If you’re looking to go biking, do not use Azealia Park. The trail is best fit for hiking not any kind of biking. If one person comes the opposite direction you will probably run into a tree because the trail is very thin.

This is our home trail, so this ride was probably our 1,000th. Starting very close to Washington, DC in Arlington, VA, the 44-mile W&OD began with a series of short hills. For about five miles, we rode through wooded neighborhoods bordered by high retainer walls that shielded us from traffic on Route 66. There are a few intersections in the town of Falls Church, but the trail has recently been widened and a few pedestrian bridges have been added. There is almost always a significant amount of traffic on this trail; weekend rides can be frustrating slogs around families with strollers, dogwalkers and children testing their training wheels.
Vienna (with one brewery steps from the trail) was the next town we passed through as we followed the soft buzz of the overhead power lines. Over the years, more and more townhouse communities have sprung up alongside the trail, but still, we frequently see deer grazing fearlessly alongside the trail, and today, we saw a fat gopher, a rabbit, and a black snake.
Next, we pedaled through Reston and along Northern Virginia’s high-tech corridor. During this segment of the trail, we passed the first of three golf courses and two ice skating rinks. A few placid miles later, we crossed through the town of Herndon where one of several good bike shops abut the trail. Things began to look decidedly rural as the trail approached Ashburn, where it traversed broad open fields and passed by a huge stone quarry. The ride through Ashburn was pleasant and traffic definitely decreased the further west we rode, but the prettiest and most peaceful part of the trail began when we passed Leesburg. Leesburg is a very cute and historic town with several breweries, and outside of town, a number of fun wineries.
The remaining 13 miles of the trail were rolling and predominately shaded with occasional barns and farmhouses visible through the trees. Alongside the trail is a 32-mile crushed gravel equestrian trail, and it is on this end of the W&OD where the rare horseback rider is likely to be seen. The trail ends on the edge of the town of Purcellville, where there are restrooms, a bakery that sells bottles of water, a very good restaurant, and more good breweries. (Actually, there are 21 breweries within two blocks of the trail which has to be some kind of record!)