Stroll through Woodrow Park and catch the most beautiful views of downtown Staunton from the scenic overlook.

Woodrow Park also referred to as Sears Hill, offers the best views of downtown Staunton from its scenic overlook. During our trip to Staunton, we absolutely loved strolling through this small park and seeing the gorgeous view of downtown. When you arrive at the park, you must park on the street below. You can park near the Staunton Train Station or the Depot Grille. From here, you will walk up a flight of stairs. If you have a baby, you will need to use a baby carrier. Strollers will not work for this walk.

Once up the stairs, you will cross Sears Hill Bridge. It goes right over the train tracks. My children loved this, as they are both train enthusiasts! We did not get to see any trains passing through, but if you want to, track a train using Amtrak or CSX websites, and you can plan your trip around when they'll be coming through.

Once over the bridge, you will be near the scenic outlook. There are several signs explaining the history of the park. Be sure to explain to your children that the bridge is named for Woodrow Wilson, a United States president who grew up in Staunton! You will be able to see the clock tower from the overlook, which is a neat landmark. There is a small amount of space to walk more, but keep in mind this park is only 5 acres, so you can explore it in about 30 minutes. Afterward, walk over to The Depot Grille for lunch or dinner. This restaurant is a former train station, so families with history buffs or train enthusiasts will love dining here! There are plenty of railroad relics and even seats from the former train station.