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

Winding Roads & Historic Gems

Winding Roads & Historic Gems

$65 USD
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.

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? 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

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:

3 hours and 5 minutes / 139 miles

From Fredericksburg*:

4 hours and 15 minutes / 224 miles

From Baltimore:

3 hours and 20 minutes / 170 miles

From Columbia:

2 hours and 55 minutes / 155 miles

From Annapolis:

3 hours and 46 minutes / 199 miles

From Dale City:

3 hours and 7 minutes / 167 miles

From Harrisonburg:

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 year round from Thursday - Sunday

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 2 reviews
100%
(2)
0%
(0)
0%
(0)
0%
(0)
0%
(0)
C
C.
Overall, how would you rate this trip?:
Excellent! I would definitely recommend this trip
It was OK, I might not recommend it to others
Rate how active the trip was:
Very active
Male
Rate how accessible the trip was:
Very accessible
40 to 60 years old
Rate how 'unique' the stops were:
Yes, very unique!
Not really
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?:
Excellent! I would definitely recommend this trip
It was OK, I might not recommend it to others
Rate how active the trip was:
Very active
Male
Rate how accessible the trip was:
Very accessible
40 to 60 years old
Rate how 'unique' the stops were:
Yes, very unique!
Not really
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.