With a rich 300-year history, colorful sites, and exceptional cuisine, Charlottesville is simply a sight to behold. It’s one of the most remarkable destinations in the United States, and (arguably) the birthplace of America (as the rough drafts of the Declaration of Independence, the Constitution, and the Bill of Rights were written here.
This is a place where people come to get away from it all, sometimes for a weekend, other times… forever. John Grisham fell in love with the area, penning numerous bestsellers here. Sissy Spacek has lived in Charlottesville for more than four decades. Dave Matthews was a bartender here. Heck, even Edgar Alan Poe attended college in Charlottesville! It wasn’t that long ago that the U.S. Bureau of Economic Research named Charlottesville, Virginia as “America’s Happiest Place.” And once you visit, you’re sure to fall for C’ville too!
Creating a world-class vacation in Central Virginia can be overwhelming, with so much for all ages and interests. We’ve narrowed down the best things to see and do during your week-long getaway in Central Virginia… and here’s our favorite suggestions for your Charlottesville vacation itinerary:
DAY 1 – WINERIES, BREWERIES & DISTILLERIES
Virginia’s love affair with wine is nothing new… in 1619, Virginia passed a law requiring each male colonist to grow at least 10 wine grapevines! Today, we’ve been named by Wine Enthusiast as one of the “Top 10 Wine Travel Destinations” in the world! Here’s some of our favorite wineries and breweries:
The leader of Virginia’s modern wine era also serves delicious lunches and dinners.
Family-owned Keswick was awarded the “Best White Wine in America” with their very first vintage.
Virginia’s largest vineyard (1,300 acres of breathtaking scenery) was a back-to-back winner of the Monticello Cup.
Dave Matthew’s music is great, his wines are better, and the views from his winery are outstanding!
“The Father of Virginia wines” has long produced Virginia’s finest wines, but locating them was difficult… not anymore with his new tasting room.
Maybe grapes aren’t your thing, but apples are! Castle Hill uses time-honored traditions to create award-winning Virginia cider.
Central Virginia’s first rural brewery. Great beer, awesome food, and stunning mountain views make this worth the trek.
In less than 10 years they’ve become America’s largest independently-owned cider company, with more than 100 awards (so far).
Brewpub in a converted brick warehouse in the heart of Downtown Charlottesville… great pub food as well.
The only mother-daughter distilling duo in the nation, they produce award-winning gin, rye whisky, and bourbon overlooking the Blue Ridge Mountains.
Using time-honored traditions, they produce an impeccable American Single Malt Whisky, “Courage & Conviction”.
DAYS 2 & 3 – “MUST-SEE” HISTORY SIGHTS
If you’re looking for a dose of history, you’ll find it in Charlottesville (three Presidents lived here, and America’s founding documents were written here). There’s some things you just shouldn’t miss, so here’s our list of “must-see” places:
No home better reflects the personality of its owner than Jefferson’s architectural masterpiece (the only home in America recognized as a U. N. World Heritage Site).
Thomas Jefferson’s “Academical Village”, the Lawn and the Rotunda are iconic figures at one of America’s premier universities. Also see Edgar Alan Poe’s room while you’re there.
The lifelong home of the 4th U. S. President and the “Father of the Constitution”, as well as his wife (Dolley), our country’s first “First Lady”.
The home of the 5th President of the U. S., author of the “Monroe Doctrine”, and close friend of Thomas Jefferson.
Once a hotel, then a Civil War hospital (serving more than 70,000 soldiers), then a Freedman’s Hospital, and now a museum.
Visit the Childhood village of Earl Hamner, Jr. (the creator of “The Walton’s”). The museum includes replicas of “Ike Godsey’s Store”, “John Boy’s Room”, and more.
DAY 4 – GET OUT AND EXPLORE
There’s no better way to get a comprehensive “lay of the land” than to hop in your car and begin driving throughout Central Virginia. Though the following sights are not in our immediate area, they make a great day-trip:
Skyline Drive (the Local’s Way)
A really nice “1/2 Day-Trip” from Prospect Hill, full of numerous roadside stands, hiking trails, scenic overlooks, country markets, and eating establishments: Take Hwy. 33 through Gordonsville, Barboursville, and Ruckersville (hit some antique shops while there, and eat lunch at Jack’s Shop Kitchen). Drive to the “Swift Run Gap” entrance to the Shenandoah National Forest, then travel South on Skyline Drive. Drive slowly, so you don’t miss the scenic overlooks and the waterfalls near the road. Exit Skyline Drive at Afton Mountain, pick up some great wines at Greenwood Gourmet Grocery (and the BEST macaroni & cheese, if you hit it right), and head back on Hwy. 250 (or Interstate 64 if you’re tired of rural roads).
Thomas Jefferson’s personal retreat near Lynchburg, he selected this property because of its distance from his public life. In keeping with his love of classical designs, this may be the first octagonal house built in the United States
Richmond’s large, sprawling cemetery with stunning views overlooking the James River. It is the final resting place of two U. S. Presidents, as well as Jefferson Davis (President of the Confederacy). In addition, there are 28 Confederate generals buried there (more than any other cemetery in the country).
Thomas Jefferson once owned this geological formation near Lexington. With a 215-foot arch (which spans 90 feet), Natural Bridge was one of the top tourist attractions of the new world during the 18th and 19th centuries, even mentioned by name in Melville’s Moby Dick. The underlying trail, a 30-foot waterfall, and a nightly laser show are accessible to guests, but unfortunately Foamhenge (a full-size styrofoam replica of Stonehenge) has been removed.
America’s oldest show cave (in operation since 1806), these limestone caverns wind for more than 3 miles underground with numerous flowstone, stalactite and stalagmite features. Located in the town of Grottoes (near Harrisonburg), the visitor’s park also has hiking and biking trails, and hosts a yearly Bluegrass Festival.
DAY 5 & 6 – OUTDOOR ACTIVITIES & ATTRACTIONS
Charlottesville and Central Virginia offer a wide array of unique, outdoor things to do. You’ll find something fun (and exhausting) for all ages during this part of your Charlottesville vacation itinerary:
Shenandoah National Park
Over 20,000 acres of waterfalls and spectacular views, including 500 miles of trails (plus 101 miles of the AT). And Skyline Drive is the breathtaking roadway that takes you through it all!
Hiking & Back-Packing
Virginia has 3 million acres of public outdoor recreation areas, including more than 2,200 hiking trails covering 3,189 miles. Our favorites include Crabtree Falls, Ragged Mountain, Humpback Rocks, and Spy Rock.
Lake Anna State Park has numerous hiking, biking, and horseback riding options (as well as panning for gold or a lazy beach day) on Virginia’s 2nd largest lake. Several marinas rent pontoon boats, jet skis, or fishing charters for the day.
With dramatic views of downtown Charlottesville, you can pick your own peaches or apples. Don’t miss the homemade apple cider doughnuts!
Built more than 150 years ago, this brick-lined tunnel carried railroad traffic beneath the Blue Ridge Mountains for three quarters of a century. Hikers and cyclists now use it to experience one of the most unique vantage points in the region.
Escape on a scenic sunrise flight over the tranquil Virginia countryside. Choose romantic flights for two, or take a group flight and meet other adventure-lovers.
Offering exciting tubing, canoeing, kayaking, rafting and camping trips down the scenic James River, this is the oldest and largest tubing company on the James River.
This nationally-recognized golf facility (#58 on Golf digest’s “America’s 100 Greatest Public Courses”) is only 4 miles from Prospect Hill!
A 20-mile rustic, urban hiking trail network that winds through the heart of Charlottesville, meandering along streams, through forested buffers, and ultimately connecting six city parks.
DAY 7 – DISCOVER OUR LOCAL’S FAVORITES
As you see, Charlottesville is packed with fun and interesting things to see and do. But there are a few which are considered “must-do” by the locals… classic C’ville, you might say. These are our favorites… not explanation necessary, as they represent the best of all things Charlottesville!
Downtown Pedestrian Mall
The centerpiece of Charlottesville, a happening tourist destination, and a defining element of our civic culture. There’s a certain laid-back hustle-and-bustle on this 8-block walkway… home to more than 120 shops, 30 restaurants, 10 art galleries, live performance venues, and a Saturday farmer’s market.
This 2-mile trail (which includes Central Virginia’s most popular park) winds its way through a native hardwood forest, ending at Jefferson’s Monticello. A 5% grade keeps it accessible to all.
A thriving “corner” of 70 bars, restaurants, bookstores, and night spots (across the street from the University of Virginia). The Corner is especially active at lunchtime, as faculty and students descend for their mid-day meals.
University of Virginia Cavaliers Sports
Leading the ACC with 27 NCAA Championships, including the 2019 NCAA Basketball Champs (and by default, the 2020?), the UVA Cavaliers always provide exciting and captivating championship-level sporting events!
WHERE TO STAY…
Just 20 minutes from Charlottesville and only 4 miles from the Interstate, as you enter Prospect Hill’s boxwood-lined driveway you’ll be captivated by the serenity of this charming estate. That will set the tone for your entire visit to Central Virginia as you work through your Charlottesville vacation itinerary. Choose a historic room or cottage at our Charlottesville bed and breakfast, let us be your “basecamp,” and your 1-week central Virginia vacation getaway will be complete. We look forward to seeing you soon!