For as long as we can remember, we’ve been heading down the Shore for waterfront fun — and we’re certain to go back sometime this year. But there’s a whole world at our fingertips on Delmarva, the 180-mile-long peninsula that includes portions of Delaware, Maryland, and Virginia. You can feast on blue crab, kayak through marshes, lounge on the beach, and visit Underground Railroad sites and the factory where some of the world’s best guitars are made. So go off and discover a new favorite vacation spot. We’ll see you there.
At Nassau Valley Vineyards , opened in 1993, you can savor the fruit-forward punchiness of the sangria-friendly chambourcin, the nuanced floral notes of the unoaked chardonnay, and the surprisingly robust flavor of the blueberry wine no New Jersey winery can match. These wines were made for easy drinking.
This route features dozens of sites related to the life and work of the famed abolitionist and Underground Railroad conductor. It starts in Dorchester County, Maryland, where Tubman was born, runs up through Delaware (which had Railroad stops), and ends here in Philly, where Tubman first lived after escaping from slavery. If you have time for only one stop, make it the Harriet Tubman Underground Railroad National Historical Park in Church Creek, Maryland.
When friends in Philly say they’re off to Ocean City, we assume they mean the dry town off the Garden State Parkway that is widely considered one of the most family-friendly destinations at the Jersey Shore. But many make the 150-mile trek to the one in Maryland , which is not that unlike New Jersey’s in that it has a bustling boardwalk and is popular with families. What’s different? You can get a cocktail or glass of wine with your dinner (how progressive!), and the restaurant scene is vastly better than that of “our” Ocean City, likely because of the presence of revenue-boosting alcohol.
Thanks to the idyllic 2,370 acres of Elk Neck State Park in Cecil County, you can go for a challenging (or downright easy) hike, take a swim in the Chesapeake Bay, catch your own crabs, have a picnic, visit a lighthouse, and paddle a canoe, all in one day.
Savor local seafood delights in Chestertown, which sits along the Upper Eastern Shore portion of the Maryland Crab and Oyster Trail . Visit treasured haunts like Blue Bird Tavern (try the fried oyster basket) and the Shanty Beach Bar , where the crab cake sandwich is a must-order. (Old Bay seasoning on crabs is the best.) Walk it off during a self-guided tour offered by the Historical Society of Kent County , or explore the grounds of Washington College (one of the oldest academic institutions in America).
You don’t see much kayaking at the Jersey Shore, but Delmarva is a decidedly different story. Locals say one of the more rewarding and less crowded places to kayak is in and around Saxis, a remote and tiny (population under 250) town on Virginia’s Eastern Shore with access to creeks — including some in the protected Saxis Wildlife Management Area, with its bounty of birds — as well as the Chesapeake Bay and Pocomoke Sound.
The isle’s off-the-beaten-path vibe is ideal for a restful weekend. Dive into a tray of steamed crab at waterfront restaurant and dock bar the Jetty , or uncork a sip at Love Point Vineyards and Winery . Experience outdoor delights at Terrapin Nature Park , from off-road biking to wandering the wildflower meadows. The indoor-inclined should tour the Paul Reed Smith Guitars factory , where guitars used by the likes of Carlos Santana, Dave Navarro, and John Mayer are crafted. A massage at Chesapeake Bay Beach Club Spa should cap off your trip.
By wildlife, we mainly mean the ponies that roam through the two parks on the island’s Maryland side. Prime viewing happens along the National Seashore’s beach during the summer, though midweek in spring and fall is less crowded. Take a self-guided bike tour (rentals are available through Assateague Outfitters ) or hop on a boat tour in Ocean City to see the creatures frolicking. There are other four-leggers too: Spot the sika deer, found throughout the state’s Eastern Shore.
July marks 100 years for the family-friendly event, when the Virginia herd, known as Chincoteague ponies, swims across the Assateague Channel . The tradition gained fame in the 1940s thanks to children’s book Misty of Chincoteague and includes a carnival, roundups, beach walks, and a “penning,” when some horses are auctioned to private owners. It’s expected to draw thousands of spectators to its namesake town, with its homey aesthetic, neighborhood shops, and fresh seafood and produce purveyors, so make your travel plans now.
The region’s most iconic enclave blends harbor-front energy with stroll-worthy downtown charm. Visit the Chesapeake Bay Maritime Museum , which covers the area’s history and culture and has a working shipyard on-site. Head to Chesapeake Trading Company , a one-stop shop for bay-themed style, decor, and books, then peruse thousands of albums at Oyster House Antiques & Vinyl Records . And for food? Crack blue crabs at the Crab Claw , order oysters at Ruse , or go casual at Carpenter Street Saloon for beer and fried crab balls.
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14 Essential Delmarva Penninsula Activities
Visit the First Winery in the First Town in the First State
Lewes, DelawareAt Nassau Valley Vineyards , opened in 1993, you can savor the fruit-forward punchiness of the sangria-friendly chambourcin, the nuanced floral notes of the unoaked chardonnay, and the surprisingly robust flavor of the blueberry wine no New Jersey winery can match. These wines were made for easy drinking.
Drive the Harriet Tubman Byway
Delaware and MarylandThis route features dozens of sites related to the life and work of the famed abolitionist and Underground Railroad conductor. It starts in Dorchester County, Maryland, where Tubman was born, runs up through Delaware (which had Railroad stops), and ends here in Philly, where Tubman first lived after escaping from slavery. If you have time for only one stop, make it the Harriet Tubman Underground Railroad National Historical Park in Church Creek, Maryland.
Discover the Other Ocean City
MarylandWhen friends in Philly say they’re off to Ocean City, we assume they mean the dry town off the Garden State Parkway that is widely considered one of the most family-friendly destinations at the Jersey Shore. But many make the 150-mile trek to the one in Maryland , which is not that unlike New Jersey’s in that it has a bustling boardwalk and is popular with families. What’s different? You can get a cocktail or glass of wine with your dinner (how progressive!), and the restaurant scene is vastly better than that of “our” Ocean City, likely because of the presence of revenue-boosting alcohol.
Go to a State Park
North East, MarylandThanks to the idyllic 2,370 acres of Elk Neck State Park in Cecil County, you can go for a challenging (or downright easy) hike, take a swim in the Chesapeake Bay, catch your own crabs, have a picnic, visit a lighthouse, and paddle a canoe, all in one day.
Follow the Crab And Oyster Trail
Chestertown, MarylandSavor local seafood delights in Chestertown, which sits along the Upper Eastern Shore portion of the Maryland Crab and Oyster Trail . Visit treasured haunts like Blue Bird Tavern (try the fried oyster basket) and the Shanty Beach Bar , where the crab cake sandwich is a must-order. (Old Bay seasoning on crabs is the best.) Walk it off during a self-guided tour offered by the Historical Society of Kent County , or explore the grounds of Washington College (one of the oldest academic institutions in America).
Hop Into a Kayak
VirginiaYou don’t see much kayaking at the Jersey Shore, but Delmarva is a decidedly different story. Locals say one of the more rewarding and less crowded places to kayak is in and around Saxis, a remote and tiny (population under 250) town on Virginia’s Eastern Shore with access to creeks — including some in the protected Saxis Wildlife Management Area, with its bounty of birds — as well as the Chesapeake Bay and Pocomoke Sound.
Live the Island Life
Kent Island, MarylandThe isle’s off-the-beaten-path vibe is ideal for a restful weekend. Dive into a tray of steamed crab at waterfront restaurant and dock bar the Jetty , or uncork a sip at Love Point Vineyards and Winery . Experience outdoor delights at Terrapin Nature Park , from off-road biking to wandering the wildflower meadows. The indoor-inclined should tour the Paul Reed Smith Guitars factory , where guitars used by the likes of Carlos Santana, Dave Navarro, and John Mayer are crafted. A massage at Chesapeake Bay Beach Club Spa should cap off your trip.
See Wildlife
Assateague Island, MarylandBy wildlife, we mainly mean the ponies that roam through the two parks on the island’s Maryland side. Prime viewing happens along the National Seashore’s beach during the summer, though midweek in spring and fall is less crowded. Take a self-guided bike tour (rentals are available through Assateague Outfitters ) or hop on a boat tour in Ocean City to see the creatures frolicking. There are other four-leggers too: Spot the sika deer, found throughout the state’s Eastern Shore.
Head to the Pony Swim
Chincoteague, VirginiaJuly marks 100 years for the family-friendly event, when the Virginia herd, known as Chincoteague ponies, swims across the Assateague Channel . The tradition gained fame in the 1940s thanks to children’s book Misty of Chincoteague and includes a carnival, roundups, beach walks, and a “penning,” when some horses are auctioned to private owners. It’s expected to draw thousands of spectators to its namesake town, with its homey aesthetic, neighborhood shops, and fresh seafood and produce purveyors, so make your travel plans now.
Hit the Hamptons of the Eastern Shore
St. Michaels, MarylandThe region’s most iconic enclave blends harbor-front energy with stroll-worthy downtown charm. Visit the Chesapeake Bay Maritime Museum , which covers the area’s history and culture and has a working shipyard on-site. Head to Chesapeake Trading Company , a one-stop shop for bay-themed style, decor, and books, then peruse thousands of albums at Oyster House Antiques & Vinyl Records . And for food? Crack blue crabs at the Crab Claw , order oysters at Ruse , or go casual at Carpenter Street Saloon for beer and fried crab balls.
