When I first moved out to the Shenandoah Valley, I had no idea of how many different hikes that would be available. There were literally hundreds of hikes all within a 1 hour drive from Winchester. So many hikes, it would be nearly impossible to complete them all.
When I first started out hiking I really did not have the skills or the confidence to venture very far. However, I was happy to find out that there were several hikes that would not only satisfy my need to be amongst the trees but would also be within my ability and confidence level.
This is a list of some of the easier, more accessible hikes that are close to Winchester. These shorter, easier hikes are kid friendly, do not require a lot of specialized gear and wont require a full tank of gas to get to if you are close to Winchester. Also, these hikes are doable as a quick walk or a half day hike.
The hikes listed are arranged from the easiest (IMHO) to slightly more challenging. Please keep in mind that this is just a sampling of some of the hikes that are both easy and close to Winchester. There are many, many more local hikes- this area is a playground for those that want to explore the woods.
Super Easy Hikes Near Winchester
These four hikes made the easiest hikes near Winchester list because of the limited elevation gain and the ease of the trail surfaces. They all had gravel or wood chip trails or in some cases the trails had paved surfaces. Many would consider them places to walk not hike- semantics! The goal of this article is not to start a debate on the difference between a hike and a walk. The goal of this article is to offer some easy, accessible hikes for those that want to get outdoors and explore a little bit.
1. Rose Hill Park
This short 1.3 mile loop trail only has an incline of 85 ft. The surface of the trail is made up of crushed stone. As you journey around this easy loop you will cross through a mixture of woods and open fields. The trail is well marked and there are benches along the way. Most notable about this trail is its history. The area that this trail is in was a part of the First Battle of Kernstown during the Civil War. As you walk along you will find signs describing this battle.
2. Museum of the Shenandoah Valley
The Museum of the Shenandoah Valley has several trails that can be linked together. In total you could get in approximately 3 miles of hiking. The unique thing about these easy trail hikes located in Winchester is that they are part of a 90 acre art park. As you walk along the fairly flat trails you will encounter different art installations. The surface of the trails is a combination of pavement, turf and mulch. The trails are dog friendly too, so feel free to bring your pup (on a leash of course).
3. Blandy Experimental Farm
The Blandy Experimental Farm is Virginia’s state arboretum. It is home to numerous gardens and trails. The Native Plant trail takes you through three different ecosystems- woodland, meadow and wetland. The wetland section is a boardwalk and will take you to a beautiful pavilion where you can look out over the wetlands. There is also an audio trail tour and many of the trees are marked with labels so that you can learn as you stroll. The arboretum also has a crushed stone loop drive that can also be walked.
4. Third Battle of Winchester
Third Battle of Winchester trail combines history and nature. This area was a battleground during the civil war. There are several interpretive signs along the way if you are interested in learning a little bit more about the history of the area.
Three loops comprise the trail system here, each loop is approximately 2.5 miles long. There are also some side trails that go a little deeper into the woods if you are feeling adventurous. There is a section that crosses over Red Bud Run with a bench that you can look out on the meandering creek.
Next level of easy:
Hikes on these trails are more of what would be classified as a “hike” instead of “walk”. The surface of these trails (for the most part) is a natural surface. Hiking on these trails also tend to be a little bit longer and also have slightly more elevation gain. However, each of these places has trails that are fairly easy.
5. Sky Meadow State Park
Sky Meadow State Park is of my favorite local spots to hike. There is a lot of variety here to explore and the views of the valley are lovely. The terrain is a mixture of open fields, woods and streams. The park is on both sides of Rte. 17. The trails on the Lost Mountain side are much flatter overall. Just be aware your trail may have a spot or two where you are stepping on stones to cross a creek.
I had a lovely experience one Winter when I was exploring the trails on the Lost Mountain side. As I walked through the snow I came across a female deer and her yearling resting in a clearing next to the creek. It was perfect. The cool crisp air, the stillness of fresh fallen snow and the mom and her baby next to a creek. It was one of those hiker moments that stays with you forever. 🙂
Also, please be aware that there is a $10 vehicle charge when entering the park. If there is no-one at the gate there is an honor system where you pay by placing your money in an envelope. Another option is to purchase an annual State Park Pass for $85.
6. Andy Guest Shenandoah River State Park
Andy Guest Shenandoah River State Park is another one of Virginia’s state parks. The fees for this park ($10) are the same as they are for Sky Meadows State Park. There are more than 24 miles of trails. 5.2 miles of this park traverse along the meandering Shenandoah River. Overall there is minimal elevation gain. The highest peaks are about 300 feet elevation. They are Pine Hill and Allen’s Peak which are both just outside of the parks boundary.
Two of my favorite trails are River Trail (1 mile) and Bluebell trai (2.1 miles)l. Both of these meander along the Shenandoah River. In the spring, the Bluebell trail is covered with bluebells. When in bloom, it is a stunning sight to see.
7. Dicky Ridge Trail
If you look up Dicky Ridge Trail on All Trails you will see this hike as being listed as moderate, 18 miles long and with an elevation gain of 3,766 feet! You may be thinking, that does not sound like a beginners trail to me- and I would completely agree if you were deciding to hike the entire trail in one day. Hear me out, there is no rule that says that you have to do an entire trail to do a hike. This trail starts outside of the park with a gentle incline through the forest. You can see remnants of former inhabitants (old stone walls) along the way. If you are feeling motivated you could hike the 3.6 miles up to the Dickey Ridge Visitor Center and back. The visitor center (when open) offers restrooms, park info and maps.
Parking for this trail just inside the park boundary on the right (before you get to the Ranger Gate). To drive into the park it is $30 for a one week pass, $55 Annual Shenandoah National Park Pass, or $80 for an America The Beautiful Pass. The America the Beautiful Pass covers the entrance fee for all national parks and national refuges.
8. Eagle Rock (parking at Dry Gap)
Of all the hikes on this list, this is the one that I keep coming back to. This is the hike I recommend when people ask me for a great local hike that is not too hard. This is the hike I take out of town visitors on. The hike up to Eagle Rock is very short (2.5 miles up and back) and the view is outstanding! There is even a stone bench at the overlook, although there is a lovely outcropping that you can sit on and take in the view.
Important: The property of Eagle Rock is owned by the family that owns Capon Springs Resort. If you do venture here please be respectful and practice “leave no trace” principles. The parking lot is small and only about 5 cars can park here comfortably and the lookout has become very popular. This short section of trail is part of the longer Tuscarora Trail. The Tuscarora trail is a 250 mile trail that runs from Duncannon, Pennsylvania to Matthew’s Arm Campground in Shenandoah National Park.
9. Harpers Ferry National Park
Harpers Ferry is also a National Park so there are fees that apply. To drive into the park it is $20 for a 3 consecutive day pass, $35 Annual Shenandoah National Park Pass, or $80 for an America The Beautiful Pass. The America the Beautiful Pass covers the entrance fee for all national parks and national refuges.
The easiest place to park is at the Visitor Center and then take the shuttle into the historic town. There is no cost to take the shuttle and there are several shuttle buses that run back and forth from the visitor center to the historic “lower town”. Another option is to drive into the lower town and hope that you find a legal spot to park. There are a few spots by the train station that you can use if you have your America the Beautiful Pass.
Once you have arrived in the lower town you can either walk along the C&O Towpath or you can explore some of the ruins along the water. Both of these options are flat along the river and are very scenic. If you want a bit of a challenge there is always the hike up to Jefferson Rock which offers a beautiful view of the Shenandoah River.
Another easy hike is to park up Bolivar Heights which has several parking spots that are a part of a self-guided driving tour. Be sure that you have your entry pass visible. I once watched a woman get a ticket because she was trying to park and hike for free. If cost is prohibitive, there are free days throughout the year that you can visit any national park.
10. Woodstock Tower
Woodstock Tower (Wagon Road Trail), located in the George Washington National Forest is an easy 2 mile hike that only ascends 510’. The cool thing about this hike is that there is an old observation tower that you can climb up that was built in 1935 by Civilian Conservation Corp. From the tower you can see beautiful views of the Shenandoah River and Fort Valley.
Please note, this trail is at the end of the list because it does require a bit more effort. You are climbing 510’ in one mile and proper footwear is a must I included it because it the views are definitely worth the hike and it is kind of cool to climb up into the tower.
How they Stack Up
Most Pet Friendly: Museum of the Shenandoah Valley
Most Pet Friendly: Museum of the Shenandoah Valley
Best for History: Harpers Ferry National Park
Overall Best for Culture: Museum of the Shenandoah Valley
Best Scenic View: Eagle Rock
Shortest: Woodstock Tower
Longest: Dicky Ridge Trail
Best for Wildflowers: Andy Guest Shenandoah River State Park
Best River Walk: Harpers Ferry National Park
Additional Reading
If you are not sure that a hike is the right level for you be sure to check out this article which helps you determine if a hike is the right level for you.
