Pizza, hoagies, and Old Bay: Eating and drinking my way from New York City to Washington, D.C.

Prior to the pandemic, I used my summer vacations as a teacher to book international flights and explore far-flung corners of the globe. The pandemic, of course, put the kibosh on this lifestyle—but certainly not on my desire to travel. Instead of waiting until the indeterminate end of the pandemic, I’ve turned to the open road. The road trips I’ve taken since early 2020—through the Great Plains, Mississippi Delta, Great Lakes, and other regions that I would have overlooked in pre-pandemic times—have shown me that long flights, currency exchanges, and Google Translate are not required for adventure. 

My girlfriend and I celebrated Thanksgiving 2021 in Washington, D.C., so I decided that the drive from New York City, my home base, would be the perfect excuse for a Mid-Atlantic road trip. As a history nerd, I wanted to check out the colonial and Revolutionary War sites en route—both Dover and Philadelphia were thriving early American cities and important to the founding of the U.S. On a less intellectual level, my appetite sizzled thinking about the delicious food to be discovered along the way: pizza in Philly, craft beer in Delaware, and Old Bay-dusted seafood from the Chesapeake Bay. 

As a bonus, the Mid-Atlantic fall foliage would be brilliant in late November, making for spectacular drives. Without stops, the trip from New York City to Washington, D.C., takes only 4 hours on Interstate 95, but we planned to spend 4 days on the road, taking ample detours while making our way south. 

Brooklyn to Philly 

The rush-hour dash to leave the city was in full force as we made our way out of Brooklyn, past Staten Island, and finally to the open highway. After another hour or so, the lights of Philly’s skyline—quaint compared to New York’s towering behemoths—came into view.  

Instead of endless bustle, relentless honking, and the buzz of manic capitalism, Philly felt subdued, even sleepy. In lieu of sleek skyscrapers, Philly’s buildings, sturdy structures of brick and brownstone, were handsomely simple. 

I met an old friend from Philly at the Bishop’s Collar, an Irish pub in the Art Museum District, a hip neighborhood close to Temple University. Rick, who worked with my dad and whom I always called “Uncle Rick,” ordered a round of lagers from Yuengling Brewery, the nation’s oldest operating brewery, located outside of Philly. Peckish from the drive, my girlfriend and I shared a roast beef sandwich made with bread from an Italian bakery next to the pub. 

As we ate and drank, Uncle Rick, a gifted raconteur by virtue of Hiberno genetics and his upbringing in a family of 14 siblings, reminisced about the raucousness of the 1970s and recent visits to Ireland. His subtle East Pennsylvania accent sounded something like a hybrid of a New Yorker and Midwesterner. Before retiring for the evening, Rick wrote down a list of places to visit while in town, including his favorite pizzeria in South Philly.

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The next morning, after a revivifying mocha at Menagerie Coffee, I set out to explore the Old City. The Old City is small enough that most of the iconic sites, like Independence Hall, Christ Church, and Ben Franklin’s headstone, are within a 10-minute walk of each other. 

No historical tour of Philly would be complete without visiting Independence Hall, the site where the Declaration of Independence and the Constitution were officialized. Since the COVID-19 pandemic, tickets ($5) to visit Independence Hall must be purchased online at Recreation.gov, and guided tours (included with the ticket) take about 30 minutes. Christ Church, where Ben Franklin worshiped, and Christ Church Burial Ground, housing the remains of the iconic Pennsylvania polymath, are also worth a visit. 

South Philadelphia, immortalized in the Rocky movies as the training ground of Philly fighters, remains a neighborhood of strong Italian, notably Sicilian, roots. Philly’s pizza style, similar to New York’s but with thicker crusts, achieves its highest expression at Angelo’s Pizzeria in South Philly—Uncle Rick’s recommendation. The waits are long and there are no tables, but it’s worth the hassle. After an unforgettable pizza, we headed to Isgro Pastries—not far from the famous rival cheesesteak joints, Gino and Pat’s—for a cannoli and an early-afternoon espresso.

To get some exercise, we walked the grounds of the University of Pennsylvania. Strolling through the Wharton School of Finance, Penn’s business school, we saluted the statue of Ben Franklin sitting on a bench reading the Pennsylvania Gazette, the newspaper he founded. 

Dinner found us at Tuna Bar, not far from the Old City. Taking cues from the restaurant’s name, we ordered a plate of tuna sashimi. Next came a couple of rolls of maki—including, of course, cream cheese-laden Philly rolls. With full bellies, we hit I-95 south toward our next destination.  

Old school East Coast 

The drive from Philly to Dover, one of the oldest cities on the East Coast, took less than 2 hours. Delaware, the second smallest state in the U.S., was the first state to ratify the U.S. Constitution, and since then holds the honorific of The First State. An anomaly among Dutch and English colonized neighboring regions, Delaware began as a Swedish settlement. 

We started the morning at the tiny House of Coffi, right next to Main Street. Awaiting caffeine, we chatted with another patron, dressed in a sharp business suit, who was a corporate attorney. Most Fortune 500 companies are incorporated in Delaware, due to the state’s unique court system, and Delaware corporate law is the gold standard for much of the world. The talkative lawyer explained that he had worked for a major law firm in Manhattan before moving to Delaware, noting that he preferred the serenity and small-town charm of Dover to the chaos of New York City. 

We spent the rest of the morning walking and admiring the red-brick Georgian-Revival architecture of Dover’s churches and storefronts, reminiscent of Alexandria, Virginia. Around lunchtime, we spied a line outside of Simaron Pizza and Steak Shop and decided to give it a try. I’ve heard Delaware called “New Jersey Light,” and similar to the Garden State, Italians are well-represented here. The “Italian Hamburger” I ordered, a beef patty topped with salami and red hots, didn’t disappoint. 

After lunch, we perused a Frida Kahlo exhibit and a collection of early American furniture at the Biggs Museum of American Art, within walking distance of Main Street. Before leaving Dover, we drove to the Fordham Brewing Company. Fordham’s beers were mainly Belgian-inspired varieties—their aged Tripel was a noteworthy standout. The bartender even gave me some recommendations for our next stop.

Maryland’s eastern shore

The Chesapeake Bay, a brackish sea that cuts through six states, is home to colonial towns, fishing villages, and remote islands, like Tangier and Taylor, whose residents have remained isolated over generations and they speak dialects of 17th-century English. 

Our first stop in Maryland was Easton, an upscale, but laid-back, village popular among retirees from nearby Washington, D.C. Frederick Douglass, the famous 19th-century freedman who became a leading abolitionist, was born on a plantation in Talbot County, Maryland, and his statue adorns Easton’s town square. 

After a coffee at Weather Gage cafe, we meandered through Easton’s colonial streets and squares. Easton boasts more than its fair share of fine dining, with chefs deftly preparing seafood from the bay. For dinner, we ate at The Wardroom, a gourmet grocery store that serves wines, plates of pasta, charcuterie, and cheese boards after hours.  

The next morning, we drove to Saint Michaels and Oxford, two other colonial towns on Maryland’s Eastern Shore. St. Michaels exuded old-school charm like Easton, but the vibe was busier and younger. We visited on a Saturday, and Main Street bustled with tourists shopping and dining outside with Old-Bay-seasoned Bloody Marys. 

We spent an hour at the Chesapeake Bay Maritime Museum ($20 per adult), a group of buildings on the Bay where visitors can tour replicas of shipbuilding workshops and traditional fisherman’s cabins. Eastern Shore Brewery, a local favorite on Main Street, offered beer flights. Tiny Oxford, a few minutes from St. Michaels, has few businesses but is home to the oldest functioning inn in the U.S., the Robert Morris Inn.  

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Returning home

We headed back north early in the morning after Thanksgiving to beat the traffic. There are plenty of other towns and detours along the corridor I want to explore, but we had to make a beeline for Brooklyn, only stopping in Trenton, the capital of New Jersey, for a quick lunch. 

As we blasted Nirvana Unplugged and raced up I-95, I reflected on how much I enjoyed the drive down: iconic historical sites in Philadelphia, foliage on Delaware country roads, and the small towns on the Chesapeake Bay. My knowledge of the Mid-Atlantic, my home region, was deepened from the half-week of slow driving. And the food—Philly’s pizza, hoagies in Delaware, and oysters from the Chesapeake—was worth the trip alone.