Imagine a food rendezvous back in 1674.
Warm, hearty dishes. Fireplace crackling. Dark hardwood floors below you and carefully hand-laid brick surrounding you. Looking out the window to see the town bustling with horses and craftsmen.
That is exactly what I got to experience today (er, sans the horses unfortunately) in Old New Castle, Delaware-one of the oldest cities in the country. In fact, it is the site William Penn first landed in America.
I have to say Old New Castle is one of the most under-appreciated spots in Delaware, and maybe America. One minute you are driving along shopping malls, Holiday Inns, gas stations, and the next minute you enter a town so anachronistic and authentic that you might get lost in the period if there weren’t modern cars parked along the road to ground you. And it’s literally in Delaware’s backyard.
As I walked around the untouched and perfectly uneven cobblestone streets, my hunger brought me to Jessop’s Tavern and Colonial Restaurant.

From the outside, I could already tell it would be a fantastic dining and culinary experience with the Swedish, Dutch, and British flags flying proudly above the building standing for over 300 years.
(Image courtesy of www.jessops-tavern.com)
The colonial inspired menu offers an array of meals reflecting the three flags flying outside, with dishes such as ”Nieuwer Amstel Strip Steak,” ”Dustch Pot Roast,” ”Olde English Flat Bread,” and their signature dish (also voted Best of Delaware) “Fish and Chips.”
‘Why these countries?’ you ask. Well, to make a long history short, the Dutch and the Swedish were the first colonial settlers in the area. In 1674, the British came to region the region (a la King Charles II.. and William Penn) and took over authority. And in that same year, the building that hosts Jessups was born. Interestingly enough, the reason the entire state of Delaware is shaped like it is (like a half-eaten sandwich with curved crust) because of Old New Castle. Since it’s original charter declared the colony to be a twelve mile radius with New Castle at it’s center, Delaware boasts it’s perfectly rounded top.
After much internal debate, I chose “Olde Dutch Tilehouse Chicken” Sandwich, which consisted of grilled chicken, smoked gouda cheese, and a tomato aoli spread.
Holding it all together was a soft and savory pretzel roll. The sandwich came with baked sweet potato fries and coleslaw.
Ultimately, the pretzel roll made the sandwich for me with the right amount of salt and sweet to compliment the chicken, cheese, and aioli. I topped off lunch with a scoop of maple walnut ice cream from a local, and personal favorite, creamery.
What really made this experience authentic for me were the period-clad waitresses and bartenders, antique metal plates hinting at the blacksmith trade, colonial inspired music featuring lutes and fifes, and furniture that brought me back to a rendezvous with William Penn himself.



(Images courtesy of www.jessops-tavern.com)
For a post-dining experience, a walk around the rest of New Castle fits the bill. All around are modern-day craftsmen shops, including art galleries, jewelry boutiques, and my favorite-antique book stores. There are also several historical buildings, courthouses, jailhouses, colonial family houses, etc. At the edge of the town lies the Delaware river, with park benches, a nice walking trail, and a dock in accompaniment.
I have learned that a restaurant rich with history always enhances a dining experience. The food is not always the only thing that matters. Although in this case, the food was as charming and satiable as this all-American town.
♡ Rendezvous with me:
Jessop’s Tavern & Colonial Restaurant
114 Delaware Street
New Castle, DE 19720
http://www.jessops-tavern.com
(added bonus!:the website also features traditional Colonial music)