Episode 4 Itinerary: Explore Lesser-Known History (Homes and Hospitality)

We’ve put together an itinerary that helps you explore lesser-known history surrounding two styles of architecture that define the built environment and hallmarks of hospitality in Charlottesville and Albemarle County.

Listen to the Founding Footprints podcast HERE or on your favorite audio streaming platform.

Itinerary Length: 2.5 – 3 days

Day 1: Federal Architecture

1. Stay in the Federal Style

Develop your itinerary around accommodations at Hollymead House or four other local inns built in the Federal style in Charlottesville and Albemarle County.

Hollymead House started life in 1780 as a log cabin. In 1813, the new owner John Jefferies had a large addition built in the Federal style. This structure serves as the centerpiece of the historic home we see today. “Federal” was a dominant architectural style in America from 1780 until about 1835 and was popular in the construction of both public and residential buildings. As the name suggests, it was a way to translate the ideals of democracy and common tenets of the United States’ founding, into physical and decorative form.

So, how can you identify the Federal style? Common exterior characteristics include

symmetry and simplicity of materials, such as wood and brick
a central door, often with fan- or sidelights, which opens into a hall
double-hung sash windows arranged in a regular pattern, and
a side-gabled roof giving the building a rather flat face.

Porches are small porticos or functional and full length. The doors of Federal-style townhomes may be off-center to reflect the arrangement of rooms inside. Interiors include well-proportioned rooms, often with high ceilings, and delicate ornamentation. Look for dentil moulding, both inside and out, urns, swags, and even bald eagles. Octagonal rooms and Palladian windows were trendy too!

Federal Style Inns and Nearby Attractions

Hollymead House

The Clifton

Crossroads Inn

Dinsmore Inn

Inn at Court Square

- Hollymead House

Hollymead House Bed & Breakfast offers six individual guest rooms, each featuring a private en-suite bath with Villa di Lusso linens and towels and cruelty-free toiletries. Rooms are named in honor of the farm’s history. Guests appreciate the sophisticated and cozy décor with antiques and art chosen by Pam and William, as well as breakfast served every morning in the Garden Room. Consider adding an afternoon tea experience with Pétale to your stay. Hollymead House is a great place to relax and walk on-site trails, or as a launchpad to explore wineries in the Earlysville and Barboursville areas. The inn is located 7 – 8 miles from the UVA Rotunda and Charlottesville’s Downtown Mall and an easy 30-minute drive to the Swift Run Gap entrance at Shenandoah National Park.

- The Clifton

The Clifton is a beautiful boutique hotel encompassing several historic buildings on 100 acres along the Rivanna River. The core of the Manor House was built in 1799 as a home for Thomas Mann Randolph who served in the Virginia House of Delegates and U.S. Congress and as Governor of Virginia. Randolph is perhaps best known as husband to Martha Jefferson Randolph and son-in-law to Thomas Jefferson! Today, Clifton guests can enjoy old-fashioned sports like croquet and horseshoes, walking trails, a private lake, and infinity pool – all on property – as well as modern interior décor. The nationally recognized 1799 Restaurant and Copper Bar are open to the public. The Clifton is about 6.5 miles east of downtown Charlottesville and conveniently located for visits to Monticello and Highland, vineyards in the Keswick area, and the Kluge-Ruhe Aboriginal Art Collection.

- Crossroads Inn

Crossroads Inn has been welcoming travelers since it was built as a tavern on the James River Turnpike. The 19th century route, also known as Plank Road, connected farms in the Shenandoah Valley to the James River port at Scottsville. The building is listed on the Virginia Landmarks Register and National Register of Historic Places because of this link to agricultural, transportation, and tavern history and for its simple and unaltered exterior. Crossroads is now part of the Easton Porter collection of properties and Pippin Hill Farm and Winery. So, guests can expect a high level of hospitality. Be sure to include a visit to the tasting room, guided estate tour, or cooking class in your stay. The Inn is also close to the charming Batesville Market and cideries and wineries in southern and western Albemarle County.

- The Dinsmore

The Dinsmore Inn takes its name from owner and architect James Dinsmore. Born in Northern Ireland, by 1798, Dinsmore had become an American citizen, and perhaps most significantly for architectural history, met Thomas Jefferson. He worked as master builder at Monticello from 1798 until 1809. Then he and countryman John Neilsen worked for James Madison to expand Montpelier between 1809 and 1812. In 1817, Jefferson called on both builders to help with construction at the recently established University of Virginia. Dinsmore recognized that the University would spur growth in Charlottesville. So, between 1818 and 1825, he built Federal style houses along West Main Street including what is the inn today. Offering nine guest rooms, the Dinsmore is within walking distance of UVA Grounds and the Amtrak Station as well as dozens of restaurants in the Midtown neighborhood. The on-site Farm Bell Kitchen, known for its Southern menu and delicious breakfast, is a favorite of students, local chefs, and visitors from around the world.

- Inn at Court Square

The Inn at Court Square consists of two historic structures, including the c.1785 Butler-Norris house – one of the oldest remaining in the heart of downtown Charlottesville. The Inn offers ten upscale guestrooms and genuine hospitality by the DeLoach family. Nationally known interior designers, Candace and her brother Michael have added their personal flair to each space. Guests can purchase antiques and decorative items on display throughout the Inn. Court Square is just a couple blocks from the Downtown Mall where you will find concert venues like Ting Pavilion and Jefferson Theater, art galleries, and a myriad of independent boutiques.

Day 2: Colonial Revival and Milton Grigg

Centennial celebrations in 1876 sparked interest in the country’s founding. The 150th anniversary in 1926, and major projects like Colonial Williamsburg, heightened the fascination for visiting historic sites and living in early American homes. Historic preservation developed as a new field of study with standards of practice. At the same time, nostalgia affected what stories and myths of the past were shared.

Milton LaTour Grigg was a preservationist and architect instrumental in restoring Virginia’s 18th and 19th century buildings as well as propagating the Colonial Revival here in Charlottesville and Albemarle County. For those who like tidy definitions, “Colonial Revival” can be difficult to pin down as it draws inspiration from many earlier sources. Prolific and popular for an extended period – most notably between 1880 and the 1950s, it influenced furniture, decorative arts, garden design, fashion, and literature. A common denominator for Colonial Revival houses: borrowing elements from a sometimes idealized past while still offering conveniences for modern living and entertaining. Grigg’s work at Hollymead House in 1937 for professor B.F.D. ‘Dee’ Runk included restoration and sympathetic renovations to introduce electricity and plumbing and expand the layout.

1. Visit Monticello and Michie Tavern

Credit: Grigg, Milton L. (Milton LaTour) (work creator). Michie Tavern: Michie Tavern - First Floor Plan.

Connect with Milton Grigg through the structures he helped protect, including Monticello where he worked on restoration projects between 1935 and 1954, and Michie Tavern, where he lived and maintained his firm’s office in the 1930s.

2. Attend an A-School Event

Attend an exhibit, lecture, or talk at UVA’s School of Architecture. The A-School was founded in 1919 under the direction of Fiske Kimball – later a mentor and colleague of Milton Grigg. Early professors and alumni included Stanislaw Makielski, Grigg, and Marshall Swain Wells, whose designs, along with those of Walter Dabney Blair and Eugene Bradbury, have become landmarks of Charlottesville and Albemarle County.

3. Celebrate Cocktails and Jazz

Honor Grigg’s penchant for martinis and jazz. The Alley Light, Lost Saint, Mas Tapas, Ten, Tonic, and Crawford’s at Keswick Hall are local favorites for grownup drinks in a grownup atmosphere. Hone your skills with a Cocktail Masterclass at the Aspen Bar, or sample the selection of martinis at Vivace.

The Charlottesville Jazz Society highlights jazz performances throughout the area and often brings big name artists to Charlottesville. Sundays Are For Jazz offers a regular jam session at Miller's Downtown. Or enjoy Gin & Jazz on Monday evenings at the Oakhurst Inn's Chateau Bar.

4. Check Out the Southern Living Idea House

Collect tips and inspirations for your personal space! Instead of looking to the colonial past, the Idea House presents a modern farmstead with deep porches, functional and fun living spaces, and thoughtful landscaping. Make a stop at Merrie Mill Farm & Vineyard. The tasting room was designed by Dalgliesh Gilpin Paxton Architects, the present-day iteration of Milton Grigg’s firm.

Day 3: The Convention Army

The Battles of Saratoga in autumn of 1777 were a major victory for American forces. British General John Burgoyne capitulated on October 17 after negotiating with American field commander Horatio Gates. Their agreement or convention stipulated that troops would be returned to Europe; however, neither government supported these terms. The British and German – collectively known as Hessian – soldiers captured at Saratoga became de facto prisoners of war. After a year imprisoned near Boston, the 4,000-strong Convention Army made the 650-mile march to Central Virginia, arriving in the exceptionally cold winter of 1779.

At the time, Albemarle County was remote, on Virginia’s western frontier, far from fighting on the eastern seaboard, and in need of more residents if the community was to succeed. The Convention Army brought highly skilled labor and the women and families who traveled with them. These thousands of individuals built a small town at the barracks, near present-day Garth Road, and regularly interacted with residents. Officers were allowed to live off site and often rented local homes, and some enlisted men labored off site. But the barracks were short-lived. By end of 1780, as the British invaded inland, the remaining members of the Convention Army were moved north. Today, it is remembered in names of places, such as Barracks and Hessian Roads, and in the history of buildings, like Hollymead House, that are miles from the former encampment.

1. Take a Tour

Book a private Revolutionary War Tour with historian Rick Britton to learn more about the Convention Army’s time in the area.

2. Shop Barracks Road

Spend time at Barracks Road Shopping Center. One of the most popular shopping districts in Charlottesville, it includes both national chains and local specialty shops like Albemarle Angler, Fluffy’s Pet Shop, Green Bean Baby Boutique, The Happy Cook, Scarpa, and The Virginia Shop.

Look for future episodes of Founding Footprints and make your travel plans now. In addition to the five Federal style accommodations mentioned above, Charlottesville and Albemarle County offer a variety of places to stay including resorts, inns, B&Bs, hotels, and vacation rentals – so you can book the lodging that aligns with your travel preferences.

Places to Stay Charlottesville and Albemarle County offer visitors a wide variety of places to stay, including resorts, hotels, inns, bed and breakfasts, cabins, and vacation rentals. Learn More