Surrounded by farms, vineyards, and verdant estates, Charlottesville is an ideal destination for celebrating local producers and bucolic scenery.
Distance from DC: 115 miles
Where to Stay
Just 15 minutes from downtown Charlottesville, Crossroads Inn has been in continuous operation since 1820, though accommodations are more luxurious than they would have been two centuries ago. A charming spot with porch rockers, a fire pit, and a small flock of chickens, it’s part of the larger property of Pippin Hill Farm & Vineyards, right next door.
Another place with a past is the Clifton, a modern boutique hotel originally built for Thomas Jefferson’s daughter and her family. A top-to-bottom renovation in 2018 transformed the 18th-century estate into a stylish hotel with well-appointed cottages and rooms in the main manor, farmhouse, and stables. It’s set on 100 acres, and guests can enjoy the private lake, walking trails, and croquet lawn, and swim in the outdoor infinity pool on still-warm fall days. The hotel has a formal restaurant, 1799, which serves New American cuisine with ingredients from the garden.
Back to Top
Things to Do
While many wineries dot the area, a few offer activities that go beyond the bottle. Book a guided tour at Pippin Hill Farm & Vineyards, meandering through vines and a field of wildflowers with a glass in hand, followed by a tasting experience. The winery’s chef also leads cooking demonstrations that utilize the farm’s herbs and produce—watch the demo while you drink sparkling wine, then sit down to a feast paired with the vineyard’s vintages. Ready to pick up a spatula yourself? Cooking classes start with a tour and end with dinner in the tasting room. Nearby, King Family Vineyards serves Petits Verdots and Viogniers to rival its countryside views. Every Sunday through October, the winery hosts polo matches. Plan to arrive early (the grounds open at 10 am, and matches begin at noon) and bring a picnic.
You can also visit two historic estates to see how the Founding Fathers lived, including the reality that the properties relied on slavery. Monticello, Thomas Jefferson’s home, is filled with the third President’s inventions as well as posh 18th-century furniture and art. Although it doesn’t get nearly as much foot traffic, James Monroe’s Highland is worth a visit. In 2016, archaeologists discovered a building hidden underground, and new exhibit spaces were unveiled in 2021, offering a fresh look at the past. Both properties are also starting points for great walks and hikes. Monticello’s 2,500 acres include the four-mile Saunders-Monticello Trail, which winds through ravines and forests, while Highland has several hikes ranging from an easy half-mile stroll to a two-and-a-half-mile mountain trail.
Back to Top
Dine and Drink
Fancy a casual, farm-to-table lunch with leafy panoramas? TheMarket at Grelen is a hybrid garden center, gift shop, and cafe with a menu of sandwiches and salads that change with the season. Don’t miss the handcrafted ice cream, churned using the market’s homegrown fruits and herbs. Another casual option near town is Dairy Market, named for its location in the brick Monticello Dairy Building. The sprawling food hall, which opened in 2020, is an easy stop to sample Charlottesville spots making everything from Himalayan momo dumplings to local IPAs.
For a more upscale meal set within a former textile mill, Broadcloth serves prix fixe tasting menus (four, six, or eight to ten courses) Thursday through Saturday and an à la carte (and slightly earlier) “supper” on Sunday. Each menu uses seasonal produce and meats from local farms and purveyors, changing weekly.
This article appears in the September 2025 issue of Washingtonian.
