Three Days, Five Adventures, Two Coastlines

Surrounded by water on three sides, the Eastern Shore is an outdoor paradise with over 78,000 acres of parks and refuges and one of only ten U.S. national seashores. Five walkable waterfront towns, with shops, galleries, museums and restaurants, hug the Atlantic and Chesapeake Bay coastlines. Come and play on this long narrow peninsula, one of the best undiscovered coastal playgrounds on the mid-Atlantic. Best of all, it’s less than a half-day’s drive from New York, D.C. and Philadelphia.

Trip Highlights:

  • Kayak out to Holly Bluff, a private, off-the-grid Atlantic island with Burnham Guides. Paddle through a delicate wildlife refuge teeming with wildlife, tour a 1930’s hunting lodge and play on the private beach, Relax and picnic on a veranda overlooking the water.
  • Boat out to Virginia’s wild barrier islands, the longest stretch of undeveloped outer banks remaining on America’s East Coast. Captain Meriwether Payne, of Seaside Ecotours, whose family has deep roots in the area, has extensive knowledge of marine life, shore birds and the history of these mystical islands.
  • Get a bird’s eye view of the stunning Eastern Shore peninsula surrounded by water on three sides. You’ll be miles above the earth, gliding like a bird in flight, with Virginia Hang Gliding.
  • Hike and paddle Kiptopeke State Park, a beachfront preserve, where you can kayak out to the concrete WWII “ghost ships” and hike miles of maritime forest with stunning views out over the Chesapeake Bay.
  • Take a sunset boat cruise out of Cape Charles as the sun sets over the vast Chesapeake Bay horizon. You’ll meet up with the Cape Charles Boat Tour Company at the town harbor, just a few steps from the town’s bustling center.

Outfitters and Guides:

Day 1

The Northampton Hotel blends southern charm and modern decor. File Photo

Wake up at the Northampton Hotel in Cape Charles, a harbor town right on the Chesapeake Bay. You’re just steps from the public beach at your hotel and every room has a spacious private veranda overlooking the beach and the town harbor. It’s a a perfect place for your first cup of coffee. Have breakfast downstairs then pack up for a day of adventures on the water and in the air.

Your first stop is the Barrier Islands Center, a beautifully restored “almshouse”, to learn about the fascinating history of the wild barrier islands that hug Virginia’s Eastern Shore. These were once thriving communities and the playgrounds of wealthy industrialists from the northeast. They are now abandoned to nature and privately owned to protect them from development.

You’ll feel like a guest at the Cobb Island Hotel when you visit the Barrier Islands Center. File Photo

Meet Captain Meriweather Payne, of Seaside Ecotours, in Wachapreague, a tiny fishing village on the Atlantic Ocean, to motor out through coastal wetlands to the undeveloped barrier islands. Learn about the fragile ecosystems of these pristine wetlands and outer banks, which are both sanctuaries for wildlife and protective vanguards against storm damage for the long Virginia Eastern Shore peninsula.

Head back to terra firma for lunch at the Island House, which perches right on the Wachapreague waterfront, for a lunch of fresh, local seafood. Sit on the outdoor patio and gaze out to the barrier islands on the horizon.

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Explore wild barrier islands with Seaside Eco Tours. File Photo

Your next stop is at Virginia Hang Gliding for a miles-high view of the Eastern Shore from a hang glider. You don’t need any experience to do this, and the instructor will be up in the air with you. This is the only tandem hang gliding outfitter on the Atlantic seaboard south of Maine. You’ll get a breathtaking view of two coastlines including the long horizon of the Atlantic Ocean to the east, with the barrier islands stretching south and north.

Back in Cape Charles, explore the bustling main drag, Mason Avenue and take a dip in the Chesapeake Bay beach that’s just steps from your hotel. Sample some moonshine at the Cape Charles Distillery or a cider at Buskey’s Cider taproom. A short car trip gets you to the Cape Charles Brewing Company with a long list of locally produced microbrews. Walk to dinner at The Shanty, just two blocks from your hotel, and savor the views out over the Bay as you relax over dinner.

Day 2

Breakfast at your hotel or walk a few blocks to the Cape Charles Coffee House, a Viennese-style cafe in an old department store that dates to the early 1900s.

Spend the day at nearby Kiptopeke State Park, a coastal playground with 562 acres of trails and separate beaches for humans and dogs. Rent a kayak and paddle out to the “ghost ships” just offshore, a remnant from World World II. Take a break for lunch at the nearby Sting-ray’s, a seafood shack right on Route 13, then take a long hike along five miles of trails. Don’t miss the trail with stunning views from high bluffs out over the Chesapeake Bay.

Get a glimpse of the concrete ships at Kiptopeke from bluffs above the Chesapeake Bay. File Photo

Head back to Cape Charles for a sunset boat tour with the Cape Charles Boat Tour Company. Meet Captain David Lee at the town harbor for an hour cruise and bring along your own cocktails and toast to the setting sun over the western skies.

Walk from the harbor across the street to Hook U Up Gourmet and classically prepared, seasonal dishes by the chef/owner.

Day 3

Begin your final day at Coach House Tavern in Cape Charles for breakfast. Located inside the golf clubhouse at Bay Creek Resort & Club, the old-world restaurant has a rustic, casual atmosphere and serves standard but quality breakfast fare daily until 10:30am. Get another boxed lunch from Rayfield’s Pharmacy and check out of the Northampton Hotel before leaving the charming town of Cape Charles.

Kayak to Holly Bluff with the Burham Guides. File Photo

Head to Wise Point boat ramp inside the Eastern Shore of Virginia Wildlife Refuge. Meet up with Mary and Bill Burnham of Burnham Guides for a trip out to a private Atlantic Ocean island. Tour an off-the-grid island retreat using a windmill and water catchment system and picnic on the wide patio overlooking the water. You’ll want to plan a longer stay at Holly Bluff, where you will take longer kayak trips along the coastline and forage for wild oysters, clams and crabs for dinner.

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