Delaware is a small state with a big talent for surprises. Some of its best restaurants are not on busy commercial strips or in obvious dining districts.
They are tucked inside a working airport, an 1822 tavern that once served ship captains, a Victorian house with no sign out front, and a building where someone used to shoe horses. The contrast between what a place looks like from the outside and what is actually happening inside is part of what makes eating out in Delaware so entertaining.
A few of these spots require a bit of a drive down an unexpected road, and at least one requires knowing that the parking lot used to belong to a blacksmith. The 12 restaurants on this list all share one thing in common: finding them is half the fun.
Le Cavalier, Wilmington, Delaware
Beneath gilded chandeliers and an ornate plaster ceiling, Le Cavalier occupies one of the most historically significant dining rooms in Delaware. The restaurant took over the Hotel Du Pont’s celebrated former Green Room, a space that opened in 1913 when the 12-story Italian Renaissance building was constructed under the direction of DuPont Company president Pierre S. du Pont.
When renovations began, workers discovered the original mosaic marble-and-terrazzo floor from 1913 perfectly preserved beneath layers of carpeting. That floor has since been carefully restored and is now visible to every diner.
The restaurant’s name, meaning “The Horseman,” pays tribute to the Brandywine Valley’s equestrian heritage. Its menu draws on culinary traditions from Provence and North Africa, with seasonal ingredients sourced locally for breakfast, lunch, dinner, and weekend brunch.
Le Cavalier earned the Historic Hotels of America’s “Best Historic Restaurant” award, a recognition that reflects both its culinary merit and its extraordinary setting.
The Quoin Restaurant, Wilmington, Delaware
The name is a clever double meaning. “Quoin” refers to the architectural corner detailing of the building and nods directly to its past as the Security Trust and Safe Deposit Company, a bank that once held silver and gold coins in its vaults.
Designed in 1885 by renowned Philadelphia architect Frank Furness, the four-story Victorian Romanesque structure underwent a $17 million renovation before reopening as a boutique hotel in September 2022. The Quoin Restaurant occupies the main dining space, seating between 100 and 155 guests around a wood-burning oven and grill that anchors an open kitchen.
Italian-inspired dishes with influences from coastal Southern France and Northern Italy fill the menu, from handmade pastas to fresh fish and premium steaks. Below the restaurant, the former bank vault is now Simmer Down, a cocktail lounge with a vaulted brick ceiling and a curved bar finished in rainforest green marble.
Esquire named Simmer Down one of the Best Bars in America in 2024.
Grey Fox Grille, Dover, Delaware
A fully restored Victorian home built in 1881 is not the most obvious place to find a full-service restaurant, but that is exactly what Grey Fox Grille offers in the heart of downtown Dover.
Current owners Barry and Cassandra Alvis took over the property in April 2024, continuing a tradition of upscale casual dining in a setting that still features original fireplaces, crown molding, and high ceilings. Dining rooms unfold through the house in a way that feels more like an invitation into a private residence than a trip to a conventional restaurant.
The menu focuses on modern American cuisine with an emphasis on quality, including steaks cut in-house, signature crab cakes, and shepherd’s pie. Sixteen beers on tap and a selection of craft cocktails round out the bar offerings.
On weekends, an outdoor patio hosts live music, and three private dining rooms can accommodate groups up to 25, with larger parties of over 150 guests also catered to.
Heirloom, Lewes, Delaware
There is no large sign out front, and that is entirely by design. When Heirloom opened in 2015, owner Meghan Lee deliberately chose to skip the signage and let word of mouth do the work instead.
The restaurant occupies an 1899 Victorian house on Savannah Road, originally built for dentist J.B. Robinson from a catalog design by architect George F.
Barber. Lee’s restoration preserved original details including wavy glass windowpanes and pine floors, while botanical drawings and lush plants fill the interior rooms.
The menu rotates with the seasons, drawing from farms and waters across the Delmarva region. Rather than a traditional single-chef kitchen, a team of cooks collaboratively develops each seasonal menu, and all staff are cross-trained in both front-of-house and back-of-house roles.
Three dining rooms seat around 65 guests, and a chef’s table with an observation window into the kitchen offers one of the more unusual dining perspectives available anywhere in coastal Delaware.
The Station on Kings, Lewes, Delaware
Breakfast here can easily turn into an unplanned shopping trip, which is not a complaint. The Station on Kings operates as a five-part concept: coffee bar, cafe, bakery, garden center, and home-and-garden market, all under one roof on Kings Highway at the entrance to Lewes.
Owner Leisa Berlin drew inspiration from Northern California establishments that blend seasonal food with thoughtful design and community focus. The culinary philosophy is direct: everything is made from scratch, from jams and dressings to freshly milled grain for bread.
The bakery team bakes croissants, breads, and pastries daily in limited quantities.
The site itself carries a quiet history. It sits on a former railroad crossing once occupied by the Lewes Coal and Gas Company, adjacent to tracks of the Queen Anne’s railroad that connected Harrington to Lewes starting in 1870.
Those old rail lines are now the popular Lewes-to-Georgetown Trail.
The outdoor garden area is dog-friendly, and the restaurant offers breakfast and lunch daily with patio and takeout options available.
Cantwell’s Tavern, Odessa, Delaware
The town was once called Cantwell’s Bridge, and this Federal-style brick building has been part of its story since 1822. Prominent businessman William Polk built it originally as the Cantwell’s Bridge Hotel and Tavern, serving travelers, merchants, and ship captains moving through what was then a thriving grain shipping hub established by the Dutch in 1662.
For roughly a century the building fulfilled its original purpose, then passed through other uses including an apartment house, private offices, and more than 30 years as an art gallery. The Historic Odessa Foundation partnered with Ashby Hospitality Group to restore it and reopen it as Cantwell’s Tavern in 2011.
The restoration preserved the first-floor flooring and a grand wood staircase, and the dining areas are arranged across intimate rooms with a dedicated bar space and additional seating upstairs. The menu offers regional, farm-to-table American cuisine alongside a raw bar, pizzas, and main courses like Twin Crab Cakes and Steak Frites.
Proceeds from the restaurant’s lease directly support the Historic Odessa Foundation’s preservation efforts and educational programming.
Krazy Kat’s, Montchanin, Delaware
Old metal rings once used to tether horses still line the dining room walls at Krazy Kat’s, and the original forge from the building’s blacksmith days remains intact as a centerpiece of the space.
The restaurant sits within Montchanin Village, a collection of 11 restored buildings dating as far back as 1799, listed on the National Register of Historic Places. It is part of the Inn at Montchanin Village in the Brandywine Valley.
The interior takes a sharp turn from its utilitarian past. Tiger-print chairs and portraits of cats and dogs dressed in military regalia cover the walls, a contrast that somehow works perfectly against the old stone surroundings.
The name itself traces back to a former tenant of the blacksmith shop whom the owner’s grandmother called “one crazy cat.” A private dining room called The Crow’s Nest on the second floor can accommodate up to 40 guests.
Jessop’s Tavern & Colonial Restaurant, New Castle, Delaware
Few restaurants in America can claim a building that predates the United States by more than a century, but Jessop’s Tavern sits in one. The structure at 114 Delaware Street dates to 1674, originally built as a private residence before Abraham Jessop, a cooper, used it for his barrel-making business in the 1700s.
After stints as the Captain’s Log Restaurant in the 1950s and The Green Frog Tavern in the 1970s, the Day Family reopened it as Jessop’s Tavern in November 1996, leaning fully into its colonial identity. Wide plank floors, original fireplaces, and colonial scenery on the walls create the backdrop, and staff members sometimes wear period attire.
The menu reflects the region’s diverse European heritage, drawing from Dutch, English, Swedish, and Belgian culinary traditions. Shepherd’s Pie and award-winning Fish and Chips are menu staples, and the restaurant’s selection of over 300 bottled Belgian beers with 30 draft options makes it a recognized authority on that particular tradition.
Outside, the cobblestone streets and brick buildings of Old New Castle make the surrounding neighborhood feel like a convincing extension of the experience inside.
Buckley’s Tavern, Centreville, Delaware
In 1817, this property along Kennett Pike was a private home on a dirt road where stagecoaches stopped and a tollgate collected fees from passing travelers. A blacksmith shop stood where the parking lot is now, and the front porch sheltered passengers waiting for the next coach.
By the 1930s the house had become a taproom and ice cream store, and in 1951 Dennis Buckley acquired it and gave the establishment its current name. Today, Buckley’s Tavern balances that layered history with a contemporary menu and what the restaurant calls “comfortable elegance.”
Exposed brickwork, warm wood tones, and intimate dining rooms characterize the interior, with a lively bar area alongside quieter spaces for a more relaxed meal. The menu covers casual American comfort food with chef-led, scratch-made dishes including Chicken Pot Pie, Twin Broiled Crab Cakes, and Shrimp and Grits.
A curious footnote from 1961: the tavern’s ladies’ room once featured a fishpond embedded in the ceiling beneath a second-floor patio, which may be the most unexpected detail in Delaware dining history.
Baywood Clubhouse Restaurant, Millsboro, Delaware
Baywood Greens has been called the Augusta of the North, a reference to its immaculate landscaping and dramatic course design. Most people assume the clubhouse is reserved for members and golfers, but the Baywood Clubhouse Restaurant is open to the public seven days a week for both lunch and dinner.
The dining room provides views across award-winning gardens that are carefully planned to display color across most of the year, with flowering bridges stretching over water features on the course. The gardens evolve with the seasons, so the backdrop changes with every visit.
The menu highlights chef-inspired American cuisine with an emphasis on fresh and locally sourced ingredients, including coastal favorites, premium steaks, and handcrafted sandwiches. Signature entrees include Filet Mignon, Lobster Francaise, and King Crab Cakes.
Beyond the restaurant, the clubhouse hosts events for up to 260 guests across multiple spaces including an outdoor veranda, a bar lounge, a library, and a corporate boardroom, making it a surprisingly versatile venue for a building most people drive past without stopping.
Grain H2O, Bear, Delaware
Most people driving through Bear, Delaware have no particular reason to turn toward a marina, which is exactly why Grain H2O tends to catch first-time visitors off guard. The restaurant sits atop Summit North Marina, a 400-slip complex on the Chesapeake and Delaware Canal, nestled within Lums Pond State Park.
Guests can arrive by car with ample parking available, by boat using transient slips at Dock G, or by bicycle via the Mike Castle Trail that runs along the C&D Canal. The combination of access options is fairly unusual for a restaurant in this part of Delaware.
Part of the Grain Craft Bar and Kitchen family, the restaurant operates as a polished casual gastropub with a bright, airy interior and both indoor and outdoor dining areas. The menu leans into its waterfront location with crab-focused dishes including Crabby Pretzel, Crab Fries, and Crab Nachos alongside burgers, wings, tacos, and a weekend brunch menu.
Grain H2O was voted Best New Restaurant by readers of Delaware Today Magazine and regularly hosts live music, Bingo, and Trivia nights with no cover charge.
Arena’s at the Airport, Georgetown, Delaware
Most restaurants ask you to leave your car outside. Arena’s at the Airport is one of the few that will happily welcome you whether you drove, or landed on the runway just beyond the window.
Located inside the terminal building of Delaware Coastal Airport in Georgetown, this outpost of the well-known Arena’s sandwich group has been serving burgers, salads, and casual American favorites since 2013. The original Arena’s started as a small Rehoboth Beach sandwich shop in 1990.
The menu includes award-winning sandwiches, nachos, and a crowd favorite called Death Fries, loaded with melted cheese, bacon, ranch, and barbecue sauce. Daily specials like Taco Night and Burger Night keep regulars coming back.
The Delaware Coastal Airport also hosts the Delaware Aviation Museum and an annual Wings and Wheels Family Event. Even without a flight to catch, showing up purely because you are hungry makes complete sense here.
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