36 Hours in Charlottesville

If you're in Virginia this summer, Charlottesville should be at the top of your must-visit places. Charlottesville is a small city nestled at the foot of the Blue Ridge Mountains and is most famous for being President Thomas Jefferson's home, Monticello. But there is so much more than that!


Let's take a look at the things you should add to your itinerary for your visit.

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Journey Through Hallowed Ground

For those of you taking a road trip through some of the states surrounding Virginia, who also love history, the Journey Through Hallowed Ground is something you must partake in. This journey which spans from Gettysburg, Pennsylvania, and culminates at Jefferson's Monticello, is brimming with Civil War history, historic homes and battlefields, farms, and other heritage sites.

Beaver Creek Reservoir

The Journey Through Hallowed Ground trek is a project from the National Parks Service and was thoughtfully designed to keep you engaged and educate you from beginning to end.

Delicious Food

Charlottesville is home to more restaurants per capita than any other American city besides New York City! From authentic Southern BBQ to elevated fine dining, Charlottesville has you covered. Local favorites include The Whiskey Jar and Le Petit Pois on the Downtown Mall and The BBQ Exchange in neighboring Gordonsville.

I always refer to Eater lists and keep up with the latest dining trends, and they have a great list for Charlottesville.

woman at farmers market

There are also several farmer's markets sprinkled throughout the city to stock up on an abundance of healthy snacks, local produce, and more if you're looking to cook your own food at an Airbnb.

Wine Country!

The people of Virginia have been producing some world-class wines for generations and the Charlottesville area is no exception. With more than 40 wineries in this down-to-earth destination, you're sure to find a bottle that'll go perfectly with your dinner tonight as well as one just waiting on special occasions!


There are many wineries to choose from, but some favorites are Pippin Hill and Jefferson Vineyards. Check out the breweries Starr Hill or the North American Sake Brewery at IX Park. 

The American Wine Girl lives in Charlottesville and has created a great guide to her local wineries.

Endless Hiking Opportunities

For those that love the outdoors, Charlottesville is an ideal getaway no matter the season. Hiking along the Shenandoah Trail, Skyline Drive, Old Rag Mountain, and Humpback Rock are all within twenty minutes of the small city.

Shenandoah Trail

Whether a novice or a pro, make sure you pack your safest hiking boots, SPF, and sunglasses (I like Maui Jims and RayBans so, of course, you know me, with all the misadventures, I also need several replacement lenses for Maui Jim sunglasses), and breathable clothes (I prefer Stio).

It's easy to spend your entire time in Charlottesville exploring the sheer majesty of The Blue Ridge. Go Hike Virginia has a great guide for all your hiking adventures.

World-Class Shopping

Maybe you're not the outdoorsy type and prefer a more leisurely vacation where you're strolling and shopping. For those who enjoy shopping, Charlottesville has as much to offer as big cities. From local favorite women's boutiques Scarpa or Eloise to famed children's toy store Shenanigans and so much more. Charlottesville is home to the country's longest pedestrian mall, known as The Downtown Mall.

Downtown Mall

This charming outdoor shopping experience is brick paved and lined with local boutiques, restaurants, and bookstores. At the end of “The Mall,” as it's known by locals, is the Ting Pavillion, which regularly features huge acts that you'd expect to see in major cities.


You can't visit Charlottesville without taking a guided tour of Thomas Jefferson's home, Monticello. This beautiful estate on the top of a little mountain is brimming with history, and the guides are eager to share more about its storied past. You get a glimpse into the dark chapter of American history – slavery – as well as a newfound appreciation for our nation's presidents.


This is my absolute favorite Presidential home, I visited it for the first time as a pre-teen and it has remained my coup de cœur.

Virginia as a state is known as the “Mother of Presidents” since more presidents are from Virginia than any other state. Plenty of those presidents spent time at Monticello with Jefferson.

In addition to the home, rich in art and historical relics, the grounds are breathtaking and feature the family cemetery and world-renowned gardens. You can even purchase some of the rare plants Jefferson had at his home from the gift shop to take home with you.


Another thing Charlottesville is known for is its many orchards. Depending on the season, you can pick fresh blueberries, apples, strawberries, peaches, or pumpkins at local orchards, Chiles or Carter Mountain.

apple orchard

Here is a list of orchards you can choose from.

The great thing about Charlottesville is you don't need to plan your visit much; there is so much to do within a very short drive or even walk one another. If you're in Virginia, this small city is a place that exudes Southern Charm but has progressed with the time and offers the most modern amenities. Happy Trails!

How about you? Have you been to Charlottesville? Are the things that you did you want to share? Do tell!

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Charlottesvilleapple orchardhiking trail

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  1. Amber Myers says:

    What an amazing area. I will have to go for sure. I would be all about the history.

  2. I’ve been to this area several years ago and Montecillo is a beautiful home to visit. The grounds are just beautiful.

  3. Melanie E says:

    It sounds like such a great place to visit. I think the hiking opportunities and food and wine sell it for me.

  4. Sounds like an amazing place to be. I’d love to visit some day. I love being able to see beautiful places like this.

  5. Tara Pittman says:

    Sounds like a nice place. My husband would love the bbq meals.

  6. Sandy N Vyjay says:

    Charlottesville has so much to offer. I am sure there can never be a dull moment here.

  7. Whitney Stewart says:

    I’ve always wanted to travel further north to like Maine and Virginia. Now I’ll really have to try and go in the near future!

  8. Melissa Dixon says:

    That sounds like a fun place to explore. I would love to take the family there and visit sometime.

  9. What a charming place to visit! Will have to plan on visiting there someday!

  10. Beautiful Touches says:

    These look like interesting places to visit, especially the journey through Hallowed Ground, the orchards, and Monticello itself!

  11. Lisa Charleston says:

    WOW, now this needs to be on my bucket list of places to visit. I would start off with the hiking opportunities!

  12. The hiking there really is nice. We always enjoy our trips up that a’way.

  13. Richelle Milar says:

    Wow! This sounds like a really wonderful and amazing place to visit! The whole family are going to love to be here!

  14. wow! Such a beautiful place that gives a lot. I would like to visit at least one of those 40 wineries.

  15. Zena's Suitcase says:

    You have given me so many reasons to visit this charming place!

  16. Marie Gizelle says:

    Hiking and wine…this resembles the area where I live….gotta love how one can be close to nature and enjoy the views. Amazing food I’m sure too!

  17. Angela Ricardo Bethea says:

    I’ve never been to Charlottesville before but that sounds like a great place to visit and explore sometime.