Road Trips Around Winchester, VA

Northern Virginia isn’t just a region of one state, but also a gateway into others like Maryland and Pennsylvania. If you’re in the area, either living or just visiting, we’ve prepared some great ideas on how to make the most out of the local road network. The simple act of getting into your car and heading along some of these roads can lead to some of the most amazing things, places, and people. Let’s take a closer look at some options:


  1. Luray Caverns (Luray, VA)

Head about an hour to the south of Winchester, and you’ll reach the well-known Luray Caverns — considered a rite of passage for many native Virginians. Head into these caves and look for the fried egg formation before listening to the “Stalacpipe Organ.” This place will put you in mind of some ancient Gothic cathedral, but you’ll also be reminded that it was entirely carved out by the marvels of nature. It was even designated a Natural Landmark by the Department of the Interior.

Road trips around Winchester


  1. Frederick, MD

An hour or so to the east will take you to Frederick, Maryland, a quirky and charming small town full of old-world charm. It may not be a big place, but you’ll see a lot while you’re there — unique old shops, street buskers, great museums, distilleries, and even a wildlife preserve. While you’re there, you must see Carroll Creek Park, Everedy Square and Shab Row (an area filled with locally-owned shops) and the town’s main street which is on North Market Street. So many unmissable sights, and just an hour away!


  1. Virginia Civil War Trails

Virginia was front and center during the Civil War; home to the capital of the short-lived Confederacy, and also the site of some of the bloodiest and most decisive battles of the war. If you’re a history buff, you couldn’t possibly miss all or part of the more-than 250 stops that make up the Virginia Civil War Trails. The routes are clearly marked on most maps and you’ll have a great time “collecting” the stops.


  1. Chesapeake Beach, MD

If you and the family are up for a longer drive (about 2 hours in total) then head southeast through Maryland, past Washington, D.C. all the way to the sea. This town is the perfect place for simple, good-old-fashioned family times. You can get fresh seafood, enjoy slot-machine games, look out at the water while you walk along the beautiful beach. It’s all here waiting for you.

Road trips around Winchester


  1. Virginia Wine Country

While history buffs have the Civil War Trails, the wine lovers have the state’s wine trails. Virginia is home to six American Viticultural Areas (AVAs) and more than 200 wineries. Take your pick of direction from Winchester – head west to the mountains, or head east to the shore. Many of Virginia’s best-known small towns, areas of natural beauty and historic sites come with a winery attached!

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

%d bloggers like this: