3 Days in Charlottesville and Shenandoah National Park

Shenandoah National Park
Shenandoah National Park

The region around Charlottesville, Virginia has something for every type of traveler – hiking, history, vineyards, craft breweries, and an impressive foodie scene.

In this comprehensive 3-Day Itinerary for Charlottesville and Shenandoah National Park, we’ll share our recommendations for how to make the most of your time. Like us, you may fall in love with the region and find yourself on repeat visits.

Day One in Charlottesville + Shenandoah National Park

Hike in Shenandoah National Park

You’ll need caffeine and carbs to power you through your morning hike. Stop by Shenandoah Joe’s on your way out of town for great coffee and pastries.

Shenandoah National Park, established in 1935, spans north to south along the Blue Ridge Mountains. The scenic roadway that runs through the park, Skyline Drive, is 105 miles in length.

Because of the oblong shape of the park, it can be quite a drive to access the park entrances, which there are four of – one at each north and south end and two equidistant in the middle. To visit the park, you’ll need to be prepared for a good amount of driving.

Fortunately, the views along Skyline Drive make the driving time worth it!

Shenandoah National Park
Shenandoah National Park

From Charlottesville, the closest section of the park is the southern region, accessible by the Rockfish Gap Entrance.

Of course, the best hikes are located in the middle of the park, closer to the Swift Run Gap Entrance.

Shenandoah National Park
Shenandoah National Park

Little Stony Man Loop

You’ll want to wake up early – the best trails fill up quickly and are significantly less enjoyable when crowded.

From Charlottesville, head to the Swift Run Gap Entrance – it’ll take about an hour.

There are two hikes near this entrance that we recommend – Hawksbill Loop Trail (2.7 miles, moderate) and Little Stony Man Loop (3.3 miles, moderate).

Shenandoah National Park
Shenandoah National Park

Between the two, Little Stony Man has more viewpoints and trail diversity.

Follow the white tree markers to the summit at Stony Man Mountain. Then, loop back and follow the blue tree markers to the longer Little Stony Man Loop. The viewpoints along the trail are stunning – and very, very windy.

It took us just under two hours to stop at each viewpoint – offering sweeping views of the treed mountainside and valley below. We took our time walking over the mossy rocks on the second half of the loop.

You’ll want sturdy hiking boots that provide ankle support.

Shenandoah National Park
Shenandoah National Park

Skyline Drive

After the hike, head south on Skyline Drive all the way to the southern end of the park at Rockfish Gap Entrance.

Put on some good road tunes and roll down the windows – the hour drive will be pleasant as you wind along the tree-lined route, passing frequent pull-off overlooks that show off the beauty of the Blue Ridge Mountains.

Skyland Visitors Center

The Skyland Visitors Center is worth a quick stop, or longer if you want to visit the on-site restaurant that comes with panoramic views from its mountain-side perch.

Lunch at Batesville Market

This country road market is the perfect post-hike sandwich stop.

Batesville is a national historic district, located on a winding country road that brings travelers alongside apple orchards, woodland, and valleys dotted with quaint farm homes – it’s incredibly charming and scenic.

batesville market in batesville virginia
Batesville Market

You can’t miss Batesville Market – it’s one of the few buildings along the main street in Batesville.

The market resides in a historic home with white siding, a large green front porch, and original wooden floors that creek as you wander around the shop.

On the autumn day we visited, there was a Model-T parked in front with pumpkins in the bed.

pumpkins at batesville market
Batesville Market

The market offers a deli with homemade soups, salads, and sandwiches served on blue and white checkered paper. You can customize your sandwich or choose from their curated menu.

The market also has baked goods from beloved Marie Bette Bakery, local beer and wine, seasonal fruit, and sundries for curating your own picnic situation to bring to a surrounding winery or brewery – just check to make sure the ones you’re planning to visit allow outside food (many do).

Afternoon Brewery Hopping

Being out in the countryside, you’re perfectly positioned to visit some local breweries.

We recommend visiting the below noteworthy breweries in the order listed, putting you on a loop that will take you back towards Charlottesville:

  • Brewing Tree Beer Co.: Located along the river, this brewery sits on five acres of beautiful countryside and features a beer garden, picnic tables, wrap around porch, and occasional live music.
  • WildManDan Brewery: Slide open the barn door and step into an eclectic tasting room, complete with brewery cats sleeping on the wooden barstools. The low-ceilinged room is adorned with metal and wooden signs, creaking floorboards, and an air of not trying too hard to impress anyone. WildManDan himself is situated behind the bar with an unkempt white beard and friendly smile. The beer itself is excellent and served in plain plastic cups alongside kettle corn. We recommend a flight of all seven beers, including the Pickalus Cage.
  • Blue Mountain Brewery: Considered a staple in the local craft brewery scene, Blue Mountain Brewery is a large operation that has been able to maintain its local brewpub feel. The brewery is spacious with both indoor and outdoor seating options. 
  • Pro Re Nata: Favorite among locals, this brewery features live music, several outdoor spaces, firepits, and excellent beers. It’s typically crowded but the variety of spaces on the property, including container bars, ensures you’ll find a seat.

Evening in Downtown Charlottesville

The most well-known feature of Charlottesville, the Downtown Mall, is a bricked eight-block stretch of local eateries, shops, boutiques, art galleries, and theatres. Strolling along the Downtown Mall, you’re greeted by a harmonious blend of historic and contemporary architecture. 

Charlottesville is a foodie town.

It’s really incredible how many great options there are considering the size of the town. It’s difficult to suggest just one, so instead we’ll suggest our favorites in the Downtown Mall area.

Regardless of which you decide on, you’ll want to make a reservation in advance.

  • Monsoon Siam: The best choice for authentic Thai food. Situated in a former house, the ambiance is intimate and cozy. The curry in particular is highly recommended.
  • The Alley Light: Tucked away in a back alley and identifiable only by a light next to an undistinguished door, dining at French-inspired The Alley Light feels like you’re being let in on a secret. The lights are turned low, adding necessity to the candlelight on the tables. The best approach here is to order several small plates and share. Dining here is truly a treat.
  • Lampo Neapolitan Pizza: This snug, artisanal eatery is where tradition meets innovation, involving the essence of Neapolitan taste in every bite. The dim lighting, exposed brick walls, and the warmth of the wood-fired oven create a cozy setting that feels both nostalgic and contemporary. Despite its compact size, the restaurant brims with energy, partly thanks to its open kitchen where diners can watch each pizza be thoughtfully crafted. 
  • C & O: The dimly lit interiors, with its wooden beams and vintage photographs, evoke a bygone era. Carefully curated, the menu changes seasonally, ensuring that every dish is a reflection of the freshest flavors available. While the dining room offers a more formal setting, the downstairs bar provides a cozy nook for those looking to unwind with a craft cocktail or locally brewed beer. The bar, with its low ceilings and intimate booths, has a speakeasy feel, making it a favorite among locals and visitors alike.

Consider getting dessert and a nightcap at one of the many wine bars on the Downtown Mall – we loved Tilman’s

Day Two in Charlottesville

Hike Humpback Rocks

Although it’s located outside of Shenandoah National Park, Humpback Rocks has a summit view that could rival many of the trails in the park.

The trail is 1.8-mile out-and-back and involves a steep incline from the beginning. Just as you catch your breath, you’ll be rewarded with peak views of the rolling hills below.

Rather than doing the out-and-back trail, you could take the loop option, which makes it a 4.2-mile jaunt.

humpback rocks
Humpback Rocks

Brunch in Belmont Neighborhood

After the hike, make your way to Charlottesville’s charming Belmont neighborhood.

Belmont is a lovely area to stroll in – there are many beautiful historic homes lining the streets around the small center of the neighborhood where Belle is located.

belle charlottesville va

Order at the counter and allow yourself to be tempted by the delectable-looking pastries. They’re proud of their house sourdough bread, and it’s definitely something to be proud of – their sandwiches and toast options are great.

They have a lovely patio, or you can opt to eat inside amongst the potted plants and wooden tables.

After brunch, stroll through cute shops next to Belle.

Afternoon Winery Hopping

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. 

pippin hill winery
Pippin Hill Winery

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: The hydrangea-lined entryway sets the tone for this upscale winery. The grounds are beautiful – views of the hillside dotted with cattle, vines surrounding the property, and lovely gardens strewn throughout. We recommend you make a table reservation for wine service on the patio, otherwise you’ll have to find an available sitting area on the grounds of the property. The only downside is the prices – this is one of the more expensive wineries in the area. We opted for just one glass.
  • King Family Vineyards: Set on a horse farm, this winery has several buildings for indoor seating, which include crackling fireplaces and winery cats curled up in corners. There is also ample outdoor seating, both on a patio with tables and out on the vast lawn where you can sit on a blanket. The Blue Ridge Mountains and horse stables serve as the backdrop for the outdoor views. During warm months, you can watch polo games on Sundays beginning at noon.
  • Mountain & Vine: Further than the others, Mountain & Vine is secluded in a valley with vineyard covered hills and a pond. The tasting room is a bit dated, but the wines are excellent, typically poured by the owner himself, and you can take your tasting outside to one of many tables that offer beautiful views of the property.
  • Eastwood Winery: Just outside of Charlottesville, this winery begins at a tasting room in a large wooden barn and moves uphill to various seating areas that provide incredible views of the rolling hills. During autumn and winter, their mulled wine is a must-try.
  • Blenheim Winery: Although you’ll find a more relaxed atmosphere than the other high-end wineries in the region, the views and quality of wine are just as great. 
  • Ablemarle CiderWorks: Technically not a winery, but more than worth a visit. The gravel road leads to you to a glass-lined tasting room where you’ll learn about their ciders, several of which have won best in the state. Whereas most commercial ciders contain 5 – 18% sugar, the most contained in these ciders is 1.5%. The options are crisp and delicious. Don’t miss out on purchasing some bags of freshly picked apples, including several varieties you likely haven’t heard of.
pippin hill winery
Pippin Hill Winery
king family vineyard
King Family Vineyard
Ablemarle Ciderworks
Ablemarle Ciderworks

Dinner in Starr Hill

Adjacent to the Downtown Mall is Starr Hill, several blocks lined with a variety of trendy eateries and shops.

Again, it is difficult to recommend just one, so we will share our favorites. You’ll want to make a reservation in advance.

  • Oakheart Social: The best meal we had in Charlottesville was at Oakheart Social. The best approach is to order several small plates and share. Their vegetable dishes, in particular, were creative and flavorful. The ambiance is intimate and the servers all friendly and attentive.
  • Orzo: Excellent option for Mediterranean. In the warmer months, opt to sit on their lovely patio. The menu is on the smaller side, but every dish is delicious.
  • Public Fish & Oyster House: If you’re from a landlocked state like us, you may seek out seafood anytime you are within a somewhat close distance to the ocean. Public Fish & Oyster House is a great option for just that!

Day Three in Charlottesville

Stroll University of Virginia

The campus of UVA is not only beautiful, it also holds historic significance, both of which make it a great option for a morning walk.

Grab a coffee from Grit Coffee Roasters in the bar district next to campus. Then, make your way towards The Rotunda.

As you walk through campus, you’ll pass brick archways, colonial-style buildings, and tree-lined paths.

The university was founded in 1819 by Thomas Jefferson 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. 

university of virginia rotunda
University of Virginia

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.

University of Virginia
University of Virginia

The row of housing just outside of the pavilions contain once-private gardens, sectioned off by brick walls and connected via white wooden gates.

The gardens are each different and make visitors feel as though they have gone back in time.

University of Virginia
University of Virginia

After your stroll, head across the street to Bodo’s Bagels. Whether you order it as a breakfast sandwich or simply the traditional route with cream cheese, their bagels are so, so good.


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.

Accessible from the visitor’s center, the Saunders-Monticello Trail is a lovely 4.3-mile out-and-back path that varies between gravel and wooden boardwalks. The trail takes you through serene woodland. 

monticello trail
Monticello Trail

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

Evening in Belmont Neighborhood

Recognized on the National Register of Historic Places, the Belmont neighborhood is both historic and eclectic.

The streets are canopied by mature trees and the architecture is varied, with early 20th-century bungalows standing alongside Victorian and Colonial Revival homes. 

There are several great eateries to choose from nestled around one another along Monticello Road. Each has a great ambiance paired with a specific cuisine: Spanish, Southern, Italian, Mexican, and New American.

Our personal favorites are Tavola for Italian and The Local for New American. You’ll want to make a reservation in advance.

belmont neighborhood
Belmont Neighborhood

If you found this guide helpful, you should also read our “Best Of” Guide to Charlottesville in Autumn

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