Friday Evening: Settle In with Seafood Galore
First stop when you arrive on Virginia’s Eastern Shore? The quaint town of Cape Charles. It's got that small-town charm with a side of beachy vibes. Check into Bay Haven Inn and get settled. We know you'll love the cozy B&B. For dinner, swing by The Shanty, where sustainable seafood is the star of the show with dishes such as Mid-Atlantic calamari, lobster rolls and baked flounder imperial. Of course, digging into a plate of local oysters while watching the sunset is a must — the kind of start to the weekend we all dream of.
(Good news: We joined forces with Visit Eastern Shore to give away a fun prize package. Take our quiz to enter!)
Saturday Morning: Birdwatching Bliss
Saturday morning, wake up with the sun (or thereabouts) and head to the Eastern Shore of Virginia National Wildlife Refuge. It's a birdwatcher's paradise, especially when the migratory birds are passing through. Binoculars in hand, go on the lookout for everything from the sneaky American avocet to the regal bald eagle. There's something about wandering through nature, with just the sound of bird calls and the peaceful crunch of leaves underfoot, that puts you in a relaxed state of mind.
After your morning adventure, sit down for breakfast at Cape Charles Coffee House. Whether you’re craving lighter pastries or a full American breakfast, the menu there will hit the spot. Plus, it’s the perfect place to chat with the locals!
Wild pony sighting is a must while on the Eastern Shore.(Courtesy Visit Eastern Shore)
Saturday Afternoon: Beach Bumming
A trip to Virginia’s Eastern Shore wouldn’t be complete without beach time, and there are plenty of beaches to choose from. Hit Assateague Island for some wild pony spotting — yes, they’re actually wild — and beach lounging. Saxis is perfect for seaglass hunting and is also the home of the Saxis Museum if you'd love a history break. Cape Charles is the perfect beach spot for families -- the tranquil, shallow bay water there is perfect for kids. Pick out some sandwiches, salads and more from Cravings for a beach picnic.
Later, find yourself in Onanco*ck, kayaking through the serene waterways as the sun dips low, painting the sunsetting sky in shades of gold and pink. Spotting herons and maybe even an otter or two makes for the perfect end to the afternoon.
Saturday Evening: Southern Eats and Starlit Nights
When dinner time comes around, grab a seat at Mallards at the Wharf. Think Southern classics with a twist, all enjoyed with a backdrop of Onanco*ck Creek. Everything on the menu will make your mouth water, from the crab bread to the miso-glazed salmon. The warm and inviting atmosphere makes you want to stay and hang out all night, but after the sun sets, the stars will be calling. Venture down to a dark spot by the water and be treated to a sky so full of stars, that it’s like nothing you’ve ever seen. It’s a magical way to end the night!
Sunday Morning: Market Moseys and Antique Adventures
Start Sunday slow with breakfast at Bay Haven Inn, then it's time to mosey through the local farmers' market. We're talking homemade jams, fresh-baked goodies and the kind of down-to-earth chats you only get at places like this. You could spend a full day just perusing the farmers’ market, but there’s so much more to explore on Virginia’s Eastern Shore!
Next up, hop between the antique shops and art galleries. Each spot is packed with stories and treasures, from sea-inspired antiques to locally made crafts. Antiques Ahead, At Altitude Gallery,Current Reflections, Blue Crow Antique Mall, Historic Onanco*ck School and BayView Engraving and Art Glass Studio are just a few of the must-visit spots to explore. It’s a leisurely wander that feels just right for a Sunday morning.
Sunday Afternoon: Vineyard Vibes and Goodbyes
Wrap up the weekend at a tucked-away vineyard, sipping on local wines and wandering among the vines. Chatham Vineyards on Church Creek is a sight to see — a four-century-old working farm that is family-owned and operated to this day. After touring the winery, enjoy a wine flight in the tasting room the tasting room and pick out a bottle to bring home. It’s a leisurely experience for a Sunday afternoon.
As you pack up, it’s a great time to reflect on the simple joys of the weekend: good food, stunning nature and new discoveries. As you drive back over the bridge to head home, you’re not just bringing home a bunch of cool photos and souvenirs — you’re carrying back a slice of the laid-back, beachy life from Virginia's Eastern Shore, reminding us that sometimes, the best escapes are closer than we think.
