“So where are we going?” I asked my husband. “You’ll see, “he slyly replied. So began
our surprise road trip adventure sponsored by Guess Where Trips’ Tiny Towns Tours.
Heading out from Washington, DC I giddily prepared for a day of…well, I had no idea.
What I did know was that there were five envelopes.
The Before You Go envelope lays out basic trip guidelines and sets the mood – as if my mood needed any more setting.
So emboldened, we headed out to our “First Stop” – as indicated on the second
envelope. An hour’s drive through scenic countryside – is there any other kind? – welcomed us to Aldie, Virginia and the Aldie Mill Historic Park.
Upon my initial foray into surprise envelopes, I learned that each stop has an option or two to explore – and a recommended eatery if sustenance is required.
The village of Aldie, established in 1810, houses one of the best-preserved historic mills
in the U.S. And not far away, we checked out an even more bucolic spot adorned by a
panoramic waterfall.
Time for “Second Stop.” The number of historical markers on our journey was a
harbinger of things to come. These Tiny Towns are historic…. Which perfectly delineated our next stop – Middleburg.
The delightful albeit upscale horse country venue dates back to the 18th century and its small charming main street is full of shops, restaurants and taverns.
A Surprise One-Day Road Trip Turns an Ordinary Day Into and Adventure
As is true of every stop, there are other options to explore. In this case, a vineyard, brewery and cider barn. Notice a pattern here? Admittedly, if I never have to take another winery tour, it’s still too soon.
But Greenhill Vineyards appealed because, as one of the oldest wineries in northern Virginia, it’s been a working farm since 1762. And it still
feels like one.
Photo by Victor Block
As historic places abound throughout the town – over 160 structures are listed on the
National Register of Historic Places – we unfortunately arrived too early to dine at the
famous Red Fox Inn. This is the oldest continually operated inn in the U.S.
Photo by Victor Block
If you’re interested in hob-knobbing with the elite – metaphorically speaking –
former residents of Middleburg include Jack and Jackie, Elizabeth Taylor and then-
husband, John Warner and the award-winning actor Robert Duvall. Also, Sheila Jackson, the first African-American female billionaire. There are probably a number of equally famous
horses around town.
Nature and History are Hallmarks of Guess Where Trips’ Surprise Getaways Through Small Towns Across America
The fourth Envelope and “Third Stop” was A Secret Bridge – and it pretty much remained so.
Any place not easily recognized by our GPS becomes a challenge and the Goose Creek Stone Bridge partially fell prey to that disadvantage.
The historic span, built in 1810, played a pivotal role in the Civil War when General Lee’s forces managed to capture it in a prelude to the Battle of Gettysburg.
The nearby town of Upperville – there’s always a nearby town – offers glimpses of other historic structures as well as dining alternatives.
Ah, but “Stop Four” brought us back up close and personal with nature. History also –
but more nature trails and gardens. A native plant trail, an herb garden, hiking trails
galore and an Experimental Farm devoted to environmental research and education.
And this, the State Arboretum of Virginia, is just one of three exploratory options on our end-of-journey journey.
300-tree Gingko Grove. Photo courtesy of Cvandyke/Dreamstime.com
Sky Meadows State Park in Northern Virginia is One of Four Stops on Our Northern Virginia One-Day Surprise Road Trip
The Sky Meadows State Park offers even more in terms of scenic overlooks and access
to early-1800 history. This comes in the form of the Mount Bleak House which showcases the life of a Virginia Farm family of that era.
For those looking for more of a challenge, there’s a two-mile loop trail over rolling hills and woodlands. Instead, we stopped by the charming tiny town of Millwood on the way home to make our day-long adventure last even longer – and to quietly revel in all that we saw and did that as of earlier today, we didn’t even know existed. Quelle surprise!
Photo by Victor Block
Guess Where Trips offers one-day self-guided, surprise road trips in 19 states and 4
Canadian provinces. Not only an unusual personal getaway for you and a partner but
what a wonderful gift idea assuming you have some adventurous friends.
For more information, visit https://guesswheretrips.com/en-us.
- Get a Taste of Americana by Exploring the Neighborhoods of US Cities - December 4, 2024
- A One-day Surprise Road Trip: You’ll Know it When You Get There - November 18, 2024
- Enjoy a Mystery Adventure With Guess Where Trips - November 5, 2024