The Eastern Shore of Maryland is a haven for rest, relaxation, and reconnections with nature. Many people visit our beautiful region in the warmer months to immerse themselves in the magnificent scenery with outdoor activities, but our area is spectacular in the winter, too. In fact, it’s one of our favorite times of the year. You might agree with us after you check out these Eastern Shore Christmas events! Plus, you can book one of our vacation rentals to put the icing on top of a magical getaway. It’s the key to unlocking a wealth of holiday cheer!

The Best Eastern Shore Christmas Events


  • Holiday Arts, Crafts & Gifts Fair

Get a head start on your shopping this year with the Annual Holiday Arts, Crafts & Gifts Fair! It takes place in early November with 25 vendors at Emily’s Produce in Cambridge, MD. You’ll find plenty of hand-crafted items that are sure to put a smile on that special someone’s face!

  • Mistletoe Market

Can’t get enough shopping during your vacation? Continue your shopping spree at the Mistletoe Market on Saturday afternoons from mid-November through mid-December at Cannery Way. There’s no shortage of unique gift options here!

  • Winter Wonderland Music and Tree Festival

Get ready for four days of holiday cheer at this year’s Winter Wonderland Music and Tree Festival! There are activities for all ages, including a holiday musical, pictures with Santa Claus, dancing, and more. Don’t forget to bid on a decorated Christmas tree — proceeds benefit the Leukemia and Lymphoma Society of the Eastern Shore.

  • Festival of Wreaths Gala

The Festival of Wreaths Holiday Gala is another excellent event to attend at the beginning of December. You can join the fun at the Pleasant Day Medical Adult Day Care Center in Cambridge for an evening of food, fun, music, and auctions for a good cause.

  • Cambridge Dorchester Christmas Parade

If you can only make it to one holiday event in Cambridge, Maryland, we highly recommend checking out the Cambridge Dorchester Christmas Parade. It’s been an annual tradition for over 70 years! Arrive early on the first Saturday of December to get a good viewing spot as the festive floats, performers, and participants make their way from Long Wharf to Washington Street.

  • Santa Swim

Do you have what it takes to jump into the Choptank River in the middle of the winter? Several brave swimmers take the plunge each year in support of the Care and Share Fund that helps less-fortunate members of the community. You’re welcome to sign up, help raise money, and have a whole lot of fun in the process.

  • Santa Trail Scavenger Hunt

Feel free to test your treasure-hunting skills toward the end of December in Downtown Cambridge! The Santa Trail Scavenger Hunt is the ideal Christmas activity for families looking to explore the area and pick up treats at a variety of local businesses. Can you solve all the clues and find Santa’s secret location?


  • RiverArts Holiday Show and Gift Sale

No matter who’s on your shopping list this season, you can find the perfect presents at the Chestertown RiverArts Holiday Show and Gift Sale. There’s a wide variety of items to choose from, and the market runs from late November all the way through late December. 

  • Dickens of a Christmas Weekend

Take a journey back in time for a Victorian celebration this December! Dickens of a Christmas is Downtown Cambridge’s premier holiday event that spans three days with historic house tours, fashion shows, bonfires, live performances, and so much more.


  • Festival of Trees

‘Tis the season of giving, and there’s no better feeling than giving to an honorable cause. The Festival of Trees in Easton is a fantastic opportunity to do that. There’s so much fun to be had here, including the new addition, Carols by Candlelight. Proceeds go toward helping terminally ill patients at Talbot Hospice.

  • Moonlight Madness

Did you know that you earn raffle tickets just for shopping at participating local businesses in Easton from November to the beginning of December? It’s true! And, you get a chance to win $10,000 worth of prizes during the drawing at Moonlight Madness. It’s an evening of late-night shopping, celebrating, photographs with Santa, and even free carriage rides through town!

  • Holiday Parade

Of course, you can expect plenty of remarkable parades during Christmas time on the Eastern Shore of Maryland. Easton, MD, is no exception! Check out the annual Holiday Parade in early December to get in the spirit of the season with a tree lighting and a one-mile parade throughout the downtown area. 

St. Michaels

  • Midnight Madness

Easton has Moonlight Madness, but it’s not to be confused with Midnight Madness in St. Michaels, Maryland. Shops remain open until midnight, as you might expect from the event name, providing extra hours of holiday cheer and fun for visitors. You can even score some exclusive deals and win more raffle prizes!

  • Christmas in St. Michaels

Make sure you don’t miss out on Christmas in St. Michaels, a must-see festival with holiday activities during three fun-filled days in mid-December. Some of the events include a gingerbread house competition, yuletide party, Breakfast with Santa, Santa’s Wonderland, and more. Don’t forget to purchase your souvenir ornament — there’s a different one each year to collect!


  • Christmas on the Creek

Christmas on the Creek is another excellent, multi-day festival that takes place in the quiet town of Oxford, Maryland. Expect plenty of fun things to do for the whole family, including the annual tree lighting and a Christmas bazaar.

Reserve Your Vacation Rental for the Holidays!

Do you know what makes these Eastern Shore Christmas events even more special? We offer beautiful properties near them all! Eastern Shore Vacation Rentals has an extensive collection of homes, cottages, and estates in each of these charming towns. Whether you’re looking to celebrate the holidays in St. Michaels, Cambridge, Oxford, Chestertown, or even Tilghman Island, we have the ideal property for you. Some of them are even pet-friendly, so you can spend this special season with the whole family, including your furry, four-legged pals.

Browse our seasonal specials and book your ideal vacation rental today! And, check out our events page to discover more celebrations you can enjoy year-round!

The living room inside Sycamore Acres