The Old Town Mall along Loudon Street in the heart of downtown has a number of coffeehouses, bakeries, and restaurants, most between Boscawen and Piccadilly streets. Best for fine dining is Village Square (tel. 540/667-8961), which has a sophisticated piano bar and excellent wine shop adjacent. The cuisine is nouveau americain, such as a roast chicken and grits casserole. I know people in Leesburg who will drive over for lunch or dinner at Violino Ristorante Italiano (tel. 540/667-8006). Thai Winchester (tel. 540/678-0055) has a very good beef salad. For informal fare, there's the publike Brewbaker's (tel. 540/667-0429) and the British-style Union Jack Pub & Restaurant (tel. 540/722-2055). All offer outdoor seating in good weather.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.