The Ultimate Guide to a Perfect Weekend in Charlottesville

Nestled in the foothills of the Blue Ridge Mountains, Charlottesville may be best known as the home to one of VA’s most prestigious universities: University of Virginia. However, the city is SO much more than that. It’s breathtaking mountain views and award-winning wine. It’s a center for arts & culture. It’s a hub for shopping local and family-owned businesses. They city hosts all the things that make for a perfect weekend getaway. Whether you’re looking for history, great food, craft wine, or the arts, you’ll find it in C’Ville. Here’s your Ultimate Charlottesville Weekend Guide and Itinerary.

How to Get to Charlottesville: Amtrak VA Northeast Regional Route

Trains are easily one of the BEST ways to keep your travel on track (pun totally intended) and get to your destination hassle-free. Instead of fighting traffic and driving from the DC Metropolitan Area, we decided to ride Business Class with Amtrak on their Northeast Regional Route. Here are a couple of the perks of traveling via Amtrak train:

  • Free WiFi and plugs allow you to stay connected on the go.
  • Each rider can bring two carry-on items AND two bags, included with your ticket (with no restrictions on liquid carry-on items).
  • The café car on-board has a full menu of snacks and hot food to enjoy, as well as beverages (even the adult ones). The car also has full-sized tables so you can spread out and watch the sights as they whoosh by!
  • With the VA Anytime Fare, Virginia residents get 15% off travel within the DC & VA area!
  • The Charlottesville Amtrak Train Station is centrally located in Downtown – and super close to the gorgeous Quirk Hotel.

Overall, riding the Amtrak VA train was such a great option for getting to Charlottesville. Since the city is super walkable (aside from a few Ubers here and there), it made the most sense to ditch the drive and let them do it for us!

Interested in overnight train travel? Click here to read about Amtrak’s Sleeper Car experience!

Where to Stay in Charlottesville: Quirk Hotel

Quirk Hotel is an art-forward hotel in the heart of Charlottesville’s Historic Downtown. The building was built around two historic homes dating back to the 19th century. Today, the boutique stay is a bright mix of chic and vintage indoor and outdoor communal spaces. When you walk into the lobby, you immediately notice the bright archways that make up the ceilings and the local art pieces that adorn the walls. On site, there are multiple spots to grab food and cocktails, including The Pink Grouse signature restaurant, laidback Quirk Café, Lobby Bar, and Q Rooftop lounge. Aside from the many places to indulge, there’s also a bi-level art gallery and artisan gift shop. It’s abundantly clear why Quirk is named Best Hotel in Charlottesville in 2021. It’s stunningly beautiful and the hospitality is top tier.

Day 1

Carter Mountain Orchard

Start your getaway off strong at one of the most beautiful places in Charlottesville: Carter Mountain Orchard! Perched at the top of Carter Mountain, the orchard and vineyard is the perfect place to live out your fall fairytale dreams. Sip wine while you take in the stunning scene of the entire valley below. Stroll rows of sweet and juicy apples and pick them straight from the tree. Even head to the Country Store to find fresh produce, locally made jams and honey, delicious apple cider donuts, and more. After working up an appetite picking all those apples and shopping for goodies, you can grab lunch at one of their on-site food trucks which rotate daily.

Stroll the Downtown Mall

The Historic Downtown Mall is one of the LONGEST pedestrian malls in the United States. Seriously – it’s 8 blocks of over 150 shops and 30 restaurants! You can find a little bit of everything handpicked by local makers – from antique shops to jewelry stores to handmade chocolate. Aside from shopping ’til you drop, the mall is a great spot to people-watch, potentially run into a live music performance, and grab a bite to eat. Don’t forget to snag a photo op at the famed Paramount Theater, built in 1931.

Have Lunch at Hamiltons’ at First and Main

There are so many great restaurants on The Historic Downtown Mall that choosing one can be a hard choice! While I didn’t get to feast my way through them all, I did try Hamiltons’ at First and Main and can confirm it’s a solid pick. Executive Chef Hannah Moster and her team bring a distinctive flare to contemporary American cuisine, serving up their take on classic dishes like Shrimp and Grits and Buttermilk Biscuits. I ordered the Blue Crab and Corn Bisque and Pan-Roasted Jumbo Lump Crabcake which were both delicious with a glass of Riesling. The restaurant itself has a cozy vibe both inside and on it the outdoor patio that feels perfect for a lunch stop.

Other top-rated restaurants on the Downtown Mall: The Whiskey Bar | Bizou | The Fitzroy

Explore the Grounds at University of Virginia

It’s no wonder that one of Charlottesville’s designated must-sees is also one of the most prestigious schools in Virginia. University of Virginia‘s grounds are 1,600 acres of perfectly manicured lawns, European architecture, and American history. Founded by Thomas Jefferson in 1819, much of the original pavilions and buildings have been preserved. You can stroll across the expansive central lawn, gaze at the larger-than-life rotunda, and get a feel for how one of our Founding Fathers wanted to reinvent higher education.

Dinner at The Ridley

As one of Charlottesville’s only Black-owned restaurants, I was thrilled to dine at The Ridley. The restaurant is an upscale-casual spot serving seafood-first Southern Cuisine and Craft-Cocktails in a swanky setting at The Draftsman, an Autograph Collection hotel by Marriott. In the modern space, you’ll find subtle nods to the institution’s namesake: Walter N. Ridley, the first African American to receive a doctorate from UVA. The menu features favorite we all know and love such as Lobster Rolls, Gumbo, Hot Chicken, Cajun Oysters, and more. We ordered the Roasted Chicken and Salmon Dishes – both were delicious!

Have a Rooftop Cocktail at Q Rooftop Bar

One thing I can’t resist is fresh air, good cocktails, and a birds-eye-view. Rooftops have my heart, no matter what city I am in. So, it was SUCH a wonderful privilege to have the Q Rooftop Bar right on top of the Quirk Hotel. During the day, you can indulge in thin crust pizzas and locally-inspired dishes. After 9PM, the space turns into a 21+ hangout. We opted to stop by after dinner, and grabbed the Pink Fizz and a Rum Old-Fashioned. Having a drink here was the perfect end to a perfect day while enjoying all the sites and sounds of the city!

Day 2

Brunch at Quirk Café

Start your morning with the most important meal of the day downstairs at Quirk Café, a welcoming space in a 19th century historic home next door to the Quirk Hotel. The restaurant mixes contemporary and vintage décor – with deep blue wall paper, lots of texture, and gold accents. On the breakfast menu, you’ll find lots of espresso-based beverages, waffles, breakfast sandwiches, eggs and more. We opted for the chicken and waffles – the chicken was crispy perfection, the waffle had a subtle sweetness to the dough, and the latte was perfect.

The Looking Glass Exhibit at IX Art Park

Fun Fact: The Looking Glass at IX Art Park is the very first immersive art exhibit in Virginia! The whimsical wonderland is a one-of-a-kind experience inviting you to leave reality at the door. (Don’t we wish we could always?) We escaped to an enchanted forest packed with lights, color, sounds, and hands-on displays that ignite the senses! Wander through a kaleidoscopic cave, solve the mazes in a neon-squiggle portal, crawl into a gnome house fully-furnished with teeny items, and finish the experience with a slot machine run by hidden coins. Can you say trippy? This was an unforgettable experience that was incredibly unique.

Wine and Views at Merrie Mill Farm & Vineyard

Stop and smell the rosé! About 9 miles east of Downtown Charlottesville is a *must see* treasure trove of fun for wine enthusiasts in a rustic town called Keswick. We visited one of the newest (and most beautiful) tasting rooms in the city, Merrie Mill Farm & Vineyard. The winery boasts a stunningly eclectic tasting room that’s expertly-decorated with bright pops of pink and teal and whimsical sculptures. Outside, your breath will be taken away by the sun shining on rows of grapes and mountain views in the distance. The wine was also spectacular – I definitely recommend ordering a wine flight with charcuterie to have a variety of flavors. The real star of the show though at Merrie Mill is the service. Our server, Katie, was such an amazing host. I WISH I could dig up Merrie Mill and move it three hours north so I could visit every weekend!

Dinner at Marigold (Get Reservations!)

Just ten minutes down the road from Merrie Mill Vineyard, you’ll find Keswick Hall – Charlottesville’s only Forbes Travel Guide Five Star resort. Located at the resort, you won’t want to miss an incredible meal at Marigold, created by French celebrity Chef Jean-Georges. The restaurant features fresh farm-to-table produce that changes seasonally set in a rustic-chic, yet elegant, dining space. You can dine al-fresco near the intimate front porch fireplace, feast in the elegant dining room, pull a seat up at the chic teal and gold bar, or even enjoy sweeping mountain views on the back patio. From the pre-dinner prosecco to the sweet dessert latte, everything about our experience was OUTSTANDING!

As I mentioned, the menu changes with the seasons. But this fall, here’s what we had:
1st Course – Crunchy Sushi with Salmon
2nd Course – Maine Lobster with Chili Butter & Shoestring Fries, Rigatoni with Meatballs & Smoked-Chili Tomato Ragu
3rd Course – Chocolate Lava Cake with Vanilla Ice Cream, Apple Pie with Pecan Ice Cream, Latte

The service was great, the ambiance is beautiful, and the food was flavorful and fresh. Run, don’t walk, to get a reservation!

There are so many adventures awaiting you in Charlottesville – from shopping galore to delicious food. Which of these activities sound the most fun to you? Let me know in the comments!

Disclaimer: This post was created in partnership with Amtrak. As always, all opinions & thoughts expressed above are 100% my own – I wouldn’t have it any other way!


  • Marissa Strang

    Marissa Strang is a full-time lifestyle and travel blogger based out of the Washington, D.C. Metropolitan area. Travel is her number one passion, and she is on a mission to empower others to make travel a reality for their own lives as well. She’s a strong believer that everyone can experience the joy of exploring the world, no matter the way they look or their socioeconomic status. Marissa creates one-of-a-kind city guides, destination inspiration, and budget-friendly travel hacks for aspiring travelers, especially young travelers and minorities. By creating travel content through her blog, The Marissa Daily, she strives to help others make lifelong memories - one destination at a time. Her journey as a blogger for the past 3 years has led her to visit amazing places and build an engaged travel community that she cares for deeply. One of the principles Marissa lives by, and encourages others to abide by, is that when you look like your passport photo, it’s time to book a trip. Let's go places.

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