If you’re searching for unspoiled natural beauty and fresh seafood on the Chesapeake Bay, you go to Tilghman Island. And, if you’re looking to celebrate everything that makes this destination special, you attend the Tilghman Island Day Festival! This exciting event takes place every October with great food and fun activities for all ages. Find out why you don’t want to miss it this year. And, browse our selection of Tilghman Island vacation rentals to make sure you have a fantastic place to stay near the celebration!

Top 3 Reasons to Enjoy Tilghman Island Day


Of course, you can expect any event here to include fresh, delicious seafood, and Tilghman Island Day is no exception. Remember to bring your appetite for boat-to-table delicacies like raw or steamed oysters, oyster stew, crabcakes, and so much more. Even if you don’t like seafood, you’re sure to find something to please your palate. Chefs and food vendors also serve up several classic options, including hot dogs, hamburgers, and barbecue chicken. 

Tip: Don’t forget to browse the nautical-themed crafts from local artisans, too! There are plenty of wares available that make ideal gifts or souvenirs to remember your visit to Maryland’s Eastern Shore.


Don’t fill up too much or spend all your time indulging in the food. (Although, we know it’s difficult to tear yourself away from all the enticing options!) You’ll also want to participate, or at least spectate, the variety of fun activities and events. Here are a few of the many options to look forward to this year:

  • Boat Docking Contest
  • Rowboat Race
  • Anchor Throw
  • Oyster Shucking Contest


One of the best reasons to visit Tilghman Island is the sense of community that this small fishing village offers. The Tilghman Island Day Festival isn’t only an excellent opportunity to spend time with the current friends and family members with you. It’s also a chance to meet new people and share lasting memories with them!

Visitor Info

  • Tickets are $5 per person.
  • The festival occurs from 10:00 a.m. to 5:00 p.m.
  • Don’t forget to attend the Tilghman Island Crab Fest in July for more food and fun!

Plan Your Trip With Eastern Shore Vacation Rentals!

Are you ready to experience the excitement of the Tilghman Island Day Festival on the Eastern Shore of Maryland? It’s worth checking out our selection of properties and vacation spots nearby, even if you’re only considering the idea of a getaway. You can secure a rental in the heart of the action with our Tilghman Island properties or unwind in a quiet retreat a little further away in the St. Michaels area and drive to the event. Either way, we’ll make sure your experience is flawless. Browse our entire list of Eastern Shore properties today to get started!

The living space inside the Clearview property on Tilghman Island

Natural beauty and memorable activities await you on Kent Island! One of its many claims to fame is that it’s the largest island in the entire Chesapeake Bay, stretching from Kent Point in the south to Love Point in the north. That means there’s plenty of room for you to enjoy all of the things to do on Kent Island, MD! And, trust us, it’s a worthwhile day-trip destination from our properties along the Eastern Shore of Maryland. If you haven’t done so already, check out all of the beautiful vacation rentals we have waiting for you in the St. Michaels, Oxford, Cambridge, Annapolis, and more!

4 of the Best Things to Do on Kent Island, MD

Enjoy the Scenery

Whether you prefer to walk, run, bike, or simply sit back and admire the views, there are so many opportunities to get out and explore the natural beauty of Kent Island. You can venture through a variety of trails like the Cross Island Trail and South Island Trail in Stevensville. Or, feel free to plan a relaxing day at the shore with scenic destinations like Matapeake Beach and Terrapin Beach Nature Park. Keep an eye out for some fascinating wildlife species, especially if you’re an avid bird watcher!

Browse Shops

Who doesn’t love checking out unique stores and boutiques? Make sure you save plenty of time for shopping on Kent Island, even if you just plan on window shopping. The downtown Stevensville area is perfect for when you want to spend a delightful afternoon searching for gifts, souvenirs, or home decor. One of the highlights here is Stevensville Antiques, where you can discover a variety of charming treasures!

Grab a Bite

Don’t worry when hunger strikes after all your outdoor adventures and shopping trips. There are so many excellent restaurants on Kent Island, MD! Of course, you might not be surprised to find out that the specialty is usually seafood due to all of the marinas and thriving fishing industry on the island. If you’d rather grab a drink rather than a full meal, you’re in luck there as well! There are plenty of Kent Island bars to check out, like the Pour House Pub on the northern end of the island and Dirty Dave’s Tiki Bar toward the southern side.

Explore History

Did you know that Kent Island was the first permanent English settlement in Maryland? That means we have good news for all of you history buffs out there. There are several must-see historical sites throughout the area. Feel free to visit the Stevensville Train Depot which dates back to 1902 and marvel at any of the historic buildings throughout Stevensville Arts and Entertainment District.

Enjoy Them All During Your Eastern Shore Vacation

Don’t simply read about this incredible place — get out there and start enjoying everything it has to offer! Eastern Shore Vacation Rentals has a wide variety of beautiful properties from the St. Michaels area to Annapolis, which are both within driving distance of Kent Island via the Kent Narrows Bridge or the Chesapeake Bay Bridge. You’ll love spending a fun-filled day on the island, then being able to head back to a stunning waterfront home, cottage, or estate. It’s not a daydream. It’s a reality, and we invite you to take the first step today. 

Browse our properties and find your happy place now!

The living room inside Fleet Street