Winding Roads & Historic Gems

Please see the approximate driving distances below. Please note this just includes round-trip driving distances and not time spent at stops.

From Washington, D.C.:

3 hours and 5 minutes / 139 miles

From Alexandria, VA:

2 hours and 47 minutes / 152 miles

From Winchester, VA:

2 hours and 11 minutes / 92 miles

From Fredericksburg, VA*:

4 hours and 15 minutes / 224 miles

From Baltimore, MD:

3 hours and 20 minutes / 170 miles

From Columbia, MD:

2 hours and 55 minutes / 155 miles

From Annapolis, MD:

3 hours and 46 minutes / 199 miles

From Harrisonburg, VA*:

4 hours and 6 minutes / 228 miles

*We recommend booking an overnight hotel if the driving distance is greater than 4 hours round-trip.

This trip can be done any day throughout the year. One farm option on stop #1 is closed from November through March.

Featured suggestions are open Thursday - Sunday; however, there are alternative options if you go outside of these days.

We recommend leaving anytime between 9:00 am and 10:00 am. The later you leave, the less time you may have to complete all of the stops.

This trip is pet-friendly! At every stop there will be at least one option for you to explore with your furry friend.

Please note that our farm suggestion on stop one does not allow dogs. There is an alternative recommendation.

We recommended bringing up to 5 people on your surprise road trip.

If you're bringing a larger group, we highly recommend having one person in charge of booking reservations at the restaurants and attractions in advance. In your confirmation email, you'll receive a copy of the itinerary.

First Stop: No fee

Second Stop: No fee

Third Stop: No fee

Fourth Stop: There is a required $20 parking fee to explore the majority of our suggestions on this stop.

*Please note: gas, tolls, and food may be additional costs.

After booking your trip, we'll send you a confirmation email with a few recommended accommodation options.