Holly and Charles have enjoyed several hikes together in Shenandoah National Park. Visitors pay $30 to enter and can cruise down Skyline Drive with commanding views of the Shenandoah Valley or hike trails like Old Rag (~9 miles) or Riprap (~10 miles). For those looking to skip the entrance fee and try a less ambitious hike, the Humpback Rocks are right down the street from the park's entrance and only ~3 miles.
The Foxfield Races are a classic horse race and happen to fall the day before the wedding. The great and good of Virginia society are out in force for turf races that start just after noon and wrap ~3:30. Visitors to the site can find ticket information there. We urge guests considering attending to arrange transportation in advance or drive, as ridesharing can be challenging.
Thomas Jefferson's home is a popular tourist destination in the area. Monticello has recently revamped its tour offerings and provides a variety of guided tours for those looking to better understand Jefferson's complex legacy, view Palladian architecture, or pick up some gardening tips.
Many of Holly and Charles' first dates consisted of walking around Grounds (guests who refer to the area as "campus" risk spontaneous combustion). The highlight is the Rotunda, the heart of the University's Academical Village , which is modeled after the Pantheon. The Rotunda is open from 9 to 5 daily (see the website for tour information). Other Grounds landmarks to check out include the Lawn and the Memorial to Enslaved Laborers. If you're hungry, head to Roots for an aggressively large salad (Holly's rec) or Take it Away for the Elliewood Club with house dressing (Charles' rec).
Charlottesville sits at the heart of Virginia's wine country. While you will experience our favorite (Pippin Hill) as the venue, we encourage you to explore some of the area's other fabulous offerings. King Family is our second favorite with stunning views and a world class polo facility attached. Sunday matches do not start until May, but visitors can book a 90 minute Intro to Polo Experience on horseback followed by a wine tasting. King Family pairs nicely with Veritas and Pro Re Nata in Crozet. For those looking East, we recommend Keswick Vineyards and Barboursville.
For golfers making the trek to Charlottesville, Charles recommends the Birdwood Golf Course at Boar's Head Resort. Recently redesigned by Davis Love III, the course provides a stern test for low handicappers and a relatively walkable design. Access and pricing is extremely preferential to UVa students and guests of the Boar's Head Resort, but limited tee times are available to the public.
Should you want to watch Liverpool win the Premier League title with a win over Tottenham Hotspur from 11:30-1:30 on Sunday, Random Row is your spot. The Liverpool bar in town, Charles has spent several Saturday and Sunday mornings supporting the Reds from the Row.