11 Great Things To Do on the Delmarva Peninsula

When I first wrote a blog post about what was going on in Delmarva, the first question I had was, “Where the heck is Delmarva?”

Where is Delmarva?

Delmarva is not in any one state but in three. The peninsula to the east of the Chesapeake Bay, which is part of Delaware, Maryland, and Virginia, apparently is “Delmarva”. I got in touch with Jim Rapp from the organization Delmarva Low-Impact Tourism Experiences (DLITE) to learn more about this region. Jim told me:

Delmarva has been in use locally and regionally for years. Off the Peninsula, the name means little. We wish we had a better, more exotic regional term – something along the lines of “Denali” or “Serengeti” or “Everglades”. We do have great names for our natural areas – Chesapeake, Chincoteague, Blackwater – but “Delmarva” doesn’t really grab you.

As a region and Peninsula, we are odd in that we are carved up so many ways – 3 states, 14 counties. This dates back to early colonial claims.

Today, each of our states & counties promote themselves, and they don’t do much together. Yet – for the nature & heritage traveler – we are just hours from millions (NYC, Philly, Balt/Wash are all within 2-4 hour drive), and LOADED with miles of scenic (& flat!) rural roads for the cyclist, miles of coastline & rivers on both sides for the kayaker, hundreds of migratory birds for the birder, and great local produce & seafood for the culinary explorer. Add in superb beaches, remote barrier islands, and some great history (John Smith explored the region in 1607-1608, birthplace of both Harriet Tubman & Frederick Douglass). You get the idea.

Here is Jim’s list of some of the best things in or about Delmarva:

1 – Beach

Assateague Island National Seashore stretches for 37 miles along the Atlantic coast, split between Maryland and Virginia, and offers some of the most unspoiled beaches on the entire U.S. East Coast. Here, white sands meet rolling surf and coastal dunes dotted with beach grass and maritime forest. The real icons of the island, though, are its wild horses, descendants of domestic animals that have adapted to the island’s salty environment over centuries. You can often see them wandering the dunes or even splashing in the surf, though visitors are reminded to keep a safe distance.

Beyond the beach, Assateague is a haven for outdoor adventure. Kayakers explore quiet back bays rich with herons and ospreys, while cyclists and hikers follow trails through pine forest and marshland. The park has campgrounds right behind the dunes, so you can fall asleep to the sound of waves under a sky full of stars. Whether you come for the wildlife, the solitude, or a refreshing swim, Assateague captures the wild beauty that makes the Delmarva Peninsula so distinctive.

2 – Beer

Founded in 1995 by Sam Calagione, Dogfish Head began as a small brewpub in Rehoboth Beach before growing into one of the pioneers of America’s modern craft beer movement. Today, its main production facility and visitor center in Milton, Delaware, draw beer fans from around the country. Calagione built the brewery’s reputation on creative, boundary-pushing recipes, think 90 Minute IPA, SeaQuench Ale, and the Ancient Ales series inspired by archaeological findings.

They have a killer brewery tour. If you know a beer lover, odds are they know about Dogfish Head, as this brewery has influenced a lot of craft beer brewers.

3 – Kayak Tour

For a peaceful and immersive way to experience Virginia’s Eastern Shore, join a guided paddle with SouthEast Expeditions, based in Cape Charles, Virginia. Founded by Dave Burden, the company has been introducing travelers to the quiet beauty of the peninsula’s tidal creeks, salt marshes, and barrier-island waterways for more than two decades. Their small-group kayak and paddleboard tours are led by experienced naturalist-guides who point out wading birds, blue crabs, and the shifting ecology of this delicate coastal environment.

One of their most popular outings is the two-hour tour of the Eastern Shore of Virginia National Wildlife Refuge, where paddlers explore calm channels and hidden coves rich in birdlife. This refuge sits at the southern tip of the Delmarva Peninsula and is part of the Atlantic Flyway, making it a key resting point for migratory species. SouthEast Expeditions also runs longer excursions through the seaside marshes and barrier-island backwaters, where you can spot ospreys, egrets, and even dolphins in the warmer months.

4 – Best-Kept Secret Restaurant

You can only reach Drum Point Market by ferry from Crisfield, a 45-minute ride across the Chesapeake Bay to Tylerton on Smith Island. The tiny, boat-filled village feels a world away from the mainland, and at its heart sits this beloved Mom-and-Pop store and café. Locals come for supplies and conversation, while visitors line up for what many call the best crab cake in Maryland—pan-fried, meaty, and made from fresh blue crab with almost no filler.

Drum Point also serves Smith Island cake, Maryland’s official state dessert, with eight to twelve thin layers of yellow cake and rich fudge icing. The recipe, created by island women generations ago, was designed to last on long crabbing trips. Between the ferry ride, friendly faces, and home-cooked food, Drum Point Market is pure Chesapeake—simple, genuine, and well worth the journey.

5 – Harriet Tubman

Harriet Tubman, born around 1822 in Dorchester County, Maryland, near Bucktown, escaped slavery and returned many times to guide others to freedom along the Underground Railroad. Today, travelers can follow her path on the Harriet Tubman Underground Railroad Scenic Byway, a 125-mile self-guided driving route with 36 sites that runs through Maryland’s Eastern Shore and into Delaware.

The byway links key sites from Tubman’s life, including the Bucktown Village Store, where she suffered a near-fatal head injury, and the Brodess Farm, where she spent her early years enslaved. Start at the Harriet Tubman Underground Railroad Visitor Center near Cambridge, set beside the Blackwater National Wildlife Refuge, where exhibits bring her story to life against the same marshland backdrop she once knew.

Though designed for drivers, parts of the route can be explored by bike, offering a slower, more reflective way to experience the landscapes that shaped one of America’s greatest heroes.

6 – Spring Shorebird Migration

Each spring, Delaware Bay comes alive with one of nature’s most remarkable migrations. Thousands of horseshoe crabs crawl ashore under the light of the new and full moons in May and early June, laying millions of eggs in the sand. At the same time, migratory shorebirds, especially red knots, ruddy turnstones, and sanderlings, arrive from as far away as South America to feast on those eggs before continuing their journey to Arctic breeding grounds. It’s a spectacle that has played out here for millennia and remains one of the great wildlife events on the Atlantic Flyway.

The best places to see the action include Slaughter Beach, Bowers Beach, and Mispillion Harbor, where the shoreline often teems with both birds and crabs during peak tides. To understand the science behind it, visit the DuPont Nature Center in Milford, Delaware, which overlooks one of the bay’s most active spawning areas. Exhibits and observation decks there help visitors spot the crabs and the shorebirds that depend on them—a vivid reminder of how the rhythms of the moon still guide life along the Delaware Bay.

7 – Winter Waterfowl Migration

Each winter, Bombay Hook National Wildlife Refuge near Dover, Delaware, transforms into a sea of white as tens of thousands of snow geese arrive from the Arctic tundra. The 16,000-acre refuge, a mix of tidal marshes and freshwater pools, provides critical habitat along the Atlantic Flyway for migrating waterfowl. On peak evenings, when the birds lift off in unison or return to roost, the sky fills with movement and sound, a living storm of wings and calls that seems to ripple across the landscape.

Most of the action centers around Shearness Pool and nearby impoundments, where geese rest and feed alongside tundra swans and pintail ducks. The best viewing is often just after sunrise or before sunset, when the flocks rise in great waves that catch the changing light. Even if you are not a dedicated birder, standing on one of Bombay Hook’s observation towers as thousands of snow geese swirl overhead is an unforgettable experience that captures the wild rhythm of Delaware’s winter coast.

8 – Fall Raptor Migration

Thousands of peregrine falcons, Cooper’s hawks, sharp-shinned hawks, and more can be seen at the Coastal Virginia Wildlife Observatory in Kiptopeke State Park near Cape Charles, Virginia. Banders catch and release birds for migration research, but you can take awesome photographs up close before they fly south.

9 – Pony Penning

Every summer, the town of Chincoteague, Virginia, celebrates one of the most distinctive traditions on the Atlantic coast: the Chincoteague Pony Swim and Auction. On the last consecutive Wednesday and Thursday in July, thousands of visitors gather to watch as the Saltwater Cowboys, volunteers from the Chincoteague Volunteer Fire Company, round up the wild ponies that live on Assateague Island.

At slack tide, when the current slows, the cowboys guide the herd across the Assateague Channel to Chincoteague. The sight of dozens of ponies swimming through open water, foals close to their mothers, is unforgettable. Once ashore, the animals are walked through town to the Carnival Grounds, where foals are auctioned the next day. The auction helps keep the herd size stable in line with U.S. Fish & Wildlife Service limits and funds the local fire department that cares for the ponies year-round.

The week also includes parades, the Fireman’s Carnival, and other small-town celebrations that honor Chincoteague’s coastal heritage. Many visitors return year after year to witness this blend of history, community, and wild spirit that continues to define life on Virginia’s Eastern Shore.

10 – Cross Island Bike Trail

Cyclists looking for a longer adventure can follow the Delmarva Bicycle Route, which stretches hundreds of miles along quiet roads from Maryland’s upper Eastern Shore to the southern tip of Virginia. Many begin near Kent Island or Chesapeake City, linking the Cross Island Trail with country roads that pass through Centreville, Easton, and Oxford. From there, the historic Oxford–Bellevue Ferry crosses the Tred Avon River to Cambridge and Crisfield, both steeped in maritime heritage.

Crossing into Virginia’s Eastern Shore, riders pedal through open farmland and salt marsh toward Kiptopeke State Park. The Southern Tip Bike and Hike Trail makes a scenic finale, and cyclists can arrange a shuttle over the Chesapeake Bay Bridge–Tunnel for the return.

Flat terrain, friendly towns, and endless water views make Delmarva ideal for multi-day rides at an easy pace. With crab shacks, lighthouses, and wildlife refuges along the way, it’s a route built for travelers who prefer discovery to speed.

11 – Waterfowl Carving Tradition

Along Maryland’s Eastern Shore, carving wooden duck decoys began as a hunting skill but became an art form through Lem and Steve Ward of Crisfield. Working from their barbershop in the early 1900s, the brothers turned working decoys into lifelike carvings that brought international attention to Chesapeake craftsmanship.

Their legacy continues through the Ward Foundation, which hosts the World Championship Wildfowl Carving Competition, and through the collection formerly displayed at the Ward Museum of Wildfowl Art in Salisbury. After the museum closed in 2023 due to structural issues, its exhibits began moving downtown to the new Museum of Eastern Shore Culture.

No, we’re serious… isn’t that offer of living at Delmarva for the Summer sounding a little more intriguing?

Where to Stay

There are a couple of options for where to stay. You can get a nice place by the shore or get something more centrally located, such as around Seaford, Delaware.

 

Traveling Soon? These useful links will help you prepare for your trip.

• Get a Car Rental
• Buy Travel Insurance