Home Travel USA A One-day Surprise Road Trip: You’ll know it when you get there

A One-day Surprise Road Trip: You’ll know it when you get there

The author’s husband prepares for their Surprise Road Trip Photo by Fyllis Hockman.

“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, 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 drive through scenic countryside – is there any other kind? – welcomed us to Aldie, Virginia – and the Aldie Mill Historic Park. And what I learned upon my initial foray into surprise envelopes is 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.

The Aldie Mill in Northern Virginia was stop #1 on our itinerary Photo by Victor Block.

Time for “Second Stop.” The number of historical markers marking 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. And 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. It still feels like one.

As historic places abound throughout the town – over 160 structures listed on the National Register of Historic Places – we unfortunately arrived too early to dine at the famous Red Fox Inn, the oldest continually operated inn in the U.S.

The Red Fox Inn in Middleburg, Virginia is the oldest continually operated inn in the U.S. Photo by Victor Block.


And if you’re interested in hob-nobbing with the elite – metaphorically speaking – former residents of Middleburg include Jack and Jackie, Elizabeth Taylor and then-husband, John Warner, award-winning actor Robert Duvall and Sheila Jackson, the first African-American female billionaire. There are probably a number of equally famous horses around town….

Fourth Envelope -“Third Stop” — 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 very 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, 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.

There are a wide variety of gardens at the State Arboretum of Virginia including a 300-tree Gingko Grove.
Photo courtesy of Cvandyke/Dreamstime.com

The Sky Meadows State Park offers even more in terms of scenic overlooks and access to early-1800’s history 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!

A mid-19th century log house on a Colonial farm in Sky Meadows State Park, Virginia Photo by Victor Block.

And Guess Where Trips offer one-day self-guided, surprise road trips in 19 states and 4 Canadian provinces. What a wonderful gift idea assuming you have some adventurous friends…..For more information, visit https://guesswheretrips.com/en-us.

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