Throughout greater Virginia, there are tons of fantastic wineries, many complete with space for dogs and others with dog-friendly events. Sometimes it's just as simple as sitting next to a nice outdoor fire and sipping some wine and sometimes it's exciting game-playing. Check your local wineries to see who hosts what during wintertime. You might be surprised to see all they offer.
Out of all the Eastern states, few boast the vast expanse of beachfront and mountains, let alone with enough hiking trails to never see anything twice. As long as you're bundled up, there are tons of winter hike spots that will give you a new lease on even your favorite old spots.