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Top 3 Winter Activities on the Eastern Shore of Maryland

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
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What You Need to Know About Eastern Shore Duck Hunting

Picture yourself in the great outdoors, surrounded by natural scenery, enjoying your favorite pastime. If your mind went straight to imagining a hunting adventure, then you’re in the right place. Maryland’s Eastern Shore is an incredible destination to make your daydream a reality, and we have all the information you need to make the most of the experience. Read on to see our complete guide to Eastern Shore duck hunting, and browse our collection of vacation rentals to find the ideal property for your trip!

Know Before You Go: Eastern Shore Duck Hunting

Rules and Regulations

Of course, the first thing you need to do is obtain the proper hunting license. Luckily, the Maryland Department of Natural Resources makes it easy — you can even apply for a license online! There are several different options available for both visitors and residents of Maryland’s Eastern Shore. If you’re a non-resident looking to plan a waterfowl-hunting expedition, we recommend the three-day Waterfowl and Small Game License. It only costs $45 and permits you to hunt waterfowl for three consecutive days in season. The duck-hunting season typically takes place in mid-October, late November, and from late December through January.

Popular Spots

The next step is to find the perfect area for your adventure, and the Eastern Shore is overflowing with opportunities. Some of the common duck-hunting destinations in Dorchester include the Blackwater National Wildlife Refuge, Fishing Bay WMA, Tar Bay WMA, and many more. There are simply so many fantastic places for duck hunting on Maryland’s Eastern Shore!

Duck-Hunting Outfitters and Guides

Did you forget your gear at home, or do you feel like picking up some new equipment for your upcoming duck hunt? Don’t worry, because there are several excellent stores that have everything you need. A few of the waterfowl-hunting outfitters and guides we recommend to visitors are Shore Sportsman, Diving Ducks, and Barneck Outfitters, among several others.

Plan Your Hunting Trip With Eastern Shore Vacation Rentals

So, now you know the essential information for an Eastern Shore duck hunting adventure. Are you forgetting anything? You can’t enjoy the ultimate hunting trip without having a fantastic place to stay in the area! Luckily, Eastern Shore Vacation Rentals has you covered with a whole list of properties with luxurious accommodations and impressive amenities. 

Whether you’d like to unwind after your hunt in St. Michaels, Oxford, Cambridge, Tilghman Island, or beyond, we have the perfect property for you. Plus, we have options for everyone from solo travelers to large groups in case you’d like to bring your friends or family along for a hunting getaway.

Don’t delay any longer. Book your favorite property and embark on an Eastern Shore adventure!

The view of Oxford Oasis from the dock
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Visit the Blackwater National Wildlife Refuge

One of the top reasons that people visit Maryland’s Eastern Shore is to unwind, enjoy some fresh air, and immerse themselves in the undisturbed beauty of nature. If this sounds like something you’re interested in, there’s one place you don’t want to miss. It’s the Blackwater National Wildlife Refuge in Maryland! This 28,000-acre space is a year-round paradise for animals and animal lovers alike in Dorchester County near Cambridge. Check out our guide to it all and embark on a scenic adventure! Just don’t forget to browse our list of vacation rentals so that you have a place to relax and rest your legs after your fun-filled day at the refuge.

Explore the Blackwater National Wildlife Refuge in Maryland

Birdwatching

Are you hoping to catch a glimpse of some rare and beautiful birds? If so, you’ll be happy to know that birdwatching is one of the most popular activities at the Blackwater National Wildlife Refuge. Consider visiting between November and February for the best chance at spotting a variety of waterfowl, including swans, geese, and over 20 different species of ducks along the walking trails. Make sure you keep an eye out for osprey, great blue heron, and bald eagles as well!

Local tip: Would you rather admire the wildlife from your automobile rather than trek through the trails? Feel free to take advantage of the Wildlife Drive and enjoy three miles of scenery from the comfort of your car!

Boating

In addition to the four hiking trails, there are also three water trails for canoeing and kayaking at the Blackwater National Wildlife Refuge. Feel free to bring your boat along on your getaway and paddle your way through nature’s magnificence on the Purple Trail, Orange Trail, and Green Trail. There’s even an interactive paddling map for your phone to help make sure you make the most of your journey on the water!

Fishing and Hunting

Get ready to reel in some lasting memories! You’re welcome to go fishing and hunting at the Blackwater National Wildlife Refuge as long as you obtain the proper licenses and abide by all rules and regulations. Anglers can cast their line and try their luck with largemouth bass, striped bass, catfish, perch, and more. If hunting is more your style, you can expect to see plenty of deer, turkey, and waterfowl.

Local tip: Bring your kids to the refuge on the first Saturday of June to enjoy the Youth Fishing Fun Day! It’s an opportunity to spend quality time together in the great outdoors with free equipment, food, and prizes.

Plan Your Visit!

Now that you know all about the Blackwater National Wildlife Refuge, it’s time to check it out for yourself! Luckily, Eastern Shore Vacation Rentals has you covered with a wide variety of properties available nearby, including several rentals in Cambridge, MD. Whether you’re looking for a cozy cottage on the shoreline or a sprawling estate with a pool and plenty of amenities, we have the perfect option for you. Plus, we go far beyond simply providing you with a place to stay. All of our properties come with superb customer service to help you plan the perfect getaway as well as seasonal specials to make the most of your experience here.

Browse our collection of beautiful properties today and get one step closer to an unforgettable vacation!

An aerial view of Bayberry Cove in Cambridge, MD
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What Are the Best Things to Do on Kent Island, MD?

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
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