Tag Archive for: Cambridge

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

Sometimes, simply thinking about Cambridge might send you into a state of serenity. It’s a paradise for family vacations where you can stroll through the downtown area, explore the town’s history, soak up the waterfront views, and set sail on scenic cruises. While it’s a fantastic destination for relaxing retreats, this community on Maryland’s Eastern Shore sure knows how to celebrate, too! Feel free to jump into all the excitement — we made a convenient guide for some of the top annual events in Cambridge, MD, to make sure you never miss out. Plus, you can enhance your experience further when you reserve one of our beautiful vacation rentals in the area!

Discover the Best Cambridge, MD, Events


There’s always something fun going on in Cambridge during the summertime, from the fireworks over the Choptank River to fun-filled festivals. When you’re not sunbathing and barbecuing with the family, feel free to check out some of the hottest events of the summer:

  • Independence Day Fireworks
  • Taste of Cambridge: Crab Cook-off 
  • Seafood Feast-I-Val
  • Light Night Cambridge!
  • GrooveFEST
  • Showcase Art Walk and Street Festival


There may not be as many festivals as the summertime, but you’re sure to fall in love with Cambridge when you attend these events. One of the biggest events of the season, and possibly the entire year, is the annual IRONMAN Maryland triathlon. It’s an opportunity to swim, bike, and run through our incredibly scenic region. You’ll get some exercise and have plenty of fun in the process! Here’s a taste of what to expect each fall in Cambridge, MD:

  • IRONMAN Maryland
  • Crabtoberfest


Happy holidays! When winter arrives, so does the holiday cheer. And, the local community loves to show off its holiday spirit with a variety of festivities. Feel free to check out these winter events in Cambridge, MD, and don’t forget to get some holiday shopping done in the downtown area. You can even warm up with a delicious meal and some hot cocoa at a cafe or restaurant.

  • Christmas Train Garden
  • Christmas Parade
  • Santa Swim


Spring back into the excitement and enjoy the beauty of springtime with wine, flowers, boating, and more! It’s already one of the best times to visit Maryland’s Eastern Shore, and the local events can make your vacation even more memorable. These are just some of the many ways to make it happen each spring:

  • Downtown Cambridge Wine Festival
  • St. Paul’s Flower Fair
  • Cambridge Classic Power Boat Regatta

Find Lodging for Your Favorite Celebrations!

It can be difficult to choose between all of these must-see events. Once you narrow your search down to your favorites, we’d love to help you select the best lodging option in the area for them. Whether you’d like to stay in the heart of the excitement or secure a relaxing escape a little further away, we have the ideal property for you. Eastern Shore Vacation Rentals is the premier property rental company in the area — and for several good reasons! 

Explore our list of Cambridge vacation rentals to take the next step toward paradise. Just don’t forget to check out our specials and book direct for the best deal. See you on the Eastern Shore this year!

The view of Indian Fields from the yard

Are you headed toward Maryland’s Eastern Shore this year? You’re already on the right track! It’s an incredibly beautiful and scenic area of the country with several different communities to visit. Luckily, we made a guide to help you decide between the top five Eastern Shore Vacation Spots. All you need to do is take a quick look and find your ideal destination. And, of course, reserve the perfect vacation rental in your chosen location. You’re in luck, again, because we’re the area’s premier boutique vacation rental provider with properties in all these remarkable communities!

Which Eastern Shore Vacation Spot Is Right for You?

St. Michaels

The view from the lawn and gardens of Osprey Point in St. Michaels, MD

Of course, you have St. Michaels in the heart of it all with a bustling historic district, beautiful homes, and upscale vacation vibes. Simply park your car and explore the charming streets that are lined with shops, restaurants, and museums. You’re also welcome to set sail on a number of boat tours from the several marinas. Make sure you save plenty of time to walk through the Chesapeake Bay Maritime Museum!

Fun fact: Did you know that the famous and successful movie, The Wedding Crashers, was filmed in St. Michaels?


An aerial view of Hudson Manor in Cambridge, MD

If you plan on visiting Cambridge, you’re in for another treat. This lovely and scenic community allows you to rent a large group or multi-family home to enjoy a destination in itself. There are 1,700 miles of shoreline, and we have beautiful cottages all along the way. Several of them have private piers where you can dip your toes in the water, fish for a variety of species, or simply enjoy the waterfront views. If you love animals and enjoy birdwatching, make sure you check out the Blackwater National Wildlife Refuge in the area.


The front view of the Thornton building in the fall

We also have a variety of properties in the Chestertown and Centreville areas, offering you quiet retreats near all the brick-lined sidewalks and charming neighborhoods. This community is ideal for relaxation and rejuvenation, but it’s also close enough to the Bay Bridge and several different fun attractions on the Eastern Shore of Maryland. If you’re headed in this direction, we recommend taking a stroll down the historic district to admire the architecture. Foodies will especially enjoy the series of local farmers markets and the variety of farm-to-table restaurants.


The front view of the Thornton building in Chestertown, MD, in the fall

Discover the true meanings of relaxation and serenity when you visit Oxford. This quiet, sleepy, small town on the Eastern Shore of MD is ideal for people who enjoy leisurely days on the waterfront. Consider renting a cozy cottage by the shoreline. You can park your car at a beautiful vacation rental and just walk to all of your favorite shops, restaurants, and fishing spots. Oxford, MD, is still somewhat of a hidden gem, meaning you won’t get a lot of the crowds that other destinations on the Eastern Shore of Maryland can attract during peak season.

Tilghman Island

The front view of Simplicity Cottage in Tilghman Island, MD

If you’re looking for another quiet, off-the-beaten-path vacation destination that’s still close enough to the charm of St. Michaels, consider a trip to Tilghman Island. It’s a charming, quaint, fishing village with a wealth of unspoiled natural beauty. If you love seafood and sailing, this is the Eastern Shore vacation spot for you. Feel free to unwind in the comfort of your property or journey out onto the Chesapeake Bay on a variety of boat charters and tours. Afterward, satisfy your hunger with the excellent restaurants in Tilghman Island and St. Michaels nearby!

Enjoy Your Favorite With Eastern Shore Vacation Rentals

Words can’t possibly do these Eastern Shore vacation spots any justice. So, that means you need to come on down and experience them for yourself! Hopefully, we helped you find your ideal community to use that PTO and treat yourself to some well-deserved relaxation.

Whether you’re leaning toward St. Michaels, Cambridge, Chestertown, Oxford, or Tilghman Island, your perfect getaway is just a click away. With our wide variety of properties, all-inclusive pricing, best price guarantee, and no pet fees, there’s no better company to trust with your trip than Eastern Shore Vacation Rentals. Why would you stay at a drab hotel on the Eastern Shore of Maryland when you can enjoy one of our stunning properties?

Browse our properties now, and get one step closer to the vacation of your dreams! Just don’t forget to browse our current specials and book direct on our website to secure the best deal on your trip.

The living room inside the Carpenter Alley unit