Middleburg, Virginia, has many unique stores to keep shoppers busy for hours. Guess Where Trips includes Middleburg in its Tiny Towns tour. Photo courtesy of Long & Foster

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Guess Where Trips mails you everything you need to know about your self-guided road trip. Locations and directions are revealed one at a time, to maintain the air of mystery. These packages make good gifts for people with a sense of adventure. Photo courtesy of Guess Where Trips

The brown cardboard box that arrived in my mailbox labeled “Ready for a Road Trip?” instantly made me want to hit the open road. Inside were five booklets: “Before You Go” and four more describing stops for a six-to-eight-hour road trip to explore “Tiny Towns.”

The box was from Guess Where Trips, a unique travel planning company founded in 2020. “Guess Where Trips will show everyone something new,” according to its website. “And because no one will have to spend hours planning, everyone can sit back and enjoy the ride.”

Last summer, the company, which offers more than 50 trips in the U.S. and Canada, introduced five new itineraries in the Washington, D.C. region, including Tiny Towns; Hikes, Haunts and History; and Waterside Bliss. The self-guided tours are suitable for anyone who wants to explore new places without a guide.

“Families, seniors, young adults — our trips are designed for everyone,” said founder Jessica Off. “People also love to give our packages as gifts, and we’ve even had several marriage proposals during trips.”

How it works

Just type in your ZIP code on the Guess Where website, choose your interests, such as wineries or outdoor activities, and one-day trip options will pop up.

The “guess” in Guess Where is the “mystery” element. You won’t get the detailed itinerary until you pay $65, which does not cover gas, food or admission fees. The website hints at destinations with trip names like “Winding Roads and Historic Gems,” but you do not get specifics until you pay.

The trip materials recommend driving to four places in one day, with optional stops. They even suggest how much time to spend at each place. All stops are free.

Guess Where provides some facts, often a little history and some tips, like restaurants to try. They provide a map and recommend using a GPS device to navigate.

The website suggests the best time of year to go and rates the activity level, accessibility, and pet- and kid-friendliness of each stop.

Guess Where experts have researched and vetted all stops. Nevertheless, reading the “before you go” packet and checking online updates can help avoid snafus.

My trip: pros and cons

I live in Northern Virginia and chose the trip called “Tiny Towns,” not knowing which direction I’d be going or to what state.

When my box arrived in the mail, I discovered that the towns turned out to be four Virginia hamlets along route 50 west of Dulles Airport: Aldie, Upperville, Middleburg and Boyce.

These towns have a range of attractions, including a 19^th-century mill, wineries, a stone bridge with Civil War connections, trendy shops and the state arboretum.

My first stop was Aldie Mill Historic Park. The Guess Where packet gave some history — President James Monroe ground his grain there — and a sign said it is the “last standing grist mill in Virginia with tandem overshot waterwheels.” I found myself wanting to know more about the mill’s mechanisms, the architecture and building materials, but with no one around, I left there wondering.

For some, the historic town of Middleburg, founded in 1787, is appealing because it offers many upscale shops and restaurants. Guess Where recommended spending an hour to an hour and a half here, but for me, that was far too short.

A deli lunch alone took 30 minutes. Sampling four recommended shops along the main street’s four blocks took another hour. Guess Where did not recommend visiting either of two local museums.

The Middleburg area is known as “horse and hunt country,” so horse and fox imagery seem ubiquitous — in statuary, in art galleries and on street flags, dishes and T-shirts. Horse trailers rumble through town.

To get a better feel for the locale, I opted to deviate from the itinerary and visit the National Sporting Library and Museum, which promotes the culture of equestrian, angling and field sports. Omitting this stop, so central to the region’s mystique and culture, seemed like a big gap in the trip materials.

Consider Googling for more info

The last stop, the State Arboretum of Virginia, could easily have taken half a day, but Guess Where recommends one to two hours. The materials describe the site’s history, including its days as a plantation that enslaved 72 people.

While that’s interesting, most visitors go to an arboretum to see trees and vegetation. Guess Where’s materials devote two sentences to the extensive tree and plant collections there and nary a mention of wildlife.

Presumably, one could go to a website and get more information while on site, but when I travel, I want to absorb the places fully and get questions answered, not fiddle with a phone or navigate websites.

Still, I appreciated Guess Where’s perks; it does the planning for you and can introduce you to new adventures. Since no reservations or tickets are involved, you can be flexible.

The trips nourish one’s sense of adventure while providing some structure. The “mystery” part is an enticing tease.

Would I do it again? Yes! I’m ready.

To find out more or send a mystery trip to a friend, visit guesswheretrips.com.