Kick The Winter Blues: Plan a Warm-Weather Highland Vacation

Written By: Dorothy Stephenson

In November, December, and even a bit into the new year, some of us enjoy seeing those white, angelic flakes fall. Especially when we’re listening to “It’s Beginning to Look A Lot Like Christmas,” and you’re gathering with family and friends for the holidays.

But about the middle-to-end of January when those puffy flakes have turned to mud, you could care less if you ever see another snowflake again. If you’re like me, you’ve got every light on in the house trying to manifest a bright environment… at 5:30 in the evening… when the sun is supposed to be shining! 

So what do you do? 

Plan Spring or Summer vacation!

Now, I’ve always said, “If I didn’t live in Highland County, I’d vacation here,” so I decided to outline what I’d do on my Highland County trip. (And, it offers a quick guide for you as well!)


#1: Reserve a Secluded Cabin

I’m an introvert. So, while I like to enjoy new places and things, I prefer to do it around as few people as possible. One thing about Highland? There are plenty of places to be alone unless you choose to be social. Personally, I’d spend most of my days soaking up the sun with a good book in my hands at any of the well-kept, quiet cabins Highland County has to offer. A few I’ve personally been to and can recommend are:

Of these, Eagle Annie’s Cottage, Laurel Point Bed & Breakfast, and Mill Gap Farms are good choices if you don’t want to be disturbed, but don’t mind people being nearby. 

Now, if an establishment isn’t on this list, I’m 99% sure you’ll still be selecting a wonderful place to stay. Like I said, these are just the ones I’ve been to.

#2: Learn About Local Culture

One thing I love to do no matter where I go is dig into local history and culture. Knowing the trials and tribulations our Highland County ancestors had to endure to settle this rugged, untamed land, I find it fascinating to simply ride back roads through areas like Bolar, Hightown, and Blue Grass (where my ancestors settled) and imagine what it would’ve been like to live, work, and survive here… when this area was truly remote. Back in the days when your “grocery store” was your garden and farm yard. A trip to the Highland County Museum can also give you real glances into the history of Highland County. One thing’s for sure though, you don’t really have to go looking for a glimpse into our county’s very early days of settlers and indians, founding families, and a wild frontier.

#3: Catch a Fish

Even if you don’t catch anything, camping out next to the river for the afternoon with your snacks and beverages is pretty darn relaxing. Toss a line in the water, and just wait for supper. Throughout my childhood, my dad and I would go fishing in the Jackson River. Unfortunately, there’s no public access to the Jackson in Highland County. (Not that I know of anyway.) However, the Bullpasture River, which is accessible via the Highland Wildlife Management Area (fishing license required) is as equally as beautiful, relaxing, and fish-friendly. Additionally, Hiner Town Trout Fishing also offers an option conveniently-located just outside of Monterey, and the Virginia Trout Company (now owned and operated by Laurel Hill Trout Farm) sells fish processed on-site and ready-to-cook. Or, you can bait a hook to catch your own. 

If you’re looking for more of an adventure, pack your camping and fishing gear and head out to the Laurel Fork Proposed Wilderness Area.

#4: Go Shopping

Ok… (Cracks knuckles) Here we go… No, Highland County doesn’t have a huge shopping mall or district; however, I LOVE the shops we have! (And for husbands who don’t like shopping, it gives wives their quick shopping fix without torturing the fellas!) For starters, Sugar Tree Country Store in McDowell is awesome. Not only are they one of our Maple Syrup producers, but they also have all kinds of fun things – pottery, other food goodies, unique kitchen items – just a cool, historic general store. Twice is Nice is a second-hand clothing store with great deals on clothing for men, women, and children as well as boots, purses, jewelry, etc. Right next door, The Curly Maple, another general store (but a recently-renovated one), has grocery items, but also local gift items as well. Though their stock changes in and out on occasion, they’ve recently featured stained glass, floral arrangements, barn quilts, photography, artwork, handmade soaps and salves, wood working, wool products, local maple syrup, local cider, baked goodies, and more. One of Monterey’s newest shops is Jenny Wren Gatherings – antiques, collectibles, vintage children’s toys, furniture, crocks, vintage baskets, old glassware, vintage kitchen utensils, woodworking, decorative shelves… a plethora of fun, little treasures!! Definitely my kinda shop!

#5: Explore the Barn Quilt Trail

Highland County’s Barn Quilt, which features almost 60 colorful works, was the first of its kind in the state of Virginia. (And, the barn quilts in the brochure aren’t the only ones in the county!) Some of the creations are traditional barn quilt patterns; however, others are unique designs. Some even have special meaning behind them, such as “Jacob’s Ladder,” which is featured at Dividing Waters Farm in Hightown and named after Jacob Hevener, a legend of a man who did so much for our county during his time here. The trail also features Virginia’s 50th LOVEworks project, which is patterned with (you guessed it!) barn quilt designs! There’s also a bonus find – a small barn quilt hidden somewhere on the trail and pays tribute to its owner’s massive salt and pepper shaker collection. Can you find it?

#6 Take a Day Trip

A friend of mine (who happens to be a former tourism director) describes Highland County as the hub to a spoke of many potential day trips. Downtown Staunton, Seneca Caverns, the Green Bank Observatory, Snowshoe Mountain, Cass Scenic Railroad, Cranberry Glades Botanical Area, and Blackwater Falls State Park (to name a few) are all within an easy, scenic 45 minute-1.5 hour drive away. If you stay in Highland County for a week or so, you can break up a couple different road trip days with some chill-axin’ (aka: relaxing) at your cabin or lodging establishment of choice.


Writing this makes me want to go on vacation now! Actually, it really makes me want to plan a “stay-cation” since I’m blessed enough to live in this wonderful place. 

Happy travel planning!


About the Author

Blog Designer & Editor-in-Chief

Dorothy Stephenson grew up on her family's cattle operation in Meadowdale, located in the southwest corner of Highland County. When she wasn't on horseback helping her father gather and work cattle, you'd likely find her (still on horseback) jumping creeks in her family's nearby "Big Pasture." Today, though she doesn't ride horses much anymore, she has her own cattle, land, and expansion plans for a farm. Additionally, (and with the inherited, Stephenson, entrepreneurial spirit) she owns two small businesses in Highland County - Sundance Media & Design and Sundance Studio & Productions, which houses another of Dorothy's long-time loves - Clogging. Dorothy loves exploring new places, skills, and ideas, and she intends to live life to the fullest as long as it will let her. (Oh! And she LOVES Christmas!)


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