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