Packed Suitcase | Itinerary: 2 days in Charlottesville, Virginia
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Itinerary: 2 days in Charlottesville, Virginia

Itinerary: 2 days in Charlottesville, Virginia

2 days in charlottesville 2


Located in the scenic foothills of the Blue Ridge Mountains, Charlottesville, Virginia is a city that really celebrates its historic roots. The area in and around Charlottesville was once home to 3 of our nation’s earliest presidents— Thomas Jefferson, James Madison and James Monroe— and today over 200 years later, their legacy can still be felt as seemingly all roads lead to a presidential estate or historic landmark dating back to the American Revolution.

However, today’s Charlottesville is as contemporary as it is reverent of the past. A bustling downtown district has seen historic buildings evolve into modernized shops and restaurants, and is a popular spot for University of Virginia students and visitors alike. The region’s thriving wine scene (which has ties back to Thomas Jefferson) has paved the way for artisan craft beer and cider-makers to join the scene. And the natural beauty of the area has led to high-end resorts that cater to an upscale crowd, with perks like fine-dining, world-class golf courses and infinity pools.

For this road trip, I’ve crafted a diverse Charlottesville itinerary that allows for plenty of historical exploration, but doesn’t pass over some of the area’s best non-historic attractions. Whether you’re in search of a rich cultural experience, or just a relaxing retreat, this Charlottesville itinerary should fit the bill!

Time needed: 48 hours

Distance from DC: 315 miles, roundtrip

Best time to visit: Year round, but April through November is particularly nice

Best suited for: Couples, Girlfriend Getaway, Families, Friends, Solo Travelers…

Charlottesville Itinerary Map:  (also can be found here)


Charlottesville Itinerary – DAY 1

1.) James Madison’s home: Montpelier (11407 Constitution Highway, Orange, VA 22960 –Tickets are $18/ adult, $7/ child and include a 1 hour guided tour of the house)

Your first stop on this road trip takes you to Montpelier, the family home of James Madison, the 4th president of the United States and “Father of the Constitution.”

After Madison’s death in 1836, Montpelier fell out of family hands until 1984, when Montpelier was donated back to the National Historic Society. Go to Montpelier, not to see a gorgeous historic house (that’s what Monticello is for)… but to witness a historic renovation of presidential proportions while learning about James Madison, one of America’s most intelligent and essential founding fathers.

Charlottesville- Montpelier exterior

A tour group heads into Montpelier

Charlottesville- Montpelier garden- me and the Madison's

Me and the Madison’s– ha!


2.) Lunch at the Barbeque Exchange in Gordonsville (102 Martinsburg Ave., Gordonsville, VA 22942 – inexpensive)

As you continue your drive, you’ll pass through Gordonsville, a charming small town about 20 miles north of Charlottesville. As you pull up to your lunch destination on the outskirts of the historic district, be sure to note a huge pile of hickory wood and 4 gigantic custom smokers. The Barbeque Exchange means business!

Opened in 2010 by a seasoned chef with roots in the fine-dining business, chef Craig Hartman has created a casual, local fixture that has garnered a loyal following of BBQ-loving devotees. House-smoked proteins like ribs, brisket, pork and even TOFU are made even better after a slathering of one of the five zingy, house-made barbeque sauces. Make your meal a platter and choose 2 freshly-made sides like hushpuppies, potato salad, pickled veggies and pumpkin muffins.

Charlottesville- BBQ Exchange- my meal

My lunch: pulled pork, brisket, potato salad, mac and cheese, pumpkin muffin and sweet tea

Charlottesville- BBQ Exchange- BBQ Sauces

The house-made sauces. The Col. Bacon has real bacon in the sauce (obviously)!


3.) Tastings at Castle Hill Cider and/or Keswick Vineyards

While you’re in the area, kick back and enjoy a tasting at Castle Hill Cider or Keswick Vineyards… or both!

Castle Hill Cider is an artisanal cidery situated on 600 acres of pastoral Virginia countryside. Visitors can enjoy a $6 tasting of 5 handcrafted ciders in the cidery’s tasting room, which resides in a spectacularly renovated cattle auction barn. Be sure to try the standout “Levity” cider, which is made of 100% Albermarle Pippin apples and fermented underground in a traditional Georgian clay vessel called a ‘kvevri.’ It’s delicately sweet and tart, and makes for a deliciously well-balanced drinking cider.

Charlottesville- Castle Hill Cider- Levity Cider

Enjoying a bottle of Levity cider on the Castle Hill grounds


Keswick Vineyards, part of the Monticello Wine Trail, is another option for wine-loving oenophiles. In 2006, Stephen Bernard became Keswick Vineyards’ Winemaker and General Manager, bringing his considerable experience as a South African winemaker to Virginia. A $5 tasting gives you samples of 7 wines, including the summer-favorite 2013 V2 white wine made of Viognier and Verdejo grapes, that refreshes the palate with dry acidity and subtly tropical undertones.

Charlottesville- Keswick Vineyards- vineyard

The view of grapes on vine at Keswick Vineyards


4.) Check into your hotel

Located 15 minutes outside of downtown Charlottesville, the historic Keswick Hall (701 Club Dr., Keswick, VA) is one of the most esteemed resorts in the U.S. Recently named one of Travel + Leisure’s 500 “World’s Best Hotels,” this historic property is a peaceful oasis set on a picturesque, 600-acre private estate in the rolling Virginia countryside. Keswick Hall is known for its impeccable service and dedicated staff as well as its highly rated Fossett’s restaurant, its upcoming Pete Dye-designed golf course and its truly gorgeous horizon pool. Summer weekend room rates start at $389/ night, but watch for reduced rates in the cooler months. (For more details, see my Keswick Hall review here.)

Keswick Hall- Horizon Pool

The horizon pool at Keswick Hall

Keswick Hall - Hallway

The decor of the 3rd floor at Keswick Hall


If you’d like the full resort experience but don’t want to spend quite that much, consider the Boar’s Head Inn (200 Ednam Dr., Charlottesville, VA). Centrally located just 5 miles from Charlottesville’s city center, the Boar’s Head Inn has 175 newly-upgraded rooms spread across 5 buildings on their pretty-as-a-picture grounds that feature walking trails and ponds. Guests of the Boar’s Head Inn can expect luxurious accommodations and lots of amenities like multiple on-site dining options featuring locally-inspired dishes by Executive Chef Russell Bradshaw, an 18-hole golf course, a spa and state-of-the-art Sports Club which houses 3 pools, basketball courts, a climbing wall and lots of squash courts… making this also a very family-friendly option. Try to plan your visit around one of the resort’s special events, such as a Wine Class with local vineyards, or during the holidays, when the Boar’s Head comes alive with festivities. (Updated in 2016!)

Charlottesville- Boar's Head Lake- JAR

One of the buildings at the Boar’s Head Inn — Photo by Jo Ann Ricchiuti

Charlottesville- Boar's Head room

One of the renovated Hunt Club rooms at the Boar’s Head Inn

A glimpse inside the Boar's Head's amazing squash facility!

A glimpse inside the Boar’s Head Inn’s gorgeous squash facility!


For thriftier travelers, Charlottesville offers a number of hotels near the University of Virginia, like the Cavalier Inn, where rooms start at around $95/ night.


5.) Dinner in downtown Charlottesville

After settling in at your hotel of choice, head back out on the town to enjoy the convergence of old and new at the historic 8-block Downtown Mall in the center of Charlottesville. Here unique restaurants and boutique shops line a brick pedestrian street where bohemian street performers and artists entertain all that are strolling by.

Charlottesville- downtown historic mall

A view along the historic mall


On a warm evening, people flock to the mall like a moth to a flame, eager to dine al fresco at one of over 50 restaurants. And there are more restaurants than meets the eye… Be sure to look down alleys, or glance up to search for hidden gems that are some of the city’s best. My favorites include:

*The Alley Light (108 2nd St. SW, moderate) is a blink-or-you’ll-miss-it culinary gem that opened in February 2014. A nondescript handwritten sign points the way to an alley with a single light above a single door, leading to this upstairs speakeasy-esque restaurant and bar featuring seasonal small plates and handcrafted cocktails.There are no passwords, no secret handshakes and —believe it or not— no pretentiousness, but for those lucky enough to snag a reservation, a delicious meal in a hip space awaits.  (Read my whole review of the Alley Light here.)

The Alley Light- interior

Inside the Alley Light

The Alley Light- Duck Confit

Duck confit with cherries and potatoes ($16)


*Look up to discover Brookville Restaurant (225 Main St., moderate). With around 95% of all ingredients sourced within 100 miles of Charlottesville, Brookville takes the prize as the most locally sourced restaurant in town. Chef and co-owner Harrison Keevil’s menu features deliciously inspired seasonal cuisine—like the slow roasted pork belly with apples ($24) and the bacon waffle with fried chicken, kim kim sauce and maple syrup($25). And, if you really like what you taste, you can opt to order a “beer for the chef” bonus which allows you to show your appreciation to the chef… by buying him a $3 beer. Fun!

Charlottesville- Brookville Restaurant- Chicken and Waffles

A bacon waffle (!) with fried chicken, kim kim sauce, egg, greens and maple syrup. SO GOOD.

Charlottesville- Brookville Restaurant giving beer to chef- JAR

Hand delivering Sous Chef Dylan Allwood a beer — Photo by Jo Ann Ricchiuti



Charlottesville Itinerary – DAY 2

6.) Spend the morning at Thomas Jefferson’s Monticello (931 Thomas Jefferson Parkway – Tickets are $25/ adult, $16/ children 12-18, $8/ children 5-11, under 5: free!)

Monticello is the only historic house in the U.S. that’s been given a spot on the UNESCO World Heritage list, and after visiting, you’ll see why. Thomas Jefferson designed his gorgeous home himself, and despite falling out of family hands for nearly 100 years, the structure has remained well preserved since its construction beginning in the 1760s. Beyond the main house, visitors will see elaborate gardens and glimpses of history at the scenic mountaintop location that is seemingly untouched by time.

A Few Monticello Tips…

  • Reserve your morning house tour ahead of time—they fill up fast.
  • Allow plenty of time for exploring the grounds—there’s a lot to do at Monticello besides just getting a house tour. All guests can participate in optional complementary tours like the “Gardens and Grounds Tour” or the “Slavery at Monticello Tour,” which are both highly recommended.
  • Be sure to bring comfortable shoes. I recommend ditching the shuttle back down to the parking area and walking the path past Jefferson’s gravesite. The walk back to the parking center is an easy, 15-20 minute walk from Monticello.
Charlottesville- Monticello- reflection


Charlottesville- Monticello- garden

The gorgeous vegetable garden at Monticello

Charlottesville - Monticello selfie

Mom and I have a nice photo op


7.) A Picnic Lunch at a Mountaintop Orchard

As you leave Monticello, you’re bound to have a bit of an appetite after all that walking around. Hop in your car and drive 5 minutes to Salt Artisan Market (1330 Thomas Jefferson Highway – inexpensive). Located in a retro 1930’s gas station, Salt features fresh and creative sandwiches and cheese & charcuterie plates that are perfect for the winery-hopping, picnicking-type.

Charlottesville- Salt Market- interior

Salt Artisan Market


Grab a sandwich (some favorites are the “Local Chicken Salad” with grapes, celery and apple — $7.75 or the “Local Soul” with miso-marinated tofu, spicy plum chutney and kimchi — $7.25) for your picnic at Carter Mountain Orchard (1435 Carters Mountain Trail), a local pick-your-own apple and peach orchard with a bustling farm market and the best views in Charlottesville.

And when they say “mountain orchard” they are not exaggerating! Driving back towards Monticello, turn onto Carters Mountain Trail and go up, up, up a steep incline until finally you break through the trees and find yourself atop a crest filled with apple tress and 35 acres of grapes on vine. At Carter Mountain Orchard, spectacular views abound and there are plenty of tables at hand to provide an excellent place for your impromptu picnic. Enjoy your lunch with a cup of peach or apple cider while enjoying the views of Charlottesville and the nearby Blue Ridge Mountains.

Charlottesville- Carter Mountain Orchard- view

The view at Carter Mountain Orchard

Charlottesville- Carter Mountain Orchard- main market

The farm market at Carter Mountain Orchard


TIP: After lunch, if you’re feeling up to it, head on over to the Carter Mountain Wine Shop for a tasting of Prince Michel wines or one of the deliciously frosty wine slushies…

Charlottesville- Carter Mountain Orchard wine with a view- JAR

Cheers to wine slushies and pretty views! — Photo by Jo Ann Ricchiuti


8.) Visit to James Monroe’s Ash Lawn-Highland (2050 James Monroe Parkway – Tickets are $14/ adult, $8/ child)

Many visitors to this area visit Monticello and Montpelier and think that their journey through history is complete. But this area’s home to a third presidential estate that also warrants a visit: James Monroe’s Ash Lawn-Highland. In 1793, Monroe purchased the home with the help of his pal, Thomas Jefferson, who selected the house’s property. Jefferson even sent his gardeners from Monticello to help Ash Lawn-Highland’s orchard get off to a successful start.

Today, visitors to Ash Lawn-Highland will see that the grounds are still lovely and beautifully maintained, with a formal garden, a vegetable garden, animals like peacocks, chickens and pigs and a beautiful countryside view from all directions. And while the house itself if simple (especially when compared to the other presidential mansions in the area) it demonstrates the more modest lifestyle of our youngest founding father.

Charlottesville- Ash Lawn-Highland- house

James Monroe’s House at Ash Lawn-Highland

Charlottesville- Ash Lawn-Highland- garden

The vegetable garden at Ash Lawn-Highland

Charlottesville- Ash Lawn-Highland- peacock

Peacock’s showing off! — Photo by Jo Ann Ricchiuti


9.) Craft Beer Tasting at Nelson 151 Breweries

In recent years, the Charlottesville area’s become as well known for their craft breweries as they have for their wineries and presidential mansions. To fully get immersed in the area’s craft beer scene in a short amount of time, there’s just one place you need to go: Nelson 151.

“Nelson 151” is actually shorthand for “Route 151 in Northern Nelson County,” and is a scenic byway that winds along the base of the Blue Ridge Mountains, passing farms, general stores, B&Bs and BBQ joints. It also happens to have several very good craft breweries (and a few wineries, a cidery and a distillery) along it.

One standout is Blue Mountain Brewery (9519 Critzer’s Shop Rd., Afton, VA 22920), which is known for gorgeous views, great food, homegrown Cascade hops and some exceptionally good craft beer. Grab a seat (outside if you can) and start with the sampler of 9 (or so) 2.5 ounce samples of their current selection of beers on tap for just $7-9. Try to choose your favorite from the popular roster of beers, like the Full Nelson Pale Ale and the Kölsch 151. If you’re hungry, or maybe even if you’re not, you should try one of the big-enough-to-share artisan pizzas ($20-22), which are so good that people have been known to travel long distances just for a slice.

Blue Mountain Brewery- ext

Blue Mountain Brewery

Blue Mountain Brewery

A Blue Mountain Brewery sampler makes for a good photo!


Another must-visit is Wild Wolf Brewing Company (2461 Rockfish Valley Hwy., Nellysford, VA 22958). With a front Biergarten, back outdoor patios, indoor dining room and sizable sports bar, there’s lots of space for lots of people. Which is a good thing, because this brewery (which opened in 2011) gets a lot of visitors eager to sit back and relax with friends over handcrafted brews and good bar food. Here, $10 gets you a tasting of all 11 beers—5 house, 6 seasonal. House standouts include the hoppy Alpha Ale and the Belgian style Blonde Hunny that taste even better when paired with an order of Wild Wolf’s BBQ Pulled Pork Nachos ($11.50).

Charlottesville- Wild Wolf exterior- JAR

The outdoor Biergarten at Wild Wolf Brewing Company — Photo by Jo Ann Ricchiuti

Charlottesville- Wild Wolf- tasting

The sampler at Wild Wolf


Finally, before you say goodbye to the Charlottesville-area, don’t miss a stop at one of the area’s newest hotspots, Virginia Distillery Company (299 Eades Lane, Lovingston, VA 22949). VDC specializes in Scottish-inspired whisky with a notably picturesque Virginia locale. Come for a tour, appropriately dubbed the Virginia Whisky Experience, where you’ll learn all about the history of single malt whisky, as get to see it being made in VDC’s distillery and cask house. Then enjoy a $10 tasting of seasonal mini-cocktails featuring their signature Virginia Highland Malt. The cocktails change monthly, allowing visitors to return again and again. The tours are available daily, and can be booked online here(Updated in 2017!)

Photo credit: Our Local Commons

Photo credit: Our Local Commons


**DISCLAIMER: Many of my meals, accommodations and activities for this trip were provided by the Charlottesville Albemarle Convention & Visitors Bureau (CACVB). I worked closely with my contacts there to customize an itinerary that best fit my travel perspective and all opinions are my own.**

  • Adam
    Posted at 21:49h, 24 July

    That BBQ place sounds incredible! I’ve been contemplating stopping off in VA on my way to Charleston next month and hmm it sounds a lot more tempting after reading this. Thanks!

  • Morgan
    Posted at 23:02h, 26 July

    You can’t visit Charlottesville without seeing UVA!

  • Dusty
    Posted at 08:22h, 27 July

    A two day trip to Charlottesville without a visit to the central Grounds of the University?

    • Weida
      Posted at 14:04h, 26 March

      agree. A little too much for food, a little less for sightseeing. UVA is a must. Still, very good itinerary.

  • Holly
    Posted at 20:12h, 27 July

    Devil’s Backbone is also another great brewery and restaurant. Also located on 151 in Nelson Co. Locals say it’s better than Wild Wolf. 😉 You should also visit UVA.

  • Tim
    Posted at 18:39h, 29 November

    Blue Mountain Brewery is easily better than Wild Wolf and Devils Backbone in both beer and food. The latter two are also quite a bit further to get to and on top of all that, the views are not as good. Wild Wolf has no view at all.

    There is a popular cidery called Bold Rock Cider in the same neighborhood as the latter mentioned breweries. Guests enjoy the free tour of the cider making process and the views are beautiful once you sit down to enjoy a drink.

    Also missing from the itinery for Charlottesvle is the free trolley bus which during a 50 min round trip ride, will take you to all the places of interest in the immediate area. You can get off and back on at stops all over the area, one of which is next to the famous rotunda on campus, thus givi g people direct access to the UVA grounds

  • Diane
    Posted at 12:45h, 03 October

    Michie Tavern near Monticello