Spend some time exploring Old Town Winchester, a historic downtown area full of charm. Take a walk down the Loudoun Street pedestrian mall, pop into a local café or restaurant, grab some ice cream at Red Fox Creamery, flip through records at Back to the Media, or browse the shelves at the Winchester Book Gallery. It’s a great spot to wander, snack, and shop!
Grab a beer and a snack at Bear Chase Brewery, we recommend the Appalachian Trail Hefeweizen and the mac n cheese. The views are awesome, the vibe is relaxed, and it’s a great spot to hang out with friends or family. If you're up for a little adventure first, head across the street to Bears Den Park Trail for a short 1.5-mile loop hike that leads to a beautiful overlook. Hike first, beer after!
Consider heading across state lines to Harpers Ferry, one of the most picturesque and historic towns in the region (and the spot where we took our engagement photos)! This scenic little town sits at the meeting point of the Potomac and Shenandoah Rivers, where Maryland, Virginia, and West Virginia all come together. Wander through cobblestone streets lined with colonial buildings, pop into museums and shops, and spot park rangers in period clothing as you step back in time. If you’re up for a hike, the Maryland Heights trail (6.5 mi) offers a tough but rewarding climb with incredible views, or take a much shorter walk to Jefferson Rock for a quick scenic stop.
Anyone who knows us knows how much we love the national parks, especially Shenandoah! It's our most-visited, thanks to how close it is to home. If you have the time, take a drive along Skyline Drive for amazing mountain views and scenic overlooks. There are tons of hikes for all levels. Some of our favorites are Bearfence Mountain (1.1 mi), Dark Hollow Falls (1.4 mi), Stony Man (3.7 mi), Hawksbill (1.6 mi), and for those looking for a serious challenge, Old Rag (9.2 mi).