North America Travel USA Virginia

How to Plan a Fun Foodie’s Weekend in Charlottesville, VA 

Pippin Hill Farm and Vineyards, Charlottesville
Hey there! This site utilizes ads to pay the bills so that we can continue bringing you free travel advice. We are also part of several affiliate programs, which means that if you click on a link and make a purchase, we may receive a small commission (at no extra cost to you). Thank you for reading and supporting Live Like it's the Weekend!

I guess I’ve been keeping Charlottesville a bit of a secret. Not intentionally, of course, but you know how sometimes when you’re so close to a thing it’s hard to get perspective and see how cool it truly is from an outsider’s view? Charlottesville (or C’ville as it’s lovingly nicknamed) is that place for me.

I spent many months living here with family in between travels before I decided to move back to Los Angeles in early 2019 — and I still come back often.

While it’s a great place to live, it’s also an awesome weekend getaway if you’re looking for a destination with a relaxed pace but all the cultural benefits of a bigger city…aka great food!

In this post I’m sharing my food and wine lover’s guide to a weekend in Charlottesville, because let’s be honest — eating and drinking are two of my favorite activities. 

But First, a Bit About C’ville

Let’s back up and give you a little context. Charlottesville is a lively small city located in central Virginia that is known for many things. Most famously, it’s been the home to two US presidents, Thomas Jefferson and James Monroe, and Jefferson’s presence and influence is still felt widely throughout the city.

There’s Jefferson’s home of Monticello (a must-visit) and the University of Virginia, which was designed by Jefferson and now holds the only collegiate UNESCO World Heritage Site designation. 

Central Virginia’s climate and topography is also ideal for growing wine grapes and many other types of produce, which is why this area has blossomed as one of the country’s best wine regions with a growing farm-to-table scene.

Charlottesville is right at the center of the Monticello Wine Trail — win! — which means a trip here puts you in perfect proximity to taste test the fruits of Jefferson’s labor (hehe see what I did there ? ), since he originally discovered that Virginia could be a premier wine growing region. 

Unfortunately, while Charlottesville’s roots are at the heart of US history, recent events have given the city some less pleasing things to be known for (to put it nicely), but it’s a bit of a bad rap that I don’t feel it deserves.

If you don’t know what I’m talking about, then look up the Charlottesville riots that happened in 2017.

I was just as shocked as anyone that such horrific, racist events could happen in a place that I’ve found to be quite forward-thinking and progressive. In fact, the people responsible for starting these events weren’t even from Virginia at all.

So if you’ve read the news in recent years and had a picture of Charlottesville in your mind, please don’t let that dissuade you from visiting! Charlottesville is a beautiful, friendly place and is safe for people of all backgrounds. 

Ok, now that we got that out of the way…


Did You Know…

In recent years, Charlottesville has been voted as one of America’s #1 Small Cities and the Happiest Places to Live by National Geographic

The Dave Matthews Band was formed in Charlottesville and Dave himself owns a winery on the Monticello Wine Trail

There are many nods around town to C’ville’s colonial-era past. Barracks Road and shopping center, for example, makes reference to its use as a camp for British and German prisoners during the Revolutionary War

There are more than 35 wineries within a 30 mile radius of Charlottesville

Charlottesville sits at the foot of the Blue Ridge Mountains and the Appalachian Trail runs through the state just 30 minutes East of C’ville 

The Downtown Mall, Charlottesville, Virginia

Plan Your Weekend in Charlottesville

How to Get to Charlottesville

Charlottesville has an extremely tiny airport (CHO), which is awesome because it makes flying in and out pretty hassle free. However, flight options are a bit more limited.

It’s currently only serviced by American, Delta and United but you’ll find non-stop options from cities like DC (Dulles), New York (Laguardia), Chicago, Philadelphia, Charlotte and Atlanta.

If you don’t find great options from your city, you can also fly into Richmond International Airport (RIC) which is about an hour and 15 minutes drive from downtown Charlottesville. 

For those living in the surrounding states, it’s pretty easy to drive into town and you can always extend your weekend in Charlottesville if you need more time to explore. For reference, the drive is about 4 and a half hours from Charlotte, North Carolina and 3 hours from Baltimore.

Northern Virginia / DC area traffic can be brutal though, so if you’re coming from that direction, plan accordingly! 


When to Plan Your Weekend in Charlottesville

I’ve been here in every season and have experienced that there really isn’t a terrible time to visit Charlottesville.

FALL: My personal favorite time to visit Charlottesville is Fall when the autumn colors come alive and there are tons of fun seasonal spots to enjoy like local favorite Carter Mountain Orchard. Plus, this time of year has the perfect mix of warm temperatures with a cooler breeze. 

WINTER: While DC to the north seems to get pretty snowy winter weather, Charlottesville feels like it’s in a bit of a bubble where it somehow manages to avoid the worst of the storms.

Some years it snows and some it doesn’t at all, but it can generally be a bit dreary and rainy though mild as far as temperatures go.

Big bonus: The wineries are much less crowded this time of year. You’ll notice from these photos that this particular trip was during the holidays which added a whole new level of charm.

If you love visiting different cities and seeing how they decorate and celebrate the holidays, Charlottesville in winter won’t disappoint. 

SPRING: Since I am allergy prone, I typically avoid spring in C’ville when the pollen comes out in full force, but the weather can still be beautiful for those that aren’t affected. Plus, there are gorgeous flowers that bloom this type of year, including cherry blossoms. 

SUMMER: Certain weeks in summer can be muggy, but for a humidity lover like myself I’m all about it.

The days are longer and you’ll get to take in all the fun summer activities like concerts, alfresco dining (although this season extends well into Fall), and if college crowds aren’t your thing, many of the UVA students will have gone home by this time of year.

All in all though, any time of year is a great one for a weekend in Charlottesville. 


Where to Stay

The Clifton Inn, Charlottesville, Virginia
Holidays at the Clifton Inn, Charlottesville, Virginia
Holidays at the Clifton Inn, Charlottesville

The Clifton Inn

There are several cute spots to stay in Charlottesville, but my personal favorite is The Clifton Inn, a boutique property comprised of five beautifully restored late 18th and early 19th century buildings, situated on 100 acres.

I know several people who’ve gotten married here (including my mom and stepdad in 2013!), and it’s got that perfect mix of traditional heritage and modern beauty.

In fact, the property was just recently renovated, so the decor feels exciting and fresh and every room offers a little something unique. 

The Clifton has more of a private feel, set a bit away from the main downtown scene and feels like its own little retreat, which is ideal for couples or those that want a more peaceful environment.

However, it’s still easy to access the best of C’ville from the Clifton. Monticello is just a 10 minute drive away and any of the wineries are the same driving distance as if you were staying downtown. 



Hotels Located Downtown

If you’re looking for something in closer proximity to downtown, my top picks for price, location and style are The Graduate, Oakhurst Inn or The Townsman: Meriwether (this one is right on the Downtown Mall). 

The Clifton Inn, Charlottesville, Virginia

Getting Around

Deciding how to get around will depend on what you plan on doing during your weekend in Charlottesville, but your basic options are: Renting a car, relying on Uber or Lyft, hiring a private driver or booking group wine tours.

As wine tasting is such a major activity here, you’re either going to want to designate a sober driver (be safe people!), hire a driver, or book a wine tour for the days when you’re out tasting. 

For all your other activities, renting a car is the easiest way to get around and will allow you to get out to some of the best spots outside of Charlottesville like Shenandoah National Park.

For this trip, my friend flew in to CHO airport to meet me and we rented a car right at the airport through Enterprise, which was literally the easiest process ever.

We were able to drive ourselves to a couple wineries when we were just doing light tastings and eating, but for our big winery tour day we decided to go with a private driver. For a more affordable option, you could book a group wine tour.

Viator Offers Some Great Wine Tours Here

It’s entirely possible to do an entire weekend in Charlottesville just using ride share services like Uber and Lyft, just expect that wait times may be a little longer for pick-ups and will cost a bit more as Charlottesville can be spread out. 

Read More Weekend Escape Posts
8 Reasons Why Savannah Is One Of The Best US Places To Travel
15 Fun Things To Do In Kennebunkport On A Long Weekend 
How To Spend The Ultimate Long Weekend In Austin


What to Eat and Drink During Your Weekend in Charlottesville

Wine Tasting at Pippin Hill

Wine Tasting Along the Monticello Wine Trail 

Wine tasting is a must-do during any trip to Charlottesville, and if you’re a wine lover like me than you’ll especially enjoy the range of varietals and tasting rooms throughout the area.

Winemaking in Charlottesville was originally the vision of Thomas Jefferson, who realized early on that the region’s climate and topography were ideal for growing grapes. However, his efforts weren’t quite realized during his time.

It wasn’t until the 1970s that winemaking in the area began to really hit its stride. It’s now one of the top activities for visitors spending a weekend in Charlottesville. 

In honor of Jefferson, the area’s wineries make up what has been named the “Monticello Wine Trail.” There are 35 wineries along the “trail” all within close proximity to Charlottesville. Below are some favorites that will give you a great intro into Charlottesville’s wine region. 

Veritas Vineyard and Wintery

Veritas Winery on the Monticello Wine Trail

Veritas Vineyard and Winery is a great year-round tasting destination. In summer, the porch and lawn come alive with families and groups of friends soaking up the sun, and in winter there are cozy spots indoors to sip wine by the fireplace. 

Veritas features a delicious wine tasting for $10 per person and offers tours of the vineyard by reservation. If you’re traveling with your dog, Veritas is the perfect place to camp out for the day because they are pup friendly ?


Blenheim Vineyards

Blenheim Vineyards is a must for any Dave Matthews Band fans. Why? Well, because the winery is owned by Dave Matthews himself, and he’s known to make surprise appearances from time to time.

Even though I was a die-hard DMB fan in my high school years, what I love even more about Blenheim is that they don’t lean on their famous owner as a crutch — in fact, they barely mention his name on the website at all. The wine here truly speaks for itself. 

We got a chance to meet their lovely winemaker Kirsty Harmon while we were visiting, and she shared how she has been experimenting with growing various types of grapes at Blenheim for over a decade.

I love their approach to wine here — make good wine that people will love, nothing stuffy or too complicated. The point at Blenheim is to have fun and they definitely accomplish that. 


King Family Vineyards

King Family Vineyards, Monticello Wine Trail

Located in nearby Crozet, King Family Vineyards is situated on a beautiful sprawling property where guests can enjoy plenty of indoor and outdoor spaces to taste, relax and spend time with friends and family. 

I love that in addition to showcasing some of the best wines in the Monticello wine growing region, King Family works with a winemaker down in Mendoza, Argentina to create a limited production of wine in collaboration with one of South America’s top wine regions. 

Pro Tip: If you’re visiting between Memorial Day Weekend and October, plan your visit on a Sunday when the winery hosts weekly polo matches. 


Pippin Hill Farm & Vineyards

Pippin Hill Farm and Vineyards, Charlottesville

When it comes to overall experience, Pippin Hill is hands down my favorite winery along the Monticello Wine Trail. Their patio and tasting room is beautifully designed (I especially love how the bistro lights add charm any time of year).

The holidays are an especially fun time to visit as the winery’s head horticulturist crafts stunning wreaths by hand from local florals and produce — many of which are grown right on site. Everything on their food and wine menus are also exceptional. 

If you’re looking for the best winery to spend a full afternoon eating lunch, tasting wines and enjoying the surrounding scenery, Pippin Hill won’t disappoint. They also have a sister restaurant on the Downtown Mall called Red Pump


Michael Shaps Winworks

While Michael Shaps Wineworks isn’t the most fancy tasting room on this list, what makes Michael Shaps so special is his unique experience and expertise in winemaking.

With a background studying winemaking in Burgundy, France, Shaps has developed quite the name for himself in the Virginia winemaking industry and not only produces his own label of wine but also acts as a consultant and winemaker for several top wineries in the state.

He also runs a successful winery in Burgundy. Fans of French wines will be happy to learn that when you visit Michael Shaps Wineworks you’ll have the chance to taste both his Virginia wines and those shipped from his winery in France. 


Where to Eat 

Petit Pois charlottesville

Petit Pois

One of the best dinners I’ve had in Charlottesville was at Petit Pois, a discreet and tiny French restaurant located right off the Downtown Mall.

It’s easy to miss but worth seeking out, especially if you have plans to catch a show at the Paramount Theater (it’s right next door) or live local music post meal.


Incredible classic Italian food run by a husband and wife duo. Located in the Belmont district, Tavola is a bit pricier than most C’ville restaurants and reservations are recommended, but it’s worth every every penny. 


My favorite spot in town for pizza is Lampos, a traditional Neapolitan pizza joint with a delicious doughy and slightly charred crust. You can tell this one’s a winner with consistent lines out the door. 


Buzzy European-style brunch with mouth watering pastries. If you don’t want to wait for a seat, just order a pastry at the counter to go. 


Located in a dark, intimate setting off the Downtown Mall, C&O is another standout fine dining option in C’ville that serves country French fare with global influences. 


For a convenient brunch on the Downtown Mall with diner vibes, try Bizou which sources all their food locally and sustainably and is one of the longest standing restaurants on the Mall. 


If You Have a Sweet Tooth

Gearthart's Chocolates in Charlottesville, VA


Want to bring some sweet treats back home with you? Head to Gearhart’s, which has been producing the finest chocolate in Charlottesville since 2001. 

Albemarle Baking Co.

One of the most beloved bakeries in Charlottesville, this is a great pit stop for a quick pick-me-up or to satisfy a sweet craving. 



Cool Foodie Experiences

Tasting dinner at the Clifton Inn, Charlottesville

Wine Pairing Dinner at The Clifton

Throughout the year, The Clifton Inn offers special wine pairing dinners to a limited number of guests. We were able to partake in a champagne pairing during the holiday season, led by a local sommelier with an extensive knowledge of champagne.

If you’re looking to do something a bit more special during your weekend trip to Charlottesville, contact the Clifton or get on their email list to find out when their next pairing dinner will be taking place. 

Flights and Bites at Pippin Hill Farms, Charlottesville

Tasting Menus and Cooking Classes at Pippin Hill

Pippin Hill offers a couple cool foodie experiences that are great to plan if you want to do something a bit more interactive during your weekend in Charlottesville — these are also perfect for groups!

The first is Flights and Bites, which is a three course tasting menu with wine pairings for $50 per person. 

For those that want to get their hands a bit dirty and learn the tricks of the trade, the winery also offers cooking classes, which are a fun way to spend an evening brushing up on your culinary knowledge. 


Tour the Gearhart’s Chocolate Factory

Pumping out 13,000 pieces of chocolate per day is no small feat and I got to witness this action firsthand at Gearhart’s during my recent visit to Charlottesville.

If you’re a chocolate lover like me, this is a great way to get a better understanding of the work and love that goes into crafting each perfect little square of deliciousness. Find Gearhart’s Events Here.  


Where to Caffeinate

Feast coffee truck Charlottesville

For coffee lovers, my favorite cups of jo can be found at Mudhouse (right on the Downtown Mall) and Shenandoah Joe.

Another go-to: Feast! market (pictured) is also a great casual eatery that features an adorable coffee truck inside their speciality foods shop and offers great seasonal drinks like pumpkin spice lattes and apple cider. 


Other Spots to Get Your Drink On

Tilman's wine and cheese shop, Charlottesville
Tilman's Wine and Cheese Shop Charlottesville

Tilman’s Wine and Cheese Shop

This great little market is right on the Downtown Mall and features a tiny wine bar in the back for those that want to sip vino or a craft cocktail in an intimate setting. This is a newer add to the Charlottesville scene and is a great addition that isn’t quite like anything else nearby. 

Alley Light

A hip cocktail bar and restaurant located by the Downtown Mall, Alley Light is — you guessed it — down a discreet alleyway, catering to those in the know. This is a great option for dinner as well. 

Three Notch'd brewery flight, Charlottesville, Virginia

Three Notch’d Brewery

Named after the historical Three Notch’d Road, which Jack Jouett traveled in the late 1700s to warn Virginia legislators that the British were coming for their capture, this brewery is a C’ville favorite and I love the nod to the state’s roots.

Head here to try a mix of wide ranging local brews from ales and IPAs to sours and stouts.

A Few Non Foodie Must-Dos in Charlottesville

Golden hour at Monticello, Charlottesville, Virginia


You simply can’t visit Charlottesville without checking out Thomas Jefferson’s home, Monticello. The grounds are beautiful, but hearing the story behind the home and Jefferson’s life in Charlottesville really gives a lot of context to the city that is hard to get anywhere else.

Shenendoah National Park in fall

Shenandoah National Park

If you have some extra time or need a break from all that eating and drinking, Shenandoah National Park is a great place to do that.

About 30 minutes East of Charlottesville, the park is stunning to drive through with great pull-off points for panoramic vistas, but I’d recommend opting for a couple short hikes if you have time.

Bittersweet fashion boutique, Downtown Mall Charlottesville

Stroll the Downtown Mall

The Downtown Mall is the heart of Charlottesville and where many of the city’s top restaurants, bars and boutiques are situated. If you plan on eating and drinking your way through a weekend in Charlottesville, then it’s likely your itinerary will take you to this area anyway.

If you’re looking to do a bit of shopping, don’t miss my favorite clothing boutique in town: BitterSweet

Did this post inspire you to take a trip to Charlottesville? Let me know in the comments below!

Planning a trip right now? Don’t miss my go-to websites for booking everything from flights and tours, to accommodation and more:

Live Like It’s the Weekend was graciously invited to explore Charlottesville as a guest of Visit Virginia, but as always, all opinions are my own and I would never promote anything I don’t freaking love.

You Might Also Like

No Comments

Leave a Reply