Winding Roads & Historic Gems
Home / Trips / Winding Roads & Historic Gems

Winding Roads & Historic Gems

Winding Roads & Historic Gems

$65.00 $55.00 CAD
Sale Sold out

One trip is required per group.

* "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)

WHAT TO EXPECT

Discover photo-worthy hidden gems along winding roads as you make your way to an iconic road trip destination filled with history and views. 

Trip Highlights

  • Make a new furry friend
  • Charming small towns to explore
  • Gorgeous drives and scenic photo ops
  • A few wineries and breweries
  • Lots of easy outdoor activities

AVAILABLE TO DEPART

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.

SUGGESTED FOR

  • Couples
  • Outdoor Adventurers
  • Weekends Away
  • Girlfriend Getaways
Winding Roads & Historic Gems
Winding Roads & Historic Gems
Winding Roads & Historic Gems
Winding Roads & Historic Gems
Winding Roads & Historic Gems

Itinerary

STOP 1

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.

STOP 2

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.

STOP 3

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.

STOP 4

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.

Region

winding_roads.png

Can depart from

Washington DC Area, Baltimore Area, Winchester VA Area, Alexandria VA Area

Before you go

What You'll Need to Bring

  • Walking Shoes
  • Camera
  • Sunscreen (lots of easy outdoor activities)
  • Water
  • Road Trip Snacks

Additional Details

  • Kid-Friendly
  • Dog-Friendly
  • Accessible

FREQUENTLY ASKED QUESTIONS

We're here to help!

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.

Customer Reviews

Based on 3 reviews
100%
(3)
0%
(0)
0%
(0)
0%
(0)
0%
(0)
C
Cynthia Hendren
Overall, how would you rate this trip?:
I would not recommend this trip
Excellent! I would definitely recommend this trip
Rate how active the trip was:
Not very active
Very active
Rate how accessible the trip was:
Not very accessible
Very accessible
Rate how 'unique' the stops were:
Not really
Yes, very unique!
Winding Roads and Historic Gems

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.

C
C.
Overall, how would you rate this trip?:
I would not recommend this trip
Excellent! I would definitely recommend this trip
Rate how active the trip was:
Male
Very active
Rate how accessible the trip was:
Not very accessible
Above 60 years old
Rate how 'unique' the stops were:
Not really
Yes, very unique!
Been before, but discovered new things!

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.

A
A.
Overall, how would you rate this trip?:
I would not recommend this trip
Excellent! I would definitely recommend this trip
Rate how active the trip was:
Male
Very active
Rate how accessible the trip was:
Not very accessible
Above 60 years old
Rate how 'unique' the stops were:
Not really
Yes, very unique!
great idea

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.