Scenic Charlottesville: A Guide to Hiking, Dining & History Near the Beautiful Blue Ridge Mountains

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Advisor - Tracy Burpee
Curated By

Tracy Burpee

  • Charlottesville

  • Active Travel

  • Arts & Culture

  • Food & Wine

  • Nature Escapes

  • Vineyard

  • Mountains

  • Outdoors

  • Foodie

  • History

Charlottesville's street view during daytime
Curator’s statement

Charlottesville, Virginia, is a college town that offers all the things one may want in one location. Perhaps best known for being the home to the University of Virginia and Thomas Jefferson’s Monticello, Charlottesville also boasts more vineyards than one can responsibly visit. It sits in the shadow of the Blue Ridge Mountains, so offers plenty of outdoor activities. When your day is done, Charlottesville offers cuisine on par with more cosmopolitan cities. Only a beautiful 2-hour drive from Washington, DC (or, there's a train!) and an hour from Richmond. It’s all too easy to run out of time on a visit to Charlottesville but it’s easy to go back!

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Where to stay in Charlottesville

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Things to do in Charlottesville

The Blue Ridge Tunnel is a historic railroad tunnel


Charlottesville is best known for its history of American Presidents who made it their home. Of the three (Jefferson, Madison and Monroe), Jefferson is revered around town and you cannot miss the references. No proper visit to Charlottesville is complete without a visit to Jefferson's house on the hill: Monticello. Tours of the home take visitors through Jefferson's life while displaying artifacts from every aspect. One will see souvenirs that Lewis & Clark sent back as well as inventions you never knew Thomas Jefferson created. Don't miss the clock in the entry!

On the other side of the same mountain one can find Ash Lawn, the home James Monroe called Highland. Quite different in style from Monticello, the two friends would ride between the two properties until their deaths.

Thomas Jefferson also had the vision and built his Academical Village in Charlottesville, known as the University of Virginia. The UVA Rotunda is a UNESCO World Heritage Site, as is the Lawn behind it. One can get a student guided tour almost daily, and it is so worth it. The most recent addition to UVA's offerings is the Memorial to Enslaved Laborers, memorializing those who built the University that we now admire. Check the schedule of events for cultural activities, sports and other things that UVA brings to the community while you're in town.


Nestled at the base of the Blue Ridge Mountains, you'll find Skyline Drive and the Blue Ridge Parkway meet just outside Charlottesville. In the Shenandoah National Park there are myriad trails of all levels, as well as south on the Parkway. Local favorite Humpback Rock is a quick hike that resembles a bumpy Stairmaster - the views from the top are worth the burn!

New, cool and flat is the reopened Blue Ridge Tunnel. Accessible in every way (strollers & wheelchairs as well as entry from both sides), you'll want to bring a flashlight for the darkest parts in the middle. This is a great thing to do with kids or on a very hot day.


If Mr. Jefferson didn't bring back the vines from France, Charlottesville wouldn't be on the list of must-visit wine locations. Regardless of your direction of travel, you'll be able to find vineyards to visit. A few highlights around town:

King Family Vineyards has award-winning wines as well as community/family-friendly polo matches on Sundays through the warmer seasons. Food trucks are plentiful and it's a picnic-style atmosphere literally at the base of the Blue Ridge.

Mt. Ida Reserve has a brick oven for pizza and amazing views to the East. A wonderful property.

Blenheim Winery is on the same mountain as Monticello. Backed by Dave Mathews (DMB), it's a fairly sustainable vineyard that will take you back to the rustic days of wine. Fun fact: Dave designs the labels for the Painted Series of wines every year!

Oakencroft Winery is quite close to town but you'd never know it when you're there. Incredibly small, (reservations are the only way to taste), it is completely sustainable and focuses on environmentally sound wines.


Heading toward Rt. 151 you'll find Pro Re Nata brewery in Crozet with trucking containers as a backdrop to the bandshell. Once you get to Rt. 151, there's a brewery every mile or so (or so it seems!) Local favorites are Blue Mountain Brewery with its great pizzas and Devil's Backbone, which has all sorts of outdoor games and music at Basecamp. Downtown, you can walk to Three Notch'd Brewery at the IX Art Park and do a little shopping on your way.

Distilleries & Cideries

Ragged Branch Distillery and Castle Hill Cider are on opposite ends of town offering beautiful farm properties to surround your time sipping their wares.


We've already mentioned it, but bears repeating: the University provides art, sports and all sorts of entertainment, so be sure to check the events calendar for your visit.

Charlottesville Opera performs many times each year at the historic Paramount Theater on the downtown mall. Hosting an emerging artist program, you never know when you'll hear the next Pavarotti!

The Front Porch and Live Arts offer community theater and music regularly. Always a good time.

Water fun

While landlocked, Charlottesville does have the Rivanna River which offers tubing and kayaking. Grab an extra tube for a cooler and have a refreshing afternoon!

Day trip

There are many options for day trips from Charlottesville. A 30-minute drive over the mountain takes you to Staunton (pronounced "Stanton") where the American Shakespeare Center Blackfriar's Playhouse regularly performs some of Shakespeare's best. Staunton is one of America's most historic cities. Think brick sidewalks, good restraints, and a little shopping (we love Burrow & Vine to pick up a trinket to take home).

One could also venture slightly north and visit James Madison's Montpelier. The house and grounds are beautiful and, depending on the timing of your visit, you might see the Jack Russell Terrier races!

Places to eat & drink in Charlottesville

Fleurie is an intimate eatery offering modern French cuisine.

Farm Bell Kitchen - Hidden gem (right on the main drag through the University) for brunch. Now offering lunch as well, the chef creates authentic southern dishes with a tasteful twist.

Fleurie - The fancy French restaurant for your special occasion. Or, every day if that's your style. Always a memorable meal.

Vivace - Close to the University, this is a local hot spot. Authentic Italian food served up by an incredibly attentive staff. The bar (the actual bar) was rescued from a 1950's establishment and is worth a peek if you can see it through the crowd of locals gathering for happy hour. Dining is much more intimate than the lounge and they boast a huge patio for al fresco dining on a nice evening.

Mas - Fantastic array of tapas, pitchers of sangria and atmosphere. Always a waiting line, but you can grab a drink and hang out on the patio.

Quirk rooftop - At the Quirk hotel, the rooftop bar provides a view of Charlottesville. Great for pre or post-dinner drinks, you can also get a bite!

Smyrna - Truly authentic Mediterranean fare. The chef hails from Turkey via New York, where they received more than a few accolades. The best hummus and eggplant dips ever and everything on the menu is truly amazing.

C & O - No list of eateries in Charlottesville would be complete without including these last two establishments. Easily missed on the street, C&O is one of the original buildings in town and has some of the best food around. Traditional menu with a great wine list.

Ivy Inn - The Ivy Inn is in an old house, so seating is intimate and great for a romantic or special meal. Family run, this restaurant never disappoints and has a very approachable (and good!) wine list.

Need to Know

Charlottesville is a beautiful, vibrant college town where there’s never a shortage of things to do!

Advisor - Tracy Burpee

Travel Advisor

Tracy Burpee

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This guide is part of our ongoing series on travel to Virginia.