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Top Tips for visiting Jefferson’s Monticello and Monroe’s Highland in Charlottesville VA PullOverandLetMeOut
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Top Tips for Visiting Jefferson’s Monticello & Monroe’s Highland

Thomas Jefferson and James Monroe were more than just presidents and founding fathers of the United States. They were also neighbors. Travel with PullOverandLetMeOut to discover the top tips for visiting Jefferson's Monticello and Monroe's Highland in Charlottesville, Virginia.
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Hi, I’m Anna Marie. I’m a wife, mother, Irish dancer, and pug mom living in North Carolina. I also love to travel. Come along for the ride! If you see something you like, don’t be afraid to say, ‘Pull over and let me out.’

Jefferson’s Monticello and Monroe’s Highland are only a few miles apart in Charlottesville, Virginia’s picturesque Blue Ridge Mountains. The two founding fathers chose this magnificent location steeped in natural beauty in Albermarle County for good reason. Today, visitors from all over the world travel to see their historic homes. Here are some top tips for planning your visit.

Tips for Visiting Jefferson's Monticello

Thomas Jefferson's Monticello
Thomas Jefferson's home, Monticello

Thomas Jefferson’s Monticello is one of those places that I could visit over and over. As a matter of fact, I have visited multiple times. Over the years, new details have emerged, the narrative has adjusted, and the experience has changed. However, with each visit there is something new to learn, see, explore, or understand that makes the visit worthwhile. Whether you’re a big history buff or a casual visitor, here are some tips to make the most of your time at this historic home.

#1 Purchase Tickets Ahead of Time

It’s not an absolute must, however, if you purchase tickets in advance, you will avoid the line. Monticello can get busy, especially during peak times, so purchasing prior to your visit will assure your entry. You will want to arrive at least thirty minutes prior to your scheduled tour time if you’re taking a guided tour to allow time for parking and catching the shuttle to the top of the mountain.

I last visited on an autumn Monday that wasn’t very busy so we were able to get tickets promptly on-site. I paid with cash and received my change back in two-dollar bills. Guess which president is featured on the two-dollar bill. 🙂

#2 Explore the Gardens

Thomas Jefferson was very interested in horticulture and various growing techniques. Consequently, he had magnificent gardens with an array of plants, flowers, herbs, and vegetables. Jefferson designed these gardens himself. Moreover, the views are breath taking. When we were there, the sky was filled with dramatic clouds, which added to the beauty of the scenery.

garden at Monticello
Jefferson had a keen interest in a variety of horticultural techniques.

#3 Visit the Visitor Center and Museum

The museum and visitor center provide context to Jefferson’s life and achievements. Likewise, a stop here gives background for what you will see during your visit. It’s also here that you’ll most likely run into Thomas Jefferson himself. Most Tuesdays through Saturdays during regularly scheduled hours, veteran interpreter, Bill Barker, frequents Monticello, greeting guests, answering questions, and portraying the third president.

I highly suggest taking the time to watch the movie about Jefferson in the theater. It gives a wonderful glimpse into the man, his life, his legacy, and his time at Monticello. They’ve also added more details about Sally Hemmings and a special focus on the enslaved people who resided at Monticello, providing fresh perspectives and concepts.

Additionally, there is a large gift shop you will want to visit, after touring, that is filled with books, souvenirs, and other Jeffersonian gifts.

#4 Take a Guided Tour

Consider taking a guided tour. They offer a variety of tours that give outstanding details and insights into Jefferson’s life, architecture, and significant contributions. And the guides do a wonderful job of captivating your attention and imparting facts. Every time I’ve visited Monticello, I’ve encountered excellent guides that make the visit all the more memorable and enjoyable.

Furthermore, there is a range of special tours such as the Highlights Tour, the Behind-the-Scenes Tour, and the From Slavery to Freedom Tour which are all first-rate, compelling, and educational narratives. I took my son several years ago and we enjoyed the Family Friendly Tour which is intended for children aged 5-11 but is suitable for both children and adults.

There are also audio self-guided tours if you prefer. These excursions are a terrific way to travel at your own pace while learning about everything you see.

#5 Study Jefferson's Innovations

In addition to being a statesman, a farmer, and a president, Jefferson was an inventor. Monticello is filled with his numerous innovations. It’s fun spotting some of his inventions such as the Great Clock, the automatic double doors, and the polygraph, which is not what we know as a polygraph today.

The home and the grounds are brimming with devices, contraptions, and a collection of inventions that were the brainchild of Jefferson. He was a true genius, and seeing so many of his gadgets gives a whole new appreciation for his mind and talents.

Thomas Jefferson's bed.
Thomas Jefferson slept here.
a mechanism on a desk
The polygraph that Jefferson invented.

#6 Explore on Foot

For a more active experience, consider hiking the Monticello Trail. It provides a scenic route through the woods and beautiful views of Monticello. Likewise, you can travel by foot to the Jefferson family cemetery to see Jefferson’s final resting place as well as the graves of his extended family.

However, should you prefer less walking, the shuttle that runs from the house to the visitor center makes a stop at the cemetery along the way. If mobility is a concern for you or someone in your party, Monticello does a wonderful job of assisting visitors with diverse abilities. You can learn more here.

Thomas Jefferson's grave behind a black gate with a coat of arms on it.
Jefferson's grave.
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Monticello and Highland are about 2 1/2 miles apart which makes it convenient to combine visits. The two properties have a noticeable difference, and time spent in either is fact-filled and insightful. Most visitors spend roughly 3.5 hours exploring Monticello and at least 90-minutes at Highland.

Tips for Visiting Monroe's Highland

a white house beside a yellow one
The back of what was the guest house at Highland.

A short drive from Monticello is the ash tree-lined drive that leads to James Monroe’s Highland. Though smaller in scale and grandeur, the story of this property is fascinating. Since my last visit in 2015, there has been confirmation of the original home’s foundation site and a new story to be told. Turns out what was assumed to be Monroe’s home was actually the guest house! Cared for by the college of William and Mary, this property is packed with history. Here are some tips for planning your visit.

#1 Combine with Monticello Visit

Because Monticello and Highland are so close to each other, it’s possible to visit both homes in one day. Monticello is larger and has much more to explore, so you can either plan to visit Highland before or after your time at Jefferson’s home.

Moreover, there are some ticket options that allow you to purchase a combination ticket for Monticello and Highland, providing a cost-effective way of touring both sites.

#2 Take a Guided Tour

Similar to Monticello, Highland offers guided tours that provide insights into Monroe’s life and the history of the property.

For our visit which was on a Monday morning, we had the guide all to ourselves. This made our time all the more special and personalized.

Our guide, Jeff, did an outstanding job of answering questions and explaining facts and details that gave us a new understanding of Monroe and his times. 

a dining table with a portrait above it
Many of Monroe's original furnishings are on display.

#3 Explore the Gardens and Grounds

Though not nearly as expansive as the grounds at Monticello, Highland has its own special charm with gardens and scenic grounds.

Take time to stroll the property, take in the views of the Blue Ridge, and examine the statuary dotting the landscape.

#4 Check for Events

Highland boasts a calendar filled with special events throughout the year. From the annual sheep shearing to the Commemoration of James Monroe’s birthday to American Girl Tea with Elizabeth Monroe to Home Educator Day, the events are many and popular.

If you discover a particular event that piques your interest, plan your visit to coincide with the festivities.

#5 Learn About Monroe's Legacy

Take the opportunity to learn more about James Monroe’s contributions to American history, including his role as the fifth President of the United States.

Monroe played an important part in the country’s founding and early days. From the American Revolution to his role in the War of 1812 to the Era of Good Feelings to the Louisiana Purchase and so much more. This is the place to immerse yourself in all things Monroe. 

Likewise, the gift shop offers a range of books about Monroe so you can take your history lesson home at the end of your tour.

I came away motivated to read up and learn more about James Monroe. For example, did you know he was Secretary of State and Secretary of War at the same time?

#6 Highland Rustic Trails

Similar to Monticello, Highland also features hiking trails. The Highland Rustic Trails make a nice addition to any visit, especially if you’re interested in encountering nature, exploring the ecosystem or catching a glimpse of some of the wildlife in the area.

 Highland is a historic property and a working farm so keep that in mind when planning your hike on the trails. Trail access is free from 11:00 a.m. to 4:00 p.m., with trail entry not permitted after 3:00 p.m.

a woman standing in front of a statue of James Monroe
You will find a statue of James Monroe in the garden.
a well with a Christmas wreath on it in a garden.
Explore the gardens and out buildings at Highland.

More Tips for Your Visit

While Monticello offers dining options at the visitor center at Farm Table and at the Farm Shop, you can also have an 18th century lunch nearby at the Michie Tavern.

This historic tavern serves a taste of the 18th century from 11:30 to 3:00 seven days a week. The tavern dates from 1784 and situated a half a mile below Monticello. They serve the tastiest fried chicken I think I’ve ever had.

Their pub is open on Friday and Saturday from 3:30 to 7 pm, should you find yourself thirsty after your tours. 

Step back in time and enjoy a hearty mid-day meal in a colonial setting. You’ll want to keep in mind that they only take reservations ahead of time for large groups of 15 or more.

Michie Tavern PullOverAndLetMeOut
Michie Tavern in Charlottesville, Virginia

The Monticello Wine Trail

Thomas Jefferson aspired for Virginia to one day produce wines that would compete with and surpass those he savored while in France. Although that didn’t happen in his lifetime, today, the Monticello Wine Trail consists of multiple award-winning wineries that would make Jefferson proud.

In fact, Wine Enthusiast Magazine has named the Monticello Wine Trail, Wine Region of the Year for 2023!

If you have time, it’s a terrific opportunity to visit one or more of the neighboring wineries. Select one of the many wineries in the Monticello AVA, sip, savor, and enjoy!

Visit Charlottesville

Charlottesville has a lot to offer beyond Monticello and Highland. This picturesque college town in the Blue Ridge Mountains, home to the University of Virginia, has a  wealth of things to do. From theater to dining to the famed downtown pedestrian promenade.

Likewise, there is a variety of tours, attractions, and places to stay that fit just about any traveler’s budget. For us, it’s a little over three hours from Raleigh, which makes it ideal for a quick over night getaway or weekend escape.

I love history, so whenever I get to include a visit to two president’s homes, a colonial tavern, and a winery, I’m a happy traveler.

a woman with a glass of wine sitting by a stone fireplace.
Enjoy one of the many beautiful wineries along the Monticello Wine Trail.

Take Away

Jefferson’s Monticello and Monroe’s Highland are two historic homes that provide visitors with an insightful glance into the life and times of the men, their families, and enslaved people who lived there. What’s more, they serve today to keep the stories alive and pass on to generations to come.

Both places do a phenomenal job of preserving history and welcoming visitors to see, learn, explore, and gain understanding. That to me, is what traveling is all about.

a fence in front of a mountain
View of the Blue Ridge from Highland.

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Top Tips for Visiting Jefferson’s Monticello & Monroe’s Highland

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