For the 50+ Traveler

On a train journey riding the Amtrak Cardinal through Virginia, I had a multi-hour layover in Charlottesville before boarding the Crescent to travel on to visit family in Greensboro, North Carolina. I was glad for the opportunity to explore Charlottesville on foot, as the train station is centrally located between the University of Virginia campus and downtown Charlottesville.

If visiting Charlottesville by train, Union Station is Amtrak’s third-busiest station in Virginia serving the Crescent, the Cardinal, and the daily Northeast Regional trains, making it easily accessible by train from Chicago, D.C., and the numerous cities along the different routes.

This charming town is known as the birthplace of American wine, so it’s a perfect destination for wine enthusiasts. There’s an abundance of history there as well. Charlottesville was home to Thomas Jefferson, author of the Declaration of Independence and the Statute of Virginia for Religious Freedom and third president of the United States. Situated in the Blue Ridge Mountains, Charlottesville’s scenery and outdoor activities are unparalleled. Plus, there’s a burgeoning culinary scene, unique luxury accommodations, and plenty of live music and art to discover.

Visit Thomas Jefferson’s Monticello

Plan on at least a few hours to visit Monticello -- a UNESCO World Heritage site. Jefferson’s mountaintop home and plantation, Monticello, is located just outside of town, and tours of the house and historic gardens are available daily, year-round. Dine on foods sourced from the Monticello gardens -- in addition to locally sourced meats, cheeses, and bread -- at the Monticello Farm Table.

Tour the house, the gardens, and the slave quarters to get to know more about Jefferson and others who lived there, and their contributions to history. While there, hike the Saunders-Monticello Trail, a four-mile easy walk that’s accessible to walkers, cyclists, and those in wheelchairs. Enjoy spectacular views of the Blue Ridge Mountains, the native hardwood forest, and deep ravines on this winding trail.

Jefferson founded the University of Virginia there in 1819. The original campus is called the Academical Village, and it’s also a must-visit.

James Monroe's Highland in Charlottesville.

Tour James Monroe’s Highland

Just a short five-minute drive from Thomas Jefferson's Monticello is the estate of James Monroe, fifth president of the United States. Spend a couple of hours at James Monroe’s Highland with a guided site tour, an augmented reality experience, and a self-guided exploration of the property.

Monroe’s story is one part of the Highland tour, but there’s also acknowledgement of the enslaved women and men who lived on the property for several generations. Monroe enslaved as many as 250 people in his lifetime yet also called for the abolition of slavery. The visitor experience looks at the contradiction between Monroe’s personal practices and his political actions.

Sip Wine At A Vineyard

The ideal setting for vineyards, the backdrop of the Blue Ridge Mountains adds to the experience of a wine tasting. There are nearly 40 wineries from which to choose. Notable wineries include Pippin Hill Farm and Vineyard, with their spectacular views, and King Family Vineyards, which has polo matches on the grounds every Sunday in the summer. There’s also Blenheim Vineyards, owned by Dave Matthews of the Dave Matthews Band, and Gabriele Rausse, considered to be the father of Virginia wine.

The wineries along the Monticello Wine Trail were inspired by Thomas Jefferson’s vision of grape growing and winemaking. Meet a winemaker, take in a wine festival, or enjoy a concert at a vineyard along the wine trail. The PDF wine trail brochure will help you plan your visit in advance.

The downtown pedestrian mall in Charlottesville.

Stroll The Historic Pedestrian Downtown Mall

With eight blocks of restaurants and cafes -- many with outdoor patios -- plus locally owned retail shops, performance venues, and lodging options, there’s plenty to see and do along this stretch of Charlottesville’s historic area. The open-air pedestrian mall is one of the most beautiful and successful in the nation. You’ll find a mix of restored and renovated buildings housing more than 120 shops and 30 restaurants.

Kayakers on the Rivanna River in Charlottesville.

Float, Kayak, Canoe, Or Fish Along The Rivanna Or James River

Take a self-guided float on the historic James River with James River Reeling and Rafting. They’ll prepare all the equipment. All you need to bring is fishing gear if you’re interested in fishing for smallmouth bass. Or bring a cooler and enjoy the river with a picnic.

Alternatively, you can explore the Rivanna River with Rivanna River Company on a self-guided or guided tour. The guided tour includes stories about the river plus tips for increasing your paddling skills. As you take in the wildlife, you’ll learn how to read whitewater and maneuver your boat.

Source Local Products

Small family farms raising organic crops and free-range livestock dot the countryside. Charlottesville residents and chefs are committed to supporting local farms. To get a taste of Charlottesville’s local flavors, goods, and produce, visit the City Market on a Saturday, Farmers in the Park on Wednesday afternoons, or Key’s Corner Indoor Market from January through March.

The Piedmont Environmental Council provides a rich resource on local fruits and vegetables, meat, dairy, beer, wine, and other local foods.

Local shops of note include Birch Street Goods, a teacher-owned company that specializes in creating materials to support and inspire young children. All items are designed and assembled by hand in a local studio. At Thicket, you’ll find minimalist jewelry inspired by the natural world. Each piece is made by hand using sustainable, reclaimed sterling silver and 14k gold. City Clay focuses on ceramic arts and is centered on the creative process and the joy of community-centered learning.

To make your own art to take home, create a pottery masterpiece at City Clay, or glass art at The Glass Palette. This interactive glass studio will provide the materials, tools, and instruction to create stained and fused-glass projects. Choose from one-day, weekend, and multi-week or immersion classes, depending on your availability and interests.

Pick Your Own Fresh Fruit While Enjoying Panoramic Views Of The City And Blue Ridge Mountains

Visit Carter Mountain Orchards to taste hot cider donuts and apple pie at the Country Store and Bakery, then pick your own fruit at the orchard. Or stay for dinner at Mountain Grill and enjoy farm-to-table fixin’s.

A meal from Michie Tavern in Charlottesville.

Indulge In The Culinary Scene

Charlottesville’s culinary scene is much larger than you would expect for a city this size. There is a multitude of restaurants serving Southern fare with a twist, many focusing on locally sourced produce and meats.

Bodo’s Bagels is legendary and has amassed quite the following for their fresh-baked authentic New York water bagels. The bagels are baked all day so they can offer hot-from-the-oven bagels at any hour. There are so many options, it’s best to check the online menu before you arrive -- and know that while the lines are long, they typically move quickly.

At the historic Michie Tavern, you can sample delicious fried chicken and other Southern favorites in an 18th-century tavern. The servers are dressed in period costumes and the meals are based on 18th-century recipes. Also on site is the General Store. Shop for Virginia-made food products such as apple butter, made-in-Virginia wines, beer, and hard cider, and even period clothing, patterns, shawls, quilts, and more.

You’ll find fine Asian fusion at Bang! The Southern fried chicken steamed buns with spicy mayo and pickles meld two cooking styles to create a hearty and tasty dish. There’s also a vegan menu, so you can enjoy tasty plant-based meals such as the grilled local mushrooms served with baby bok choy and basil.

Macaroni and cheese is a Southern specialty, and you’ll find some of the best at The Virginian, Charlottesville’s oldest restaurant, open since 1923. In addition to their famous mac ’n’ cheese, enjoy burgers, crab cakes, sandwiches, and salads.

Ole’ Virginia Fried Chicken is the specialty at Wayside. The restaurant, listed in Southern Living’s “Best of the South,” has been a favorite eatery for more than 50 years. In addition to chicken, try their hearty breakfasts and seafood platters.

The pool at Keswick Hall in Charlottesville.

Stay At A Luxury Hotel

Immerse yourself in history while sleeping in a grand mansion at Keswick Hall. This luxury resort located amidst scenic rolling hills near the Blue Ridge Mountains has period pieces such as brass room keys and oversized claw-foot bathtubs mixed with modern luxuries such as an infinity pool. Enjoy an onsite golf course, tennis courts, a spa, and a fitness center with classes when the hotel reopens later this year or in spring 2021.

The Boar’s Head Resort is a AAA four-diamond country resort that mixes the beauty of the historic mountain town with state-of-the-art amenities such as a spa and racquet and fitness club.

For a more rustic experience, Montfair Resort Farm immerses you in nature, comfort, and simplicity. Stay in one of the lakeside cottages and enjoy nature trails, canoes, bikes, and fishing. Both the cottages and Beauchamp House are fully equipped with appliances, gas heaters, and air conditioning yet set in a gorgeous rural mountainside setting.