Join the Fun at the Best Annual Events in Cambridge, MD

fireworks in the night sky

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