For over five years now, the better half and I have been taking road trips throughout the Washington region. From the Blue Ridge Mountains to the coastal plains, we’ve visited more than two-dozen places.
Looking at our stickpin map, one conclusion can be easily drawn. Direction-wise, we enjoy heading westward from Alexandria the most. That, of course, means we’ve visited towns in the piedmont and mountains of Virginia. But Maryland also reaches to the west. And that reminded us we’ve visited Virginia and Maryland about an equal number of times.
So which state have we enjoyed the most? Which one has the best destinations?
Yea, it is a bit silly to think in these terms, but we figured why not have a little fun and conduct what we’ll call -- “The Tournament of the Towns?”
Trying to judge all the places we’ve been to is beyond our scope, so we’ll narrow the field. Then we’ll match up towns (and cities) with similar populations. A few are not as equal in size as we would like, but we’ve discovered biggest is not always best.
So, who will take the prize? The Commonwealth or the Old Line State?
Let’s hit memory road and see.
Division 1, Semifinals
Annapolis vs. Fredericksburg
Fredericksburg makes a strong case with its connections to George Washington and James Monroe, the Civil War, and its tidewater history. “Read All Over” book store is one of our favorites, and Bistro Bethem provides good coffee and a great people watching location. Fredericksburg’s historic district impresses with a good stock.
This contest was close in the first half, but Fredericksburg slowed down and Annapolis pulled away in the second. The capital city has too much going for it, including a beautiful setting, lovely historic homes, the Museum Store, the Naval Academy, and zipping down Highway 50 is almost always a better experience than I-95.
Leesburg vs. Frederick
Leesburg combines its own set of history with a great downtown and Main Street feel. Their arts festivals are wonderful, and several restaurants, including Doner Bistro Café, are always good. One of our favorite coffee spots is their King Street Café. Leesburg is also easier to get to now, provided you’re willing to pay the HOT Lane and Greenway tolls.
Frederick has an impressive lineup too, which includes a new Visitors Center located in an old spoke factory, shopping along Market Street, and the lovely waterway near Market Street. Their star player is Volt and we think Gladchuk’s Yankee Stew is pert near fair. Frederick is clicking on all cylinders right now, with its Francis Scott Key connections and how about that dramatic view look into the valley with the mountains in the background?
Leesburg put up a good fight but Frederick takes this one.
Division I Final
Annapolis vs Frederick
This showdown was dubbed “The War of 1812 Special.” The odds-makers showed Frederick a three-point favor, pointing to their population advantage. Annapolis was just too much, however, with its long history, the Naval Academy’s support and all those sail boats making the difference.
Division I Winner: Annapolis
Division II, Semifinals
Cambridge vs Front Royal
This match up pits a town lying peacefully at the foot of the mountains against a flat Eastern Shore locale.
Front Royal’s balanced approach – its lovely Shenandoah Mountain setting, Overall Run’s solitude, dining at Apartment 2-G and The Element - kept it in the game. Cambridge proved too much, however, with a powerhouse performance from its star – the Harriet Tubman Museum. Cambridge’s newly revamped lighthouse shone bright too.
Chestertown vs Culpepper
Smaller in size, Culpepper was a five-point underdog coming in. Chestertown, with its enchanting waterfront, shady historic stock, tales of tea parties, and Monument Row, took the early lead.
Culpepper came roaring back with its Civil War connections, and downtown renaissance. One of its stars in this regard is the Raven’s Nest Coffee House where locals relax and talk about the 2008 Presidential election when the BBC’s Matt Frei chose their downtown spot to report live updates. Culpepper also recruited Michael & Rose Herrity, a friendly force in local politics. Culpepper’s excellent shops chipped in, and its friendly people cheered them on to a stunning runaway victory.
Finals, Cambridge vs Culpepper
This one came down to the final seconds. Cambridge got a great performance by Patrick Fanning, master chef at High Point Restaurant. But with the Harriet Tubman National Park not yet opened, their fans were worried. Cambridge was also slowed down by a back up at the Bay Bridge.
Culpepper’s star, their Great American Main Street Award in 2012, proved to be the difference.
Division III, Semifinals
St. Michaels vs. Middleburg
Two towns small in size and population, but two titans in reputation. St. Michaels has been called the “Hamptons of Washington,” while Middleburg’s reputation with the jet set is well-known, to say nothing of its mystique.
Both sides gave it all they had in terms of pre-game publicity and hype. It even got ugly with mudslinging. Middleburg’s tony P.R. machine asked -- “Where exactly is St. Michaels?” The latter responded by wondering if blue jeans were allowed in Middleburg.
The game lived up to the hype, going to three overtimes. St. Michaels won by a nose, er, a bow.
Winner: St. Michaels
Boonsboro - Waterford
Fans of Nora Roberts filled their half of the arena and half of Waterford’s side. Tony Horwitz, Waterford’s coach, complained the match up was unfair. But in the end, it was this tiny town’s spirit and refreshing lack of commercialism that made it an upset winner over Boonsboro. “Noraville” showed no hard feelings, and even suggested the two hilly towns become sister cities.
Finals, Waterford vs St. Michaels
Waterford stunned everyone in attendance by employing Dean Smith’s infamous “Four Corners” offense. St. Michaels decided not to press until the second half. When they did, they brought out the big boats and sailed to victory.
Winner: St. Michaels
So there you have it, two titles for Maryland and one for Virginia. Bragging rights for this year goes to the team in red.
Until we meet at next year’s tourney, we take this opportunity to remind everyone that you can’t go wrong visiting places in either state. We love both states, and West Virginia too!