Fall Getaways

History Buffs Will Savor a Trip to Charlottesville, Virginia

Visit Monticello, stay in a historic inn, pick apples, see the leaves change--you can go full fall in Charlottesville.

By Kay Kipling September 28, 2016 Published in the October 2016 issue of Sarasota Magazine

Monticello zbh70e

A leisurely 13-hour drive or a quick flight into Washington, D.C., or direct to the local airport in Charlottesville, Virginia, takes you to the home of Thomas Jefferson and his beloved University of Virginia in the foothills of the Blue Ridge Mountains. You don’t have to be a UVA alum to love walking the campus, especially when autumn colors dominate the grounds. Originally designed by Jefferson as a U-shaped “Academical Village” with terraced lawns and the library/rotunda as the head, UVA feels just the way a university campus ought to. In fact, it’s the only college designated by UNESCO as a World Heritage Site.

Beyond UVA, Charlottesville has a wealth of captivating historic buildings. (You can actually stay at some of them.) You have to visit at least one of the presidential homes occupying the gently rolling hills here; there are three in all, from Jefferson’s famous Monticello (complete with gardens where he experimented with plants as sources for both food and beauty) to the lesser-known but still fascinating Montpelier of James Madison and James Monroe’s Ash Lawn-Highland. Film buffs turn up annually for the Virginia Film Festival (Nov. 3-6 this year), led by former Sarasota Film Festival director Jody Kielbasa. And you might get to hear native son Dave Matthews perform; his band shows up regularly.


The Inn at Court Square (410 E. Jefferson St., 434-295-2800) has guest rooms and suites in two historic, beautifully restored homes, the Butler-Norris House and the Molly Johnson House. Both are across from Stonewall Jackson Park and well-located for strolling and dining; Southern cuisine served in the inn’s dining room for lunch. Rates about $149 to $359 a night.

The Dinsmore House (1211 W. Main St., 434-974-4663) was built by Thomas Jefferson’s master builder in 1817 and has eight guestrooms right in the heart of town. Besides a daily hot breakfast, the owners can provide an in-room farm basket packed with scones, fruit, jams and more. Rates $149-$279.

The Boar’s Head Inn (200 Ednam Drive, 434-296-2181) is a 4-Diamond resort set on 573 acres of Virginia countryside, with 175 renovated rooms and suites, plus fine dining, golf, a spa and other resort experiences. Rates $195-$265

Www.visitcharlottesville.org thomas hill nyp112

The Downtown Mall.


Fall is apple-picking time. Head to Carter Mountain Orchard (1435 Carters Mountain Trail, 434-977-1833) for fresh fruit in varieties from Gala to Jonathan to Fuji and Winesap. A country store here sells apple butter, jams and apple cider doughnuts, too.

Shenandoah National Park  is 20 miles or so outside town, and a must-see. Set your sights on the park’s historic Skyline Drive for gorgeous fall foliage and plentiful chances to spot deer and other wildlife. Hike a trail (more than 500 miles of them here), have a meal at the rustic lodge and take in some homegrown folk music or clogging at Skyland or Big Meadows Lodge.

The historic Downtown Mall boasts more than 120 shops, 50 restaurants and plenty of live music, theater and cinema in its eight blocks; it’s one of the longest outdoor pedestrian malls in the nation.

October is Wine Month in Virginia, with more than 250 local wineries uncorking their best for you by the glass. Or take home a bottle or two. For a complete list of wine tasting ops, click here.

Orzo tb3wxf


Image: Courtesy Orzo


Lawyers and bankers mingle with UVA students and artists at the Court Square Tavern (500 Thomas Jefferson Parkway, 434-296-6111) for fare both light (Tavern Caesar Salad) and hearty (shepherd’s pie), and for its 130-plus imported and micro-brewed beers.

The Threepenny Café (420 W. Main St., 434-995-5277) takes an artistic approach to dishes like fried goat cheese salad, roasted duck breast and global artisan pizzas, carefully prepared and plated with style.

Public Fish & Oyster (513 W. Main St., 434-995-5542), a newer addition to town right across from Threepenny, specializes in fresh East Coast seafood, with a raw bar, craft beer and use of Virginia farm produce.

Orzo (416 W. Main St., 434-975-6796) also believes in fresh ingredients from local farms, changing its menu seasonally but always employing a modern take on traditional Mediterranean recipes.

Filed under
Show Comments