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

Historically known as “The Town that Fooled the British,” St. Michaels, MD is the most popular destination in our collection of waterfront towns. Offering a variety of activities, shops, and restaurants, there are countless attractions and things to do in St. Michaels for everyone in the family to enjoy.

Things to Do in St. Michaels, Maryland

1. Visit the Chesapeake Bay Maritime Museum

The Chesapeake Bay Maritime Museum is in the center of St. Michaels and offers visitors a chance to learn about the heritage of the Chesapeake Bay. The waterfront campus includes interactive exhibitions, tours, and scenic boat rides, demonstrations, hands-on education programs for children and adults, and annual festivals that celebrate the Chesapeake Bay culture.

During the year, there are several fun events hosted by the Museum to enjoy–OysterFest in October, July 4 fireworks, the Charity Boat Auction, Big Band Night and Waterman’s Appreciation Day are all local and guest favorites.

2. Discover Kid-friendly Things to Do in St. Michaels

The best part about this community are the variety of kid-friendly things to do in St. Michaels! Kids love the opportunity to: tour a real lighthouse, and the Chesapeake Bay Maritime Museum also offers family sleepovers for children to experience the life of a lighthouse keeper.

3. Check out The Historic Mill Complex

The Historic Mill Complex is an industrial hip-chic atmosphere and features a winery, brewery, and distillery. Spend some time tasting local wines, enjoying some spirits and learning about the beer-making process.

4. Enjoy a Wide Variety of Dining Option

There is a fantastic array of restaurants in St. Michaels, and you are in for a treat as you stroll along the charming town. From waterfront crab houses where you can learn to pick crabs and enjoy the best local seafood while taking in bay breezes and scenic water views, to upscale restaurants with fine dining for a special evening out, you will want to bring your appetite along. Some of our favorites include:

  • Limoncello for authentic Italian cuisine
  • Ava’s for delicious wood-fired pizza
  • Theo’s Steak House, for an upscale steakhouse experience
  • St. Michaels Crab & Steak. The Crab Claw is a local icon offering an authentic crab house experience overlooking the harbor.
  • Justine’s for a sweet treat. This is a local favorite for ice cream
  • Gina’s Bakery for homemade goodies perfect to take home to enjoy along with your morning cup of coffee.

5. Get On the Water

Want to get on the water? There are many water activities and things to do outdoors in St. Michaels. Take a boat ride or charter, or for the more active vacationer, you can rent kayaks or paddleboards. A guest favorite is the H.M. Krentz, a working skipjack offering daily tours to learn about oyster dredging and local history and experience the life of a waterman by helping pull up sails. The Patriot offers narrated cruises aboard a replica of a 1930’s steam ferry, or for an upscale sailing experience, the Selina II is perfect for an intimate sunset cruise. Shore Pedal and Paddle has an array of kayaks and paddleboards for you take out or stop by the Maritime Museum to rent a boat there.

6. Rent a Bike and Explore

Biking is very popular in St. Michaels whether you’d like to just explore the town at a slow pace or take on a more ambitious ride along some of our scenic bicycle trails. Several shops offer bike rentals for all ages and levels of experience.

7. Spend the Day Shopping

The historic district of St. Michaels is also home to some of the best shopping around! You can find a keepsake treasure in the local antique shops, browse the many upscale boutiques, discover a new favorite artist in one of the eclectic art galleries or get some inspiration for your home by visiting some of the furniture and accessories shops. Kids love the candy and Christmas shops, as well as the souvenir stores (crab hats, anyone?) to find that perfect keepsake for your visit.

8. Experience the Offseason

An offseason trip to St. Michaels will not disappoint. Starting in October, St. Michaels hosts a variety of fall events where you can enjoy the cooler temperatures, beautiful foliage and seasonal delicacies such as oysters and crab soup. Fall into St. Michaels weekend in October is a family-friendly event or be sure to visit for Oysterfest for great seafood, music, and local flavor.

St. Michaels is one of the best Christmas destinations on the East Coast. The town pulls out all of the stops with spectacular holiday decorations, parades, homes tours and more.

Book Your Next St. Michaels vacation with Eastern Shore Vacation Rentals

Eastern Shore Vacation Rentals is proud to offer a variety of St. Michaels Vacation Rentals for your next visit. Browse and book these beautiful properties today!

View Our St. Michaels Vacation Rentals

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