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Restaurant Review: Cherries Jubilee & Spirits!— Middleton Tavern

Jan 22, 2016 11:40AM ● By Cate Reynolds

Middleton Tavern

2 Market Space, Annapolis // 410-263-3323 //

By Rita Calvert // Photography by Tony Lewis, Jr.

Middleton Tavern in Annapolis serves up a side of history along with a spirit or two. The tavern is one of the oldest continuously operating taverns in America. To this day, they are open every single day of the year. Jerry Hardesty, owner and operator, calls his staff family. To prove it, his chef has been with him for three and a half decades while a bartender has run the show for four.

The tavern is housed in a circa-1740 former private residence. Purchased by Horatio Middleton in 1750, the building operated as an “inn for seafaring men” and as the base for Middleton’s Ferry Service that connected Annapolis to Maryland’s Eastern Shore. It is said to be haunted by a ghost nicknamed Roland who has been seen in the first-floor dining rooms, usually in the very wee hours. He wears Revolutionary War-era clothing, smells of cigar smoke, and looks out the window toward the water. He has been known to knock plates and glasses, one at a time, off shelves and throw a few pots around in the kitchen. When I asked Jerry about Roland, he says he basically leaves him alone and doesn’t venture in during the wee hours. Witnesses report seeing shadowy figures in the dining rooms, furniture that moves on its own, and the wall lanterns being turned upside down.

Established and timeless, with walls peppered with friendly memorabilia, pine wainscoting, and checkered blue tablecloths, Middleton can please raw bar, classic seafood, and beef lovers alike. Even with a brisk crowd, and local guitar talent Shawn Owen later in the evening, conversation was easy, a most-welcome plus.

From the lengthy wine list, Keith, our friendly obliging server, recommended Terraza Malbec as highly favored. The individual portion carafe of wine was a hefty pour for the large bulbous glass. Very satisfying, this deep rich Argentinian Malbec was an excellent value, which is so rare these days for wines by the glass under $10. I would have guessed at least $10, and would not have been unhappy if $12. (But Jerry, keep the price as is!)

No need to coax me for oysters. I paved my path into the Annapolis scene with the famous Middleton Oyster Shooters. If you can handle it, you are an “old salt” and across the country, no establishment seems to make these oyster specialties with such flair. The “a la moment” shucked oysters are large and plump while the cocktail sauce topping the juicy bivalve has a kick. One can get a floater of Stoli Peppar, (or other vodka) which takes the shooter up to top-notch! A chaser of beer is served alongside each shooter. Don’t just stop at the shooters though, for the raw bar is a legend as well.
Hailing back to the day of tradition and flair, a few items still remain on the menu with the drama of being “Prepared Tableside for Two”—Caesar or Spinach Salad, Chateaubriand, Bananas Foster, and Cherries Jubilee. Keep in mind that the dinner entrees do include a starter and we were told a tableside salad as well, would be just too much food.

Without a doubt, we had to try the Seafood de Mer appetizer special. Big chunks of fresh lobster, two sweet sea scallops, and a pair of large shrimp were nicely baked in tarragon butter sauce—unlike so many mixed seafood dishes where the bake time misses the mark and leaves something underdone or overdone. These had a twist with Italian bread crumbs. We’d love to see chef cut back on the crispy crumb just a smidge to let the seafood itself really shine.

We each picked the salad from the soup or salad option and I chose the tangy feta, kalamata, herb dressing while my fellow diner indulged in a rich creamy chunky blue cheese. My dining friend says you can tell everything you need to know about a place from the bread and salad dressings. Middleton obliges with dressings that tasted house made. Fresh Cuban bread arrived, which Jerry Hardesty “imports” from Tampa’s Ybor City neighborhood, widely acclaimed for its Cuban cuisine. Served warm, with whipped butter, it was a comforting starter. By the way, this bread originally was selected for Middleton Tavern’s Cubano Sandwich, which is the real deal with marinated slow-roasted pork shoulder.

Another irresistible special, Pan-Seared Softshell Crabs, delivered two nice size crabs with just the right coating and crisp, served atop fresh mesclun greens and “dressed” with a hefty serving of lump crab meat and mushrooms. My companion wished she hadn’t devoured so much Cuban bread.

Filet Mignon Oscar Tenderloin Medallions served with lump crab meat, asparagus, and topped with Béarnaise sauce had a definitive dry-aged mellowness in the meat. A few lumps of crab meat were strewn on the top with a drizzle of the sauce. I indulged in additional lemony sauce without an extra charge.

Full as we were, we simply couldn’t stop ourselves from ordering the timeless and decadent Cherries Jubilee (although Middleton Tavern spells it like the comic strip, Cherry’s Jubilee), prepared tableside with dramatic flair by Keith. What an elegant finish that has all but disappeared from menus in today’s all-too-fast-paced dining scene. And what a memory for my dining companion who years ago had a late night Christmas Eve family tradition at Middleton for dessert and Irish coffees before moving away. Unlike so many memories from yesteryear, Middleton still does it right, with the richest, creamiest ice cream in king-size portions (it actually could serve four), drizzled with sweet cherries, lightly sautéed in melted butter, sugar, cherry juice, Cherry Kirschwasser, and just the right hint of brandy.

Lift some spirits to the spirit!

As a food writer, blogger, food stylist, photographer, Rita Calvert has partnered in writing cookbooks and developed product lines to showcase the inspiration, art and nourishment of food. She is an advisor for the food world. The Grassfed Gourmet Fires It Up! is her most recent book with co-author farmer, Michael Heller. After owning a successful restaurant in California, she has now been an Annapolis resident for close to 30 years.