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3 Destinations, 4 Founding Fathers

Charlottesville, Orange and Fredericksburg, VA – George Washington, Thomas Jefferson, James Madison & James Monroe
Discover the stories of 4 of America’s most iconic leaders as you travel through the Central Virginia Piedmont region.

Summary

Contact

Fredericksburg
Victoria Matthews, Tourism Sales Manager
[email protected]
540-372-1216
groupsatfred.com

Charlottesville
Teresa Lamb, Sales Manager
[email protected]
434-972-4138
visitcharlottesville.org

America’s 250th Anniversary

On July 4, 2026, our nation will celebrate the 250th anniversary of the signing of the Declaration of Independence. This historic milestone is an opportunity for the country to pause and reflect on all that we have achieved in the last 250 years and consider all that work that is still unfinished. The signing of the Declaration of Independence may have started a revolution, but that revolution is far from complete. The Founding Fathers knew at the time of the Declaration’s signing that this was an experiment. They did not have all the answers, but they knew that future generations would work to improve upon the framework they created. By studying the events of the past and honoring the contributions of those who have come before, we inform the continued efforts towards a future that includes the rights to life, liberty, and the pursuit of happiness for all.

The State of Virginia played a significant role in the creation of the United States of America. From the first permanent English colony at Jamestown in 1607 to the ultimate battle of the Revolutionary War at Yorktown in 1781, Virginia’s history is central to this story. Many of the nation’s most distinguished and notable Founding Fathers resided in Virginia. Commander of the Continental Army, General George Washington, called the Commonwealth home throughout the entirety of his life. Learn more about the man who played such an important role in the outcome of the American Revolution by visiting the places he called home.

To stay informed about events related to the America’s 250th celebration in individual localities and throughout the country, visit the following sites below. Events will populate on a rolling basis so check back often for the most up to date information.

State of Virginia 250th Commission:
https://va250.org/
National 250th Commission:
https://america250.org/

Day 1

Arrive in Charlottesville in the afternoon and check into hotel.

Enjoy dinner on Charlottesville’s historic Downtown Mall. The Downtown Mall is a vibrant collection of over 120 shops and 30 restaurants housed in historic buildings along the city’s main street. Enjoy dining al fresco at a number of fine restaurants. After dinner enjoy shopping at one of a number of unique boutiques or listen to live music at one of several performance venues.

Charlottesville Downtown Mall lit up at night

Day 2

Front entrance of Monticello

Begin the day with a visit to Thomas Jefferson’s Monticello and get to know the author of the Declaration of Independence and the Statute of Virginia for Religious Freedom, the third President of the United States and the Founder of the University of Virginia. A self taught architect, Jefferson referred to Monticello as his “essay in architecture,” with construction continuing on the mountaintop for forty years. The final product is a unique blend of beauty and function that combines the best elements of the ancient and old worlds with a fresh American perspective. In addition to taking a guided tour of the House, explore the gardens and grounds, including Mulberry Row, the main street of the 5,000 acre plantation. Thomas Jefferson enslaved over six hundred people throughout his life. Learn about the men, women, and children who built Jefferson’s home, planted his crops, tended his gardens, and who helped run his household and raise his children.

After a morning of touring, make time for lunch and a little shopping at historic Michie Tavern (ca. 1784). Michie Tavern is located 1/2 mile below Thomas Jefferson’s Monticello. Servers in period attire offer bountiful Southern Midday Fare. The rustic restaurant setting renders a lunch dining experience rich in southern culture and hospitality for groups to enjoy. “The Ordinary”, is open daily and lunch is served from 11:30 am-3:00 pm. After lunch, guests may enjoy browsing in unique shops – all housed in distinct historic structures. The Tavern Shop and The General Store each provide a one-of-a-kind experience in addition to plentiful shopping opportunities. 

Michie Tavern building and stairs
aerial view of multiple structures on the Highland property

Approximately 4 miles away is James Monroe’s Highland. The former plantation, nestled in the hills of Albemarle County, was a working plantation in the early American economy, and home to scores of enslaved men, women, and children who performed the bulk of Highland’s production and maintenance. It was also the sporadic residence of fifth president, James Monroe, from the years 1799 to 1826. For years, public understanding of the site relied on incomplete evidence, so now historians and archaeologists are peeling back the layers of mystery and misunderstanding to uncover more of Highland’s past. The untold lives of enslaved people, a fire that destroyed the original main residence, alterations by later owners: these are some of the many stories coming to light in recent work. While on site, take a self-guided tour of the 1818 guest house and explore exhibits that focus on Monroe’s presidential years and show how Highland is a lens for understanding the early American history and present day legacies.

Complete your day with a visit to a nearby winery such as Jefferson Vineyards. Located just 10 minutes from downtown Charlottesville, Jefferson Vineyards is located in the heart of America’s most historic winemaking region, neighboring Monticello and Highland. Their award-winning wines range from delicate and refreshing, to elegant, full-bodied and rich.  Alternatively, pay a visit to Carter Mountain Orchard located just minutes from downtown Charlottesville and Monticello. At the orchard, visitors overlook lush groves and breathtaking views of the valley below. Against this stunning backdrop, families and friends pick sun-ripened peaches and crisp apples while breathing in the fresh mountain air. From season to season, there’s always something fun!

Day 3

Take a scenic drive through rolling hills and lush horse county on Constitution Highway (US-20) as you travel to James Madison’s Montpelier. Montpelier is the lifelong home of James Madison, Father of the Constitution and fourth President of the United States. Montpelier is more than just the home of one of America’s Founding Fathers; it’s a place where visitors can learn how the Constitution affects our everyday lives. It’s an ongoing archaeological dig that tells us more about 18th century life every day. It’s a destination for anyone who wants to know more about how the thinking of James Madison changed the world by engaging the public with the enduring legacy of Madison’s most powerful idea: government by the people. While on site take a “Highlights of Montpelier Tour” to explore the histories and legacies of James and Dolley Madison, the Enslaved Community and the Constitution as you journey through the landscape and inside the Madison’s home. Visit the award winning Mere Distinction of Colour exhibit to understand Montpelier’s connection to the national story of slavery – and discover the economic, ideological, and political factors that cemented it in the newly-created American nation and Constitution.

Montpelier mansion with trees in the background and large lawn in the foreground
Mary Washington House

Located 4 miles north of Montpelier is the town of Orange, VA. Stop for lunch at Orange’s Silk Mill Grill. Located in the historic site of a 1930’s era silk mill, this restaurant offers classic American surf ‘n’ turf dishes amid antique décor. Continue your drive on Constitution Highway (US-20) as you make your way north to Fredericksburg, VA. Acquaint yourself with Fredericksburg by visiting Mary Washington House. In 1772, George Washington purchased this home in Fredericksburg, Virginia for his mother. Mary Ball Washington spent her last seventeen years in this comfortable home. The white frame house sits on the corner of Charles and Lewis Streets and was in walking distance to Kenmore, home of Mary’s daughter Betty Washington Lewis. Tradition has it that, during the Revolution, General Lafayette came by the home seeking a visit with Mrs. Washington and found her working in her garden. The President-to-be came to this home to receive his mother’s blessing before attending his inauguration in 1789.

Next, pay a visit to the Rising Sun Tavern. Built by George Washington’s youngest brother Charles around 1760 as his home, this frame building became a tavern in 1792 when it was purchased by the Wallace family. It operated for 35 years as a stopover for travelers in the bustling port town of Fredericksburg. While it is no longer an operating Tavern, historical interpreters in period attire guide guests through the Tavern experience as if you were an 18th century traveler.

Dogwood tree next to the front porch of the Rising Sun Tavern

Day 4

A young George Washington walking towards Ferry Farm

Continue your exploration of Fredericksburg with a visit to George Washington’s boyhood home, Ferry Farm. George Washington’s Ferry Farm is where young Washington spent his formative years. The future general and first president was 6 years old when his family moved to King George County (now Stafford County), Virginia, in 1738.The guided tour of the Washington house replica explores the lives of George, his mother Mary, other Washington family members, and the enslaved community. The tour recounts the adversity these individuals faced after the death of Augustine Washington, George’s father. You can walk Ferry Farm’s grounds before and after your house tour. The Visitor Center features the introductory exhibit The Science of History at Ferry Farm with colonial and Civil War artifacts excavated at Ferry Farm and windows into the Archaeology Lab, where you can see archaeologists identify and study thousands of artifacts found at Ferry Farm.

From Ferry Farm, travel approximately 2 miles to the James Monroe Museum and Library. The James Monroe Museum is dedicated to the study, interpretation, and presentation of the life and times of the fifth President of the United States, James Monroe. The museum holds the country’s largest collection of artifacts and documents related to the fifth president of the United States. The museum was first opened in 1927 by Monroe descendants as a place to house their personal collections, which had been handed down through generations of the family. Eventually, the museum was turned over to the Commonwealth of Virginia and is now administered by the University of Mary Washington.

Mother and son walking in front of portrait of James Monroe

As you make your way to lunch, make a quick stop at Thomas Jefferson’s Religious Freedom Monument located on the Washington Avenue Mall at Pitt Street. It commemorates Jefferson’s Virginia Statute for Religious Freedom. The Statute became the basis for the religion clause of the First Amendment.

After a morning full of history, take a break and have lunch at one of over 40 chef or family owned restaurants in Downtown Fredericksburg. Whether you are looking for fine-dining or a quick sandwich, there is something to meet your cravings.

Bottles of Bowman whiskey sitting on top of a barrel

In the afternoon, sip and savor at A. Smith Bowman Distillery – Virginia’s oldest distillery, located just 5 minutes from Downtown Fredericksburg. Winner of multiple awards for their spirits, visitors to the area can experience a behind-the-scenes glimpse into the production of hand crafted spirits. Tours explore distillation, barreling and bottling of high quality bourbon. Products are available for tasting and purchase. 

Finally, enjoy a farewell dinner and a show at Riverside Center for the Performing Arts – Winner of the 2019 Theater of the Year for Central Virginia Award by Broadway World. Approximately 15 minutes from Downtown, the theatre is a traditional proscenium stage boasting Virginia’s only dinner theatre fly loft for exquisite sets and seamless transitions between scenes. It’s ever-widening reputation and recognition for production excellence has attracted performers from the Broadway stage and national-tour casts. Dinner Theatre patrons enjoy a three-course, chef-prepared meal served by an experienced staff of waiters, a service not generally found in dinner theaters elsewhere. 

group watching a show at Riverside Dinner Theater