Print Full Itinerary
Itinerary: Subject to change due to local conditions, unforeseen events, or more interesting as yet unplanned awesome experiences that become available
Overview:
There are special places hidden throughout the U.S. where the past still speaks through the natives and immigrants who sowed the seeds of innovation and independence to create the spaces that exist today.
The small mountain towns in the rolling foothills of the Blue Ridge Mountains of Virginia are such a place where intriguing history is waiting to be discovered and experienced. Join us as we explore a region filled with winding scenic roads that pass through farmlands, quaint towns and wonderful wineries.
We’ll stroll tree-lined streets of delightful downtowns, visit the roots of history at Monticello and Montpelier where the past is abundantly present, see breathtaking views from the mountain tops and wander through magical gardens. From old jails and antiques to gorgeous plantation homes and a giant nutcracker head, there’s an adventure around every corner.
Why not leave NJ behind and step back to a simpler time where fast-paced life melts away and relaxation can be rediscovered. And who knows, along our historic journey we may just uncover secrets from the past that connect us and help to inform the path ahead.
Day One: Sweet Shepherdstown
As we make our way south, we must stop by the quaint town of Shepherdstown nestled along the banks of the Potomac River.
Stretch your legs and take a wander along the charming streets to see what fun surprises are in store. You just may run into the cute Little House or feel like you’re being watched by the Seeing Eye on the historic Public Library building with a very storied past.
Don’t miss taking a step back in time at O’Hurley’s General Store and be on the lookout for the Town Run fed by six natural springs that allow its flow to meander all throughout town. You’ll be surprised at where it might just pop up next!
And of course, grab some lunch at one of the many restaurant choices along your wanders.
Hidden Bamboo Forest:
The adventures don’t end here. A hidden bamboo forest lies near the State Arboretum of Virginia, so let’s see if we can find it!
Once inside this captivating green space, have a quiet, peaceful meditative moment.
Mayhurst Estate:
Soon we’ll arrive at the Mayhurst Estate, a special historic place that stands as a testament to the elegance and grandeur of a bygone era. Once you step inside, you’ll immediately sense how its timeless beauty of the past meets the luxury of the present.
Take a stroll in the gardens emerging from spring that will ignite your sense of wonder, witness a sea of ivory and pink blossoms from the Magnolia Grove or venture out on a meandering nature trail through the woodlands and meadows.
Since it’s too lovely here to leave, we’ll enjoy an included takeout dinner from a nearby local spot.
Day Two: LOVEworks
Wake up to a home cooked breakfast as you enjoy the serenity of the Mayhurst Estate.
Today will be filled with history and also fun. Along our journey keep an eye out for Virginia’s iconic LOVEworks. Since Virginia is for lovers, artistic LOVE creations can be found in every corner of the state.
James Madison's Montpelier:
Step into history at the lifelong home of James Madison, fourth president of the U.S., father of the constitution, and architect of the Bill of Rights.
On the guided Highlights Tour, we will have a look inside Montpelier and hear stories that focus on James and Dolley Madison’s cultural and political impact along with an understanding of the lives of the enslaved community and their descendants’ struggle for freedom and equal rights.
Take time to wander the grounds and visit the family cemeteries, Annie duPont Formal Gardens, and Mr. Madisons Temple and see if you can spot the LOVEworks.
Market at Grelen Lunch:
Onto an included lunch at a most spectacular spot, The Market at Grelen.
As we wait for our lunch to arrive, browse the enchanting European style Garden shop filled with lush greenery, vibrant blooms, and décor treasures and another LOVEworks spot.
Monticello:
Our second brush with history is at Thomas Jefferson’s Monticello, an autobiographical masterpiece that’s been designed and redesigned and built and rebuilt for over forty years.
The Highlights tour will guide us through Monticello’s first floor rooms and outdoor spaces as we learn about Thomas Jefferson’s life and slavery on the plantation.
Wander the expansive grounds, join another guided outdoor tour, and visit the various exhibits and daily programs.
Downtown Orange:
This evening let’s take a moment to explore downtown Orange while finding a great restaurant for a delicious dinner on your own.
Day Three: Giant Nutcracker Head
Our adventures start with a Giant Nutcracker Head! An old tar silo has been whimsically transformed into a 30-foot-tall nutcracker head, quite a rare sight!
Charming Culpeper:
The scenic country roads lead us to the charming small town of Culpeper where there’s a story behind every storefront and a reason behind every restaurant.
Discover all the town’s secrets at the Museum of Culpeper History that reveals stories from the time the dinosaurs roamed here to when soldiers camped and fought here.
Take a walk along Main Street and find a tasty lunch or browse the shops along the way. It’s worth a wander on Culpeper’s oldest and most picturesque streets, South East Street, lined with Greek and Colonial Revival homes dating back to 1831.
Barboursville Vineyard:
If you weren’t already aware, Virginia has a great climate for winemaking, a dream of Thomas Jefferson.
At the Barboursville Vineyard we’ll get a taste of the area’s best wines while exploring what was once one of Jefferson’s true architectural gems.
The Landmark Ruins with its elegant Palladian proportions set upon a gentle knoll. Cheers to a great day!
Gordonsville:
The cute southern town of Gordonsville lies at the crossroads of history, so we must make a stop.
Take a stroll and wander down Main Street and side streets among historic buildings to sense all the town’s character and charm.
Let’s return to our serenity at the Mayhurst Estate and enjoy a quiet, relaxing evening here with an included takeout dinner with a specialty from Gordonsville and a story to boot!
Day 4: Old Town Warrentown
More fascinating history awaits discovery in two old jail buildings from the 1800s at the Fauquier History Museum in the quaint town of Warrenton.
Let curiosity lead your way through the past and see what exciting things are revealed.
Now take a wander along the brick sidewalks through Historic Old Town Warrenton, find a tasty lunch, then explore the galleries and shops.
Historic Oatlands:
Step into a historic landmark at Oatlands and walk where generations before us lived, worked, and dreamed.
A guided tour will immerse us in the site’s history as we walk through the mansion’s elegant spaces, then we’ll step into the lovely walled gardens for some springtime colors.
Let’s make our way back home to the solitude of the Mayhurst Estate and enjoy our last night here with an included takeout dinner.
Day 5: Birdsong Pleasure Garden
A delightful scenic drive into the Shenandoah Valley will lead us to a special private garden paradise at the Birdsong Pleasure Garden.
Wander through the picturesque native garden spaces with broad mountain visits as you hear a distant sound of water from a fountain or a creek.
Like the Pleasure Gardens of Georgian England, stroll with leisure over the many grassy and smooth woodland paths and let the cares of the world melt away.
Bonnie Blue Lunch:
Hope you’re hungry because the downright best BBQ spot is not too far for an amazing, included lunch at Bonnie Blue Southern Market & Bakery.
Old Town Winchester:
If we’re up for a quick walk after consuming so many calories, we’ll take a short stroll into Old Town Winchester, a quaint pedestrian walking promenade with historic buildings and charming ambiance.
Now that we’re ready for a rest, nap away and we’ll be back in New Jersey before you know it.
Pricing & Departures:
Departs Ridgewood’s Graydon Pool at the corner of Linwood Ave & Northern Parkway at 7:00 AM and returns at approximately 8:30 PM
Departs Madison’s Kings Road Parking Lot, 62 Kings Rd. at 7:45 AM and returns at approximately 7:45 PM
Departs South Plainfield High School at the end of Lane Ave at 8:30 AM and returns at approximately 7:00 PM
Price per person is $2,250 Twin & $2,850 Single. No reservations accepted without a deposit of $350 per person. Make checks payable to “Group Tours & Travel” and mail to our address above. Final payment is due February 1, 2026. There are no refunds if cancellation occurs after February 1, 2026. Travel protection/cancellation coverage is available and highly recommended, but not included. Educated Wanderer is not responsible for any delays, cancellations, injuries or circumstances beyond its control and reserves the right to change the itinerary. All trip components are subject to change in accordance with Government, State and Local guidelines and/or mandates. This tour will run rain or shine.
Upon submitting final payment you are agreeing to our new policy.
Wet Blanket Policy:
Wet blanket
– a person who makes it difficult for other people to enjoy themselves by complaining, acting negatively, creating drama, etc.
– one that quenches or dampens enthusiasm or pleasure
- Our philosophy of travel involves getting out of the ordinary to experience other cultures and places with an open minded attitude and flexibility. Since as in daily life, anything can and will happen, let’s embrace these situations with acceptance and understanding because they will either lead to an unexpected, amazing experience or positive learning experience.
- If anyone brings along excess baggage such as incessant complaining, under the breath rude comments, outward negativity or other such behaviors that infect the entire group or individuals, we have the exclusive right to remove them from the tour at their own cost with no refunds. (yes, this means you)
- If any major concerns arise during a tour, please just come talk to us and we’ll work it out!
The Educated Wanderer
Group Tours & Travel
PO Box 35 Henryville, PA 18332
973-513-9001
