celebrate

As the holiday season approaches, it’s the perfect time to plan a winter road trip to Maryland’s Coast. With festive events, cozy small-town charm, and endless opportunities to enjoy the seasonal beauty of the coast, each of the four towns—Ocean City, Ocean Pines, Berlin, Snow Hill, and Pocomoke—offers something unique for families, friends, and couples. 

Whether you're watching twinkling lights, exploring holiday parades, indulging in artisanal shopping, or taking scenic winter walks, this guide will show you 100 ways to experience the holiday magic of Maryland’s Coast.

Ocean City, MD

Ocean City turns into a winter wonderland, with plenty of festive activities to warm your heart. From the dazzling Winterfest of Lights at Northside Park to the excitement of the Christmas Parade, there are endless ways to embrace the season.

  1. Stroll through Winterfest of Lights at Northside Park.
  2. Warm up with hot chocolate at Bayside Skillet.
  3. Join the fun at the Ocean City, MD Christmas Parade.
  4. Dress up for SantaCon and spread holiday cheer.
  5. Go ice skating at the Carousel Hotel Ice Rink.
  6. Shop for unique gifts at the Ocean City Art League Holiday Artisan Fair.
  7. Enjoy the festive light show at Cain Woods Christmas House.
  8. Dress up for Comic Con and celebrate fandom in the winter.
  9. Watch the holiday boat parade from Harpoon Hanna’s.
  10. Take your pup for a festive beach walk.
  11. Have breakfast with Santa at Ropewalk Restaurant.
  12. Tour and taste at Seacrets Distilling Company.
  13. Play a free round of mini golf on Christmas Day at Old Pro Golf.
  14. Create holiday art at T&C Studios family paint night.
  15. Enjoy a weekend brunch at Spain Wine Bar.
  16. Catch a holiday show at the Performing Arts Center.
  17. Sip house-made eggnog at Annabelle’s BBQ & Creamery.
  18. Watch The Polar Express while dining at Nick’s House of Ribs.
  19. See the toy trains at the Train Garden at the Convention Center.
  20. Take the plunge at the Penguin Swim on New Year’s Day.
  21. Watch the New Year’s Eve fireworks over the beach.
  22. Book a stay at a beachfront hotel for a cozy winter getaway.
  23. Holiday shop along Coastal Highway for unique gifts.
  24. Gather for a winter beach bonfire.
  25. Treat yourself to holiday-inspired sweets from Dolle’s Candyland.

Berlin, MD

Known for its quaint Victorian charm, Berlin becomes a magical destination during the holiday season. From horse-drawn carriage rides to holiday parades, this town offers festive activities that will make you feel like you’ve stepped into a winter postcard.

  1. Stroll through downtown during Berlin’s Victorian Christmas.
  2. Take a cozy horse-drawn carriage ride through historic Berlin, MD.
  3. Explore local movie locations with a walking tour brochure.
  4. Savor a warm Peach Dumpling from Baked Dessert Cafe.
  5. Take a candlelight tour of the Taylor House Museum.
  6. Watch artisans at Beach Memories Glass Studio create unique gifts.
  7. Attend the Berlin Christmas Parade, a holiday tradition.
  8. Sip a seasonal craft beer at Sinepuxent Brewing.
  9. Watch a classic holiday movie at the Globe Theater.
  10. Indulge in Lemon Lust at the Atlantic Hotel Bistro Bar.
  11. Drive through the Light up the Pines holiday display.
  12. Enjoy fondue in a heated igloo at Windmill Creek Vineyard.
  13. Create a custom ornament at Jeffrey Auxer Designs.
  14. Explore nostalgic toys at World of Toys.
  15. Shop during Sip and Shop Fridays downtown.
  16. Enjoy a holiday treat and pick out the perfect Christmas tree at the Snow Ball Stand.
  17. Craft your own holiday wreath at a wreath-making workshop.
  18. Discover hidden gnomes in Ocean Pines Fairy Woods.
  19. Take festive photos with Berlin's holiday murals.
  20. Experience a traditional wassail event at the Taylor House Museum.
  21. Sip seasonal brews at Burley Oak Brewery.
  22. Ring in the New Year at Berlin’s Ball Drop.
  23. Savor seasonal dishes at Blacksmith Berlin.
  24. Browse holiday treats at the Ocean Pines Farmers Market.
  25. Cozy up with hot chocolate and an electric blanket at The Atlantic Hotel.

Snow Hill, MD

If you’re looking for a peaceful holiday experience, Snow Hill offers a relaxed, charming vibe. From holiday markets to winter kayaking, this town is a great spot for those who love to enjoy nature and historic charm.

  1. Attend the festive Snow Hill Christmas Parade.
  2. Shop for handmade gifts at the Holiday Market.
  3. Kayak the serene Nassawango Creek.
  4. Spot Bald Eagles along the Pocomoke River.
  5. Watch tundra swans and snow geese migrate across farm fields.
  6. Find mistletoe while exploring Snow Hill's forests.
  7. Listen for frogs in late winter.
  8. Stay in a cozy cabin at Shad Landing.
  9. Hike the winter trails at Pocomoke River State Park.
  10. Fish for winter bass using crankbaits.
  11. Stroll Snow Hill's charming historic streets.
  12. Book a peaceful stay at a bed and breakfast.
  13. Get cozy and listen to live music at Tides and Vines.
  14. Burn energy at the Imagination Village or shop for children at Snow Hill Toys.
  15. Shop for handmade gifts at Snow Hill’s Christmas Market.
  16. Enjoy cocktails at Oaked 110 Whiskey & Wine Bar.
  17. Indulge in handmade sweets at Royal Port Candy Co.
  18. Spend an afternoon at Bishop’s Stock for art and wine.
  19. Explore the Snow Hill Model Train Gardens.
  20. Attend holiday storytime at the library.
  21. Celebrate history at the Frosty Furnace Festival at Furnace Town.
  22. Enjoy a winter picnic at one of Snow Hill’s parks.
  23. Take a guided winter nature walk at Pocomoke River State Park.
  24. Admire the holiday lights on an evening walk through Snow Hill.
  25. Watch the goat drop for New Year’s Eve

Pocomoke City, MD

Located along the banks of the Pocomoke River, Pocomoke City is a small-town treasure with its own unique holiday charm. Whether you're sipping on Peppermint Mochas, catching a holiday movie at the historic Mar-Va Theater, or touring the town's beautifully decorated historic homes, Pocomoke offers something special for everyone during the festive season.

  1. Sip on a Peppermint Mocha at Christmas Sweet.
  2. Unwind with a massage at Simply Sublime Massage & Bodywork.
  3. Book a family holiday photo shoot along the river.
  4. Visit holiday exhibits at the Delmarva Discovery Museum.
  5. Attend the Pocomoke Tree Lighting Ceremony.
  6. Watch a holiday movie at the Mar-Va Theater.
  7. Explore Santa’s Train Wonderland at the Discovery Museum.
  8. Join a Christmas Eve candlelight service.
  9. Take a scenic drive on the View 100 trail.
  10. Explore antiques at The Vault.
  11. Send flowers from Enchanted Florist for a holiday surprise.
  12. Enjoy a cozy stay at The River Gem B&B.
  13. Adopt an animal for the year at the Discovery Museum.
  14. Sip hot cocoa while strolling Pocomoke’s decorated streets.
  15. Tour historic homes dressed for the holidays.
  16. Hike festive nature trails.
  17. Attend holiday events at Sturgis One Room School Museum.
  18. Visit the Costen House Museum for Christmas tours.
  19. Craft for the otters Mac and Tuck at the Discovery Museum.
  20. Listen to holiday stories at the library.
  21. Savor a Christmas Crush at Dockside Restaurant.
  22. Shop at the Christmas Open House.
  23. Sip Pocomoke Punch at Cypress Roots Brewery.
  24. Enjoy a winter picnic in one of Pocomoke’s parks.
  25. Hunt for vintage treasures at Black Water Relics.

So, gather your loved ones, bundle up in your favorite sweaters, and take a holiday road trip to Maryland’s Coast. Whether it’s the festive lights of Ocean City, the Victorian charm of Berlin, the historic streets of Snow Hill, or the cozy escapes in Pocomoke, there’s no shortage of ways to make this season unforgettable. Let the coastal beauty and holiday spirit of Worcester County, MD turn your winter getaway into a cherished memory