Tag Archive for: Events

Daily life on the Eastern Shore of Maryland almost always involves two things: water and seafood. Not only is this landmass flanked by the Chesapeake Bay and the Atlantic Ocean, but it’s also filled with intricate waterways that are serene and picturesque. The area’s proximity to fresh and saltwater means there’s always an abundance of delicious seafood to enjoy. And, while the summer is a popular tourist season, winter on the Eastern Shore of Maryland presents its own unique opportunities for a fun-filled Maryland-style getaway. Don’t miss out!

The foundation of any vacation begins with the perfect place to stay. Select one of our Eastern Shore Vacation Rentals to experience the best of Eastern Shore living any time of year. Choose from quaint historic cottages to waterfront homes to luxurious estates.

What Is There to Do in Maryland in the Winter?

The short answer is, a lot! Colder weather means fewer crowds at the top attractions. You can use that to your advantage and book a trip to the Eastern Shore this winter!

1. Explore a Wildlife Refuge

If you love to get outside, no matter the weather, the Eastern Shore of Maryland is a wonderful place to go birding. The Eastern Neck National Wildlife Refuge in Rock Hall offers winter walks in sanctuary areas. Don’t miss the chance to explore areas that aren’t usually open to the public. Keep your binoculars and your camera ready to capture sightings of tundra swans, scaup, Canada geese, ruddy ducks, mallards, buffleheads, and more. You might also see foxes, deer, and groundhogs.

The Blackwater National Wildlife Refuge in Cambridge is another great spot for birding. Look for bald eagles, golden eagles, tundra swans, great horned owls, and a variety of ducks.

2. Eat, Drink, and Be Merry

Easton Shore restaurants understand the best way to capture a traveler’s heart (and keep them coming back) is through an unforgettable meal. As we mentioned earlier, seafood is just about the center of every dish in this area. Try the crab cakes at Theo’s in St. Michaels, baked oysters on the half-shell at Latitude 38 in Oxford, or the oyster stew at Mason’s in Easton.

If you love wine, you’ll enjoy exploring Chesapeake Wine Country. Stop for a tasting at Cascia Vineyards, Triple Creek Winery, and St. Michaels Winery. Don’t forget to pick up something to pair with a delicious meal back home!

3. Holiday Festivities on the Eastern Shore of Maryland

The holidays might be one of the best reasons for a winter trip to the Eastern Shore of Maryland. You’ll get a healthy dose of traditional cheer, plus you can shop for locally made gift items, and sample local delicacies while you’re at it! A few of our favorite Eastern Shore Christmas Events include:

The Eastern Shore Winter Weather Report

Be sure to pack your warm coat, scarf, gloves, and maybe even snow boots if you’re planning a winter getaway. Daily highs range between 39 and 49 degrees Fahrenheit and the National Weather Service keeps us up-to-date on the occasional chance of snow and freezing rain. We think you’ll agree that a little blanket of the white stuff will only further enhance your trip. Imagine waking up one morning to a snow-covered landscape. You’ll have the perfect excuse to stay at your vacation rental all day to sip hot coffee, read, and relax!

Where to Stay in the Winter on the Eastern Shore of Maryland

The best way to enjoy a winter escape to the Eastern Shore of Maryland is to book one of our vacation rental properties. Our large collection of homes, cottages, and estates span St. Michaels, Cambridge, Oxford, Chestertown, and Tilghman Island.  We even have pet-friendly options and last-minute deals!

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 the Carpenter Alley Cottage

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