Exploring the Small Towns of the Shenandoah Valley The Shenandoah Valley stretches from Harpers Ferry, West Virginia to Roanoke, Virginia. The Valley is 200 miles across, bordered by the Blue Ridge Mountains and Allegheny Mountains. During the Civil War, this region was nicknamed the “breadbasket of the Confederacy.” Today, this area is an outdoor wonderland, with bucolic farms and country roads. There are natural wonders like the Luray and Shenandoah Caverns, and Natural Bridge, as well as gorgeous scenic drives along the Skyline Drive and Blue Ridge Parkway.The Shenandoah Valley also includes Shenandoah National Park and the popular Bryce and Massanutten Resorts. There are plenty of outdoor adventures to be had including biking, hiking, paddle sports and horseback riding. It has been memorialized in songs like “Oh, Shenandoah!” Families can explore this area along the Shenandoah Valley Kids Trail — a website and mobile app design to let kids steer the family vacation.This summer, we had a chance to explore part of the Valley during our two-week mother-daughter road trip through Virginia. One of the many LOVE signs throughout Virginia, this one was found in Harrisonburg, VAHarrisonburg, VirginiaWe began our stay in Harrisonburg, after driving a portion of the Skyline Drive on our way up from Charlottesville. Unfortunately that detour meant that we had to skip Staunton, which I’ve heard is quite a lovely town, but Harrisonburg was a nice introduction to the small towns of Shenandoah Valley. Located just minutes from Shenandoah National Park, Massanutten Resort, and the Skyline Drive, Harrisonburg is also the home to James Madison University, giving it that distinct college town vibe. Downtown Harrisonburg, flowers from the Harrisonburg farmer’s market, enjoying ice cream from Kline’s Dairy Bar, and cows at the Rockingham County Fair.We began our stay with a stroll through the Harrisonburg Farmers Market and a stop at the Hardesty-Higgins House Visitor Center. From there, we strolled down Main Street, working on a letter boxing hunt set up throughout town. Downtown features a number of small museums, such as the Explore More Discovery Museum, the Valley Turnpike Museum & Civil War Orientation Center, Harrisonburg Fire Department Museum and the Virginia Quilt Museum, and plenty of college-student friendly locally owned restaurants.Nearby, visitors can enjoy hikes at the Edith Carrier Arboretum at James Madison University, Hillandale Park, and the Grand Caverns Grottoes. We had hoped to explore a bit more but after a week on the road, we need an afternoon of relaxation. Instead, we stopped for ice cream at Klines Dairy Bar before taking in an authentic county fair experience at the Rockingham County Fair. At the end of the day, it was time to head on to our next stop in Woodstock in Shenandoah County.Woodstock, VirginiaWoodstock is actually the fourth oldest town in Virginia, and is centered along Route 11 with a small but quaint downtown district. Since we were to spend a few days enjoying Shenandoah County from our home base in Woodstock, we had the opportunity to spread out and enjoy our surroundings in a cabin in the woods. This stylish vacation rental had more than enough space for the two of us with a large master suite and a bedroom with two double beds on the lower floor. The main floor featured an open plan kitchen and family room and another bathroom. Conveniently, the cabin also had full laundry facilities so we were really able to relax and feel like we were at home for a few days. Our vacation rental River Ridge Roost in Woodstock, VAOur time in Shenandoah County was all about enjoying the outdoors and local culture. We climbed to the top of the Woodstock Tower, high up on the mountain, overlooking a few of the seven bends of the mighty Shenandoah River. The view from the top of Woodstock TowerWe also spent an afternoon kayaking on the Shenandoah River with Route 11 Outfitters. We had hoped to go river tubing, since we haven’t tried that yet, but the river was too low in late summer. The best time for tubing would be in the spring or early summer when the mighty Shenandoah is a bit mightier. Kayaking on the Shenandoah RiverOur adventures continued underground at the Shenandoah Caverns, the only caverns with an elevator access. The caverns have been open since 1922 and welcoming visitors through a one-mile circuit on one-hour tours. The Caverns are a steady 56-degree in the summer or winter, so visitors should bring a sweater or sweatshirt. These were not too terribly different from our visit to Howe Caverns, but they did have one special feature I haven’t seen before — cave bacon! They interesting rock formations look temptingly like bacon.Our guide walked us through other features like the Rainbow Lake, Capital Dome, Cardross Castle, and the Breakfast Bacon. The teenage guide seemed to think it was a virtue to repeat his spiel by rote memory, with heavily-practiced intonations, driving us a bit crazy, but we tuned him out as much as we could while being shepherded through each area. Next door, we popped in to the surprisingly interesting American Celebration on Parade — a collection of parade floats from the Rose Parade, Presidential Inaugurals, and the Thanksgiving Day Parades covering 40,000 square feet.Click on any photo in the gallery to enlarge it: If you visit the Caverns, take a few minutes to stop at the Route 11 Potato Chips Factory. You can’t take pictures but you can look through the windows at the production line and get to sample many of their tasty chips. Pitstop at Route 11 Potato Chip FactorySince I had a little adventure seeker as a travel companion, we got our thrills in at the Bryce Resort. A ski resort the winter, in the summer Bryce transforms into an adventureland with ziplining, grass tubing, Euro Bungy, mountain biking and even grass skiing. The ziplining was fun and easy, you just take the ski lift to the top and then proceed down and across the mountain on a series of ziplines — none of which are too high or too fast. Hannah loved the grass tubing, which is really on a plastic netting and they wipe the bottom of the tube with silicone to make it go faster. I did a couple of runs but then appointed myself photographer. Since I sit a little lower in the tube than she does, I didn’t like the way my bottom bumped along. Grass Tubing at Bryce ResortJust keep in mind that not all activities are available on all days, so you’ll want to call ahead to check the schedule and plan according to what you want to do most. Ziplining at Bryce ResortIf you plan on heading out to the Shenandoah Wine Trail, you may also want to schedule a stop at the Posey Thisisit Llama Farm (just be sure to call ahead) in Toms Brook, Virginia. They offer tours and a chance to meet and feed their llama and have handcrafted items and llama wool for sale. We were surprised to learn that llamas aren’t actually nasty, as we have been led to believe, but that it all depends on how they are treated. These llamas were very well loved and it showed with their friendliness. Hannah with Zapper at the Posey Thisisit Llama FarmEven though our cabin included a full kitchen, we also like to eat locally when we are traveling (and frankly when on a road trip and solo parenting the last thing I feel like doing at the end of a long day is cooking.) We were able to try out a few of the local eateries in and around Woodstock, starting with Sunday brunch at The Woodstock Cafe and Shoppes. This cute cafe in downtown Woodstock is part country store, part cafe, full of local characters and flavors. We also had dinner at the higher end Joe’s Steak, part of a small local chain, featuring steaks, seafood and chicken. It was good but pricey and not at the level of a big city steakhouse.One night we headed up to the next town of Strasburg and got some yummy Mexican food at Jalisco’s, although Christina’s Cafe also looked really charming. Our favorite stop in Woodstock though has to be the Woodstock Brewhouse. This converted denim factory has a hip interior that I would expect to see in…well, frankly a hipper town…like maybe Charlottesville. They have a limited food menu because the focus is on their craft beers, but if you happen to be in town when they are smoking some brisket or making BBQ then YOU MUST GO! We had leftover BBQ brisket on a flatbread pizza and it was delicious. Woodstock Brewhouse, BBQ brisket pizza at Woodstock Brewhouse, enchiladas at Jalisco’s, strip steak at Joe’s Steak and inside Woodstock Brewhouse (clockwise.)Winchester, VirginiaSoon it was time for us to head north, but we had one more stop in the Shenandoah Valley in Virginia before our next stop in Harpers’ Ferry, West Virginia. This town is just full of history, largely from the Civil War but some dating back to George Washington’s early days. In fact, some historians claim that this small town changed hands up to 72 times during the Civil War, going back and forth between the North and the South! Just walking through the quaint downtown, you can learn about some of this history at the George Washington’s Office Museum or the Old Court House Civil War Museum.Nearby, you can also visit Stonewall Jackson’s Headquarters, the Cedar Creek Battlefield, and the Museum of the Shenandoah Valley. Kids should love the Shenandoah Valley Discovery Museum. We peeked in and it looked super fun, but geared primarily for kids 10 and under. Since we only had a short time to spend in Winchester, we gravitated to the Historic Downtown.Winchester has a pedestrian mall, very similar to what we saw in Charlottesville, which is lined with shops and restaurants with outdoor tables. We found a yummy Thai restaurant for lunch and then cooled off a bit at the community splash pad. Downtown Winchester VirginiaWinchester was the prettiest of the towns we visited in the Shenandoah Valley and I wish we had more time to explore here, but if we head back down Interstate 81 someday, I’ll be sure to stop in.I wasn’t sure what to expect when visiting this region, but we had a nice taste of rural Virginia and small town living. We definitely couldn’t forget we were in the south. I’m not sure if it was because of the recent controversy over the Confederate flag last summer or not, but we saw a whole lot more Confederate flags flying than this Yankee was comfortable with. I hadn’t noticed any during the rest of our trip to Virginia in the Newport News, Hampton, Williamsburg and Charlottesville — so they really caught my attention. But overall, the people were warm and welcoming to us.PLAN YOUR TRIPFly into Charlottesville, Virginia or Washington’s Dulles Airport (if you aren’t road tripping!)…check fares using SkyScannerBook a hotel — we stayed at the Residence Inn in Harrisonburg, which is a great choice for families with kitchenettes, breakfast, pools, laundry facilities and lots of spaceOr, stay at a cabin in the country. We stayed at River Ridge Roost in Woodstock (get a $20 credit when you sign up for Airbnb with my referral link)PIN THIS FOR LATERNote: Our accommodations and activities in Woodstock were hosted by Shenandoah County Tourism to enable us to enjoy the area and share our experiences with you. All opinions are 100 percent my own.Find this useful? Share it!PinShareTweetFlipboardEmail Written by We3Travel and was last updated on October 2, 2018. Read more about United States, Family Trips, Destinations, VirginiaRelated Posts What to do in Charlottesville Virginia with Kids Achieve the Impossible! Make U.S. History Fun on a Northeast Road Trip Tips for Visiting Monticello with Kids Comments are closed. 2 Comments on “Exploring the Small Towns of the Shenandoah Valley”You were in my neck of the woods! I live between Winchester and Harpers Ferry. I love exploring up and down the Shenandoah Valley since I’m not originally from here. I love learning along with my daughter the great history this area has to offerSuch a lovely area!! I was charmed by both towns and love the activities in the Harpers Ferry area too!