Your Guide to the Best Weekend Getaways From Delaware

Access Our Eastern Shore of Maryland Travel GuideAre you in need of a romantic escape, a fun girl’s getaway, or a relaxing solo trip? When it comes to the best weekend getaways from Delaware, look no further than the Eastern Shore of Maryland for a memorable vacation. Get ready to explore historic Chestertown, sail along the Chesapeake Bay, or unwind in luxurious accommodations at Brampton Inn. Here’s what makes this gorgeous region the ultimate destination for a weekend escape!  

From fabulous shopping and dining to exciting activities and events, it’s easy to see why the Eastern Shore of Maryland is one of the best weekend getaways from Delaware. Before you start packing your bags, make sure to request a copy of our free Travel Guide. It’s full of recommendations about things to do, restaurants to try, and attractions to see during your trip!

The Eastern Shore of Maryland: One of the Best Weekend Getaways From Delaware

Things to See and Do:

Chestertown, MD, is one of the best East Coast weekend getaways, and it’s just a short drive from Delaware! This Eastern Shore of Maryland historic town is known for its rich and fascinating past. Take a self-guided walking tour downtown, enjoy a stroll around Washington College, or visit the Harriet Tubman Underground Railroad Byway

Next, head over to Chestertown’s Main Street to explore the thriving arts and cultural scene. Grab a cup of coffee and take your time browsing the many boutiques and art galleries. After sunset, make sure to catch the latest show at one of the local theaters or entertainment venues. There is always something exciting happening at The Mainstay in Rock Hall or The Garfield Center for the Arts.

Whether your ideal vacation consists of relaxation or adventure, you’ll discover both along the Eastern Shore of Maryland. Sail your way to a better vacation aboard a Chesapeake Bay Boat Tour or the Chester River Packet. Or, relax and reconnect with nature at the Eastern Neck Wildlife Refuge, Adkins Arboretum, or Calico Fields. No matter what you decide to do during your Eastern Shore of Maryland getaway, we guarantee it will be an experience you will always remember!

Where to Dine:

Chestertown is the ultimate destination for foodies, wine-lovers, and craft beer enthusiasts alike. Here, you’ll find a plethora of excellent restaurants, wineries, brewpubs, and distilleries. Are you craving fresh fish, shrimp, crab, or oysters? Enjoy some of the most delicious seafood you will ever taste at one of these local restaurants. Or, head over to Luisa’s for authentic Italian cuisine like antipasto, pizza, and pasta. Some of our other favorite eateries are 98 Cannon Riverfront Grille, Evergrain Bread Company, and Play it Again Sam’s

If you’re interested visiting one of the area’s top wineries, be sure to enjoy a tasting at Crow Vineyard and Winery. Sample the award-winning Maryland wines, tour the lush vineyard, and bring home a bottle of your favorite wine as a souvenir. Perhaps you’d prefer an ice-cold brew to a glass of wine? Stop by Bad Alfred’s in historic Chestertown for local craft beer and house-made spirits. 

Where to Stay:

When searching for the best weekend getaways in Maryland, we invite you to stay at Brampton Inn! Our romantic bed and breakfast is just minutes from all of these incredible attractions and offers the ideal accommodations for your stay. Our spacious guest rooms and cottages are designed with your ultimate comfort in mind. Many of them even feature amenities such as wood-burning fireplaces, plush linens, and modern en-suite bathrooms. 

Located at the edge of the woods, our Mulberry Cottage is a wonderful choice for weekend getaways from Delaware. Perfect for guests who prefer privacy and seclusion, it includes a hammock for two, a luxurious spa tub, and an elevated bedroom area with King-sized bed. Enjoy serene meadow views from your private outdoor sanctuary, or warm up by the fire during those cold winter months. Are you ready to experience the Eastern Shore of Maryland to the fullest? Check our availability and book your stay today!

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