An Autumn Weekend in Charlottesville, Virginia

Shenandoah National Park
Shenandoah National Park

The saying goes that “Virginia is for Lovers,” but after many visits to the region, we have found that Charlottesville, Virginia has something for everyone!

An autumn visit in particular makes for an unforgettable trip – the crisp air combined with the backdrop of Shenandoah National Park’s orange and gold hues leaves visitors eager to come back, as we have done!

The region embraces autumn with tastes of cider, spiced apple, and pumpkin on every menu. Charlottesville, Virginia is certainly for autumn-lovers!

After many visits to this beloved destination, this autumn travel guide was thoughtfully curated with our “best of” suggestions for the Charlottesville region.

Charlottesville is for Wine Lovers

Charlottesville is nestled in the Monticello Wine Trail region, which is designated an American Viticultural Area (AVA).

The region is named after Thomas Jefferson’s mountaintop home, Monticello. Jefferson dreamed of surrounding vineyards that would produce high quality wine that could rival the best Old World wines. So began his foray into bringing French vines to Virginia and the first New World vines were planted in 1774, giving birth to American wine. 

There is no shortage of those vines in this region – in fact, there are 43 wineries in this AVA. Of all of those, our most-loved are listed below, all located to the south and west of Charlottesville.

  • Pippin Hill Vineyard: an estate vineyard with expansive views and highly rated restaurant
  • King Family Vineyard: sprawling grounds include a working ranch and polo field set in the Blue Ridge Mountains
  • Blenheim Vineyard: easy-going winery owned by Dave Matthews
  • Eastwood Farm and Winery: choose between a cozy wooden barn or seating with a view up the hill, a highlight of this winery is their mulled wine during autumn months

Many of these wineries have food menus, but we also suggest stopping for a sandwich and sundries in between wine tastings at The Batesville Market or Greenwood Grocery.

Delfosse Vineyard
pippin hill winery
Pippin Hill Winery

Charlottesville is for History Lovers

The history of the Charlottesville region dates back to the mid-1700’s. From a historical perspective, it is most known for its association with Founding Father Thomas Jefferson, who chose it as the location for his estate home, Monticello.

For history lovers, a tour of the estate is highly recommended. There are several options to choose from; many opt for the 45 minute guided tour. It would be easy to spend an entire afternoon exploring the estate grounds and various exhibits available.

If you visit Monticello, be sure to stop down the road at Carter Mountain Orchard for apple cider donuts, fall-inspired sips, and truly incredible views of Charlottesville.

In addition to Monticello, history lovers would enjoy a morning stroll – coffee in hand, of course – around the University of Virginia’s campus. The university was founded in 1819 by Thomas Jefferson (are you seeing a pattern here?) and has many historically significant buildings.

If you’re planning a short stroll, don’t miss The Lawn, a UNESCO World Heritage Site, which is part of Jefferson’s Academical Village. Meandering through The Lawn, you’ll pass the pavilions – original student and faculty housing – as well as The Rotunda, the architectural centerpiece, and Old Cabell Hall. 

If your stroll through the campus leaves you wanting more, you can join a guided historical tour through the University Guide Service.These tours cover the original University and Lawn area, and they begin from the Lower East Oval Room of the Rotunda, Sunday – Friday at 11 am, and Saturday at 11am and 3pm, no reservation required. 

Another morning stroll location is the historic and eclectic Belmont neighborhood, which is recognized on the National Register of Historic Places. The streets are canopied by mature trees and the architecture is varied, with early 20th-century bungalows standing alongside Victorian and Colonial Revival homes. You’ll want to grab and coffee – and perhaps breakfast – from Belle before embarking on your Belmont explorations.

James Madison’s estate, Montpelier, is also in the area and offers guided tours.

University of Virginia
University of Virginia
Breakfast at Belle

Charlottesville is for Craft Beer Lovers

In addition to more than forty wineries, the Charlottesville area is home to a thriving community of independent craft breweries and cideries.

Charlottesville’s love for craft beer aligns with the national movement that began in the late 20th century. The city’s emphasis on locality, combined with the agricultural abundance of Virginia, makes it a prime spot for craft breweries. Over time, numerous establishments have taken root, each offering its own unique flavors and atmospheres.

If you’re into brewery tours, you can organize your own self-guided walking tour – within Charlottesville, there are several craft breweries within walking distance of one another. The bolded options are our recommendations, but they are all worth visiting: Three Notch’d, Starr Hill, South Street, Rockfish, Random Row, North American Sake, and Champion.

For those interested in deepening their knowledge, many breweries offer behind-the-scenes tours. This gives enthusiasts a chance to understand the brewing process, meet the brewers, and, of course, sample a diverse range of beers.

If you’re looking to get outside of Charlottesville into the beauty of the Blue Ridge Mountains, there are great breweries nestled amongst wine country. Following a morning hike in Shenandoah National Park, stop at Blue Mountain Brewery and reward yourself with a crisp brew on their scenic patio.

Another countryside option is Pro Re Nata – excellent beer and live music on the weekends. Starr Hill Brewery down the street in Crozet is also worthwhile.

Charlottesville is for Nature Lovers

The main draw to the region for many travelers is Shenandoah National Park, which stretches for more than one hundred miles along the Blue Ridge Mountains.

For those who are not into hiking, consider visiting the park’s most famous feature, Skyline Drive, a paved road that extends the length of the park and offers incredible views. During the drive, make a stop at Big Meadows Lodge where they have a full service restaurant.

Planning to bring hiking boots? There are plenty of options, including several hikes that feature waterfalls.

Our recommendation is the Hawksbill Summit hike (approx. 2 hrs) – the incline leads to the most incredible summit views. From Charlottesville, the South District section of the park is the shorter drive.

Shenandoah National Park
Shenandoah National Park

Charlottesville is for Culinary Lovers

Those who consider themselves foodies will be pleased with the culinary scene in Charlottesville.

Because of the popularity of the region in autumn, it cannot be emphasized enough the importance of making dinner reservations prior to your visit.

Below are cuisine-specific recommendations based on our several visits to Charlottesville. On your way to dinner, consider strolling through the Downtown Mall, an outdoor pedestrian thoroughfare home to more than one hundred shops, eateries, and art galleries.

  • Italian Cuisine: Tavola, Lampo (pizza)
  • French Cuisine: a quick note that there is a significant French influence in Charlottesville, so there are several great options – The Alley Light, C&O, Brasserie Saison, Fleurie (prix fixe menu), Cafe Frank
  • Thai Cuisine: Monsoon Siam
  • Mediterranean Cuisine: Orzo, Sultan Kebab
  • Southern Cuisine: Mockingbird, Tonic, Farm Bell Kitchen
  • Latin Cuisine: Passiflora, Conmole
  • American Cuisine: Tavern & Grocery, Public Fish & Oyster, The Fitzroy, The Local
  • Breakfast/Brunch: Belle, Chickadee, Petit MarieBette (bakery), Bodo’s Bagels (grab a sandwich for the road and enjoy it at the Hawksbill summit)
  • Coffee Shop: Shenandoah Joe, Petit MarieBette, Grit Coffee

If you found this guide helpful, you should read our 3-Day Itinerary for Charlottesville and Shenandoah National Park

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