The Milton Inn

Within a 272-year-old fieldstone building, the aroma of pan-seared seafood and glazed meat drifts through dining rooms as patrons clink together glasses of fine wines. The location didn't always have such a refined air; throughout its history it served as a rest area for travelers and a prestigious school for boys. It wasn't until 1947, when Ivan Drechsler purchased the location, that it was restored and established as a country inn.

Today, executive chef and owner Brian Boston, who was recently named 2011 Chef of the Year by the Restaurant Association of Maryland, crafts upscale American dishes in the Inn's bustling kitchen. Plates of artisan cheeses and steaming bowls of fresh Maryland crab soup travel to the dining room, warming up stomachs for later courses more efficiently than a series of lunges beside one's table. Entrees such as the 12-ounce grilled rib-eye steak and wild-mushroom-stuffed phyllo star in the inventive, upscale menu next to sides of grilled summer vegetables.

Nearly 200 handpicked red and white wines age gracefully in an underground wine cellar, which rests beneath colonial-style dining rooms illumined by tabletop candles and crackling flames from a rustic stone fireplace. The Milton Inn Restaurant requests that male guests don jackets, a prerequisite that arose after the short-lived “shirtless cummerbund” fad of the late 1980s. Diners that commute via four-wheeled steed can deposit their vehicles in the eatery's free parking lot.