We had a great turnout on Monday, April 13 with 40+ members of AIA Northern Virginia joining us for the Middleburg Architecture & Historic Buildings Walking Tour + Wine Tasting led by AIA NoVA Member and local architect Timothy Clites, AIA — a 20+ year Middleburg resident, small-firm owner, and Chair of the town’s Historic District Review Committee.

While Middleburg is known today for its equestrian estates, scenic landscapes, and wineries, the town has a layered past that reveals a far more complex story than its current reputation as a wealthy enclave. To unveil this history, the tour began at the Middleburg Community Center and continued with stops (for cookies!) at the Toll House, Middleburg Elementary School, and even a peek inside the recently renovated Boyd-Burn House (now a bed & breakfast).

Walking along Washington and Marshall Streets, we stopped at notable historic homes and commercial buildings to learn about their origins, evolution, and present-day use. A key stop was Asbury Church, the oldest surviving African American church in Loudoun County, where we discussed its historical and cultural significance along with current restoration efforts. As we walked through the West side of town, Tim made sure to point out contrasts in building quality, style, and use, in addition to several works by William “Billy” Dew, one of Middleburg’s most recognized architects.

And then there was WINE! In case you are wondering how we fit a wine tasting into an architecture event, Boxwood Estate Winery offers a thoughtful look at how architecture, landscape, and winemaking come together in one cohesive place. Designed by architect Hugh Newell Jacobsen, the winery blends clean, modern forms with materials that feel right at home in rural Virginia. Fieldstone walls, standing seam metal roofs, and glass cupolas reference the area’s historic character while maintaining a distinctly contemporary presence. Recognized with a 2007 Merit Award for Architecture from the AIA Northern Virginia Design Awards, the winery demonstrates how contemporary design can support agriculture, respect history, and create a meaningful visitor experience. We were able to enjoy such an experience ourselves with the final tasting artfully arranged in the stainless steel fermenting room. This dynamic day concluded by pairing four of Boxwood’s premiere and “everyday” wines with a curated selection of dried meats and cheeses.

We would like to extend immense gratitude to our tour guides, Timothy Clites, AIA for bestowing his knowledge about the history of Middleburg and Simon Jacobsen of Jacobsen Architecture, LLC for the insightful architectural tour of Boxwood Winery. We would also like to thank our sponsors who made this fun, enlightening, and delicious expedition possible: CLITES ARCHITECTS, VERITAS CONTRACTING, HUNTLANDS Landscape Architecture, HORN & Co., and GRUVER COOLEY.

In case you are eager for more architecturally focused connection and conversation, check out some of the amazing programming we have lined up for Spring. Additionally, in an ongoing effort to reach our members across the vast region that is Northern Virginia, if you have a project or community for which you would like to coordinate a tour, please reach out to the Chapter!

Leesa Mayfield, AIA, 2026 AIA NoVA Board Director