You don’t have to be type-A to enjoy a well-planned, historic trip to Charlottesville. To ensure your stay at our Virginia bed and breakfast is all you had hoped for, we have personally crafted a 3-day Charlottesville history tour. Keep reading and make sure to take note of any activity that will make your East Coast getaway one for the books!
Day 1: Meet Past U.S. Presidents
8:30-9:30 am: Breakfast at Prospect Hill – Served everyday between 8:30 and 9:30 a.m. at your choice of a private table in our dining room, or delivered directly to your room, begin your day with Chef’s hot, scratch-made breakfast.
10:30 am – 1:30 pm: Thomas Jefferson’s Monticello – After your bellies are happy and you have had your morning coffee, head to the home of Thomas Jefferson, the 3rd President of the United States. Once a 5,000-acre plantation, Jefferson began designing Monticello after inheriting land from his father at age 26. Monticello is a National Historic Landmark, is the only private home in the United States to be designated a UNESCO World Heritage Site, and is a must-see stop on any Charlottesville history tour. Images of Monticello are on the reverse side of both the United States nickel and the two-dollar bill. If you plan on visiting this pristine establishment, we recommend blocking off 2.5 – 3.5 hours of your day to fully experience all Monticello has to offer. Some of our favorite things to do onsite include:
- The main house at Monticello
- Jefferson’s gravesite and cemetery
- Exhibits under the house, including colonial cooking, travel, the legacy of slavery, & Sally Hemmings
- Kids discovery room
- Grounds and gardens
- Legacy of Declaration of Independence, the construction of Monticello, and more
- Gift shop, café, bookstore, and more
- With native hardwood forest, deep ravines elevated walks and spectacular views, the Saunders-Monticello Trail is Central Virginia’s most popular park
1:30 – 2:30 pm: Lunch at Michie Tavern – Located just outside the gates of Monticello, this circa 1784 tavern once served as the social center of its community and provided travelers with food, drink, and lodging. Servers in period attire offer traditional 18th-century Southern fare, including southern fried chicken, hickory-smoked barbecue, stewed tomatoes, black-eyed peas, and buttermilk biscuits, in a rustic and historic restaurant setting. After lunch guests may enjoy browsing in one of four unique shops – all housed in distinct historic structures.
3:00- 5:30 pm: Highland – The Highland Estate of James Monroe, 5th President of the United States. Encouraged by his close friend, Thomas Jefferson, Monroe purchased one thousand acres of land adjacent to Monticello in 1793. By 1815, Monroe increasingly needed to sell his land to pay off debt, and in 1825, was forced to sell Highland completely. The estate is now owned, operated and maintained by Monroe’s alma mater, the College of William & Mary. Highland was featured in Bob Vila’s A&E Network production, Guide to Historic Homes of America.
- Guided Tours
- Monroe’s career
- Monroe’s style in furnishing a new nation
- How Monroe’s home was lost and re-discovered
- Monroe’s friendships Washington, Adams, Jefferson & Madison
- Slavery at Highland
6:30 – 8:00 pm: Dinner at Prospect Hill – After a long day of fun-fill history lessons, come back to the inn and enjoy an award-winning, savory dinner, right here at Prospect Hill Bed and Breakfast. After you have satisfied your hunger, mosey back to your room for a relaxing evening.
*Dinner is served between 6:00 pm and 8:00 pm nightly, except Tuesdays
Day 2: Step Back in History
8:30-9:30 am: Breakfast at Prospect Hill – To start the day off right, wake up to a scratch-made breakfast from our talented Chef. His “chef’s choice” offerings include such classics as poached eggs with prosciutto, roasted asparagus, and chive oil; classic Eggs Benedict; Belgian waffles with warm peach compote and Applewood smoked bacon, and fresh seasonal fruit (or something on the lighter fare, like a yogurt parfait).
10:00 am – 12:00 pm: Montpelier – The Plantation House of the Madison family, including fourth President of the United States, James Madison, and his wife Dolley. The 2,650-acre property was declared a National Historic Landmark and listed on the National Register of Historic Places in 1966. Owned by the National Trust for Historic Preservation, Montpelier is open seven days a week with the mission of engaging the public with the enduring legacy of Madison’s most powerful idea: government by the people. Twenty-first-century archeological investigations have revealed new information about African-American life at the plantation and spurred recent restorations of the slave quarters (with research-based, in part, on Prospect Hill’s original structure, the Boy’s Cabin) in the South Yard.
- Guided Tours
- The Montpelier House and Artifacts
- Dolley Madison, America’s FIRST First Lady
- Madison, the Constitution, and the Bill of Rights
- Madison’s friendship with Jefferson
- Slavery at Montpelier
12:30 – 2:30 pm: Lunch and Wine Tasting at Barboursville Winery – Today, Virginia is home to more than 250 wineries and ranks 5th in America in grape production with 6500 tons of grapes produced each year. This growth was led, in part, by the 1976 opening of Barboursville Vineyards by the Zonin family of Italy. Located on the former estate of James Barbour (the 19th Governor of Virginia), Barboursville Vineyards has been one of Virginia’s premier wineries for more than 40 years.
The entire estate is open for wine tastings & tours, outdoor strolls of the splendid lawns, or a relaxing picnic lunch. In addition, you can explore the historic ruins of Governor Barbour’s home (which burned in 1884). This house was significant in that it was the only home in Orange County designed by Thomas Jefferson himself. Delicious lunches are served in the onsite restaurant, Palladio.
3:00-4:00 pm: Exchange Hotel and Civil War Medical Museum –The Exchange Hotel Civil War Medical Museum contains exhibitions on the history of Gordonsville as a railroad town, the elegance of the Exchange Hotel and its transformation and remarkable history as the Gordonsville Receiving Hospital. Prior to the Civil War, the Gordonsville’s Exchange Hotel with its Georgian architecture (including high ceiling parlors and grand verandas) welcomed passengers from two intersecting rail lines. Once the war began, the railroads were used to transport troops, supplies, and the wounded to Gordonsville where the Exchange Hotel became a battlefield receiving hospital. By the end of the war, the Gordonsville Receiving Hospital provided care for 70,000 soldiers, both Confederate and Union.
Following the Civil War, the hospital served newly-freed slaves as a Freedman’s Bureau. Original letters that students wrote to their teacher, as well as documents from court cases held in the building during that period, are on display. As the United States healed and the railroads once again boomed, this elegant building returned to its role as a hotel. On display are world-renowned collections of artifacts relating to medical care during the Civil War, including surgical instruments, pharmaceutical bottles, containers, medical knapsacks, panniers, stretchers, litters, prosthetic devices, and dental tools.
Dinner at Restaurant Rochambeau in downtown Gordonsville – Take a break in between activities and get a taste of authentic French cuisine at Restaurant Rochambeau. Their classic Soupe aux Homards or Foie Gras Maison Comme Un Mille Feuilles are great options.
Day 3: Choose Your Charlottesville History Adventure
8:30 – 9:30 am: Breakfast at Prospect Hill – It’s only fitting to enjoy another delicious breakfast on your last day at the inn! Expect another tasty offering today… perhaps our whole-wheat pumpkin-pancakes topped with wild Virginia blueberries or raspberries or an assortment of frittatas and quiche with savory hams and sausages.
For day three, we recommend choosing from any of these wonderful and history packed attractions.
- Major Civil War Battlefields Tour – Information-packed guided tours of the most fought-over territory in America, with local historian Phil Audibert. The all-day tour includes Fredericksburg, Chancellorsville, Wilderness & Spotsylvania Courthouse; Half-day includes Chancellorsville (Lee’s greatest victory) and Wilderness (the beginning of the end).
- The Battle of Trevilian Station – Located 6 miles from Prospect Hill, this is a self-guided driving tour of major sites of the largest all-cavalry battle of the Civil War. There is no visitor center or battlefield, per se; Rather, the tour stops at a number of road-side markers that detail the events that happened on or around those lands.
- The Rotunda at the University of Virginia – Designed by Thomas Jefferson as the architectural and academic heart of his “Academical Village”, the University of Virginia was based on Jefferson’s principle that learning is a lifelong process, and that interaction between faculty and students is vital to the pursuit of knowledge. Jefferson modeled the Rotunda after the Pantheon, a second-century temple in Rome. Construction began in 1822 and was completed in 1826, shortly after Jefferson’s death (on July 4 of that year). Built at a cost of almost $60,000, it was the last structure to be finished on the Lawn. Together with Monticello, the Academical Village is designated as a UNESCO World Heritage site.
Lunch and Wine Tasting at Virginia’s Finest Wineries: Favorites of our guests include Blenheim Vineyards, Trump Winery, Keswick Vineyards, Jefferson Vineyards, 53rd Winery & Vineyard, Pippin Hill, and Michael Shaps Wineworks.
Shopping & Antiquing on Main Street, Gordonsville – Visit the quaint and charming town of Gordonsville with beautiful storefronts offer unique wares.
- Alpaca Boutique offers alpaca products, apparel & bedding; pottery and copperware
- Cavallo an art gallery with custom framing
- Floradise Orchids is a premier quality orchids, arrangements, and installations
- Gordonsville Emporium is an eclectic thrift shop
- Krecek Kakes & Coffeeshop offers a variety of cakes, muffins, pies, and specialty coffees and teas
- Laurie Holladay Interiors is the coolest décor shop with a surprise at each display
- Lindenlaan Antiques is a fine European antique store
- Posh offers vintage jewelry and custom jewelry made-to-measure
- Stokes of England showcases blacksmith work, including blade cutlers, architectural ironwork
Dinner in Town – End your amazing Virginia getaway with a tasty meal from one of the many fine eateries or restaurants in town.
Now that we have outlined all the details for a fun and educational Charlottesville history adventure, book your cozy room, grab your favorite history buff, and get ready for a vacation like no other!