June 17, 2024|Around Charlottesville

How to Spend a Weekend in Wine Enthusiast’s Wine Region of the Year

Have you visited Wine Enthusiast’s Wine Region of the Year yet? Now is the time to discover everything the Charlottesville region and the Monticello American Viticultural Area (AVA) have to offer.

Whether you’re interested in touring the celebrated Monticello Wine Trail, exploring historical landmarks, enjoying outdoor adventures in the Blue Ridge, or savoring local dining, Charlottesville promises a memorable experience for visitors of all interests.

We’ve compiled an essential guide to Cville for casual visitors and wine connoisseurs alike, to enjoy the best of Virginia Wine Country.

Where to Stay

Crossroads Inn
Originally a historic tavern dating back to 1820, Crossroads Inn features unbeatable mountain views, a historic legacy, and a convenient location close to both central Charlottesville and neighboring wineries. A timeless escape with modern comforts that guarantee an idyllic getaway.

Kimpton The Forum Hotel
For those looking to pick a home base close to UVA Campus, the Forum Hotel is the perfect spot for a stylish stay featuring amenities such as elegantly designed rooms and a rooftop bar.

Oakhurst Inn
A boutique hotel offering a cozy and inviting retreat also located central to the University of Virginia Campus. Enjoy charming accommodations, a serene pool, and a delightful café onsite. The perfect spot for a relaxing weekend. 

Boar’s Head Resort
A countryside oasis with upscale accommodations, fine dining, and a variety of amenities such as a spa, golf course, and scenic walking trails. It’s the perfect choice for those seeking a weekend retreat in a tranquil setting with plenty of opportunities for adventure.


Photo: Sera Petras

Vineyard Adventures

With over 40 wineries in the Charlottesville area, including 30+ on the Monticello Wine Trail, the region is home to a wide variety of wine ventures of all sizes, each with their own unique varietals and tasting experiences. The area boasts a perfect climate for grape growing due to fertile soil and unique topography. The most common grape varieties include Cabernet Franc, Petit Verdot, Chardonnay, Merlot, Cabernet Sauvignon, and Viognier, often regarded as the region’s signature grape.

The Monticello Wine Region celebrates Thomas Jefferson’s early efforts to pioneer winemaking in the Charlottesville area and is recognized as the birthplace of American wine. Honored as Wine Region of the Year by Wine Enthusiast, this region has surpassed other renowned regions in Italy, France, and South Africa. This award positions Charlottesville as a world-class wine destination and highlights the area’s unmatched quality and unique terroir—a success that brings Jefferson’s initial aspirations to life.

This award-winning trail is a must-do for those looking to experience the best of Virginia Wine Country. Savor different varietals, learn about winemaking and unwind to the backdrop of rolling hills and picturesque vineyards.

Explore and Enjoy

The Downtown Mall
Stroll through the pedestrian mall in the town center, surrounded by historic buildings and a mix of shops, restaurants, galleries, and more.

Photo: Richard Hedrick

A Haven of History
A visit to Charlottesville isn’t complete without exploring Monticello, Thomas Jefferson’s former estate and plantation. Experience Virginia’s colonial heritage with a visit to Michie Tavern, featuring 18th-century Southern cuisine.

Don’t miss a walk on the University of Virginia “grounds” to see the iconic Rotunda, also built by Jefferson. Those looking to dive deeper into local American history can visit James Monroe’s Highland, which is now a historic museum.

The Best of the Blue Ridge
Blue Ridge Mountains and Shenandoah National Park provide scenic trails like Old Rag Mountain and Humpback Rocks, great for both novice and experienced hikers. Those looking to stay closer to town can explore the Rivanna Trail surrounding the city. If a river adventure is calling your name, the Rivanna River is great for kayaking and tubing.

What to Eat

Petite MarieBette
Conveniently located in downtown Charlottesville, this charming bakery and café is known for its freshly baked goods and delectable artisanal pastries. A seasonal latte and petite canelés are the perfect way to start your day exploring the city.

You can’t go wrong with authentic Italian cuisine and an intimate setting, perfect for special occasions. Located in the heart of Charlottesville’s charming Belmont neighborhood.

A historic facade welcomes you into an elegant yet cozy interior, where French-based cuisine is paired with global flavors. A Charlottesville staple with exceptional cuisine and rustic charm.

Oakhart Social
A trendy spot featuring a diverse menu, stylish atmosphere, and curated selection of wine and cocktails, this is the ideal place for an outdoor hangout with friends and family during the warm weather months.

If you’re looking for an evening of ambiance, opt for sophisticated sushi creations and contemporary Japanese flavors at Ten on the Downtown Mall. It’s a perfect spot for a date night or a girls’ weekend dinner.

Parting Bite
On your way out of the small but lively city, hopefully with ample wine in tow, make a stop at the beloved Bodo’s Bagels, the quintessential Charlottesville breakfast spot. 

An idyllic setting for wine enthusiasts, outdoor adventurers, and foodies alike—we invite you to visit Charlottesville, taste our exceptional wines, and immerse yourself in the rich experiences this charming region has to offer.