A Philadelphian’s Guide to the Delmarva Peninsula

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.

14 Essential Delmarva Penninsula Activities

Visit the First Winery in the First Town in the First State

Lewes, Delaware
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.

Drive the Harriet Tubman Byway

Delaware and Maryland
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.

Discover the Other Ocean City

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.

Go to a State Park

North East, Maryland
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.

Follow the Crab And Oyster Trail

Chestertown, Maryland
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).

Hop Into a Kayak

Virginia
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.

Live the Island Life

Kent Island, Maryland
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.

See Wildlife

Assateague Island, Maryland
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.

Head to the Pony Swim

Chincoteague, Virginia
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.

Hit the Hamptons of the Eastern Shore

St. Michaels, Maryland
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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Have a Small-Town Stopover in Easton, Maryland

This tiny enclave often gets overlooked in favor of the glitzy St. Michaels, just down the road, but it’s worth a pit stop. Not only does it offer history — Frederick Douglass was imprisoned in the courthouse and later spoke here as an activist — but it’s rich with things to do. The pièce de résistance is its dining scene: Think a prix fixe dinner at Bas Rouge, prepared by James Beard Award-winning executive chef Harley Peet, light lunch at Sunflowers & Greens, and fresh-made ice cream at the Insta-worthy Bonheur. (The wallpaper is hand-painted by Gracie Studios, whose work is also found in the White House.) Beyond that, the Academy Art Museum’s Bugatti exhibit (on view through April 13th) features five impeccably restored cars, while the Modern Bulldog feels like a shoppable gallery of mid-century-modern furniture.

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Go Lighthouse Spotting

These beacons have brightened the shore for more than a century.

Turkey Point Lighthouse

From May to October, you can enjoy views of the Chesapeake Bay and the Elk and North East rivers from the top of this circa-1833 light, thanks to its prime position on a 100-foot bluff. Fun fact: Four of its 10 keepers were women. North East.

Hooper Strait Lighthouse

The “screwpile” building (built on iron pilings that were tipped with a screw to fasten them to the sea floor for stability) wasn’t always perched on Navy Point. It started its life on Hooper Strait in 1879 and was moved in 1966 to its current home, where visitors can step inside to see preserved artifacts from the keepers or tend the lens. St. Michaels.

Delaware Breakwater East End Lighthouse

Between May and October, Cape Water Tours and Taxi provides narrated boat rides to this isolated lamp, so you can get the historic details while taking in scenic shore views. The tour includes a visit to the four-story building, with its circular watch room and octagonal lantern room. Tours leave from the Lewes Ferry Terminal. Lewes.

Fenwick Island Lighthouse

Situated on the Delaware-Maryland state line, the 166-­year­-old Gothic-style light was decommissioned between 1978 and 1982, when lovers of the lamp fought to have it restored to its glory — and it still shines bright today. You can’t climb to the top, but you can visit the museum and grounds from May to November. Ocean City.

Assateague Lighthouse

The picture-perfect red-and-white-striped beauty stands 142 feet tall and is still in operation. It was built in 1833 and rebuilt in 1867, and on weekends from April to November you can climb the 175 spiraling steps to the top. The panoramas are worth the trek. Assateague Island.

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Make It a Weekend

Book one of these hotels or inns to immerse yourself for a few days.

Dogfish Inn

After a fun-filled day shopping in historic downtown Lewes, riding bikes (available to rent) to Cape Henlopen State Park, and hanging out at the beach, unwind at Dogfish Inn. Operated and run by Dogfish Head Brewery, the inn is a home base for intrepid beer lovers exploring from Cape Henlopen to Rehoboth Bay. (Note: Beer is not for sale at the inn.) Hang out in the back yard, do a puzzle by the fireplace on a chilly night, or just head back to your room and sprawl out on the cozy bed. Rooms from $189; Lewes.

Great Oak Manor

For Eastern-Shore-meets-English-countryside vibes, book one of the 12 stately rooms (or the carriage house!) at this Georgian-style manse on the Chesapeake Bay. It has a colorful past — think JFK, Hemingway, and an illegal casino — but it’s now an all-inclusive adults-only retreat. Food lovers should not miss the new Taste series featuring visiting award-winning chefs. Afterward? Kick back in an Adirondack chair at the private beach and catch the sunset. Rooms from $329; Chestertown.

Kent Island Resort

The island’s namesake resort revels in dualities. The manor house is historic (a little more than 200 years old) yet elegantly updated, meals at its on-site restaurant 18TWENTY are regional and comforting yet modern, and the 220-acre location is rural yet lively. In warmer months, enjoy access to the waterfront area, which is outfitted with a private dock and a range of watercraft including Jet Skis, pontoons, and kayaks. Rooms from $239; Stevensville.

Inn at Perry Cabin

Tourism in St. Michaels orbits around Inn at Perry Cabin, a 26-acre property set against a backdrop of yachts. (The reception scene in Wedding Crashers was filmed here.) Nautical luxury abounds throughout spacious, modern accommodations, championship golf, a boutique spa, elegant and sustainable dining with glistening water views, an outdoor pool, and boating excursions. (Sailing season begins in early April with a Return of the Fleet celebration.) An evening toast at the resort’s “Don’t Give Up the Ship” flag closes the day. Rooms from $386; St. Michaels.

Ashore Resort & Beach Club

It’s fair to say that many of the hotels and motels in Ocean City are a bit dated and, well, dusty. Avoid that by staying at this recently renovated (as in 2023) resort. Be absolutely sure to book an oceanfront suite with a balcony, and grab a boozy Orange Crush at the hotel’s Wahoo Beach Bar. Rooms from $114; Ocean City.

Watson Guest House

Eschew the bigger resorts and stay at this quaint B&B on Chincoteague Island. The rooms are filled with antique wares, and each has its own name (we were in the aptly hued Rose Room). The B&B provides chairs and beach towels for lounging on the sand, and bikes and binoculars for exploring the nearby wildlife refuge. And mornings begin with a delicious spread of breakfast treats, which you can enjoy on the wraparound porch. Rooms from $340; Chincoteague Island.

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Dig in Along Delaware’s Coast

Chart a culinary course, from Milton to Fenwick Island.

1. Dogfish Head Brewery • After taking a tour of Delaware’s first craft brewpub, grab a personal pizza or a bratwurst on a pretzel bun. You’ll need the carbs to absorb all those samples of their 90 Minute IPA and Blue Hen pilsner.

2. Lewes Bake Shoppe & Notting Hill Coffee Roastery • Fresh-roasted coffees and loose-leaf teas line the walls and countertops. Start your morning off strong with a smooth cuppa and one of their famous Lewes sticky buns.

3. Nectar Cafe & Juice Bar • Nestled in the heart of the Lewes Historic District, Nectar serves up homey breakfast platters, hearty sandwiches, and, for vacationers looking for a boozy brunch, vibrant cocktails.

4. Crooked Hammock Brewery • With events from Trivia Tuesdays to movie nights, it’s always a family-friendly party. Kick back with a Sway IPA and watch the kids play between bites of mini corn dogs and Old Bay crab dip.

5. Starboard Claw • This seafood-focused sports bar/beach hangout will make you feel like a local, with deals on crab legs, seafood pots, and crushes fit for a Dewey Beach native.

6. Sunshine Crepes • This sweet beach-adjacent spot has a crave-worthy strawberry, banana, and Nutella crepe, though you can’t go wrong with any of the pastries.

7. Story Hill Farm • Stock up on heritage meats, farm-fresh eggs, locally harvested Henlopen sea salt, and house-made peanut butter; pick wildflowers in the meadow; or take an herbal tea blending class.

8. One Coastal • From the menu of seasonal­ ingredients intentionally sourced from local farmers and fishermen to the decor’s nautical charm, it’s easy to forget that this James Beard-nominated restaurant is in an unassuming strip mall.

Published as “We’re Going to Delmarva!” in the March 2025 issue of Philadelphia magazine.