Highland Hiking Trails and Tips

Highland County offers gorgeous views on hiking trails; however the lack of cell service on the more remote trails can be a bit intimidating. Rest assured. Pre-planning and safe hiking practices can lower the risk of potential issues and reduce your worry during excursions.

Here are a few pieces of advice for anyone planning a trail adventure:

  • Communication: Be sure to tell someone where you are going, when you will leave, and when you will return. It can be someone you’re staying with, a friend in the area, or (at the very least) a family member or friend back home, who can track you. In addition to supplying them with the where’s and when’s of the hike, also give them the number of the Highland County Sheriff’s Office (540-468-2210) to report any issues that may arise. (Take it one step further – Leave the same info taped to the inside of your car window in case a law enforcement officer or fellow traveler stops to check on you.)
  • Beware of Wildlife: Critters, large and small, are always a possibility when hiking, and Highland County is no exception. Stay aware of your surrounds, pay attention to the trail in front of you, and look where you plan to step. Additionally, hikers should thoroughly check themselves afterwards for ticks.
  • Remember the Survival Rules of Three: A human can last three weeks without food, three days without water, and three hours without shelter. (FYI: Hypothermia can kill in less than an hour if you are wet and the temperature drops below 40 degrees!)

    Steves Safety Kit
    Sample Survival Safety Kit
  • Carry The Proper Supplies: Whether you’re planning a short or long hike, ALWAYS be prepared with a sufficient amount of supplies. You’re in luck because Steve Pullinger, an owner of Blue Grass Cabin, is a survival specialist. Here is his hiking supplies packing list, all of which should easily fit in a small backpack or large fanny pack:
    • Cell Phone – Service is a bit sketchy, but sometimes you can get lucky.
    • Pepper Spray or a pistol – For protection from aggressive wildlife.
    • Walking Staff – For climbing and assistance.
    • A Map – For obvious reasons. 🙂
    • Survival Blanket and Rain Poncho – To use for shelter and warmth.
    • Sawyer Mini-Straw – To filter drinking water.
    • Fire – Two lighters, a pack of matches, and a roll of 0000 steel wool for tinder will ensure warmth.
    • Food – Carry a couple protein bars and some GORP.
    • Super Glue – It fixes so many things and can be used as backwoods wound care.
    • Other Helpful Items – A leatherman tool, paracord or similar cordage, a small AAA flashlight, an extra pair of glasses (if needed), and any medications needed.



Photo Credit: Winifred Stephenson/Hike Highland
Photo Credit: Winifred Stephenson/Hike Highland

Take a trail through history when you hike the same grounds the Civil War soldiers did during the Battle of McDowell. This approximate two-mile hike is an easy to moderate excursion that will take hikers to the top of Sitlington Hill for an expansive view. There’s not much shade on this hike so be prepared with necessary sunscreen, water, and other provisions and protection.

Trailhead: From Monterey, travel east on Rt. 250 over Jack Mountain heading towards McDowell. Pass through the town of McDowell, and continue another two miles (approximately) to the parking lot and trailhead, which is located at the start up Shaw’s Ridge. (Still on Rt. 250 east).

Additional Tip: Stop in the Highland County Museum before your hike to learn more about the historic happenings that took place on the hill.





Laurel Fork Photo Credit Todd Frye
A view from Laurel Fork Trail, which can be accessed via the Locust Spring and Buck Run Trails. Photo Credit: Todd Frye

Laurel Fork is definitely a remote location; however with some of the most diverse scenery and old growth forests in the state of Virginia, it’s something all nature lovers should see. At approximately 4,000 feet, this adventure offers a cool break from high temperatures of other locales. And for the advanced hiker and adventurer, trails within the Laurel Fork area can be combined for a multi-day backpacking excursion. (Definitely exercise good communication if you decide on the backpacking option!)

Trailhead: From Monterey, travel west of town on Rt. 250 over Monterey and Allegheny mountains. A short distance past the Virginia/West Virginia border, turn right onto WV28. Then, turn right onto FR106 and travel .4 miles, left onto FR60 for .3 miles, right onto FR142 for .2 miles, and finally, park at the Locust Spring Picnic Area. You will see the trail head for the Locust Spring Run Trail at the bottom right of the picnic area.

For more detailed information, we recommend visiting the Laurel Fork profile on HikingUpward.com.



Highland WMA2
Photo Credit: Department of Game & Inland Fisheries

Approximately three to four miles east when traveling on Route 250 out of Monterey is a pull off on the right at the top of Jack Mountain. Upon further inspection, you will see a gravel road, which leads to the Highland Wildlife Management Area. (Click on the link for usage fees!) When you travel this road (AKA: Sounding Knob Road), you’ll find a small piece of the larger 14,000+ acre area that includes diverse habitats, a plethora of wildlife, and a variety of views – an area where you can customize the length and features of your hike! As always, be aware of wildlife such as snakes, bear, fox, and more. These critters are usually fairly elusive but are present, nonetheless.

Trailhead: From Monterey, travel east on Rt 250 up Jack Mountain and look for a gravel pull off area labeled “Sounding Knob Road” at the top of the mountain. Drive in, decide on a hiking area, find a parking spot, and enjoy!

For more info, visit the Highland Wildlife Management Area profile on the Virginia Department of Game and Inland Fisheries website.


For other hiking recommendations, contact the Highland County Chamber of Commerce or check out the “Hike Highland” Facebook group page, which was created by a local resident.


Living Room cropped
Relax in Front of our Cozy Fireplace

If you’re looking for inner peace, inspiration, or spiritual rejuvenation, plan a trip to Highland County, Virginia.

Those who live here, visit here, and (most importantly) RECOVER here, can’t deny it – If you’re at a point in life where you feel stuck, uninspired, or just plain burnt out, a getaway to the refreshing, wide open spaces of Highland County can be invigorating, uplifting, and sometimes even life-changing.

At Blue Grass Cabin, we offer a tranquil getaway to calm down, collect yourself, cool off, take a break, kick your boots off, put your feet up, or whatever relaxation phrase is right for you. Additionally, we recommend these local activities or services to aid in your restorative, mountain therapy:



Massage picMassage therapy is a go-to for relaxing. Licensed Massage Therapist Nicole Frye at Heart & Soul Massage in Monterey can quickly assess what your body and mind (and heart and soul!) need for repair. Therapeutic massage, deep-tissue massage, hot stone massage, and Reiki are just a few services she offers. However, one huge thing Nicole gives each and every client is her open ears, full attention, and compassion. From almost the moment you walk through the door, she can tell what you need. With her years of experience and knowledge, she will have you feeling lighter, less knotted, and refreshed when you leave.

To book an appointment, call Heart and Soul Massage at (540) 292-0568.




Emerald Mountain SanctuaryOriginally from Germany, retired clinical psychologist Annette Naber now lives at her Emerald Mountain Sanctuary, a 58-acre farm home that consists of pastures, forests, and a few small ponds. Given her professional history, desire to empower women, and passion for helping others, Annette along with her husband, Dan, have opened their little slice of Highland heaven to guests as a retreat and small conference center. Together, the couple offers workshops in self-care, stress management, life simplification, forest bathing, nature walks, journaling for self-therapy, backyard foraging, individual and group coaching sessions, and Yoga classes.

If you’re feeling lost with no direction, Annette is an absolute treasure that will provide valuable insight to experiences and methodology that could help you gain significant clarity.

For more info on her services, visit the Emerald Mountain Sanctuary website!

HOT TIP: For the motorcycle enthusiasts out there, Annette’s husband, Dan, also owns and operates Allegheny Motorcycle Tours, which offers guided rides throughout Highland County and surrounding areas! He is in the process of building a motorcycle campground, which should be open to the public in spring of 2021.



Monterey Walking TrailMany come to Highland County for outdoor recreation. While there are several hiking trails in the area, most options are remote and out of cell service range. For those who just want a quick, relaxing stroll, check out the Monterey Walking Trail, which loops through the charming town and past our LOVEworks sign. (Park at the Highland Pool Complex to start walking. The entrance to the complex can be found off Route 220 heading south out of Monterey.) The trail is equal parts nature, community, and quiet neighborhood and offers an approximate mile to mile-and-a-half trail.

When your walk is through, step through the rest of the town. Shop through thrift stores and flower and gift shops. Stop by the Walk of Honor and pay respect to Highland County’s veterans, and take in the view of our historic courthouse. (History Factoid: The current courthouse building is the second structure, which was rebuilt after a fire JUMPED THE STREET(!!!) from a two-story store formally-situated on the current Summit Community Bank lot.)



Barn QuiltImagine… Cruising along the back roads of Highland County with a kind-of treasure map. What are you in search of? Colorful, locally-created barn quilts. Like bright blooms popping from a green garden, these delightful pieces of artwork are creatively-scattered throughout the countryside for travelers to enjoy on the first and largest barn quilt tour in Virginia (to our knowledge).

How to find them? Stop by the Highland Visitor Center at The Highland Center on Spruce Street in Monterey or download the online brochure to find these vibrant treasures throughout the county.

Not only can you enjoy local artwork, but you can also experience Highland County’s scenic back roads and spectacular views while doing it!



HikingExperiencing nature up-close and personal is a sure-fire way to rejuvenate the senses and find calm. Highland County offers hiking trails that are serene, educational, and feature views to relax and inspire inner peace.

Learn about the Battle of McDowell on the McDowell Battlefield hiking trail. Explore wildlife, trees, rivers, and fishing in the Laurel Fork Wilderness Area. Take in expansive views from overlooks and a restored firetower in the Highland Wildlife Management Area.

Bring a friend, or enjoy a solo expedition. If you’re hiking alone, we encourage you to tell someone where you’re going, when you’ll leave, and when you’ll return. Also consider practicing our other hiking tips to ensure safety during your adventure.

Six Picks for Locally-Sourced Foods

Our beloved Blue Grass Cabin features a fully-furnished kitchen perfect for meal prep. With its open concept, one can prepare a locally-sourced meal in the kitchen while visiting with family and friends who may be perched at the adjacent dining room table or kicking it back on the couch.

Now the question is: In a county so plentiful with local foods, where is the best place to find the succulent selections? Pick one (or a combination of!) our six picks for locally-sourced food and find all you need for a homegrown meal while you’re visiting our Blue Grass Cabin!


Highland Farmers Market

The Highland Farmers’ Market opens in late-May and runs through mid-October. (Usually the last market of the season is Hands & Harvest weekend.) So that means, on Friday evenings from 3:30 to 6:00 pm, you can drive to The Highland Center on Spruce Street in Monterey to shop a selection of seasonal produce, meats, baked goods, maple syrup, and other locally-raised and locally-made foods. (And sometimes there’s even an arts and crafts vendor or two sprinkled in!)

To stay up-to-date with Highland Farmers’ Market news, follow them on their Facebook page, which also features the occasional fun giveaway or a delicious recipe!



Big Fish CiderBig Fish Cider Co. is a microcidery located on Spruce Street in Monterey, Virginia. (If you get lost in the complex town of Monterey, just look for the BIG trout behind the Monterey Courthouse!) Local Cidermaker Kirk Billingsley and his crew create uniquely-flavored ciders using locally-grown apples and traditional techniques. Additionally, their cider is available in a range of off-dry to semi-sweet blends and seasonal offerings. (One of our favorites is Church Hill Blush!)

The Big Fish Tasting Room is open Fridays from 4:00 to 7:00 pm and Saturdays from 2:00 to 7:00 pm. Stop by and see which selection tickles your taste buds the most! (And if you happen to be free on a Friday, visit between 5:00 and 7:00 pm. There’s usually a jam session featuring local bands and musicians!)





The Curly MapleIn the mood for a sweet treat? The Curly Maple has you covered! In addition to carrying locally-sourced products, such as meats and maple syrup, this former general store turned coffee shop/eatery/grocery stop is also home to one of the county’s most beloved bakers – Melissa Moyers, who is famous county-wide for her culinary talents.

On any given day, you can handpick your favorites from a selection of cookies, cakes, and candies. Recent creations are presented with rustic elegance in an old antique display, which was donated by Dorothy Colaw Shepherd, a cherished 92-year-old lady who visits the establishment for coffee every morning. (Sit down and talk with her. She doesn’t know a stranger, and she can tell some great Highland County stories! As do her compadres that sit with her! )




Virginia Trout CompanyOne thing Highland County is know for besides that iconic maple syrup is their delectable Allegheny Mountain Trout, which is available at the Virginia Trout Company on route 220 north approximately 4-5 miles from Monterey. Here you will find a selection of whole, filleted, or smoked trout that you can bring back to Blue Grass Cabin and pop in the oven or throw on the grill.

While you’re there, gander at the fish swimming in ponds fed by a natural stream that flows right out from under the mountain. This is a great activity for kids and families! You can even feed the fish or toss in a line and catch your own! (Just bring your own pole.) The guys at the Virginia Trout Company will even clean your catch for you!




Alleghany MeatsAlleghany Meats is located just a couple miles north of the Virginia Trout Company. So you can get your fish and meats in two close, conveniently-located locations! Customers can visit the facility and market from 8:00 a.m. to 5:00 p.m. and shop a rotating stock of frozen beef, bison, hog, goat, and lamb from local producers. You can call ahead to see what’s in stock and even place an order for pick-up.

Established in 2012, Alleghany Meats is a USDA-inspected, Animal Welfare Approved, value-added slaughter and processing facility that bridges a gap between local meat producers and their customers. This facility works with local meat producers to offer the finest quality USDA-inspected and custom meat processing options, including smoked products. For more info about Alleghany Meats, visit their website!



Sugar Tree Country StoreSugar Tree Country Store and Sugar House is a small retail and wholesale store located just off route 250 in the village of McDowell. Owned and operated by Glenn and Fern Heatwole and family, the store stocks a variety of pure maple products, jellies, honey, candles, hand-crafted toys, baskets, pottery, and many other products (including homemade Apple Butter!) If you love old general stores, this is a great one to explore!

The Heatwoles gather “sugar water” from local sugar maple trees growing at elevations of 3,000 to 4,000 feet. After collection, they bring the “water,” or sap to the sugar house, which is located behind the store, for boiling and syrup creation. Want to know more about the process? Ask them! They love answering maple questions! (Just don’t plan your visit on a Sunday as they close to observe a day of rest and spend time with their family.)

An Extra Tip! Sugar Tree Country Store is located next to the Highland Historical Society! Visit two attractions in one trip!