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.

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.

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This trip can be done year-round from Thursday - Sunday. We do not recommend traveling Monday through Wednesday. One farm option on stop #1 is closed from November - March.

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

Wander through a gorgeous 19th century town and learn more about the historic buildings. A roadside farmers market and a couple of antique stores make the perfect pit-stop. Drive time to the third stop is 20 minutes.

* "PDF Instant Download" means the trip will be sent by email as a PDF document, and not by mail (the email is sent immediately after completing your purchase)

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We had so much fun getting away. We didn’t do this on one day but spent one night at the last stop which made the trip more relaxing. We went at our own pace knowing we did not need to rush through. Will definitely do another trip.

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.

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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.

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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.

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had a nice time seeing new places around us. family friends were in town and this felt like the perfect thing to do together. very impressed.

Your end destination packs a punch. With so much to do, we've recommended a ton of our favorite things. From outdoor adventures to historic photo ops, you won't be disappointed.

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.

First Stop: No fee Second Stop: No feeThird Stop: No feeFourth 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.

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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.

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This area attracts epic brewmasters and award-winning wine makers and now you get to experience all they have to offer. Drive time to the fourth stop is 20 minutes.

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 milesFrom Alexandria, VA:2 hours and 47 minutes / 152 milesFrom Winchester, VA:2 hours and 11 minutes / 92 milesFrom Fredericksburg, VA*:4 hours and 15 minutes / 224 milesFrom Baltimore, MD:3 hours and 20 minutes / 170 milesFrom Columbia, MD: 2 hours and 55 minutes / 155 milesFrom Annapolis, MD: 3 hours and 46 minutes / 199 milesFrom 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.

Who wouldn't want to start their day with cute farm animals or a stroll around a historic park with gorgeous gardens? Note that the farm option is closed from November to March. Drive time to the second stop is 15 minutes.

I've been to this particular area before but we were impressed with how many more things there are to do in this area. Can't wait to try another trip! Tiny Town Tour is next on my list.

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